SIOC English
有机化学
高级检索

有机化学 >

2022 , Vol. 42 >Issue 6: 1687 - 1693

DOI: https://doi.org/10.6023/cjoc202112012

研究论文

一种具有大斯托克斯位移和高光学稳定性的线粒体靶向近红外染料及其细胞成像应用

  • 周红梅 ,
  • 唐永和 ,
  • 卢辉旭 ,
  • 张倩 ,
  • 林伟英
展开
  • 广西大学化学化工学院 广西电化学能源材料重点实验室 广西大学光功能材料与化学生物学研究院 有色金属及材料加工新技术教育部重点实验室 广西有色金属及特色材料加工重点实验室 广西南宁 530004

收稿日期: 2021-12-06

  修回日期: 2022-02-17

  网络出版日期: 2022-03-22

基金资助

国家自然科学基金(21672083); 国家自然科学基金(21877048); 国家自然科学基金(22077048); 国家自然科学基金(22104019); 广西省自然科学基金(2021GXNSFDA075003); 广西省自然科学基金(AD21220061); 广西省自然科学基金(2019GXNSFBA245068); 广西大学启动基金(A3040051003)

收起

A High Photostability Mitochondrial Targeted Near-Infrared Dye with Large Stokes Shift and Cell Imaging Application

  • Hongmei Zhou ,
  • Yonghe Tang ,
  • Huixu Lu ,
  • Qian Zhang ,
  • Weiying Lin
Expand
  • Guangxi Key Laboratory of Electrochemical Energy Materials, Institute of Optical Materials and Chemical Biology, MOE Key Laboratory of New Processing Technology for Nonferrous Metals and Materials,Guangxi Key Laboratory of Processing for Non-ferrous Metals and Featured Materials,School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004
*E-mail:

Received date: 2021-12-06

  Revised date: 2022-02-17

  Online published: 2022-03-22

Supported by

National Natural Science Foundation of China(21672083); National Natural Science Foundation of China(21877048); National Natural Science Foundation of China(22077048); National Natural Science Foundation of China(22104019); Natural Science Foundation of Guangxi Province(2021GXNSFDA075003); Natural Science Foundation of Guangxi Province(AD21220061); Natural Science Foundation of Guangxi Province(2019GXNSFBA245068); Startup Fund of Guangxi University(A3040051003)

Fold

摘要

线粒体功能障碍与阿尔茨海默病(AD)、高血压、糖尿病和神经退化性疾病等严重疾病密切相关, 开发可高度靶向线粒体的荧光染料对于研究线粒体的生理功能至关重要. 但市场上的线粒体染料斯托克斯位移很小, 容易受到自吸收效应的影响. 基于线粒体膜电位的特性设计了一种线粒体靶向染料, 命名为Mito-ql. 染料Mito-ql具有优异的光学特性, 例如大斯托克斯位移(约165 nm)良好的化学和光稳定性以及低细胞毒性. 此外, 细胞成像实验表明, 染料Mito-ql具有优异的线粒体定位能力, 不受线粒体膜电位变化的影响.

关键词： 大斯托克斯位移; 荧光成像; 线粒体; 荧光染料

本文引用格式

周红梅 , 唐永和 , 卢辉旭 , 张倩 , 林伟英 . 一种具有大斯托克斯位移和高光学稳定性的线粒体靶向近红外染料及其细胞成像应用[J]. 有机化学, 2022 , 42(6) : 1687 -1693 . DOI: 10.6023/cjoc202112012

Abstract

Mitochondrial dysfunction is closely related to serious diseases such as Alzheimer’s disease (AD), hypertension, diabetes and neurodegenerative diseases. The development of a fluorescent dye that can be highly targeted to mitochondria is essential for studying the physiological functions of mitochondria. However, the Stokes shift of the mitochondrial dyes on the market is very small and is easily affected by the self-absorption effect. Herein, a new mitochondria targeted dye was designed, named as Mito-ql, based on the properties of mitochondrial membrane potential. The dye Mito-ql has excellent optical properties such as large Stokes shift (about 165 nm), good chemical and photo stability, and low cytotoxicity. In addition, the cell imaging experiments demonstrated that the dye Mito-ql has excellent mitochondrial localization ability, which is not affected by changes in mitochondrial membrane potential.

