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Facile Synthesis of Highly Sensitive, Red‐Emitting, Fluorogenic Dye for Microviscosity and Mitochondrial Imaging in Embryonic Stem Cells
Author(s) -
Raja Sufi O.,
Sivaraman Gandhi,
Mukherjee Ananya,
Duraisamy Chellappa,
Gulyani Akash
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700463
Subject(s) - microviscosity , fluorescence , biophysics , embryonic stem cell , live cell imaging , mitochondrion , chemistry , stem cell , fluorescence lifetime imaging microscopy , microbiology and biotechnology , biology , biochemistry , cell , membrane , optics , physics , gene
Bright, sensitive fluorescent probes that respond to changes in the cellular microenvironment are extremely valuable for imaging cellular dynamics. We report a simple, one‐step synthesis of a new hemicaynine (HC‐ 1 ) dye as a sensitive, red‐emitting (λ max ‐610 nm) fluorogenic probe for micro‐viscosity and local order in diverse environments, including live cells. HC‐ 1 responds to increasing micro‐viscosity through changes in fluorescence intensity and lifetime, and is sensitive enough to report dynamic micellar self‐assembly. While HC‐ 1 shows properties of a molecular ‘rotor’, time‐dependent density functional theoretical analysis reveals that in HC‐ 1 , an inhibition of photo‐isomerization in viscous environment is the likely cause of fluorescence enhancement. HC‐ 1 localizes to mitochondria in live cells and responds to mitochondrial ordering through a significant increase in fluorescence. Strikingly, we show that HC‐ 1 is also a sensitive probe for the spatial heterogeneity of mitochondrial organization in embryonic stem cells as well as dynamic remodeling of the mitochondria in early‐differentiated cells.