Deep-red and near-infrared xanthene dyes for rapid live cell imaging
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1 Deep-red and near-infrared xanthene dyes for rapid live cell imaging Guangle Niu,, Weimin Liu,*, Bingjiang Zhou,, Hongyan Xiao, Hongyan Zhang, Jiasheng Wu, Jiechao Ge, and Pengfei Wang Key Laboratory of Photochemical Conversion and Optoelectronic Materials and CityU-CAS Joint Laboratory of Functional Materials and Devices, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, , China University of Chinese Academy of Sciences, Beijing, , China Present Addresses: Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, , China Table of Contents 1. Crystallographic data s2 2. Photophysical data s7 3. Cell data s10 4. The details of DFT calculations S12 5. NMR spectra s18 6. HR-MS spectra s21 S1
2 1. Crystallographic data Table S1. Crystal data and structure refinement for H-hNR. Item analys Data Empirical formula C 23 H 27 ClN 2 O 5 Formula weight Temperature Wavelength Crystal system Space group K Å Monoclinic P121/n1 Unit cell dimensions a = (17) Å a= 90. Volume Z 4 Density (calculated) Absorption coefficient F(000) 944 b = (4) Å b= (3). c = (4) Å g = (8) Å Mg/m mm-1 Crystal size 0.47 x 0.37 x 0.07 mm 3 Theta range for data collection to Index ranges Reflections collected <=h<=9, -21<=k<=21, -22<=l<=22 Independent reflections 4979 [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 4979 / 0 / 284 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Extinction coefficient Largest diff. peak and hole and e.å -3 n/a S2
3 Figure S1. Thermal ellipsoid plots (ORTEP drawing) of H-hNR. (the ellipsoid contour: 50 % probability levels) S3
4 Table S2. Crystal data and structure refinement for TF-hNR. Item analys Data Empirical formula C 24 H 26 ClF 3 N 2 O 5 Formula weight Temperature K Wavelength Å Crystal system Monoclinic Space group C12/c1 Unit cell dimensions a = (4) Å a= 90. b = (14) Å b= (3). c = (7) Å g = 90. Volume (18) Å3 Z 8 Density (calculated) Mg/m3 Absorption coefficient mm-1 F(000) 2144 Crystal size 0.67 x 0.19 x 0.18 mm3 Theta range for data collection to Index ranges -21<=h<=26, -9<=k<=9, -44<=l<=35 Reflections collected Independent reflections 5441 [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 5441 / 16 / 343 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Extinction coefficient n/a Largest diff. peak and hole and e.å -3 S4
5 Figure S2. Thermal ellipsoid plots (ORTEP drawing) of TF-hNR. (the ellipsoid contour: 50 % probability levels) S5
6 Figure S3. Single-crystal X-ray structures of (a) H-hNR and (b) TF-hNR. C, gray; N, blue; O, red; F, yellow; Cl, green. S6
7 2. Photophysical data Figure S4. The linear plots for H-hNR, TF-hNR and two standard samples. The data for Zinc phthalocyanine (Zp) was measured in PhMe (containing 1% pyridine). Figure S5. Normalized absorption and fluorescence spectra of H-hNR and TF-hNR in CH 2 Cl 2. S7
8 Figure S6. Normalized absorption and fluorescence spectra of H-hNR and TF-hNR in EtOH. Figure S7. The DFT optimized structures of H-hNR, TF-hNR and CP. S8
9 Figure S8. ph-dependence of the absorption of (a) H-hNR and (b) TF-hNR. Figure S9. Absorption spectra of (a) H-hNR and (b) TF-hNR in TE buffer (ph 7.4) before (black line) and after (red line) addition of 10 mm GSH. S9
10 3. Cell data Figure S10. Mean fluorescence intensity of H-hNR and TF-hNR in HeLa cells at different time-points. Figure S11. Confocal fluorescence microscopy images of A549 & HeLa cells (a) stained with LTG (200 nm) and H-hNR (0.8 µm) and (b) stained with MTG (100 nm) and TF-hNR (2 µm). Scale bar: 10 µm. S10
11 Table S3 Pearson's coefficient and overlap data Cells Commercial dyes Data H-hNR TF-hNR A549 cells HeLa cells MTG [a] Pearson's coefficient Overlap LTG [b] Pearson's coefficient Overlap MTG [a] Pearson's coefficient Overlap LTG [b] Pearson's coefficient Overlap [a] MTG = MitoTracker Green FM. [b] LTG = LysoTracker Green DND-26. Figure S12. The cytotoxicity of H-hNR and TF-hNR in A549 & HeLa cells. S11
12 4. The details of DFT calculations Table S4. Atomic coordinates and absolute energy for H-hNR at the B3LYP/6-31G(d) level of theory. Atom X Y Z O N N C H H H C H H C H H H C H H C C H C H C C C H C H C C C S12
13 C C H H C H H C H C C H C H C H H H C H H H E(RB3LYP) = hartree or ev S13
14 Table S5. Atomic coordinates and absolute energy for TF-hNR at the B3LYP/6-31G(d) level of theory. Atom X Y Z F F F O N N C H H H C H H C H H H C H H C C H C H C C C H C C C C S14
15 C C H H C H H C H C H C C H C H H H C H H H C E(RB3LYP) = hartree or ev S15
16 Table S6. Atomic coordinates and absolute energy for CP at the B3LYP/6-31G(d) level of theory. Atom X Y Z O N N C H H C H H C C H C H C C C H C H C C C C C C H C C C H C C S16
17 H H H H H O O C C H H H H H H E(RB3LYP) = hartree or ev S17
18 5. NMR spectra Figure S13. 1 H NMR (400 MHz, DMSO-d 6 ): H-hNR. Figure S C NMR (100 MHz, DMSO-d 6 ): H-hNR. S18
19 Figure S15. 1 H NMR (400 MHz, DMSO-d 6 ): TF-hNR. Figure S C NMR (100 MHz, DMSO-d 6 ): TF-hNR. S19
20 Figure S F NMR (376 MHz, DMSO-d 6 ): TF-hNR. S20
21 6. HR-MS spectra Figure S18. ESI-HRMS spectra of H-hNR. S21
22 Figure S19. ESI-HRMS spectra of TF-hNR. S22
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