Supporting Information for Unique X-ray Sheet Structure of 1,8- Bis(imidazolium) Anthracene and Its Application to Fluorescent Probe for DNA and DNase

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1 Supporting Information for Unique X-ray Sheet Structure of 1,8- Bis(imidazolium) Anthracene and Its Application to Fluorescent Probe for DA and Dase Ha a Kim, a Jisoo Lim, b Han a Lee, a Ju-Woo Ryu, c Min Jung Kim, a Joohee Lee, b Dong-Ung Lee, c Youngmee Kim, a Sung-Jin Kim a, Kap Duk Lee,* c Hee-Seung Lee* b and Juyoung Yoon* a,d a Department of Chemistry and ano Sciences, Ewha Womans University, Seoul , Korea b Molecular-Level Interface Research Center, Department of Chemistry, KAIST, Daejeon , Korea c Department of Chemistry, Dongguk University, Kyungju, Kyungbuk , Korea d Department of Bioinspired Science (WCU), Ewha Womans University, Seoul , Korea jyoon@ewha.ac.kr; hee-seung_lee@kaist.ac.kr; kdlee@dongkuk.ac.kr Experimental Section... S2 page Figure S1 Partial 2D COSY spectrum of 1 (2 mm) in DMSO-d 6... S5 page Figure S2 Partial 2D OESY spectrum of 1 (2 mm) in DMSO-d 6....S5 page Figure S3 Fluorescent changes of 1 with anions....s6 page Figure S4 UV absorption changes of S6 page Figure S5 Fluorescent spectra and CD spectra changes of S7 page Figure S6 Effect of salt concentration on the fluorescence changes...s7 page Figure S7 1 H MR (CDCl 3, 250 MHz) spectrum of S8 page Figure S8 13 C MR (CDCl 3, 62.5 MHz) spectrum of S8 page Figure S9 1 H MR (CDCl 3, 250 MHz) spectrum of S9 page Figure S10 13 C MR (CDCl 3, 62.5 MHz) spectrum of S9 page Figure S11 1 H MR (CDCl 3, 250 MHz) spectrum of S10 page Figure S12 13 C MR (CDCl 3, 62.5 MHz) spectrum of S10 page

2 Experimental Section General methods. Unless otherwise noted, materials were obtained from commercial suppliers and were used without further purification. Flash chromatography was carried out on silica gel 60 ( mesh ASTM; Merck). Thin layer chromatography (TLC) was carried out using Merck 60 F 254 plates with a thickness of 0.25 mm. Preparative TLC was performed using Merck 60 F 254 plates with a thickness of 1 mm. Transferrin was purchased from Sigma as an iron free from. Melting points were measured using a Büchi 530 melting point apparatus, and are uncorrected. 1 H MR and 13 C MR spectra were recorded using Bruker 250 or Varian 500. Chemical shifts were expressed in ppm and coupling constants (J) in Hz. Mass spectra were obtained using a JMS-HX 110A/110A Tandem Mass Spectrometer (JEOL). UV absorption spectra were obtained on UVIKO 933 Double Beam UV/VIS Spectrometer. Fluorescence emission spectra were obtained using RF-5301/PC Spectrofluorophotometer (Shimadzu). 1, 8-dibromoanthracene (4) was synthesized following the reported procedure. 1 Br Br H CuI / Cs 2 CO 3 /DMF 4 H H 3 CH 3 I 2 PF 6 - H 4 + PF 6 - I - I Scheme S1. Synthesis of probe 1. Compound 3. To the 1,8-dibromoanthracene (200mg, 0.55 mmol) and imidazole (101 mg, 1.49 mmol) in DMF (5 ml), CuI (10mg) and, -diethylethylenediamine 20 ul, Cs 2 CO 3 (870mg, 1.34 mmol) were added. The resulting mixture was refluxed for 48 hours. After filtration and cooling down to room temperature, solvent was evaporated under vacuum and the crude product was purified by column chromatography using S2

