The fluorescent markers based on oxazolopyridine unit for imaging organelles

Ya-Nan Wang; Bing Xu; Li-Hua Qiu; Ru Sun; Yu-Jie Xu; Jian-Feng Ge

doi:10.1016/j.bmcl.2020.126996

The fluorescent markers based on oxazolopyridine unit for imaging organelles

Bioorg Med Chem Lett. 2020 Apr 1;30(7):126996. doi: 10.1016/j.bmcl.2020.126996. Epub 2020 Jan 29.

Authors

Ya-Nan Wang¹, Bing Xu², Li-Hua Qiu³, Ru Sun¹, Yu-Jie Xu², Jian-Feng Ge⁴

Affiliations

¹ College of Chemistry, Chemical Engineering and Material Science, Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, PR China.
² State Key Laboratory of Radiation Medicine and Protection, School of Radiation Medicine and Protection and Collaborative Innovation Center of Radiation Medicine of Jiangsu Higher Education Institutions, Soochow University, Suzhou 215123, PR China.
³ College of Chemistry, Chemical Engineering and Material Science, Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, PR China. Electronic address: qiulihua@suda.edu.cn.
⁴ College of Chemistry, Chemical Engineering and Material Science, Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, PR China; Jiangsu Key Laboratory of Medical Optics, Suzhou Institute of Biomedical Engineering and Technology, Chinese Academy of Sciences, Suzhou 215163, PR China. Electronic address: ge_jianfeng@hotmail.com.

PMID: 32033852
DOI: 10.1016/j.bmcl.2020.126996

Abstract

Bioactive oxazolopyridine unit was used in the synthesis of fluorescent markers for specific organelles in this paper. The compounds 1a-c are linked with double bond between oxazolopyridine ring and photogenic precursors (3a-c). Compound 1a showed higher fluorescence yield (0.86 in THF), compounds 1b-c showed larger stokes shifts in DMSO. In lipid vesicles environment, they also showed good optical properties. In addition, the three compounds are biomarkers with lower cytotoxicity. Among them, compound 1a based on oxazolopyridine and coumarin unit is a dual targetable fluorescent marker for mitochondria and lipid droplets; while the other two compounds 1b-c are only biomarkers for lipid droplets.

Keywords: Bioactive; Dual targetable; Fluorescent markers; Oxazolopyridine; Photogenic precursors.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Cell Line
Fluorescent Dyes / chemical synthesis
Fluorescent Dyes / chemistry*
Fluorescent Dyes / radiation effects
Light
Lipid Droplets / metabolism*
Mice
Microscopy, Confocal
Microscopy, Fluorescence
Mitochondria / metabolism*
Oxazoles / chemical synthesis
Oxazoles / chemistry*
Oxazoles / radiation effects
Pyridines / chemical synthesis
Pyridines / chemistry*
Pyridines / radiation effects

Substances

Fluorescent Dyes
Oxazoles
Pyridines