Supporting Information for

Size: px
Start display at page:

Download "Supporting Information for"

Transcription

1 Supporting Information for Probing the Anticancer Action of Oridonin with Fluorescent Analogues: Visualizing Subcellular Localization to Mitochondria Shengtao Xu,#, Shanshan Luo,#, Hong Yao, Hao Cai, Xiaoming Miao,$, Fang Wu, *, Dong-Hua Yang, Xiaoming Wu, Weijia Xie, Hequan Yao, Zhe-Sheng Chen, Jinyi Xu, * State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing , P. R. China Department of Pharmacology, School of Pharmacy, Fudan University, Shanghai , P. R. China State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Tianjin , P. R. China Key Laboratory of Systems Biomedicine (Ministry of Education), Shanghai Center for Systems Biomedicine, Shanghai Jiao Tong University, Shanghai, , P. R. China College of Pharmacy and Health Sciences, St. John's University, 8000 Utopia Parkway, Queens, New York, NY 11439, USA Contents General procedures for the synthesis of starting materials Page S2-S4 1 H NMR and 13 C NMR spectra of probes S5-S10 Figure S1 Figure S2 Figure S3 2D NMR of probe 17d Spectra date Purity of probes S11 S12 S13 S13-S18 S18-S36 S36-S40 S1

2 Stability test of probe 17d in cells References S41-S45 S45 General Procedures for the Synthesis of Starting Materials The titled compound 14 was prepared according to the literature procedure 1. Ethyl-7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate (13) was synthesized according to the literature procedure 1 as a yellow crystalline solid: (62%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.23 (t, J = 6.0 Hz, 6H), 1.38 (q, J = 6.0 Hz, 3H), 3.44 (q, J = 6.0 Hz, 4H), 4.36 (q, J = 6.0 Hz, 2H), 6.44 (d, J = 2.4 Hz, 1H), 6.60 (dd, J = 9.0, 2.4 Hz, 1H), 7.35 (d, J = 9.0 Hz, 1H), 8.41 (s, 1H); MS(ESI) m/z: [M+H] +. 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylic acid (14) was synthesized from compound 13 according to the literature procedure 1 as a yellow crystalline solid: (91%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.26 (t, J = 6.0 Hz, 6H), 3.49 (q, J = 6.0 Hz, 4H), 6.54 (d, J = 2.4 Hz, 1H), 6.70 (dd, J = 9.0, 2.4 Hz, 1H), 7.45 (d, J = 9.0 Hz, 1H), 8.65 (s, 1H), (br, 1H); MS(ESI) m/z: [M+H] +. 2-hydroxyethyl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate (Compound 15a) A solution of 14 (1 g, 3.83 mmol, 1 equiv.) and ethylene glycol (2.38 g, mmol, 10 equiv.) in dry dichloromethane (20.0 ml) was stirred at room temperature for 24 h. After concentration, the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with water and brine, dried over Na 2 SO 4 and concentrated. Column chromatography (MeOH/CH 2 Cl 2 1:150, v/v) offers the titled product 15a (1.02 g, 85%) as a yellow solid, mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.25 (t, J = 6.0 Hz, 6H), 2.86 (br, 1H), 3.44 (q, J = 6.0 Hz, 4H), 3.92 (m, 2H), 4.44 (m, 2H), 6.46 (d, J = 2.4 Hz, 1H), 6.61 (dd, J = 9.0, 2.4 Hz, 1H), 7.36 (d, J = 9.0 Hz, 1H), 8.45 S2

3 (s, 1H); MS(ESI)m/z: 306.2[M+H] +. Analogous reactions of coumarin with propanediol, butanediol or diethylene glycol gave compounds 15b, 15c, and 15d respectively as yellow solids. 3-hydroxypropyl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate (Compound 15b) (yield 83%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.24 (t, J = 6.0 Hz, 6H), 2.01 (m, 2H), 3.33 (br, 1H), 3.44 (q, J = 6.0 Hz, 4H), 3.84 (t, J = 6.0 Hz, 2H), 4.47 (t, J = 6.0 Hz, 2H), 6.46 (d, J = 2.4 Hz, 1H), 6.61 (dd, J = 9.0, 2.4 Hz, 1H), 7.36 (d, J = 9.0 Hz, 1H), 8.48 (s, 1H); MS(ESI)m/z: 320.2[M+H] +. 4-hydroxybutyl 7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate (Compound 15c) (yield 85%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.23 (t, J = 6.0 Hz, 6H), 1.26 (m, 2H), 1.89 (m, 2H), 2.08 (br, 1H), 3.44 (q, J = 6.0 Hz, 4H), 3.73 (t, J = 6.0 Hz, 2H), 4.35 (t, J = 6.0 Hz, 2H), 6.46 (d, J = 2.4 Hz, 1H), 6.61 (dd, J = 9.0, 2.4 Hz, 1H), 7.36 (d, J = 9.0 Hz, 1H), 8.44 (s, 1H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 164.0, 158.0, 152.5, 149.0, 130.6, 109.1, 107.2, 96.2, 64.7, 61.5, 44.6, 29.0, 24.5, 12.0; MS(ESI) m/z: [M+H] +. 2-(2-hydroxyethoxy)ethyl-7-(diethylamino)-2-oxo-2H-chromene-3-carboxylate (Compound 15d) (yield 80%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.16 (t, J = 6.0 Hz, 6H), 2.53 (br, 1H), 3.37 (q, J = 6.0 Hz, 4H), 3.62 (m, 2H), 3.70 (m, 2H), 3.78 (m, 2H), 4.40 (m, 2H), 6.38 (d, J = 2.4 Hz, 1H), 6.53 (dd, J = 9.0, 2.4 Hz, 1H), 7.27 (d, J = 9.0 Hz, 1H), 8.38 (s, 1H); MS(ESI)m/z: [M+H] +. 4-(2-((7-(diethylamino)-2-oxo-2H-chromene-3-carbonyl)oxy)ethoxy)-4-oxobutanoic acid (Compound 16a) A solution of 15a (0.5 g, 1.64 mmol, 1 equiv.) and glutaric anhydride (0.18 g, 1.80 mmol, 1.1 equiv.) in dry dichloromethane (20.0 ml) was stirred at room temperature in the presence of catalytic amount of DMAP for 72 h. After concentration, the residue was partitioned between EtOAc and water. The aqueous layer was extracted S3

4 with EtOAc, and the combined organic layers were washed with water and brine, dried over Na 2 SO 4 and concentrated. Column chromatography (MeOH/CH 2 Cl 2 1:120, v/v) offers the titled product 16a (0.58 g, 87%) as a yellow oil; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.24 (t, J = 6.3 Hz, 6H), 2.68 (m, 4H), 3.45 (q, J = 6.3 Hz, 4H), 4.47 (m, 4H), 6.45 (s, 1H), 6.61 (d, J = 8.1, 1H), 7.36 (d, J = 7.8 Hz, 1H), 8.44 (s, 1H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 172.1, 163.8, 158.5, 153.1, 149.8, 131.4, 109.8, 107.7, 96.6, 62.6, 45.1, 29.1, 12.4; MS(ESI)m/z: [M+H] +. Analogous procedures starting with 15a-d gave compounds 16b-e as yellow oils. 5-(2-((7-(diethylamino)-2-oxo-2H-chromene-3-carbonyl)oxy)ethoxy)-5-oxopentanoic acid (Compound 16b) (yield 76%); 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.16 (t, J = 6.9 Hz, 6H), 1.88 (m, 2H), 2.38 (m, 4H), 3.36 (q, J = 6.6 Hz, 4H), 4.38 (m, 4H), 6.37 (d, J = 2.1 Hz, 1H), 6.52 (dd, J = 9.0, 2.1 Hz, 1H), 7.29 (d, J = 9.0 Hz, 1H), 8.36 (s, 1H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 172.8, 163.9, 158.5, 153.1, 149.7, 131.3, 109.7, 107.7, 96.6, 62.7, 62.3, 45.1, 33.0, 33.9, 29.7, 19.8, 12.4; MS(ESI)m/z: [M+H] +. 5-(3-((7-(diethylamino)-2-oxo-2H-chromene-3-carbonyl)oxy)propoxy)-5-oxopentanoi c acid (Compound 16c) (yield 71%); 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.16 (t, J = 6.9 Hz, 6H), 1.86 (m, 2H), 2.03 (m, 2H), 2.34 (m, 4H), 3.36 (q, J = 6.6 Hz, 4H), 4.17 (t, J = 6.0 Hz, 2H), 4.31 (t, J = 6.0 Hz, 2H), 6.37 (d, J = 2.1 Hz, 1H), 6.54 (dd, J = 9.0, 2.1 Hz, 1H), 7.28 (d, J = 9.0 Hz, 1H), 8.35 (s, 1H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 173.0, 164.2, 158.5, 153.0, 149.5, 131.2, 109.7, 96.6, 61.6, 61.2, 45.1, 33.2, 29.7, 28.0, 19.9, 12.4; MS(ESI)m/z: [M+H] +. 5-(4-((7-(diethylamino)-2-oxo-2H-chromene-3-carbonyl)oxy)butoxy)-5-oxopentanoic acid (Compound 16d) (yield 78%); 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.23 (t, J = 6.0 Hz, 6H), 1.79 (m, 4H), 2.02 (m, 2H), 2.46 (m, 4H), 3.45 (q, J = 6.0 Hz, 4H), 4.17 (t, J = 6.0 Hz, 2H), 4.35 (t, J = 6.0 Hz, 2H), 6.46 (d, J = 2.4 Hz, 1H), 6.61 (dd, J = 9.0, S4