3 ethyl acetate-methanol (3:1, v/v) as eluent to give 3 as brown solid in a yield of 17%: mp 206 o C; 1 H-MR (DMSO-d 6, 250 MHz)δ 8.95 (s, 1H), 8.3 (d, 2H, J = 8.29 Hz), 8.06 (d, 2H, J = 8.29 Hz), 8.04 (s, 1H), (m, 6H), 7.14 (s, 2H); 13 C-MR (DMSOd 6, 125 MHz) δ 117.2, 122.6, 124.4, 126.5, 128.0, 128.6, 129.7, 129.7, 132.6, 134.6, 139.1; HRMS (FAB) m/z = (M+H) +, calcd. For C 20 H 14 4 = Compound 2. 3 (80mg, 0.26 mmol) and CH 3 I (0.8 mmol) was dissolved in 10 ml of acetonitrile, and the solution was refluxed overnight. The volatiles were removed, and the solid obtained was triturated with ether and dried in vacuo to give 2 in 95% yield: mp 334 o C; 1 H-MR (DMSO-d 6, 250 MHz) δ 4.01 (s, 6H), 7.85 (t, 2H, J = 7.2 Hz), 7.98 (d, 2H, J = 6.9), 8.06 (s, 2H), 8.13 (s, 1H), 8.32 (s, 2H), 8.52 (d, 2H, J = 8.5), 9.15 (s, 1H), 9.75 (s, 2H); 13 C-MR (DMSO-d 6, 62.5 MHz) δ 36.2, 115.6, 124.1, 125.4, 125.8, 125.8, 128.8, 131.2, 131.7, 138.4; HRMS (FAB) m/z = (M) +, calcd. For [C 22 H 20 I 4 ] + = Compound 1. The resulting iodide salt 2 (21.09 mg, mmol) was dissolved in minimum amount of DMF and added with saturated solution of ammonium hexafluorophosphate dropwise. The precipitate obtained was filtered, washed thoroughly with water and dried under vacuum to give mg (86%) of hexafluorophosphate salt 1: solid: mp >352 o C decomposed ; 1 H-MR (CD 3 C, 250 MHz) δ 4.06 (s, 6H), ,60 (m, 2H), (m, 2H), 7.76 (s, 1H), (m, 4H), 8.44 (dd, 2H, J = 2.0 & 7.6 Hz), 8.80 (s, 2H), 8.98 (s, 1H); 13 C-MR (CD 3 C, 62.5 MHz) δ 35.9, 114.4, , 125.3, 125.7, 128.9, 130.8, 131.5, 131.9, 137.1, 143.7; HRMS (FAB) m/z = (M) +, calcd. For [C 22 H 20 F 6 4 P] + = Fluorescent study for anions and CT-DA. Stock solutions (10 mm) of anions (the sodium salts of F -, Cl -, Br -, I -, CH 3 CO 2 -, HSO 4 -, H 2 PO 4 -, and pyrophosphate ions) and, ATP, CTP, GTP, TTP and UTP in distilled water were prepared. Stock solutions of probe 1 (1 mm) were also prepared in CH 3 C. Stock solution of calf thymus DA was prepared in 10 mm sodium phosphate buffer (100 mm acl, 0.1 mm EDTA and 10 mm sodium phosphate, ph 7.0) 2 and the concentration of CT DA was determined by UV absorbance at 260 nm using the molar extinction coefficient (6600 M -1 cm -1 ). Test solutions were prepared by placing 30 µl of the probe stock solution into a test tube, adding an appropriate aliquot of each metal stock, and diluting the solution to 3 ml with ph 7.0, 10 mm sodium phosphate buffer (5% CH 3 C). S3

4 DA Hydrolysis study The test solution contained CT DA (60 µm) with the probe 1 (3 µm) and Mg(ClO 4 ) 2 (300 µm) were prepared. 3 After adding of Dase (25 µg/ml) to the solution, the fluorescent emission change was measured by using RF-5301/PC spectrofluorophotometer (Shimadzu). The excitation and emission wavelength were 368 and 418 nm, respectively. Circular Dichroism (CD) measurement The CD spectra were obtained on a JASCO J-810 spectropolarimeter. Solutions containing the probe and CT DA were placed in a quartz cell (1 cm path length), and the spectra were recorded in the nm region. The parameters of measurement were 1 nm bandwidth, standard sensitivity and response time of 4 s. Each sample was scanned 3 times and the averages were obtained. Reference 1. (a) Benites, M. d. R.; Fronczek, F. R.; Hammer, R. P.; Maverick, A. W. Inorg. Chem. 1997, 36, (b) Haenel, M. W.; Jakubik, D.; Krüger, C.; Betz, P. Chem. Ber. 1991, 124, Wittung, P.; E. ielsen, P.; Buchardt, O.; Egholm, M.; orde n, B. ature 1994, 368, Hong S. Y.; Czarnik A.W. J. Am. Chem. Soc. 1993, 115, S4

5 Figure S1. Partial 2D COSY spectrum of probe 1 (2 mm) in DMSO-d 6. Figure S2. Partial 2D OESY spectrum of probe 1 (2 mm) in DMSO-d 6. S5

6 250 Intensity only 1 + HSO Cl I CH 3 COO Br F PPi 1 + Pi Wavelength (nm) Figure S3. Fluorescent changes of probe 1 (3 µm) upon the addition of anions (100 equiv.) in CH 3 C (excitation at 368nm). Figure S4. UV titration of probe 1(50 µm) in the presence of various concentration of Calf thymus DA in CH 3 C : 10 mm sodium phosphate buffer(ph 7.0) = 5 : 95 (v/v). S6

7 Figure S5. (A) Fluorescent emission changes of Proflavine (6 µm) in the presence of various concentration of Calf thymus DA at excitation wavelength 443 nm (B) CD spectra changed of CT DA with 3, 6, 12, 18, 30, 42, 60, 90 and 120 µm of Proflavine in CH 3 C : 10 mm sodium phosphate buffer(ph 7.0) = 5 : 95 (v/v). Figure S6. Effect of acl concentration on the emission changes of probe 1(3 µm) with 20 equiv. of CT DA in HEPES buffer(5% CH 3 C). S7

8 Figure S7. 1 H MR (250 MHz) of compound 3 in DMSO-d 6. Figure S8. 13 C MR (62.5 MHz) of compound 3 in DMSO-d 6. S8

9 Figure S9. 1 H MR (250 MHz) of compound 2 in DMSO-d 6. Figure S C MR (62.5 MHz) of compound 2 in DMSO-d 6. S9

10 Figure S11. 1 H MR (250 MHz) of compound 1 in CD 3 C. Figure S C MR (62.5 MHz) of compound 1 in CD 3 C. S10

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