Key words： large Stokes shift; fluorescent imaging; mitochondria; fluorescent dye

参考文献

[1]
Finkel, T. Nature 2006, 444, 151.
[2]
Murfin, L. C.; Weber, M.; Park, S. J.; Kim, W. T.; Lopez-Alled, C. M.; McMullin, C. L.; Pradaux-Caggiano, F.; Lyall, C. L.; Kociok- Kohn, G.; Wenk, J.; Bull, S. D.; Yoon, J.; Kim, H. M.; James, T. D.; Lewis, S. E. J. Am. Chem. Soc. 2019, 141, 19389.
[3]
Park, S. H.; Shin, I.; Kim, Y. H. Anal. Chem. 2020, 92, 12116.
[4]
Magi, S.; Piccirillo, S.; Preziuso, A.; Amoroso, S.; Lariccia, V. Cell Calcium 2020, 86, 102162.
[5]
Nakamura, Y.; Park, J. H.; Hayakawa, K. Exp. Neurol. 2020, 324, 113114.
[6]
Scantland, S.; Tessaro, I.; Macabelli, C. H.; Macaulay, A. D.; Cagnone, G.; Fournier, E.; Luciano, A. M.; Robert, C. Biol. Reprod. 2014, 91, 75.
[7]
Zhang, Y.; Cui, P.; Li, Y.; Feng, G.; Tong, M.; Guo, L.; Li, T.; Liu, L.; Li, W.; Zhou, Q. FASEB J. 2018, 32, 1891.
[8]
Li, J.; Wu, D. D.; Zhang, J. X.; Wang, J.; Ma, J. J.; Hu, X.; Dong, W. G. World J. Gastroenterol. 2018, 24, 1901.
[9]
Druck, T.; Cheung, D. G.; Park, D.; Trapasso, F.; Pichiorri, F.; Gaspari, M.; Palumbo, T.; Aqeilan, R. I.; Gaudio, E.; Okumura, H.; Iuliano, R.; Raso, C.; Green, K.; Huebner, K.; Croce, C. M. Cell Death Dis. 2019, 10, 1.
[10]
Gorman, G. S.; Chinnery, P. F.; DiMauro, S.; Hirano, M.; Koga, Y.; McFarland, R.; Suomalainen, A.; Thorburn, D. R.; Zeviani, M.; Turnbull, D. M. Nat. Rev. Dis. Primers 2016, 2, 1.
[11]
Singhal, N. K.; Alkhayer, K.; Shelestak, J.; Clements, R.; Freeman, E.; McDonough, J. Mol. Neurobiol. 2018, 55, 8051.
[12]
Kawamata, H.; Manfredi, G. Mech. Ageing Dev. 2010, 131, 517.
[13]
Malhi, S. S.; Murthy, R. S. R. Expert Opin. Drug Delivery 2012, 9, 909.
[14]
Fan, L.; Zan, Q.; Wang, X. D.; Wang, S. H.; Zhang, Y. W.; Dong, W. J.; Shuang, S. M.; Dong, C. Chin. J. Chem. 2021, 39, 1303.
[15]
Pokorn, J.; Kobilková, J.; Jandová, A.; Vrba, J. Prague Med. Rep. 2014, 115, 104.
[16]
Missiroli, S.; Perrone, M.; Genovese, I.; Pinton, P.; Giorgi, C. EBioMedicine 2020, 59, 102943.
[17]
Liu, M. J.; Ren, X. L.; Meng, X. W.; Li, H. B. Chin. J. Chem. 2021, 39, 473.
[18]
He, L. W.; Yang, X. L.; Ren, M. G.; Kong, X. Q.; Liu, Y.; Lin, W. Y. Chem. Commun. 2016, 52, 9582.