5 2.4 Hz, 1H), 7.36 (d, J = 9.0 Hz, 1H), 8.43 (s, 1H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 152.5, 148.8, 130.6, 109.1, 96.2, 64.1, 63.6, 44.6, 32.7, 32.3, 29.2, 24.9, 24.8, 19.4, 11.9; MS(ESI)m/z: [M+H] +. 5-(2-(2-((7-(diethylamino)-2-oxo-2H-chromene-3-carbonyl)oxy)ethoxy)ethoxy)-5-oxo pentanoic acid (Compound 16e) (yield 76%); 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.37 (m, 6H), 1.95 (m, 2H), 2.45 (m, 4H), 3.46 (q, J = 6.6 Hz, 4H), 3.77 (t, J = 6.0 Hz, 2H), 3.85 (t, J = 6.0 Hz, 2H), 4.28 (t, J = 6.0 Hz, 2H), 4.46 (t, J = 6.0 Hz, 2H), 6.45 (d, J = 2.1 Hz, 1H), 6.61 (dd, J = 9.0, 2.1 Hz, 1H), 7.37 (d, J = 9.0 Hz, 1H), 8.46 (s, 1H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 153.0, 149.6, 131.2, 109.6, 96.7, 69.1, 64.1, 63.6, 45.1, 33.1, 32.8, 29.7, 19.8, 12.4; MS(ESI)m/z: [M+H] +. The titled compound 21 was prepared according to the literature procedure [1] as a brown solid, 2-(7-(dimethylamino)-2-oxo-2H-chromen-4-yl)acetic acid (21) (29% over two steps); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 3.30 (s, 6H), 3.77 (s, 2H), 6.04 (s, 1H), 6.55 (s, 1H), 6.72 (d, J = 9.0 Hz, 1H), 7.45 (d, J = 9.0 Hz, 1H), (br, 1H); 13 C NMR (75 MHz, DMSO): δ (ppm) 171.4, 161.4, 156.1, 153.5, 150.9, 126.7, 110.3, 110.3, 109.8, 108.8, 98.2, 40.3, 38.0; MS(ESI)m/z: [M+H] +. 2-hydroxyethyl 2-(7-(dimethylamino)-2-oxo-2H-chromen-4-yl)acetate (Compound 22a) A solution of 21 (1 g, 4.04 mmol, 1 equiv.) and glycol (2.51 g, mmol, 10 equiv.) in dry dichloromethane (20.0 ml) was stirred at room temperature for 24 h. After concentration, the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with water and brine, dried over Na 2 SO 4 and concentrated. Column chromatography (MeOH/CH 2 Cl 2 1:100, v/v) offers the titled product 22a (1.01 g, 86%) as a pale yellow solid; mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.98 (br, 1H), 3.06 (s, 6H), 3.74 (s, 2H), 3.82 (m, 2H), 4.27 (m, 2H), 6.09 (s, 1H), 6.56 S5

6 (d, J = 2.4 Hz, 1H), 6.72 (dd, J = 9.0, 2.4 Hz, 1H), 7.41 (d, J = 9.0 Hz, 1H); 13 C NMR (75 MHz, DMSO): δ (ppm) 168.9, 161.6, 155.4, 152.5, 147.9, 124.7, 110.0, 108.6, 107.8, 97.8, 66.5, 60.2, 39.6, 37.4; MS(ESI)m/z: [M+H] +. An analogous procedure starting with 21 gave 4-hydroxybutyl 2-(7-(dimethylamino)- 2-oxo-2H-chromen-4-yl)acetate (Compound 22b) as a pale yellow solid (81%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.55 (m, 2H), 1.68 (m, 2H), 3.04 (s, 6H), 3.62 (t, J = 6.3 Hz, 2H), 3.68 (s, 2H), 4.15 (t, J = 6.3 Hz, 2H), 6.05 (s, 1H), 6.52 (d, J = 2.4 Hz, 1H), 6.62 (dd, J = 9.0, 2.4 Hz, 1H), 7.40 (d, J = 9.0 Hz, 1H); MS(ESI)m/z: [M+H] +. 4-(2-(2-(7-(dimethylamino)-2-oxo-2H-chromen-4-yl)acetoxy)ethoxy)-4-oxobutanoic acid (Compound 23a) A solution of 22a (0.5 g, 1.72 mmol, 1 equiv.) and glutaric anhydride (0.19 g, 1.89 mmol, 1.1 equiv.) in dry dichloromethane (20.0 ml) was stirred at room temperature in the presence of catalytic amount of DMAP for 72 h. After concentration, the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with water and brine, dried over Na 2 SO 4 and concentrated. Column chromatography (MeOH/CH 2 Cl 2 1:120, v/v) offers the titled product 23a (0.60 g, 89%) as a yellow solid; mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 2.45 (m, 4H), 3.00 (s, 6H), 3.89 (s, 2H), 4.22 (t, J = 6.3 Hz, 2H), 4.27 (t, J = 6.3 Hz, 2H), 6.05 (s, 1H), 6.53 (d, J = 2.4 Hz, 1H), 6.71 (dd, J = 9.0, 2.4 Hz, 1H), 7.44 (dd, J = 9.0, 2.4 Hz, 1H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 173.2, 172.0, 169.2, 160.6, 155.4, 152.8, 149.3, 125.9, 109.7, 109.0, 107.8, 97.4, 62.6, 61.8, 36.7, 28.5; MS(ESI)m/z: [M+H] +. An analogous procedure starting with 22b gave 5-(4-(2-(7-(dimethylamino)-2-oxo-2H -chromen-4-yl)acetoxy)butoxy)-5-oxopentanoic acid (Compound 23b) as a yellow solid (yield 82%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.67 (m, S6

