Polarity Mapping of Cells and Embryos by Improved Fluorescent Solvatochromic Pyrene Probe.

Analytical Chemistry
Jurga ValanciunaiteAndrey S Klymchenko

Abstract

Solvatochromic dyes enable sensing and imaging of biomolecular organization in living systems by monitoring local polarity (lipophilicity), but most such dyes suffer from limited brightness, photostability, lack of a convenient spectral range, and limited sensitivity to polarity. Moreover, the presence of an electron acceptor group, typically a carbonyl, in its push-pull structure raises concerns about its potential chemical reactivity within the biological environment. In order to achieve robust bioimaging, we synthesized a push-pull pyrene probe bearing a ketone acceptor group (PK) and compared it with a recently developed aldehyde analogue (PA). We found that in live cells the aldehyde analogue PA transforms slowly (in ∼100 min) into blue-emissive species, assigned to in situ formation of an imine analogue, whereas the PK probe is stable in the presence of primary amines and inside cells. Like the parent PA, the new probe shows strong solvatochromism and an emission color response to lipid order in membranes (ordered vs disordered liquid phases), while its blue-shifted absorption is more optimal for excitation with 400 nm light sources. In live cells, the PK probe enables high-contrast polarity mapping of organelles using tw...Continue Reading

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Citations

Feb 18, 2021·Proceedings of the National Academy of Sciences of the United States of America·Wulin TeoPeter K Stys
Jul 3, 2021·Journal of Biochemistry·Yosuke Niko, Andrey S Klymchenko
Oct 13, 2020·Analytical Chemistry·Dmytro I DanylchukAndrey S Klymchenko
Jan 9, 2021·Journal of the American Chemical Society·Dmytro I DanylchukAndrey S Klymchenko
Oct 7, 2021·Chembiochem : a European Journal of Chemical Biology·Di ShenYu Liu

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