1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) An activatable fluorescent probe with an ultrafast response and large Stokes shift for live cell bioimaging of hypochlorous acid Feng Liu, Ying Tang, Yongqing Kuang, Dan Pan, Xianjun Liu, Ru-Qin Yu*, Jian-Hui Jiang* State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha , P. R. China * Corresponding authors. Tel.: ; Fax:
2 Table of Contents 1. Instrumentation 2. Comparison of this method and other assays 3. Structure characterizations of HPBD, HPBD-1, HPBD-2 4. Detection limit and linear range of HPBD for HOCl detection 5. Colorimetric response of HPBD to various ROS and RNS 6. Sensing mechanism study 7. MTT assay
3 1. Instrumentation Mass spectra (MS) were performed using an LCQ Advantage ion trap mass spectrometer from Thermo Finnigan or Agilent 1100 HPLC/MSD spectrometer. 1 H NMR and 13 C NMR spectra spectra were recorded on a Bruker DRX-400 NMR spectrometer (Bruker) using tetramethylsilane (TMS) as an internal standard. UV-vis absorption spectra were plotted using a Shimadzu UV-2450 spectrophotometer with a wavelength interval of 2 nm. Fluorescence spectra were obtained on a HORIBA Fluoromax-4 spectrofluorometer (JobinYvon, Japan) with both excitation and emission slits set to 5.0 nm. The ph was verified using a Mettler-Toledo FE20 ph meter. The fluorescence imaging of cells was performed using a confocal laser scanning microscopy (Olympus, FV-1000).
4 2. Comparison of this method and other assays Table S1. Comparison of this method and other assays Methods Materials Linear range Detection limit Ref. Colorimetric Method N,N -diethyl-p-phenylenediamine (DPD) 0-40 μm - 1 Electrochemical Method a commercial 2B pencil lead-based graphite sensor 0-6 ppm μa ppm -1 cm Chemiluminescence Method carbon nitride quantum dots (g-cnqds) μm 0.01 μm 3 Fluorescent probe Probes λ ex /λ em Sensing Detection medium and 0-5 μm 25 nm 4 (nm) moieties [probe] AC-ClO 480/576 1,8-diamino naphthalene PBS buffer (ph 10.0, 20 mm) and DMF (1/4, v/v), 5 μm nanoprobe (MTPE-M) 340/ dicyanoviny l PBS buffer solutions (ph 7.4, 10 mm, containing 0-45 μm 0.47 μm 5 1% DMSO and 1 mm CTAB) 10 μm HKOCl-3 490/527 2,6- dichlorophe nol PBS solution (10 mm, ph 7.4, DMF 0.1%) 10 μm BClO 480/505 pyrrole PBS/EtOH (ph 7.4, 1:9); 0-10 μm 0.33 nm nm 0.56 nm 7 1 μm HBP 480/508 heterocyclic hydrazone PBS buffer-meoh (v/v = 50/50, 50 mm PBS, ph7.4) 1-8 μm 2.4 nm 8 5 μm Probe 1b 464/ /585 diaminomal eonitrile PBS buffer/dmf (ph 7.4, 8:2) μm 0.2 μm 9 3 μm probe 1 450/556 oxime H 2 O:CH 3 CN (99.5 : 0.5, 0-25 μm 163 nm 10 v/v) buffered with HEPES (50 mm), ph = μm Flu-1 -/530 oxime HEPES/DMSO (ph ,1:9) 10 μm
6 References 1 L. Moberg and B. Karlberg, Anal. Chim. Acta., 2000, 407, S. Pan, M. J. Deen, R. Ghosh, Anal. Chem., 2015, 87, Y. R. Tang, Y. Y. Su, N. Yang, L. C. Zhang, Y. Lv, Anal. Chem., 2014, 86, J. L. Fan, H.Y. Mu, H. Zhu, J. Y. Wang, X. J, Peng., Analyst, 2015, 140, Y. Huang, P. S. Zhang, M. Gao, F. Zeng, A. J. Qin, S.Z. Wu and B. Z. Tang, Chem. Commun., 2016, 52, J. J. Hu, N.-K. Wong, M. Y. Lu, X. M. Chen, S. Ye, A. Q. Zhao, P. Gao, R. Y.-T. Kao, J. G. Shen and D. Yang, Chem. Sci., 2016, 7, H. Zhu, J. L. Fan, J. Y. Wang, H. Y. Mu and X. J. Peng, J. Am. Chem. Soc., 2014, 136, W.-C.Chen, P. Venkatesan, S.-P. Wu, Anal. Chim. Acta., 2015, 882, L. Yuan, W. Y. Lin, J. Z. Song and Y. T. Yang, Chem. Commun., 2011, 47, S. I. Reja, V. Bhalla, A. Sharma, G. Kaur and M. K, Chem. Commun., 2014, 50, X. H. Cheng, H. Z. Jia, T. Long, J. Feng, J. G. Qin and Z. Li, Chem. Commun., 2011, 47, G. H. Cheng, J. L. Fan, W. Sun, J. F. Cao, C. Hua and X. J. Peng, Chem. Commun., 2014, 50, G. P. Li, D. J. Zhu, Q. Liu, L. Xue and H. Jiang, Org. Lett., 2013, 15, S. R. Liu and S. P. Wu, Org. Lett., 2013, 15, L. Yuan, W. Y. Lin, Y. N. Xie, B. Chen and J. Z. Song, Chem. Eur. J., 2012, 18, Q. L. Xu, K.