7 4H), 1.92 (m, 2H), 2.42 (m, 4H), 3.06 (s, 6H), 3.69 (s, 2H), 4.05 (t, J = 6.3 Hz, 2H), 4.14 (t, J = 6.3 Hz, 2H), 6.07 (s, 1H), 6.52 (d, J = 2.4 Hz, 1H), 6.63 (dd, J = 9.0, 2.4 Hz, 1H), 7.40 (d, J = 9.0, 1H); MS(ESI)m/z: [M+H] +. 1 H NMR and 13 C NMR spectra of probes Compound 17a Compound 1 (100 mg, 0.27 mmol, 1 equiv.) was dissolved in dichloromethane, then 16a (110 mg, 0.27 mmol, 1 equiv.), EDCI (62 mg, 0.32 mmol, 1.2 equiv.) and catalytic amount of DMAP were added. The reaction mixture was stirred at room temperature for 1 h. Then the mixture was washed with 10% HCl. The organic layer was washed with brine, dried over anhydrous Na 2 SO 4. After flash chromatography (dichloromethane/methanol 100:1), compound 17a was obtained as a yellow solid (185 mg, 91%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.11 (s, 6H), 1.28 (t, J = 6.6 Hz, 6H, N(CH 2 CH 3 ) 2 ), 1.50 (m, 10H), 1.96 (m, 1H), 2.19 (m, 1H), 2.60 (m, 4H), 3.15 (d, J = 10.2 Hz, 1H), 3.45 (4H, q, J = 6.6 Hz, -N(CH 2 CH 3 ) 2 ), 3.75 (m, 1H), 4.27, 4.06 (dd, J A = J B = 10.8 Hz, each 1H, 20-CH 2 ), 4.10 (m, 1H), 4.41 (t, J = 4.5 Hz, 2H), 4.48 (t, J = 4.5 Hz, 2H), 5.52 (s, 1H), 5.88 (s, 1H), 6.06 (d, J = 10.8 Hz, 1H), 6.14 (s, 1H), 6.49 (s, 1H, Ar-H), 6.6 (d, J = 9.0 Hz, 1H, Ar-H), 7.44 (d, J = 9.0 Hz, 1H, Ar-H), 8.43 (s, 1H, Ar-H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 206.6, 171.4, 170.5, 165.2, 157.3, 152.1, 149.2, 149.1, 130.9, 119.9, 109.2, 107.4, 96.2, 95.0, 73.7, 72.9, 66.9, 63.1, 62.1, 59.0, 54.1, 44.6, 40.8, 38.1, 34.8, 33.2, 32.1, 29.9, 29.4, 29.0, 28.3, 27.1, 21.2, 19.3, 11.9; MS (ESI) m/z: [M-H] -, [M+H] +, [M+Na] + ; HR-MS (ESI) m/z: calcd for C 40 H 49 NNaO 13 [M+Na] , found An analogous procedure starting with 16b gave compound 17b as a yellow solid, (yield 84%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.11 (s, 6H), 1.28 (t, J = 7.2 Hz, 6H, N(CH 2 CH 3 ) 2 ), 1.70 (m, 8H ), 1.94 (m, 4H), 2.27 (m, 1H), 2.34 (m, 4H), 2.61 (m, 1H), 3.18 (d, J = 9.9 Hz, 1H), 3.44 (q, J = 7.2 Hz, 4H, N(CH 2 CH 3 ) 2 ), S7

8 3.76 (m, 1H), 4.28, 4.04 (dd, J A = J B = 10.8 Hz, each 1H, 20-CH 2 ), 4.16 (s, 1H), 4.39 (m, 2H), 4.49 (m, 2H), 5.50 (s, 1H), 5.87 (s, 1H), 6.04 (d, J = 10.5 Hz, 1H), 6.14 (s, 1H), 6.46 (s, 1H, Ar-H), 6.63 (d, J = 9.0 Hz, 1H, Ar-H), 7.37 (d, J = 9.0 Hz, 1H, Ar-H), 8.42 (1H, s, Ar-H); MS(ESI)m/z: [M+H] + ; HR-MS (ESI) m/z: calcd for C 41 H 51 NNaO 13 [M+H] , found An analogous procedure starting with 16c gave compound 17c as a yellow solid, (yield 88%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.11 (s, 6H), 1.27 (t, J = 7.2 Hz, 6H, N(CH 2 CH 3 ) 2 ), 1.29 (m, 2H), 1.66 (m, 7H ), 1.94 (m, 3H), 2.08 (m, 2H), 2.27 (m, 1H), 2.34 (t, J = 7.5 Hz, 4H), 2.61 (m, 1H), 3.18 (d, J = 9.9 Hz, 1H), 3.46 (q, J = 7.2 Hz, 4H, N(CH 2 CH 3 ) 2 ), 3.76 (m, 1H), 4.28, 4.09 (dd, J A = J B = 10.8 Hz, each 1H, 20-CH 2 ), 4.17 (s, 1H), 4.25 (t, J = 6.3 Hz, 2H), 4.37 (t, J = 6.3 Hz, 2H), 5.51 (s, 1H), 5.88 (s, 1H), 6.06 (d, J = 10.5 Hz, 1H), 6.14 (s, 1H), 6.46 (d, J = 2.4 Hz, 1H, Ar-H), 6.63 (dd, J = 9.0, 2.4 Hz, 1H, Ar-H), 7.37 (d, J = 9.0 Hz, 1H, Ar-H), 8.41 (1H, s, Ar-H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 206.2, 172.2, 170.8, 163.6, 158.1, 152.4, 149.5, 148.8, 130.8, 119.8, 109.1, 107.1, 96.2, 95.6, 73.5, 73.0, 62.9, 61.1, 59.2, 54.1, 44.6, 40.8, 38.1, 33.4, 33.3, 32.4, 32.0, 30.0, 29.6, 29.3, 27.5, 21.2, 19.2, 11.9; MS(ESI)m/z: [M+H] + ; HR-MS (ESI) m/z: calcd for C 42 H 53 NNaO 13 [M+H] , found An analogous procedure starting with 16d gave compound 17d as a yellow solid, (yield 80%); mp C; 1 H NMR(CDCl 3, 300 MHz), δ (ppm) 8.42 (1H, s), 7.37 (1H, d, J = 8.94 Hz), 6.62 (1H, dd, J = 8.97, 2.34 Hz), 6.46 (1H, d, J = 2.16 Hz), 6.05 (1H, s), 6.07 (1H, d, J = Hz), 5.88 (1H, s), 5.51 (1H, s), (3H, m, 20-CH 2 ), (4H, m), 3.73 (1H, m), (5H, m), 3.17 (1H, d, J = 9.81 Hz), 2.60 (1H, m), (4H, m), 2.29 (1H, m), 1.97 (1H, m), 1.90 (2H, m), (4H, m), 1.73 (1H, m), 1.68 (1H, m), 1.58 (1H, m), 1.44 (1H, m), 1.30 (1H, m), (2H, m), 1.24 (6H, t, J = 7.14 Hz), 1.88 (6H, s); 13 C NMR(CDCl 3, 75 MHz), δ (ppm) 206.5, 172.7, 171.3, 164.2, 158.4, 158.2, 152.9, 149.9, 149.2, 131.1, S8

9 120.0, 109.5, 108.8, 107.7, 96.7, 96.1, 76.4, 74.1, 73.4, 64.5, 64.0, 63.4, 61.9, 59.7, 54.6, 45.0, 41.3, 38.7, 33.7, 33.5, 33.0, 32.5, 30.5, 30.0, 29.6, 25.4, 25.3, 21.6, 19.8, 19.8, 12.4; MS (ESI) m/z: [M-H] -, [M+H] + HR-MS (ESI) m/z: calcd for C 43 H 56 NO 13 [M+H] , found An analogous procedure starting with 16e gave compound 17e as a yellow solid, (yield 72%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.11 (s, 6H), 1.23 (t, J = 7.2 Hz, 6H, N(CH 2 CH 3 ) 2 ), 1.29 (m, 2H), 1.66 (m, 6H ), 1.92 (m, 2H), 1.99 (m, 1H), 2.27 (m, 1H), 2.34 (t, J = 7.5 Hz, 4H), 2.61 (m, 1H), 3.18 (d, J = 9.9 Hz, 1H), 3.47 (q, J = 7.2 Hz, 4H, N(CH 2 CH 3 ) 2 ), 3.52 (m, 1H), 3.76 (m, 1H), 3.75 (t, J = 4.5 Hz, 2H), 3.82 (t, J = 4.5 Hz, 2H), 4.28, 4.09 (dd, J A = J B = 10.8 Hz, each 1H, 20-CH 2 ), 4.15 (s, 1H), 4.25 (t, J = 6.3 Hz, 2H), 4.46 (t, J = 6.3 Hz, 2H), 5.51 (s, 1H), 5.87 (s, 1H), 6.06 (d, J = 10.5 Hz, 1H), 6.14 (s, 1H), 6.46 (d, J = 2.4 Hz, 1H, Ar-H), 6.63 (dd, J = 9.0, 2.4 Hz, 1H, Ar-H), 7.37 (d, J = 9.0 Hz, 1H, Ar-H), 8.44 (1H, s, Ar-H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 206.1, 172.3, 170.9, 163.6, 157.8, 152.5, 149.3, 149.0, 130.7, 119.7, 109.2, 107.1, 96.1, 95.6, 76.1, 73.6, 72.8, 68.5, 63.5, 63.0, 62.9, 61.3, 59.2, 54.1, 44.6, 40.8, 38.1, 33.2, 32.9, 32.4, 32.0, 30.0, 29.3, 21.1, 19.2, 11.9; MS(ESI)m/z: [M+H] + ; HR-MS (ESI) m/z: calcd for C 43 H 55 NNaO 14 [M+H] , found An analogous procedure starting with 23a gave compound 24a as a pale yellow solid, (yield 73%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.09 (s, 3H), 1.11 (s, 3H), 1.26 (m, 4H), 1.61 (m, 7H), 1.97 (m, 1H), 2.22 (m, 1H), 2.57 (m, 4H), 3.07 (s, 6H, N(CH 3 ) 2 ), 3.15 (m, 1H), 3.50 (m, 1H), 3.74 (s, 2H), 4.05 (d, J = 8.7 Hz, 1H), 4.28 (m, 5H), 5.52 (s, 1H), 5.90 (s, 1H), 6.04 (m, 1H), 6.09 (s, 1H), 6.15 (s, 1H, Ar-H), 6.57 (s, 1H, Ar-H), 6.66 (d, J = 9.0 Hz, 1H, Ar-H), 7.43 (d, J = 9.0 Hz, 1H, Ar-H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 206.0, 171.3, 170.3, 168.5, 161.3, 155.4, 152.5, 149.4, 147.7, 124.8, 119.7, 110.2, 108.6, 107.9, 97.8, 95.6, 75.7, 73.8, 72.9, 62.8, 62.5, 61.7, 61.5, 59.0, 54.2, 40.8, 39.6, 38.2, 37.3, 33.2, 32.1, 30.0, 29.8, 29.4, 29.1, 21.2, 19.3; MS (ESI) m/z: [M-H] -, [M+H] + ; HR-MS (ESI) m/z: calcd for S9

