Development of a spectrophotometric method for assessment of the relative reactivity of monocarbonyl analogs of curcumin with 2-(dimethylamino)ethanethiol

Lozanovski, Zlatko and Petreska Stanoeva, Jasmina and Bogdanov, Jane (2023) Development of a spectrophotometric method for assessment of the relative reactivity of monocarbonyl analogs of curcumin with 2-(dimethylamino)ethanethiol. Macedonian Journal of Chemistry and Chemical Engineering, 42 (1). ISSN 1857-5552

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Abstract

In order to improve the bioavailability of curcumin, studies have been undertaken to prepare the so-called monocarbonyl analogs of curcumin (MACs) and assess their biological activity. These analogs contain an electrophilic α,β-unsaturated carbonyl moiety (Michael acceptor). Several key biological processes are connected/controlled with thiol alkylation (glutathione, cysteine, cysteine peptide residues). The most likely reaction is the Michael addition between the α,β-unsaturated acceptor and a corresponding thiol. 2,6-Bisarylidenecyclohexanone and 3,5-bisarylidenepiperidin-4-one scaffolds offer convenient tunability of electrophilicity and redox properties of the Michael acceptor by the introduction of various substituents. In this study, several MACs were prepared by Claisen-Schmidt condensation reaction, and their reactivity with 2-(dimethylamino)ethanethiol was evaluated. For this purpose, based on the UV-Vis spectra of the analogs and thiol(s), a proper method for spectrophotometric evaluation of their reactivity with 2-(dimethylamino)ethanethiol was optimized. The relative reactivity of the analogs was 7 > 2 > 5 > 4 > 1 ≈ 6. The developed method is simple, and it can be extended to assess the reactivity of other MACs.

Item Type:	Article
Subjects:	Scientific Fields (Frascati) > Natural sciences > Chemical sciences Scientific Fields (Frascati) > Medical and Health Sciences > Other medical sciences
Divisions:	Higher Medical School
Depositing User:	PhD Zlatko Lozanovski
Date Deposited:	19 Sep 2024 14:17
Last Modified:	19 Sep 2024 14:17
URI:	https://eprints.uklo.edu.mk/id/eprint/10260

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