Issue 47, 2020

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
08 Mai 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
Creative Commons BY-NC license

Chem. Sci., 2020,11, 12695-12700

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, 11, 12695 DOI: 10.1039/D0SC02623A

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