一种苯并噻唑衍生物对H2S的荧光识别及细胞成像
收稿日期: 2016-08-04
修回日期: 2016-09-19
网络出版日期: 2016-10-11
基金资助
国家自然科学基金（Nos.21476029，U1608222）及辽宁省高等学校优秀人才支持计划（No.LR2015001）资助项目.
Fluorescence Recognition of H2S by a Benzothiazole Derivative and Its Live Cell Imaging
Received date: 2016-08-04
Revised date: 2016-09-19
Online published: 2016-10-11
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21476029, U1608222) and the Liaoning Excellent Talents in University (No. LR2015001).
以3-（2-苯并噻唑基）-2-羟基-5-甲基苯甲醛为原料，合成了一种基于苯并噻唑类衍生物的荧光探针2-（4-叠氮苄氧基）-3-（2-苯并[d]噻唑基）-5-甲基苯甲醛（HBTA），表征了其结构，研究了HBTA对H2S的识别性质.实验结果表明，HBTA在水溶液中（Tris-HCl 0.01 mol·L-1，pH=7.4，含0.005 mol·L-1 CTAB）对H2S具有良好的选择性和灵敏度，且响应快速，抗干扰能力强，并且在较宽的pH范围内有较好的荧光响应，其检测限为9.09×10-7 mol·L-1.细胞成像实验表明，HBTA可用于检测细胞内的H2S.
何平 , 汤立军 , 钟克利 , 侯淑华 , 燕小梅 . 一种苯并噻唑衍生物对H2S的荧光识别及细胞成像[J]. 有机化学, 2017 , 37(2) : 423 -428 . DOI: 10.6023/cjoc201608003
A new benzothiazole-derived fluorescence probe 2-(4-azidobenzyl)oxy-3-(benzo[d]thiazol-2-yl)-5-methylben-zaldehyde (HBTA) was synthesized from 3-(benzo[d]thiazol-2-yl)-2-hydroxy-5-methylbenzaldehyde, and the structure of HBTA was characterized. The recognition behaviors of HBTA to H2S were investigated and the results show that HBTA exhibits good selectivity and sensitivity to H2S with fast response and good anti-interference ability. The probe can be applied to detect H2S in a broad pH range, and the detection limit of HBTA for H2S was estimated to be 9.09×10-7 mol·L-1. Cell imaging studies reveal that HBTA is capable of detect H2S in live cells.
Key words： hydrogen sulfide; fluorescent probe; benzothiazole; cells imaging
[1] Li, L.; Rose, P.; Moore, P. K. Annu. Rev. Pharmacol. Toxicol. 2011, 51, 169.
[2] Lovatt, E. C. Q. J. Exp. Physiol. Cogn. Med. Sci. 1967, 52, 231.
[3] (a) Eto, K.; Asada, T.; Arima, K.; Makifuchi, T.; Kimura, H. Biochem. Biophys. Res. Commun. 2002, 293, 1485.
(b) Kamoun, P.; Belardinelli, M. C.; Chabli, A.; Lallouchi, K.; Chadefaux-Vekemans, B. Am. J. Med. Genet., Part A 2003, 116A, 310.
(c) Yang, W.; Yang, G.; Jia, X.; Wu, L.; Wang, R. J. Physiol. 2005, 569, 519.
(d) Fiorucci, S.; Antonelli, E.; Mencarelli, A.; Orlandi, S.; Renga, B.; Rizzo, G.; Distrutti, E.; Shah, V.; Morelli, A. Hepatology 2005, 42, 539.
[4] (a) Qian, L.; Lancaster, J. R. Nitric Oxide 2013, 35, 21.
(b) Yang, C.; Yang, Z.; Zhang, M.; Dong, Q.; Wang, X.; Lan, A.; Zeng, F.; Chen, P.; Wang, C.; Feng, J. PLoS One 2011, 6, e21971.
[5] (a) Qandil, A. M. Int. J. Mol. Sci. 2012, 13, 17244.
(b) Lefer, D. J. Br. J. Pharmacol. 2008, 155, 617.
[6] (a) Choi, M. G.; Cha, S.; Lee, H.; Jeon, H. L.; Chang, S. K. Chem. Commun. 2009, 47, 7390.
(b) Lawrence, N. S.; Davis, J.; Compton, R. G. Talanta 2000, 52, 771.
(c) Hannestad, U.; Margheri, S.; Bo, S. Anal. Biochem. 1989, 178, 394.
[7] (a) Yu, F.; Han, X.; Chen, L. Chem. Commun. 2014, 50, 12234.
(b) Guo, Z.; Chen, G.; Zeng, G.; Li, Z.; Chen, A.; Wang, J.; Jiang, L. Analyst 2015, 140, 1772.
(c) Lin, V. S.; Chen, W.; Xian, M.; Chang, C. J. Chem. Soc. Rev. 2014, 44, 4596.
[8] Liu, C.; Pan, J.; Li, S.; Zhao, Y.; Wu, L. Y.; Berkman, C. E.; Whorton, A. R.; Xian, M. Angew. Chem., Int. Ed. 2011, 50, 10327.
[9] Fang, F.-L.; Jing, J. Q.; Chen, X. M. Chin. J. Org. Chem. 2014, 34, 2178 (in Chinese).(范方禄, 靖金球, 陈雪梅, 有机化学, 2014, 34, 2178.)
[10] Hou, F.; Huang, L.; Xi, P.; Cheng, J.; Zhao, X.; Xie, G.; Shi, Y.; Cheng, F.; Yao, X.; Bai, D.; Zeng, Z. Inorg. Chem. 2012, 51, 2454.
[11] Tian, H.; Qian, J.; Bai, H.; Qian, S.; Zhang, L.; Zhang, W. Anal. Chim. Acta 2013, 768, 136.
[12] (a) Kabil, O.; Banerjee, R. J. Biol. Chem. 2010, 285, 21903.
(b) Chegaev, K.; Rolando, B.; Cortese, D.; Gazzano, E.; Buondonno, I.; Lazzarato, L.; Fanelli, M.; Hattinger, C. M.; Serra, M.; Riganti, C.; Fruttero, R.; Ghigo, D.; Gasco, A. J. Med. Chem. 2016, 59, 4881.
[13] (a) Zhang, J.; Guo, W. Chem. Commun. 2014, 50, 4214.
(b) Zheng, Y.; Zhao, M.; Qiao, Q.; Liu, H.; Lang, H.; Xu, Z. Dyes Pigm. 2013, 98, 367.
(c) Paul, S.; Goswami, S.; Mukhopadhyay, C. D. New J. Chem. 2015, 39, 8940.
[14] Yin, J.; Wu, Q.; Chang, X. Talanta 2014, 121, 122-126.
[15] Jian, X.; Yan, Z.; Hui, Y.; Gao, X.; Shao, S. Anal. Chem. 2015, 88.
[16] (a) And, T. J. D.; Julius Rebek, J. J. Am. Chem. Soc. 2006, 128, 4500.
(b) Huang, Z.; Ding, S.; Yu, D.; Huang, F.; Feng, G. Chem. Commun. 2014, 50, 9185.
(c) Roy, A.; Kand, D.; Saha, T.; Talukdar, P. Chem. Commun. 2014, 50, 5510.
[17] Tang, L.; Dai, X.; Wen, X.; Wu, D.; Zhang, Q. Spectrochim. Acta, Part A 2015, 139, 329.
[18] Belkheira, M.; Abed, D. E.; Pons, J.-M.; Bressy, C. Chem.-Eur. J. 2011, 17, 12917.
/
| 〈 |
|
〉 |
