Supporting Information for
|
|
- Clarissa Woods
- 5 years ago
- Views:
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+ Weimin Xuan, a Chen Chen, b Yanting Cao, a Wenhan He, a Wei Jiang, a Kejian Li, b* and Wei
More informationFluorescent 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 informationSupporting 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 informationElectronic 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 informationElectronic 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 informationMolecular 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 information1G (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 informationA 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 informationSupporting 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 informationSupplementary 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 informationAminoacid 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 informationAntibacterial 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 informationSupporting 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 informationPalladium-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 informationAn 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 informationSynthesis 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 informationDomino 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 informationAbsorbance (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 informationSynthesis 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 informationElectronic 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 informationSupporting 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 informationSupporting 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 informationSignificant 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 informationElectronic 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 informationElectronic 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 informationYujuan 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 informationSupporting 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 informationfor 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 informationReactive 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 informationSupporting 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 informationSupporting 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 informationSupporting 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 informationSupporting 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 informationSupporting 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 informationSupporting 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 informationCompound 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 informationSupporting 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 informationSUPPLEMENTARY 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)
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 informationSupporting 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 informationSupporting 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 informationSupporting Information
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2017 Supporting Information Direct copper-catalyzed oxidative trifluoromethylthiolation
More informationCu-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 informationSupporting 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 informationSupporting 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 informationA 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 informationThe 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 informationSupporting 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 informationBoronate 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 informationQile 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 informationRed 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 informationA 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 informationElectronic 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 informationMonitoring 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 information2017 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 informationSynthesis 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 informationSUPPORTING 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 informationA 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) 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 informationSYNTHESIS 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 informationSupporting 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 informationTetrahydrofuran (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 informationSUPPLEMENTARY 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 informationwith 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 informationA 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 informationSupporting 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 informationSimplified 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 informationRegioselective 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 informationAll 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 informationRevisiting 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 informationSupporting 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 informationSupplementary 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 informationSupporting 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 informationSYNTHESIS 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 informationSUPPLEMENTARY 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 informationSpirotrichilins 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 informationSuper-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 informationSupporting 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 informationSupporting 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 informationSupplementary 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 informationSupporting 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 informationSupporting 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 informationCurtius-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 informationSupporting 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 informationCobalt-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 informationHow 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 informationBio-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 informationSilver-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 informationSupplementary 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 informationElectronic 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 informationA 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 informationSupporting 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 informationSupporting 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 informationSupporting 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 informationRatiometric 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 informationSupporting 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 informationSynthesis 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 informationA 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 informationA 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 informationSupporting 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