Methyl 5-MeO-N-aminoanthranilate, a minimalist fluorogenic probe for sensing cellular aldehydic load. Issue 7 (19th November 2018)

• Record Type: Journal Article
• Authors: Suchý, Mojmír; Lazurko, Caitlin; Kirby, Alexia; Dang, Trina; Liu, George; Shuhendler, Adam J.
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 7(2019)
• Page Start: 1843
• Page End: 1853
• Publication Date: 2018-11-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob02255k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A minimalist fluorogenic probe is presented capable of the mapping of aldehydic load through live cell microscopy. 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.