[19]
Zheng, K. B.; Lin, W. Y.; Tan, L. Org. Biomol. Chem. 2012, 10, 9683
[20]
Stephens, D. J.; Allan, V. J. Science 2003, 300, 82.
[21]
Sang, R.-Y.; Xu, X.-P.; Wang, Q.; Fan, Q.-L.; Huang, W. Acta Chim. Sinica 2020, 78, 901. (in Chinese)
[21]
( 桑若愚, 许兴鹏, 王其, 范曲立, 黄维, 化学学报, 2020, 78, 901.)
[22]
Yue, Y.; Huo, F.; Ning, P.; Zhang, Y.; Chao, J.; Meng, X.; Yin, C. J. Am. Chem. Soc. 2017, 139, 3181.
[23]
Dong, B.; Song, X.; Kong, X.; Wang, C.; Tang, Y. H.; Liu, Y.; Lin, W. Y. Adv. Mater. 2016, 39, 8755.
[24]
Gujrati, V.; Mishra, A.; Ntziachristos, V. Chem. Commun. 2017, 53, 4653.
[25]
Hua, C.; Dong, B.; Tang, Y.; Lin, W. Acc. Chem. Res. 2017, 50, 1410.
[26]
Koide, Y.; Urano, Y.; Kenmoku, S.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2007, 129, 10324.
[27]
Cheng, D.; Pan, Y.; Wang, L.; Zeng, Z.; Yuan, L.; Zhang, X.; Chang, Y. J. Am. Chem. Soc. 2017, 139, 285.
[28]
Zheng, X.; Xu, L. Chem. Inform. 2016, 52, 1094.
[29]
Yang, Z.-G.; Xiong, J.; Zhang, W.; Li, W.; Pan, W.-H.; Zhang, J.-G.; Gu, Z.-Y.; Huang, M.-N.; Qu, J.-L. Acta Chim. Sinica 2020, 78, 130. (in Chinese)
[29]
( 杨志刚, 熊佳, 张炜, 李文, 潘文慧, 张建国, 顾振宇, 黄美娜, 屈军乐, 化学学报. 2020, 78, 130.)
[30]
Minamikawa, T.; Sriratana, A.; Williams, D. A.; Bowser, D. N.; Hill, J. S.; Nagley, P. J. Am. Chem. Soc. 1999, 112, 2419.
[31]
Wang, J. L.; Lin, W. Y. Biomaterials 2013, 34, 7429.
[32]
Gopika, G. S.; HariPrasad, P. M.; Lekshmi, A. G.; Lekshmypriya, S.; Sreesaila, S.; Arunima, C.; Kumar, M. S.; Anil, A.; Sreekumar, A.; Pilla, Z. S. Mater. Today: Proc. 2021, 46, 3102.
[33]
Shindy. H. A. Dyes Pigm. 2017, 145, 505.
[34]
He, L.; Yang, X.; Xu, K.; Kong, X.; Lin, W. Chem. Sci. 2017, 8, 6257.
[35]
Li, X.; Long, C.; Cui, Y.; Tao, F. R.; Yu, X.; Lin, W. ACS Sens. 2021, 6, 1595.
[36]
Li, K.; Li, L. L.; Zhou, Q.; Yu, K. K.; Kim, J. S.; Yu, X. Q. Coord. Chem. Rev. 2019, 388, 310.
[37]
Bionda, C.; Portoukalian, J.; Schmitt, D. Biochem. J. 2004, 382, 527.
[38]
Aliaga, M. E.; Gazitua, M.; Rojas-Bolaños, A.; Fuentes-Estrada, M.; Durango, D.; GarcíaBeltrán, O. Spectrochim. Acta, Part A 2020, 224, 117372.
[39]
Xiang, M.; Huang, H.; Liu, X.; Tong, Z.; Zhang, C.; Wang, F.; Yu, R.; Jiang, J. Anal. Chem. 2019, 91, 5489.
Options
文章导航

/

〈 〉