Novel Coumarin-Based Fluorescent Probes for Detecting Zn2+ in Living Cells

doi:10.6023/cjoc201511016

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (4): 787-794.DOI: 10.6023/cjoc201511016 Previous Articles Next Articles

ARTICLE

新型香豆素类Zn²⁺荧光探针的合成及细胞成像研究

李长伟, 杨栋, 尹兵, 郭媛

西北大学化学与材料科学学院西安 710127

收稿日期:2015-11-10 修回日期:2015-12-08 发布日期:2015-12-21
通讯作者: 郭媛 E-mail:guoyuan@nwu.edu.cn
基金资助:
国家自然科学基金(Nos.21472148,21072158)、陕西省教育厅专项基金(No.12JK0580)和西北大学优秀青年学术骨干支持计划资助项目.

Novel Coumarin-Based Fluorescent Probes for Detecting Zn²⁺ in Living Cells

Li Changwei, Yang Dong, Yin Bing, Guo Yuan

College of Chemistry and Materials Science, Northwest University, Xi'an 710127

Received:2015-11-10 Revised:2015-12-08 Published:2015-12-21
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21472148, 21072158), the Special Foundation of the Education Committee of Shaanxi Province (No. 12JK0580), and the Academic Back-bone of Northwest University Outstanding Youth Support Program.

1. Novel Coumarin-Based Fluorescent Probes for Detecting Zn²⁺ in Living Cells.PDF(1123KB)

Abstract

Zinc ion (Zn²⁺) is one of the most important transition-metal ions in the human body which is involved in many important life activities and many diseases can be displayed by its situation. Thus, monitoring of Zn²⁺ is very meaningful to diagnosis of diseases. Compared to the traditional detection methods, fluorescence probe is safer and more practical. Because coumarin derivatives possess several advantages in optics, we choose them as key structures to prepare new fluorescent probes. Based on the mechaism of photoinduced electron transfer (PET), the water-soluble fluorescent probes 1 and 2that are coumarin-based derivatives were designed, which demonstrated sensitivity for Zn²⁺ and exhibited high selectivity to Zn²⁺ over other metal ions. The receptor unit serves as an electron donor in the absence of Zn²⁺, quenching the fluorophore excited state that makes the probe have no fluorescence. However, when Zn²⁺ binds to the receptor, photoinduced electron transfer is prevented and the quenching is blocked, resulting the fluorescence intensity significantly enhanced. There is a good correlation between fluorescence intensity and Zn²⁺ concentration. With the increase of Zn²⁺ concentration, fluorescence intensity becomes stronger. Furthermore, the two probes were successfully labelled on the MCF-7 cell and B. subtilis. The single crystals of the coumarin-based compounds 1~4 and zinc complex [Zn(2)] were also obtained. The X-ray crystal structure of the zinc complex [Zn(2)] reveals that the hydroxyl group and the 2,2-dipicolylaminomethyl group participate in coordination. Zn²⁺ is five-coordinated with three nitrogen atoms from the pyridine rings, the substituted amino group and two oxygen atoms from the 7-site hydroxyl group, also coordinated with water molecule forming a pentacoordinated bipyramid geometry.

Key words: coumarin, Zn²⁺ fluorescent probe, cell imaging

Cite this article

Li Changwei, Yang Dong, Yin Bing, Guo Yuan. Novel Coumarin-Based Fluorescent Probes for Detecting Zn²⁺ in Living Cells[J]. Chin. J. Org. Chem., 2016, 36(4): 787-794.

