Coumarin/BODIPY Hybridisation for Ratiometric Sensing of Intracellular Polarity Oscillation

Yang Bai; Xiangchao Shi; Yuncong Chen; Chengcheng Zhu; Yang Jiao; Zhong Han; Weijiang He; Zijian Guo

doi:10.1002/chem.201800915

Coumarin/BODIPY Hybridisation for Ratiometric Sensing of Intracellular Polarity Oscillation

Chemistry. 2018 May 23;24(29):7513-7524. doi: 10.1002/chem.201800915. Epub 2018 Apr 30.

Authors

Yang Bai¹, Xiangchao Shi¹, Yuncong Chen¹, Chengcheng Zhu¹, Yang Jiao¹, Zhong Han¹, Weijiang He¹, Zijian Guo¹

Affiliation

¹ State Key Laboratory of Coordination Chemistry, Coordination Chemistry Institute, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P.R. China.

PMID: 29575108
DOI: 10.1002/chem.201800915

Abstract

With different polarity responses, coumarin and 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) were hybridised to construct polarity fluorescent sensors, CBDP and iso-CBDP, to overcome the disadvantages of solvatochromic sensors in ratiometric polarity sensing. Only CBDP displayed an emission ratio (I_Cou /I_BDP , coumarin to BODIPY emissions) that increased with an exponential dependence on medium relative permittivity over a wide polarity range (ϵ_r <57.9). This sensing ability of CBDP was not affected by medium pH; viscosity; and most intracellular species, especially reactive oxygen, nitrogen, and sulfur species. Apart from local cytoplasmic polarity quantification through lambda imaging, CBDP enables real-time ratiometric imaging for intracellular polarity oscillation induced by oxidative stimulation. Ratiometric polarity flow cytometry was developed, for the first time, with CBDP, which demonstrated that a high concentration H₂ O₂ induced cytoplasmic polarity enhancement, whereas pre-incubation with N-acetyl-l-cysteine inhibited this effect.

Keywords: dyes/pigments; flow cytometry; fluorescence; imaging agents; sensors.