10 C 39 H 48 NO 13 [M+H] , found An analogous procedure starting with 23b gave compound 24b as a pale yellow solid, (yield 68%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.01 (s, 6H), 1.20 (m, 3H), 1.72 (m, 8H), 1.85 (m, 4H), 2.24 (m, 1H), 2.34 (m, 5H), 2.50 (m, 1H), 2.98 (s, 6H, N(CH 3 ) 2 ), 3.10 (m, 1H), 3.42 (m, 1H), 3.63 (s, 2H), 3.75, 4.02 (dd, J A = J B = 10.8 Hz, each 1H, 20-CH 2 ), 4.10 (m, 4H), 4.25 (m, 2H), 5.44 (s, 1H), 5.79 (s, 1H), 5.97 (s, 1H), 6.07 (m, 2H), 6.44 (d, J = 2.2 Hz, 1H), 6.54 (dd, J = 9.0, 4.8 Hz, 1H, Ar-H), 7.33 (d, J = 9.0 Hz, 1H, Ar-H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 206.1, 172.2, 170.9, 168.6, 161.3, 155.4, 152.5, 149.3, 148.0, 128.3, 124.8, 119.7, 110.0, 108.6, 107.9, 97.7, 95.6, 75.9, 73.6, 72.7, 64.5, 63.3, 63.0, 61.4, 59.1, 54.1, 40.8, 39.6, 39.6, 38.1, 37.7, 33.2, 33.0, 32.5, 32.1, 30.0, 29.3, 24.6, 24.6, 21.2, 19.2; MS(ESI)m/z: [M+Na] + ; HR-MS (ESI) m/z: calcd for C 42 H 53 NNaO 13 [M+Na] , found An analogous procedure starting with 21 gave compound 24c as a pale yellow solid, (yield 89%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.11 (s, 6H), 1.26 (m, 3H ), 1.45 (m, 4H), 1.77 (m, 2H), 2.11 (m,1h), 2.95(m, 1H), 3.08 (6H, s), 3.60 (s, 2H), 3.75 (m, 1H), 4.03, 4.08 (dd, J A = J B = 10.8 Hz, each 1H, 20-CH 2 ), 4.39 (s, 1H), 4.59 (m,1h), 4.66 (s, 1H), 5.12 (s, 1H), 5.52 (s, 1H), 6.01 (s, 1H), 6.14 (s, 1H, Ar-H), 6.28 (d, J = 11.4 Hz, 1H), 6.55 (d, J = 2.7 Hz, 1H, Ar-H), 6.64 (dd, J = 9.0, 2.7 Hz, 1H, Ar-H), 7.35 (d, J = 9.0 Hz, 1H, Ar-H); 13 C NMR (75 MHz, DMSO-d 6 ): δ (ppm) 212.3, 171.8, 164.6, 159.4, 156.9, 155.3, 153.2, 130.1, 123.6, 113.6, 113.0, 111.8, 101.4, 100.7, 79.7, 76.8, 76.3, 66.1, 65.0, 63.2, 54.9, 46.4, 41.3, 37.0, 36.1, 33.3, 28.5, 25.3, 21.5; MS(ESI)m/z:592.2 [M-H] - ; HR-MS (ESI) m/z: calcd for C 33 H 29 NNaO 9 [M+H] , found An analogous procedure starting with 16d gave compound 27 as a yellow solid, (yield 82%); mp C; 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 1.01 (s, 3H), 1.06 (m, 3H), 1.14 (s, 3H), 1.16 (t, J = 7.2 Hz, 6H, N(CH 2 CH 3 ) 2 ), 1.52 (m, 7H), 1.85 (m, 5H), S10

11 1.90 (m, 4H), 2.21 (m, 1H), 2.34 (m, 4H), 2.58 (m, 1H), 2.78 (m, 1H), 3.41 (q, J = 7.2 Hz, 4H, N(CH 2 CH 3 ) 2 ), 3.60 (m, 1H), 4.19, 3.96 (dd, J A = J B = 10.8 Hz, each 1H, 20-CH 2 ), 4.08 (m, 2H), 4.27 (m, 2H), 5.72 (d, J = 11.4 Hz, 1H), 5.90 (d, J = 1.2 Hz, 1H), 6.39 (d, J = 2.4 Hz, 1H, Ar-H), 6.54 (dd, J = 9.0, 2.4 Hz, 1H, Ar-H), 7.30 (d, J = 9.0 Hz, 1H, Ar-H), 8.35 (1H, s, Ar-H); 13 C NMR (CDCl 3, 75 MHz): δ (ppm) 221.9, 172.1, 170.7, 158.0, 152.5, 130.6, 125.0, 109.1, 107.2, 96.2, 95.4, 76.5, 73.8, 72.9, 64.1, 63.6, 63.0, 61.0, 60.2, 59.5, 54.0, 53.0, 45.6, 44.6, 40.5, 38.2, 38.0, 36.6, 33.2, 33.1, 32.6, 32.0, 31.7, 29.8, 29.2, 24.9, 24.8, 20.8, 19.3, 13.4, 11.9, 9.3; MS (ESI) m/z: [M-H] -, [M+H] + ; HR-MS (ESI, M+H) m/z: calcd for C 43 H 58 NO 13 : , found Figure S1. Images were collected using fluorescence microscopy with different concentrations of coumarin 15a. (a) HepG2 cells were treated with 50 µm 15a for 60 min; (b) HepG2 cells were treated with 100 µm 15a for 60 min; (a) HepG2 cells were treated with 500 µm 15a for 60 min, bars denote 50 µm. S11

12 Figure S2. Time-course uptake of 1 µm probe 17d in A549 cells. (A) Uptake of probe 17d, images were collected using fluorescence microscopy. (a) A549 cells were treated with 17d for 5 min; (b) for 15 min; (c) for 30 min; (d) for 60 min; (e) for 90 min; (f) for 120 min; (g) for 480 min; (h) for 720 min; (i) for 1440 min; bars denote 50 µm. (B) Kinetic fluorescence analysis of 17d, the diagram represents the percentage of the mean fluorescence of maximum signal intensity, values are the means of three separate experiments. S12

13 Figure S3 The location of oridonin fluorescent probes 17d or 24a in HepG2 cells. HepG2 cells were treated with 1 µm probe 17d (a) or 24a (b) for 12 h. Images were collected with excitation of probe 17d or 24a at λ ex = 405 nm and emission at λ em = 460 nm, cells were imaged at 40x with an inverted confocal microscope (LSM710 NLO, Zeiss). DIC: differential interference contrast field. 2D NMR of probe 17d S13