-A. Lee, S. Y. Lee, K. M. Lee, W.-J. Lee, and J. Y. Yoon, J. Am. Chem. Soc., 2013, 135, Q. L. Xu, C. H. Heo, J. A. Kim, H. S. Lee, Y.Hu, D. Y. Kim, Anal. Chem., 2016, 88, J. Zhou, L. H. Li, W. Shi, X. H. Gao, X. H. Li and H. M. Ma, Chem. Sci., 2015, 6, L. J. Liang, C. Liu, X. J. Jiao, L.C. Zhao and X. S. Zeng, Chem. Commun., 2016, 52, Q. A. Best, N. Sattenapally, D. J. Dyer, C. N. Scott, and M. E. McCarroll, J. Am. Chem. Soc., 2013, 135, H. D. Xiao, K. Xin, H.F. Dou, G. Yin, Y. W. Quana and R. Y. Wang, Chem. Commun., 2015, 51, F. S. Tian, Y.Jia, Y.N. Zhang, W. Song, G. J. Zhao, Z. J. Qu, C.Y. Li, Y. H. Chen, P. Li, Biosensors and Bioelectronics, 2016, 86, L. Yuan, L. Wang, B. K.Agrawalla, S.-J. Park, H. Zhu, B. Sivaraman, J. J. Peng, Q.-H. Xu and Y.- T. Chang, J. Am. Chem. Soc., 2015, 137, This workccc
7 3. Structure characterizations of HPBD, HPBD-1, HPBD-2 Fig. S1. 1 H NMR spectrum of HPBD in d 6 -DMSO. Fig. S2. 13 C NMR spectrum of HPBD in d 6 -DMSO.
8 lf #5 RT: 1.00 AV: 1 NL: 8.84E5 T: + c EI Full ms [ ] Relative Abundance m/z Fig.S3. EI spectrum of HPBD in Methanol. Fig. S4. HRMS (EI) spectrum of HPBD in Methanol.
9 Fig.S5. 1 H NMR spectrum of HPBD-1 in d 6 -DMSO. Fig. S6. 13 C NMR spectrum of HPBD-1 in d 6 -DMSO.
10 lf #16 RT: 2.74 AV: 1 SB: NL: 1.48E6 T: + c EI Full ms [ ] Relative Abundance m/z Fig.S7. EI spectrum of HPBD-1 in Methanol. Fig.S8. HRMS (EI) spectrum of HPBD-1 in Methanol.
11 Fig.S9. 1 H NMR spectrum of HPBD-2 in d 6 -DMSO. Fig. S C NMR spectrum of HPBD-2 in d 6 -DMSO.
12 lf #19 RT: 3.33 AV: 1 SB: NL: 1.14E6 T: + c EI Full ms [ ] Relative Abundance m/z Fig.S11. EI spectrum of HPBD-2 in Methanol. Fig.S12. HRMS (EI) spectrum of HPBD-2 in Methanol.
13 4. Detection limit and linear range of HPBD for HOCl detection. The spectrum of free HPBD (10 μm) was collected for 10 times to determine the background noise σ. Then the solution was treated with various concentration of HOCl from 0-40 μm. A linear regression curve was then fitted according to the emission intensity at 585 nm in the range of 0-40 μm. As exhibited in Fig.S13, HPBD can quantitatively detect HOCl in the range from 0 to 40 μm with good linearity (R 2 = ). Another linear regression curve was then fitted according to the data in the range of HOCl from 0 to 4 μm, and the slope of the curve was obtained (Fig. S14). The detection limit (3σ/slope) was then determined to be 50 nm. Fig. S13. The titration curve plotted with the fluorescnece intensity of HPBD (10 μm) at 585 nm as a function of HOCl concentration in range of 0-40 μm. λ ex = 455 nm.
14 Fig. S14 The titration curve plotted with the fluorescnece intensity of HPBD (10 μm) at 585 nm as a function of HOCl concentration in range of 0-4 μm. λ ex = 455 nm.
15 5. Colorimetric response of HPBD to various ROS and RNS Fig.S15 (a) Absorption spectra of HPBD (10 μm) upon adding various ROS and RNS (40 μm) in a PBS buffer-ch 3 CN(v/v=4/1, 20 mm PBS, ph 7.4). (b) Colorimetric (upper row) and fluorometric (lower row, irradiated at 365 nm) photographs of HPBD (25 μm) in a PBS buffer-ch 3 CN (v/v=4/1, 20 mm PBS, ph 7.4). Left to right: HPBD, HOCl,. OH, H 2 O 2, 1 O 2, NO 2-, NO 3-, NO, ONOO -, O - 2 and t- BuOOH.
16 6. Sensing mechanism study pd #27 RT: 0.44 AV: 1 NL: 2.08E7 T: + c ESI ms [ ] Relative Abundance m/z Fig.S16. ESI-MS spectrum of HPBD/HOCl mixture. Fig.S17. Mechanistic study of probe reacting with HOCl and indentification of adduct using HPLC method. (a) 100 µm probe HPBD; (b) 100 µm DBDC; (c) the reaction products of 100 µm probe with HOCl. Detection: UV-vis (398 nm) detector. Flow rate: 1mL/min. T: 20 C. Injection volume: 100 µl. Mobile phase: methanol/water=80/20 (v/v).
17 7. MTT assay Fig. S18. Cytotoxicity assay of RAW cells were treated in the presence of HPBD (0-25 µm) incubated for 24 h.
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