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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 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.

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

The article was received on 12 Sep 2018, accepted on 01 Nov 2018 and first published on 08 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02255K
Citation: Org. Biomol. Chem., 2018, Accepted Manuscript
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    Methyl 5-MeO-N-aminoanthranilate, a minimalist fluorogenic probe for sensing cellular aldehydic load

    M. Suchy, C. Lazurko, A. Kirby, T. Dang, G. Liu and A. Shuhendler, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8OB02255K

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