14 12 13 OH O OH H OH O O 17 22' 23' O 20' 19' 21' O O 17' 15' 18' 16' O O O 3' 4' 5' 10' 2' 9' 1' O 8' 6' 7' N 13' 14' 11' 12' Carbon no. δ C ppm, type δ H ppm, mult. (J in COSY HMBC a HZ) , C 17, 14, 13, , C 18, 20, , C 14, 22, , C 4, , C 5, 4, , C 4, , C 5, 11, , C 14, 17, 13, 12a, 12b , CH 8.42, s , CH 7.37, d (8.94) , C 14, , CH 6.62, dd (8.97, 2.34) , C , C 5, 6, , CH 6.46, d (2.16) 6 4, , C 6, 6OH, 7OH, 20, , CH 5.88, s 13, 9, , CH 3.73, m 5, 6OH 6OH, 7OH, , CH 3.52, m 2 2, , CH , m , CH , m , CH , 4.33, m 20 1, , C 6, 7OH, 13, 9, , CH 1.24, m 6 20, 6, , CH 1.97, m 14, 20, 1, 12, , CH , m 12, 14 12, , CH 3.17, d (9.81) 17, 11, , CH , 1.44, m 2, 5, , CH , m 21 21, , CH , m 21 21, , C 6, 5, , CH , s 5, 3 S14

15 , CH , 1.58, m 11, 13, 14, , CH , 1.22, m 1, , C 5, , CH , m 18 15, 16, , CH , m 15 15, 17, 18, , CH , s 19, 5, , CH , m 20, 22 20, , CH , 1.73, m 12, , CH , t (7.14) 11, 13 11, 13 a Assignments were made based on analysis of COSY, HMBC, and HSQC data. HMBC correlations are from the proton(s) stated to the indicated carbons. 1 H NMR(CDCl 3, 300 MHz), δ (ppm) 8.42 (1H, s, 4 -CH), 7.37 (1H, d, J = 8.94 Hz, 5 -CH), 6.62 (1H, dd, J = 8.97, 2.34 Hz, 6 -CH), 6.46 (1H, d, J = 2.16 Hz, 8 -CH), 6.05 (1H, s, 17-CH 2 ), 6.07 (1H, d, J = Hz, 6-OH), 5.88 (1H, s, 14-CH), 5.51 (1H, s, 17-CH 2 ), (3H, m, 20-CH 2, 15 -CH 2 ), (4H, m, 20-CH 2, 18 -CH 2, 7-OH), 3.73 (1H, m, 6-CH), (5H, m, 11 -CH 2, 13 -CH 2, 1-CH), 3.17 (1H, d, J = 9.81 Hz, 13-CH), 2.60 (1H, m, 12-CH 2 ), (4H, m, 20 -CH 2, 22 -CH 2 ), 2.29 (1H, m, 11-CH 2 ), 1.97 (1H, m, 9-CH), 1.90 (2H, m, 21 -CH 2 ), (4H, m, 16 -CH 2, 17 -CH 2 ), 1.73 (1H, m, 11-CH 2 ), 1.68 (1H, m, 2-CH 2 ), 1.58 (1H, m, 12-CH 2 ), 1.44 (1H, m, 3-CH 2 ), 1.30 (1H, m, 3-CH 2 ), (2H, m, 2-CH 2, 5-CH), 1.24 (6H, t, J = 7.14 Hz, 12 -CH 3,14 -CH 3 ), 1.88 (6H, s, 18-CH 3, 19-CH 3 ). 13 C NMR(CDCl 3, 75 MHz), δ (ppm) (15-C), (19 -C), (23 -C), (3 -C), (9 -C), (1 -C), (7 -C), (16-C), (4 -C), (5 -C), (17-C), (6 -C), (2 -C), (10 -C), 96.7 (8 -C), 96.1 (7-C), 76.4 (14-C), 74.1 (6-C), 73.4 (1-C), 64.5 (15 -C), 64.0 (18 -C), 63.4 (20-C), 61.9 (8-C), 59.7 (5-C), 54.6 (9-C), 45.0 (11 -C, 13 -C), 41.3 (13-C), 38.7 (3-C), 33.7 (22 -C), 33.5 (20 -C), 33.0 (10-C), 32.5 (19-C), 30.5 (12-C), 30.0 (2-C), 29.6 (4-C), 25.4 (17 -C), 25.3 (16 -C), 21.6 (18-C), 19.8 (21 -C), 19.8 (11-C), 12.4 (12 -C, 14 -C). S15

16 1 H NMR of Probe 17d 13 C NMR of Probe 17d S16

17 H-H COSY of Probe 17d HMQC of Probe 17d S17

18 HMBC of Probe 17d Spectra date S18

19 S19

20 S20

21 S21

22 S22

23 S23

24 S24

25 S25

26 S26

27 S27

28 S28

29 S29

30 S30

31 S31

32 S32

33 S33

34 S34

35 S35

36 HPLC data of tested compounds Chromatographic Condition Column Mobile phase Conditions Phenomenex Gemini C18 4.6*150mm,5um A phase:water;b phase:acetonitrile Time (min) A Phase B Phase Solvent Acetonitrile Temperature 30 S36

37 UV wavelength 240nm Speed 1mL/min Compound Purity 17a 95.88% 17c 95.49% 17d 95.58% 24a 97.34% 24b 95.05% 24c 93.56% % HPLC of 17a HPLC of 17c HPLC of 17d S37

38 HPLC of 24a HPLC of 24b HPLC of 24c S38

39 HPLC of 27 Chromatographic Condition Column Mobile phase Conditions Agilent SB C18 4.6*150mm,5um A phase:water;b phase:acetonitrile Time (min) A Phase B Phase Solvent Acetonitrile Temperature 30 S39

40 UV wavelength 240nm Speed 1mL/min Compound Purity 17b 95.32% 17e 94.56% HPLC of 17b HPLC of 17e S40

41 Stability test of probe 17d in cells A549 cells were seeded on 75 cm 2 cell culture flasks. After ~90% confluence, cultured cells were treated with 20 µm Probe 17d or DMSO (solvent control) for different time (0, 1, 3, 24 h), After incubation, cells were lysed by three freeze-thaw cycles and compounds were extract with ethyl acetate. 17d and oridonin were determined by HPLC. As can been seen in Table 1, only a very small part of the A was cleaved after 24 h, and no oridonin could be detected. Table 1. Stability test of probe 17d with HPLC analysis. Peak Time (min) Area (%) Probe 17d % Oridonin % Conditions Area of the probe 17d (%) 17d with lysed cells 17d incubated with cells for 0 h 17d incubated with cells for 1 h 17d incubated with cells for 3 h 17d incubated with cells for 24 h % % % % % Blank S41

42 HPLC of compound 17d HPLC of Oridonin S42

43 HPLC of 17d with lysed cells HPLC of 17d cultured with cells for 0 h HPLC of 17d cultured with cells for 1 h S43

44 HPLC of 17d cultured with cells for 3 h HPLC of 17d cultured with cells for 24 h S44

45 Reference [1] Ma, Y.; Luo, W.; Quinn, P. J.; Liu, Z.; Hider, R. C. Design, synthesis, physicochemical properties, and evaluation of novel iron chelators with fluorescent sensors. J. Med. Chem. 2004, 47, S45

Rational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+

Rational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+ Rational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+ Weimin Xuan, a Chen Chen, b Yanting Cao, a Wenhan He, a Wei Jiang, a Kejian Li, b* and Wei

More information

Fluorescent Chemosensor for Selective Detection of Ag + in an. Aqueous Medium

Fluorescent Chemosensor for Selective Detection of Ag + in an. Aqueous Medium Electronic supplementary information For A Heptamethine cyanine -Based Colorimetric and Ratiometric Fluorescent Chemosensor for Selective Detection of Ag + in an Aqueous Medium Hong Zheng *, Min Yan, Xiao-Xing

More information

Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline

Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Chunpu Li 1,2, Lei Zhang 2, Shuangjie Shu 2 and Hong Liu* 1,2 Address: 1 Department of Medicinal

More information

Electronic Supplementary Information for. A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective