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References

[1] Xu, Z. C.; Yoon, J.; Spring, D. R. Chem. Soc. Rev. 2010, 39, 1996.
[2] Prasad, A. S., Biochemistry of Zinc, Plenum Press, New York, 1993.
[3] Geiser, J.; Venken, K. J. T.; De Lisle, R. C.; Andrews, G. K. PLoS Genet. 2012, 8, e1002766.
[4] Thambiayya, K.; Wasserloos, K.; Kagan, V. E.; Stoyanovsky, D.; Pitt, B. R. Am. J. Physiol. 2012, 302, 1351.
[5] Maret, W.; Jacob, C.; Vallee, B. L.; Fischer, E. H. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 1936.
[6] (a)Nikseresht, S.; Etebary, S.; Karimian, M.; Nabavizadeh, F.; Zarrindast, M. R.; Sadeghipour, H. R. Arch. Iran. Med. 2012, 15, 306.
(b) Morris, D. R.; Levenson, C. W. J. Toxicol. 2012, 785647.
[7] Fraustoda Silva, J. J. R.; Williams, R. J. P. The Biological Chemistry of the Elements,Oxford University Press, Oxford, 1991, p. 561.
[8] Fischer Walker, C. L.; Lamberti, L.; Roth, D.; Black, R. E. Biomed. Health Res. 2011, 76, 234.
[9] Grabrucker, A. M.; Rowan, M.; Garner, C. C. Drug Delivery Lett. 2011, 1, 13.
[10] Gower-Winter, S. D.; Levenson, C. W. BioFactors 2012, 38, 186.
[11] Bicer, M.; Gunay, M.; Baltaci, A. K.; Uney, K.; Mogulkoc, R.; Akil, M. Br. Med. J. 2012, 113, 199.
[12] Chen, X.; Yu, H. N.; Shen, S. R.; Yin, J. J. J. Trace Elem. Med. Biol. 2007, 21, 125.
[13] (a) Srichaikul, B. Adv. Nat. Sci. 2012, 5, 1.
(b) Lee, J. Y.; Cho, E.; Seo, J. W.; Hwang, J. J.; Koh, J. Y. J. Neuropath. Exp. Neur. 2012, 71, 211.
[14] (a) Jayabharathi, J.; Thanikachalam, V.; Jayamoorthy, K. Spectrochim. Acta, Part A 2012, 95, 143.
(b) Liu, Z. P.; Zhang, C. L.; Chen, Y. C.; He, W. J.; Guo, Z. J. Chem. Commun. 2012, 48, 8365.
(c) Mandal, A. K.; He, T. C.; Maji, S. K.; Sun, H. D.; Zhao, Y. L. Chem. Commun. 2014, 50, 14378.
(d) Tang, L. J.; Zheng, Z. X.; Bian, Y. J. Chem. Online 2015, 78, 388 (in Chinese). (汤立军, 郑竹轩, 边延江, 化学通报, 2015, 78, 388.)
[15] (a) Tsien, R. W.; Tsien, R. Y. Rev. Cell Biol. 1990, 6, 715.
(b) Jitendra, B.; Umesh, F.; Banashree, B.; Simanpreet, K.; Narin- der, S.; Anupam, B.; Rajesh, D.; Ratnamala, B.; Anil, K. J. Mol. Recognit. 2015, 28, 369.
(c) Liu, M.; Tan, H. L.; Liu, Z. G.; Wang, W.; Zeng, W. B. Chin. J. Org. Chem. 2013, 33, 1655 (in Chinese). (刘敏, 谭慧龙, 刘治国, 王维, 曾文彬, 有机化学, 2013, 33, 1655.)
[16] (a) Priya, C.; Sivaramapanicker, S.; Ayyappanpillai, A. Chem. Asian J. 2007, 2, 338.
(b) Nolan, E. M.; Lippard, S. J. Acc. Chem. Res. 2009, 42, 193.
(c) Wong, B. A.; Friedle, S.; Lippard, S. J. J. Am. Chem. Soc. 2009, 131, 7142.
