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A new pentacyclic pyrylium fluorescent probe that responds to pH imbalance during apoptosis

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Abstract

Efficient fluorophores with easy synthetic routes and fast responses are of great importance in clinical diagnostics. Herein, we report a new, rigid pentacyclic pyrylium fluorophore, PS-OMe, synthesised in a single step by a modified Vilsmeier–Haack reaction. Insights into the reaction mechanism facilitated a new reaction protocol for the efficient synthesis of PS-OMe which upon demethylation resulted in a “turn-on” pH sensor, PS-OH. This new fluorescent probe has been successfully used to monitor intracellular acidification at physiological pH. From the fluorescence image analysis, we were able to quantify the intracellular dynamic pH change during apoptosis. This new pH probe is a potential chemical tool for screening, drug discovery and dose determination in cancer therapy.

Graphical abstract: A new pentacyclic pyrylium fluorescent probe that responds to pH imbalance during apoptosis

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Supplementary files

Article information


Submitted
08 May 2020
Accepted
14 Jul 2020
First published
17 Jul 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

A new pentacyclic pyrylium fluorescent probe that responds to pH imbalance during apoptosis

S. Chakraborty, M. M. Joseph, S. Varughese, S. Ghosh, K. K. Maiti, A. Samanta and A. Ajayaghosh, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC02623A

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