Electronic Supplementary Information for. A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective Electronic Supplementary Information for A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective and Sensitive Detection of H 2 S: Synthesis, Spectra and Bioimaging Changyu Zhang, 1 Runyu Wang,

More information

Electronic Supplementary Material

Electronic Supplementary Material Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly

More information

Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe

Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Supporting Information for Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Ho Yu Au-Yeung, Jefferson Chan, Teera Chantarojsiri and Christopher J. Chang* Departments

More information

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow

More information

A near-infrared colorimetric fluorescent chemodosimeter for the detection of glutathione in living cells

A near-infrared colorimetric fluorescent chemodosimeter for the detection of glutathione in living cells Electronic Supplementary Material (ESI) for Chemical Communications Electronic Supplementary Information (ESI) A near-infrared colorimetric fluorescent chemodosimeter for the detection of glutathione in

More information

Supporting Information. Cells. Mian Wang, Yanglei Yuan, Hongmei Wang* and Zhaohai Qin*

Supporting Information. Cells. Mian Wang, Yanglei Yuan, Hongmei Wang* and Zhaohai Qin* Electronic Supplementary Material (ESI) for Analyst. This journal is The Royal Society of Chemistry 2015 Supporting Information Fluorescent and Colorimetric Probe Containing Oxime-Ether for Pd 2+ in Pure

More information

Supplementary Information

Supplementary Information Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)

More information

Aminoacid Based Chiral N-Amidothioureas. Acetate Anion. Binding Induced Chirality Transfer

Aminoacid Based Chiral N-Amidothioureas. Acetate Anion. Binding Induced Chirality Transfer Aminoacid Based Chiral -Amidothioureas. Acetate Anion Binding Induced Chirality Transfer Fang Wang, a Wen-Bin He, a Jin-He Wang, a Xiao-Sheng Yan, a Ying Zhan, a Ying-Ying Ma, b Li-Cai Ye, a Rui Yang,

More information

Antibacterial Coordination Polymer Hydrogels Consisted of Silver(I)-PEGylated Bisimidazolylbenzyl Alcohol

Antibacterial Coordination Polymer Hydrogels Consisted of Silver(I)-PEGylated Bisimidazolylbenzyl Alcohol Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Supporting Information for Antibacterial Coordination Polymer Hydrogels Consisted of Silver(I)-PEGylated

More information

Supporting Information. A turn-on fluorescent probe for detection of Cu 2+ in living cells based on signaling mechanism of N=N isomerization

Supporting Information. A turn-on fluorescent probe for detection of Cu 2+ in living cells based on signaling mechanism of N=N isomerization Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016 Supporting Information A turn-on

More information

Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles

Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles Supporting Information for Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles Xiao-Li Lian, Zhi-Hui Ren, Yao-Yu

More information

An unexpected highly selective mononuclear zinc complex for adenosine diphosphate (ADP)

An unexpected highly selective mononuclear zinc complex for adenosine diphosphate (ADP) This journal is The Royal Society of Chemistry 213 Supplementary Information for An unexpected highly selective mononuclear zinc complex for adenosine diphosphate (ADP) Lei Shi, Ping Hu, Yanliang Ren and

More information

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi

More information

Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes

Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,

More information

Absorbance (a. u.) Wavelength (nm) Wavelength (nm) Intensity (a. u.) Wavelength (nm) Wavelength (nm)

Absorbance (a. u.) Wavelength (nm) Wavelength (nm) Intensity (a. u.) Wavelength (nm) Wavelength (nm) Intensity (a. u.) Absorbance (a. u.) a UV UV b Wavelength (nm) Wavelength (nm) UV UV Wavelength (nm) Wavelength (nm) Supplementary Figure 1. UV-Vis absorbance spectral changes of (a) SP-Gal (left, 10 μm),

More information

Synthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property

Synthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property Supporting Information for: Synthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property Wen-Bin Jia, Hao-Wei Wang, Long-Mei Yang, Hong-Bo Lu, Lin Kong, Yu-Peng

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information Rapid detection of intracellular Cys

More information

Supporting Information. for A Water-Soluble Switching on Fluorescent Chemosensor of. Selectivity to Cd 2+

Supporting Information. for A Water-Soluble Switching on Fluorescent Chemosensor of. Selectivity to Cd 2+ Supporting Information for A Water-Soluble Switching on Fluorescent Chemosensor of Selectivity to Cd 2+ Weimin Liu, a Liwei Xu, a Ruilong Sheng, a Pengfei Wang,*,a Huaping Li*,b and Shikang Wu a a Laboratory

More information

Supporting information. An improved photo-induced fluorogenic alkene-tetrazole reaction for protein labeling

Supporting information. An improved photo-induced fluorogenic alkene-tetrazole reaction for protein labeling Supporting information An improved photo-induced fluorogenic alkene-tetrazole reaction for protein labeling X. Shang, 1 R. Lai, 1,3 X. Song, 1 H. Li, 1,3 W. Niu, 2 and J. Guo 1 * 1. Department of Chemistry,

More information

Significant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes

Significant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes Significant improvement of dye-sensitized solar cell performance by a slim phenothiazine based dyes Yong Hua, a Shuai Chang, b Dandan Huang, c Xuan Zhou, a Xunjin Zhu, *a,d Jianzhang Zhao, c Tao Chen,

More information

Electronic Supplementary Information. ligands for efficient organic light-emitting diodes (OLEDs)

Electronic Supplementary Information. ligands for efficient organic light-emitting diodes (OLEDs) Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 27 Electronic Supplementary Information bis-zn II salphen complexes bearing pyridyl functionalized

More information

Electronic supplementary information. Strong CIE activity, multi-stimuli-responsive fluorescence and data

Electronic supplementary information. Strong CIE activity, multi-stimuli-responsive fluorescence and data Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2015 Electronic supplementary information Strong CIE activity, multi-stimuli-responsive

More information

Yujuan Zhou, Kecheng Jie and Feihe Huang*

Yujuan Zhou, Kecheng Jie and Feihe Huang* Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 A redox-responsive selenium-containing pillar[5]arene-based macrocyclic amphiphile: synthesis,

More information

Supporting Information

Supporting Information Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and

More information

for Brønsted Base-Mediated Aziridination of 2- Alkyl Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-1,4-Dicarbonyl Compounds by Iminoiodanes

for Brønsted Base-Mediated Aziridination of 2- Alkyl Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-1,4-Dicarbonyl Compounds by Iminoiodanes 10.1071/CH16580_AC CSIRO 2017 Australian Journal of Chemistry 2017, 70(4), 430-435 Supplementary Material for Brønsted Base-Mediated Aziridination of 2- Alkyl Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-1,4-Dicarbonyl

More information

Reactive fluorescent dye functionalized cotton fabric as a Magic Cloth for selective sensing and reversible separation of Cd 2+ in water

Reactive fluorescent dye functionalized cotton fabric as a Magic Cloth for selective sensing and reversible separation of Cd 2+ in water Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2015 Supplementary Information Reactive fluorescent dye functionalized cotton

More information

Supporting Information

Supporting Information Supporting Information Towards Singlet Oxygen Delivery at a Measured Rate: A Selfreporting Photosensitizer Sundus Erbas-Cakmak #, Engin U. Akkaya # * # UNAM-National Nanotechnology Research Center, Bilkent

More information

Supporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones

Supporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Supporting Information Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Marco Bandini,* Riccardo Sinisi, Achille Umani-Ronchi* Dipartimento di Chimica Organica G. Ciamician, Università

More information

Supporting Information. An AIE active Y-shaped diimidazolylbenzene: aggregation and

Supporting Information. An AIE active Y-shaped diimidazolylbenzene: aggregation and Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information An AIE active Y-shaped diimidazolylbenzene: aggregation

More information

Supporting Information

Supporting Information Supporting Information Total Synthesis and Structural Reassignment of (±)-Cereoanhydride Zhiqiang Ren, Yu Hao, Xiangdong Hu* Department of Chemistry & Material Science, Key Laboratory of Synthetic and

More information

Supporting Information. Visualization of Phagosomal Hydrogen Peroxide Production by A Novel Fluorescent Probe That Is Localized via SNAP-tag Labeling

