Issue 7, 2019

Methyl 5-MeO-N-aminoanthranilate, a minimalist fluorogenic probe for sensing cellular aldehydic load

Abstract

Methyl 5-MeO-N-aminoanthranilate, a fluorogenic probe comprising a single substituted benzene ring has been applied towards the fluorescence detection of endogenous carbonyls through rapid, catalyst-free complexation of these bio-derived markers of cell stress under physiological conditions. The products formed during the reaction between the probe and aldehydic products of lipid peroxidation, including malondialdehyde and long-chain aliphatic aldehydes relevant to the oxidative decomposition of cell membranes, have been evaluated. Live cell imaging of diethyl maleate-induced oxidative stress with or without pretreatment with α-tocopherol was carried out, with the result suggesting that the presented molecule might serve as a minimalist molecular probe capable of cellular “Aldehydic Load” detection by fluorescence microscopy. This work also outlines functional constraints of the fluorogenic probe (i.e. intramolecular cyclization), providing a realistic evaluation of methyl 5-MeO-N-aminoanthranilate for fluorescence-based aldehyde detection.

Graphical abstract: Methyl 5-MeO-N-aminoanthranilate, a minimalist fluorogenic probe for sensing cellular aldehydic load

  • This article is part of the themed collection: New Talent

Supplementary files

Article information

Article type
Paper
Submitted
12 Sept. 2018
Accepted
01 Nov. 2018
First published
08 Nov. 2018

Org. Biomol. Chem., 2019,17, 1843-1853

Methyl 5-MeO-N-aminoanthranilate, a minimalist fluorogenic probe for sensing cellular aldehydic load

M. Suchý, C. Lazurko, A. Kirby, T. Dang, G. Liu and A. J. Shuhendler, Org. Biomol. Chem., 2019, 17, 1843 DOI: 10.1039/C8OB02255K

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