(d) Walkup, G. K.; Burdette, S. C.; Lippard, S. J.; Tsien, R. Y. J. Am. Chem. Soc. 2000, 122, 5644.
(e) Mizukami, S.; Okada, S.; Kimura, S.; Kikuchi, K. Inorg. Chem. 2009, 48, 7630.
(f) Song, Z. K.; Dong, B.; Lei, G. J.; Peng, M. J.; Guo, Y. Tetrahedron Lett. 2013, 54, 4945.
[17] (a) Domaille, D. W.; Zeng, L.; Chang, C. J. J. Am. Chem. Soc. 2010, 132, 1194.
(b) Yang, Z.; She, M. Y.; Yin, B.; Hao, L. K.; Obst, M.; Liu, P.; Li, J. L. Anal. Chim. Acta 2015, 868, 53.
(c) Fan, J. L.; Xu, Q. L.; Zhu, H.; Peng, X. J. Chin. J. Org. Chem. 2014, 34, 1623 (in Chinese). (樊江莉, 徐群利, 朱浩, 彭孝军, 有机化学, 2014, 34, 1623.)
[18] (a) Yuan, L.; Lin, W. Y.; Yang, Y. T.; Song, J. Z.; Wang, J. L. Org. Lett. 2011, 13, 3730.
(b) Jung, H. S.; Han, J. H.; Kim, Z. H.; Kang, C. H.; Kim, J. S. Org. Lett. 2011, 13, 5056.
(c) Perry, C. C.; Tang, V. J.; Konigsfeld, K. M.; Aguilera, J. A.; Milligan, J. R. J. Phys. Chem. B 2011, 115, 9889.
(d) Huo, F. J.; Sun, Y. Q.; Su, J.; Chao, J. B.; Zhi, H. J.; Yin, C. X. Org. Lett. 2009, 11, 4918.
(e) Peng, M. J.; Yang, X. F; Yin, B; Guo, Y.; Suzenet, F.; En, D.; Li, J.; Li, C. W.; Duan, Y. W. Chem. Asian J. 2014, 9, 1817.
[19] (a) Ciesienski, K. L.; Hyman, L. M.; Derisavifard, S.; Franz, K. J. Inorg. Chem. 2010, 49, 6808.
(b) Park, J. E.; Choi, M. G.; Chang, S. K. Inorg. Chem. 2012, 51, 2880.
(c) Ezeh, V. C.; Harrop, T. C. Inorg. Chem. 2012, 51, 1213.
(d) En, D.; Guo, Y.; Chen, B. T.; Dong, B.; Peng, M. J. RSC Adv. 2014, 4, 248.
(e) Hong, T.; Song, H. L.; Li, X.; Zhang, W. B.; Xie, Y. S. RSC Adv. 2014, 4, 6133.
[20] (a) Wu, J. S.; Sheng, R. L.; Liu, W. M.; Wang, P. F.; Ma, J. J.; Zhang, H. Y.; Zhuang, X. Q. Inorg. Chem. 2011, 50, 6543.
(b) Yuan, L.; Lin, W. Y.; Xie, Y. N.; Chen, B.; Zhu, S. J. Am. Chem. Soc. 2012, 134, 1305.
(c) Zhou, Y.; Liu, K.; Li, J. Y.; Fang, Y.; Zhao, T. C.; Yao, C. Org. Lett. 2011, 13, 1290.
(d) Choi, M. G.; Hwang, J. Y.; Moon, J. O.; Sung, J. Y.; Chang, S. K. Org. Lett. 2011, 13, 5260.
(e) Reddie, K. G.; Humphries, W. H.; Bain, C. P.; Payne, C. K.; Kemp, M. L.; Murthy, N. Org. Lett. 2012, 14, 680.
[21] (a) Runge, E.; Gross, E. K. U. Phys. Rev. Lett. 1984, 52, 997.
(b) Dreuw, A.; Head-Gordon, M. Chem. Rev. 2005, 105, 4009.
(c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
(d) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.

新型香豆素类Zn²⁺荧光探针的合成及细胞成像研究

Novel Coumarin-Based Fluorescent Probes for Detecting Zn²⁺ in Living Cells

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新型香豆素类Zn2+荧光探针的合成及细胞成像研究