Supporting Information. Visualization of Phagosomal Hydrogen Peroxide Production by A Novel Fluorescent Probe That Is Localized via SNAP-tag Labeling Supporting Information Visualization of Phagosomal Hydrogen Peroxide Production by A Novel Fluorescent Probe That Is Localized via SNAP-tag Labeling Masahiro Abo, Reiko Minakami, Kei Miyano, Mako Kamiya,

More information

Supporting Information

Supporting Information Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,

More information

Compound Number. Synthetic Procedure

Compound Number. Synthetic Procedure Compound Number 1 2 3 4 5 Synthetic Procedure Compound 1, KY1220, (Z)-5-((1-(4-nitrophenyl)-1H-pyrrol-2-yl)methylene)-2-thioxoimidazolidin-4-one was purchased from Chemdiv, Catalog #3229-2677, 97% HPLC

More information

Supporting Information

Supporting Information Supporting Information for Dual-stimuli responsive fluorescent supramolecular polymer based on a diselenium-bridged pillar[5]arene dimer and an AIE-active tetraphenylethylene guest Yan Wang, Ming-Zhe Lv,

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION doi:10.1038/nature14137 1. Supplementary Methods 2. Supplementary Text 2.1 Physico-Chemical Properties and Structural Elucidation of Compound 1. 2.2 Physico-Chemical Properties and Structural Elucidation

More information

(Supplementary Information)

(Supplementary Information) Foldamer-mediated Structural Rearrangement Attenuates Aβ Oligomerization and Cytotoxicity (Supplementary Information) Sunil Kumar* 1, Anja Henning-Knechtel 2, Ibrahim Chehade 2, Mazin Magzoub 2, and Andrew

More information

Supporting Information. for

Supporting Information. for Supporting Information for Near-Infrared Fluorescent Turn-On Probe with a Remarkable Large Stokes Shift for Imaging Selenocysteine in Living Cells and Animals Weiyong Feng, Meixing Li, Yao Sun, and Guoqiang

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2017 Supporting Information Direct copper-catalyzed oxidative trifluoromethylthiolation

More information

Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines. and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary

Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines. and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Amines as Carbon Sources Changqing Rao, Shaoyu Mai and Qiuling Song* Institute of Next

More information

Supporting Information

Supporting Information Supporting Information In Situ Ratiometric Quantitative Tracing Intracellular Leucine Aminopeptidase Activity via an Activatable Near- Infrared Fluorescent Probe Kaizhi Gu, Yajing Liu, Zhiqian Guo,*,,#

More information

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,

More information

A selenium-contained aggregation-induced turn-on fluorescent probe for hydrogen peroxide

A selenium-contained aggregation-induced turn-on fluorescent probe for hydrogen peroxide Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information (ESI) A selenium-contained aggregation-induced

More information

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,

More information

Supporting Information

Supporting Information Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook

More information

Boronate based fluorescence (ESIPT) probe for peroxynitrite

Boronate based fluorescence (ESIPT) probe for peroxynitrite Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 216 Supplementary Information Boronate based fluorescence (ESIPT) probe for peroxynitrite

More information

Qile Wang, and Nan Zheng* Department of Chemistry and Biochemistry, University of Arkansas. Fayetteville, Arkansas,

Qile Wang, and Nan Zheng* Department of Chemistry and Biochemistry, University of Arkansas. Fayetteville, Arkansas, Supporting Information A Photocatalyzed Synthesis of Naphthalenes by Using Aniline as a Traceless Directing Group in [4+2] Annulation of AminoBenzocyclobutenes with Alkynes Qile Wang, and Nan Zheng* Department

More information

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated

More information

A water-soluble and fast-response mitochondria-targeted fluorescent

A water-soluble and fast-response mitochondria-targeted fluorescent Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) A water-soluble and fast-response mitochondria-targeted

More information

Electronic Supplementary Information (12 pages)

Electronic Supplementary Information (12 pages) Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A C 2 -responsive pillar[5]arene: synthesis and self-assembly in water Kecheng Jie, Yong Yao, Xiaodong

More information

Monitoring of Au 3+ in plant with a ratiometric fluorescent probe

Monitoring of Au 3+ in plant with a ratiometric fluorescent probe Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information Monitoring of Au 3+ in plant with a ratiometric fluorescent

More information

2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide

2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide 217 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide O O Cl NH 3 NH 2 C 9 H 7 ClO (166.6) (17.) C 9 H 9 NO (147.2) Classification Reaction types and substance classes reaction of

More information

Synthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods

Synthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods Synthesis and Use of QCy7-derived Modular Probes for Detection and Imaging of Biologically Relevant Analytes Supplementary Methods Orit Redy a, Einat Kisin-Finfer a, Shiran Ferber b Ronit Satchi-Fainaro

More information

SUPPORTING INFORMATION. A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore

SUPPORTING INFORMATION. A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore SUPPORTING INFORMATION A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore Serdar Atilgan,, Tugba Ozdemir, and Engin U. Akkaya * Department

More information

A ratiometric fluorescent probe for specific detection of cysteine over. homocysteine and glutathione based on the drastic distinction in the

A ratiometric fluorescent probe for specific detection of cysteine over. homocysteine and glutathione based on the drastic distinction in the Supporting Information for A ratiometric fluorescent probe for specific detection of cysteine over homocysteine and glutathione based on the drastic distinction in the kinetic profiles Lin Yuan, Weiying

More information

(Supplementary Information)

(Supplementary Information) (Supplementary Information) Peptidomimetic-based Multi-Domain Targeting Offers Critical Evaluation of Aβ Structure and Toxic Function Sunil Kumar 1*, Anja Henning-Knechtel 2, Mazin Magzoub 2, and Andrew

More information

SYNTHESIS OF A 3-THIOMANNOSIDE

SYNTHESIS OF A 3-THIOMANNOSIDE Supporting Information SYNTHESIS OF A 3-THIOMANNOSIDE María B Comba, Alejandra G Suárez, Ariel M Sarotti, María I Mangione* and Rolando A Spanevello and Enrique D V Giordano Instituto de Química Rosario,

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany SUPPRTIG MATERIAL Base Dependence in Copper-catalyzed Huisgen Reactions: Efficient Formation of Bistriazoles Yu Angell and Kevin Burgess *

More information

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION Synthetic chemistry ML5 and ML4 were identified as K P.(TREK-) activators using a combination of fluorescence-based thallium flux and automated patch-clamp assays. ML5, ML4, and ML5a were synthesized using

More information

with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15

with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 2. A solution of Rhodamine B (14.2 g, 30.0 mmol) in CH 2 Cl 2 (40 ml) was treated with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 g, 30.0 mmol) and TEA (4.21 ml, 3.03 g, 30.0

More information

A Highly Selective Fluorescent Probe for Fe 3+ in Living Cells: A Stress Induced Cell Based Model Study

A Highly Selective Fluorescent Probe for Fe 3+ in Living Cells: A Stress Induced Cell Based Model Study Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information A Highly Selective Fluorescent Probe

More information

Supporting Information

Supporting Information Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy

More information

Simplified platensimycin analogues as antibacterial agents

Simplified platensimycin analogues as antibacterial agents Simplified platensimycin analogues as antibacterial agents Dragan Krsta, a Caron Ka, a Ian T. Crosby, a Ben Capuano a and David T. Manallack a * a Medicinal Chemistry and Drug Action, Monash Institute

More information

Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable

Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable 1 Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable immobilized AlCl 3 on γ-al 2 O 3 SUPPLEMETARY DATA Typical Procedure to the preparation of Azides Phenyl azide Phenyl azide was

More information

All solvents and reagents were used as obtained. 1H NMR spectra were recorded with a Varian

All solvents and reagents were used as obtained. 1H NMR spectra were recorded with a Varian SUPPLEMETARY OTE Chemistry All solvents and reagents were used as obtained. 1H MR spectra were recorded with a Varian Inova 600 MR spectrometer and referenced to dimethylsulfoxide. Chemical shifts are

More information

Revisiting the complexation between DNA and polyethylenimine when and where S S linked PEI is cleaved inside the cell

Revisiting the complexation between DNA and polyethylenimine when and where S S linked PEI is cleaved inside the cell Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B. This journal is The Royal Society of Chemistry 214 Revisiting the complexation between DNA and polyethylenimine when and where

