A mitochondria-targeted probe containing multi-rotors for visualizing the viscosity change in living cells
Shuting Shen A # , Kun Yu A # , Yaxuan Wang A # , Zhiyu Wang A , Lei Hu A * and Hui Wang
A *
A Department of Chemistry, Anhui provincial engineering research center for polysaccharide drugs, Wannan Medical College, Wuhu 241002, People’s Republic of China.
Australian Journal of Chemistry 75(6) 381-386 https://doi.org/10.1071/CH22018
Submitted: 26 January 2022 Accepted: 3 April 2022 Published: 30 May 2022
© 2022 The Author(s) (or their employer(s)). Published by CSIRO Publishing.
Abstract
Fluorescent probes based on molecular rotor are expected to be a powerful tool to uncover the relationship between intracellular viscosity and organelle functions as well as related diseases. Herein, a fluorophore MV-indol containing multiple rotors was constructed by linking triphenylamine group and benzindole unit. It was found that MV-indol can quantitatively detect viscosity with a high selectivity and a 75-fold enhancement in quantum yield (QY). Moreover, the viscosity-sensitive property could be ascribed to the inhibition of molecular rotation and restriction of twisted intramolecular charge transfer (TICT) in a high-viscous environment, which was confirmed by time-dependent density functional theory (TD-DFT). Importantly, we also demonstrated that MV-indol can precisely localize in mitochondria and monitor the change of mitochondrial viscosity at the cellular level.
Keywords: benzindole, bioimaging, fluorescent probe, mitochondria, molecular rotor, TD‐DFT, triphenylamine, viscosity.
References
[1] XD Wang, L Fan, SH Wang, YW Zhang, F Li, Q Zan, WJ Lu, SM Shuang, C Dong, Anal Chem 2021, 93, 3241.| Crossref | GoogleScholarGoogle Scholar |
[2] J Cui, HL Nie, SP Zang, S Su, MX Gao, J Jing, XL Zhang, Sens. Actuators B Chem 2021, 331, 129432.
| Crossref | GoogleScholarGoogle Scholar |
[3] HB Xiao, P Li, B Tang., Chem Eur J 2021, 27, 6880.
| Crossref | GoogleScholarGoogle Scholar |
[4] HY Li, W Shi, XH Li, YM Hu, Y Fang, HM Ma., J Am Chem Soc 2019, 141, 18301.
| Crossref | GoogleScholarGoogle Scholar |
[5] HY Tan, KX Zhou, JW Yan, H Sun, M Pistolozzi, MC Cui, L Zhang, Sens Actuators B Chem 2019, 298, 126903.
| Crossref | GoogleScholarGoogle Scholar |
[6] CG Ma, W Sun, LM Xu, Y Qian, JN Dai, GY Zhong, YD Hou, JL Liu, BX Shen., J Mater Chem B 2020, 8, 9642.
| Crossref | GoogleScholarGoogle Scholar |
[7] JJ Cui, YH Yao, C Chen, R Huang, WB Zhang, JH Qian, Chin. Chem Lett 2019, 30, 1071.
| Crossref | GoogleScholarGoogle Scholar |
[8] L Cai, H Li, X Yu, LL Wu, XQ Wei, TD James, CS Huang., ACS Appl Bio Mater 2021, 4, 2128.
| Crossref | GoogleScholarGoogle Scholar | 35014341PubMed |
[9] JA Robson, M Kubánková, T Bond, RA Hendley, AJP White, MK Kuimova, JDET Wilton-Ely., Angew Chem Int Ed 2020, 59, 21431.
| Crossref | GoogleScholarGoogle Scholar |
[10] Z Yang, Y He, JH Lee, N Park, M Suh, WS Chae, J Cao, X Peng, H Jung, C Kang, JS Kim, J Am Chem Soc 2013, 135, 9181.
| Crossref | GoogleScholarGoogle Scholar | 23713894PubMed |
[11] Y Zhang, Z Li, W Hu, Z Liu., Anal Chem 2019, 91, 10302.
| Crossref | GoogleScholarGoogle Scholar | 31272148PubMed |
[12] B Shen, LF Wang, X Zhi, Y Qian., Sens Actuators B Chem 2020, 304, 127271.
| Crossref | GoogleScholarGoogle Scholar |
[13] W Miao, CJ Yu, ER Hao, LJ Jiao., Front Chem 2019, 6, 825.
| Crossref | GoogleScholarGoogle Scholar |
[14] MT Sun, T Wang, X Yang, H Yu, SH Wang, DJ Huang., Talanta 2021, 225, 121996.
| Crossref | GoogleScholarGoogle Scholar |
[15] H Wang, FZ Cai, L Zhou, J He, DX Feng, Y Wei, ZJ Feng, XX Gu, U Kajsa, ZJ Hu., New J Chem 2019, 43, 8811.
| Crossref | GoogleScholarGoogle Scholar |
[16] H Wang, L Zhou, FZ Cai, XB Shen, JQ Sun, Y Wei, DX Feng, ZJ Feng, J He., Chem Pap 2020, 74, 1071.
| Crossref | GoogleScholarGoogle Scholar |
[17] M Fu, Y Sun, Kenry, M Zhang, H Zhou, W Shen, Y Hu, Q Zhu, Chem Commun 2021, 57, 3508.
| Crossref | GoogleScholarGoogle Scholar |
[18] YB Li, YL Zhu, XZ Cai, JM Guo, CP Yao, QL Pan, XF Wang, K-N Wang., Spectrochim Acta A Mol Biomol Spectrosc 2021, 251, 119457.
| Crossref | GoogleScholarGoogle Scholar |
[19] MK Kuimova, G Yahioglu, JA Levitt, K Suhling., Molecular rotor measures viscosity of live cells via fluorescence lifetime imaging. J Am Chem Soc 2008, 130, 6672.
| Molecular rotor measures viscosity of live cells via fluorescence lifetime imaging.Crossref | GoogleScholarGoogle Scholar | 18457396PubMed |
[20] G Zhang, YM Sun, XQ He, WJ Zhang, MG Tian, RQ Feng, RY Zhang, XC Li, LF Guo, XQ Yu, SL Zhang., Anal Chem 2015, 87, 12088.
| Crossref | GoogleScholarGoogle Scholar | 26585577PubMed |
[21] R Guo, YY Ma, YH Tang, P Xie, QA Wang, WY Lin., Talanta 2019, 204, 868.
| Crossref | GoogleScholarGoogle Scholar | 31357375PubMed |
[22] MG Ren, BB Deng, K Zhou, XQ Kong, J-Y Wang, WY Lin, Anal Chem 2017, 89, 552.
| Crossref | GoogleScholarGoogle Scholar |