More information

Supporting Information

Supporting Information Supporting Information Control the Structure of Zr-Tetracarboxylate Frameworks through Steric Tuning Jiandong Pang,,,,# Shuai Yuan,,# Junsheng Qin, Caiping Liu, Christina Lollar, Mingyan Wu,*, Daqiang

More information

Supplementary Information (Manuscript C005066K)

Supplementary Information (Manuscript C005066K) Supplementary Information (Manuscript C005066K) 1) Experimental procedures and spectroscopic data for compounds 6-12, 16-19 and 21-29 described in the paper are given in the supporting information. 2)

More information

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde

More information

SYNTHESIS AND ANTIBACTERIAL EVALUATION OF NOVEL 3,6- DISUBSTITUTED COUMARIN DERIVATIVES

SYNTHESIS AND ANTIBACTERIAL EVALUATION OF NOVEL 3,6- DISUBSTITUTED COUMARIN DERIVATIVES SYNTHESIS AND ANTIBACTERIAL EVALUATION OF NOVEL 3,6- DISUBSTITUTED COUMARIN DERIVATIVES 1 Ravibabu Velpula, 1 Ramesh Gondru, 2 Yashodhara Velivela and 1 Rajitha Bavantula* 1 Department of Chemistry, National

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION doi:10.1038/nature24451 Chemical synthesis of USP7 compounds General 1 H, 13 C and 19 F nuclear magnetic resonance (NMR) spectra were obtained on either Bruker or Varian spectrometers at 300 or 400 MHz,

More information

Spirotrichilins A and B: Two Rearranged Spirocyclic Limonoids from Trichilia connaroides

Spirotrichilins A and B: Two Rearranged Spirocyclic Limonoids from Trichilia connaroides Spirotrichilins A and B: Two Rearranged Spirocyclic Limonoids from Trichilia connaroides Fa-Liang An, Jun Luo, Rui-Jun Li, Jian-Guang Luo, Xiao-Bing Wang, Ming-Hua Yang, Lei Yang, He-Quan Yao, Hong-Bin

More information

Super-Resolution Monitoring of Mitochondrial Dynamics upon. Time-Gated Photo-Triggered Release of Nitric Oxide

Super-Resolution Monitoring of Mitochondrial Dynamics upon. Time-Gated Photo-Triggered Release of Nitric Oxide Supporting Information for Super-Resolution Monitoring of Mitochondrial Dynamics upon Time-Gated Photo-Triggered Release of Nitric Oxide Haihong He a, Zhiwei Ye b, Yi Xiao b, *, Wei Yang b, *, Xuhong Qian

More information

Supporting Informations for. 1,8-Naphthyridine-based molecular clips for off-on fluorescence sensing

Supporting Informations for. 1,8-Naphthyridine-based molecular clips for off-on fluorescence sensing Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Supporting Informations for 1,8-aphthyridine-based molecular clips for off-on fluorescence

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 217 Electronic Supplementary Material

More information

Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry Supplementary data

Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry Supplementary data Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2012 Supplementary data Cu-catalyzed in situ generation of thiol using xanthate as thiol

More information

Supporting Information

Supporting Information Supporting Information Synthesis of the natural product Marthiapeptide A Yuqi Zhang 1, Md. Amirul Islam 1 and Shelli R. McAlpine 1* 1 School of Chemistry, University of New South Wales, Sydney, NSW 2052

More information

Supporting Information for

Supporting Information for Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,

More information

Curtius-Like Rearrangement of Iron-Nitrenoid Complex and. Application in Biomimetic Synthesis of Bisindolylmethanes

Curtius-Like Rearrangement of Iron-Nitrenoid Complex and. Application in Biomimetic Synthesis of Bisindolylmethanes Supporting Information Curtius-Like Rearrangement of Iron-itrenoid Complex and Application in Biomimetic Synthesis of Bisindolylmethanes Dashan Li,, Ting Wu,, Kangjiang Liang,, and Chengfeng Xia*,, State

More information

Supporting Information

Supporting Information Supporting Information (Tetrahedron. Lett.) Cavitands with Inwardly and Outwardly Directed Functional Groups Mao Kanaura a, Kouhei Ito a, Michael P. Schramm b, Dariush Ajami c, and Tetsuo Iwasawa a * a

More information

Cobalt-Porphyrin /Dansyl Piperazine Complex Coated Filter. Paper for Turn on Fluorescence Sensing of Ammonia Gas

Cobalt-Porphyrin /Dansyl Piperazine Complex Coated Filter. Paper for Turn on Fluorescence Sensing of Ammonia Gas Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 215 Electronic Supplementary Information Cobalt-Porphyrin /Dansyl Piperazine Complex Coated Filter

More information

How to build and race a fast nanocar Synthesis Information

How to build and race a fast nanocar Synthesis Information How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,

More information

Bio-based Green Solvent Mediated Disulfide Synthesis via Thiol Couplings Free of Catalyst and Additive

Bio-based Green Solvent Mediated Disulfide Synthesis via Thiol Couplings Free of Catalyst and Additive Bio-based Green Solvent Mediated Disulfide Synthesis via Thiol Couplings Free of Catalyst and Additive Yunyun Liu, ab Hang Wang, b Chunping Wang, b Jie-Ping Wan* ab and Chengping Wen* c a Key Laboratory

More information

Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media

Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous

More information

Supplementary Table S1: Response evaluation of FDA- approved drugs

Supplementary Table S1: Response evaluation of FDA- approved drugs SUPPLEMENTARY DATA, FIGURES AND TABLE BIOLOGICAL DATA Spheroids MARY-X size distribution, morphology and drug screening data Supplementary Figure S1: Spheroids MARY-X size distribution. Spheroid size was

More information

Electronic Supplementary Information. for. A New Strategy for Highly Selective Fluorescent Sensing of F - and

Electronic Supplementary Information. for. A New Strategy for Highly Selective Fluorescent Sensing of F - and Electronic Supplementary Information for A New Strategy for Highly Selective Fluorescent Sensing of F - and Zn 2+ with Dual Output Modes Yinyin Bao, Bin Liu, Fanfan Du, Jiao Tian, Hu Wang, Ruke Bai* CAS

More information

A dual redox-responsive supramolecular amphiphile fabricated by selenium-containing pillar[6]arene-based molecular recognition

A dual redox-responsive supramolecular amphiphile fabricated by selenium-containing pillar[6]arene-based molecular recognition Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 A dual redox-responsive supramolecular amphiphile fabricated by selenium-containing pillar[6]arene-based

More information

Supporting Information - I: Experimental Procedures and Characterization

Supporting Information - I: Experimental Procedures and Characterization Supporting Information - I: Experimental Procedures and Characterization The Direct Reductive Amination of Electron-deficient Amines with Aldehydes: the Unique Reactivity of Re 2 O 7 Catalyst 1 Braja Gopal

More information

Supporting information

Supporting information Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 205 A simple and greener approach

More information

Supporting Information for

Supporting Information for Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for

More information

Ratiometric Fluorescence Imaging of Cellular Glutathione

Ratiometric Fluorescence Imaging of Cellular Glutathione Supporting Information for: Ratiometric Fluorescence Imaging of Cellular Glutathione Gun-Joong Kim, Kiwon Lee, Hyockman Kwon, and Hae-Jo Kim, * Department of Chemistry, and Department of Bioscience and

More information

Supporting Information. Light-Induced Hydrogen Sulfide release from Caged gem-dithiols

Supporting Information. Light-Induced Hydrogen Sulfide release from Caged gem-dithiols Supporting Information Light-Induced Hydrogen Sulfide release from Caged gem-dithiols elmi O. Devarie-Baez, Powell E. Bagdon, Bo Peng, Yu Zhao, Chung-Min Park and Ming Xian* Department of Chemistry, Washington

More information

Synthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity

Synthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic

More information

A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one

A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one Haoyue Xiang and Chunhao Yang* State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy

More information

A colorimetric and fluorescent turn-on sensor for pyrophosphate. anion based on dicyanomethylene-4h-chromene framework

A colorimetric and fluorescent turn-on sensor for pyrophosphate. anion based on dicyanomethylene-4h-chromene framework Electronic Supplementary Information (ESI) A colorimetric and fluorescent turn-on sensor for pyrophosphate anion based on dicyanomethylene-4h-chromene framework Xiaomei Huang, Zhiqian Guo, Weihong Zhu*,

More information

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS

More information