Publication

Studies on the Mechanism of Action of Isoniazid and Ethionamide in the Chemotherapy of Tuberculosis

Kai Johnsson
1995
Journal Articles

Abstract

The inactivation of the enoyl-reductase InhA from Mycobacterium tuberculosis by reactive intermediates formed during the oxidn. of isoniazid and ethionamide was studied. Both drugs can generate electrophilic intermediates capable of reacting with a nucleophilic group of InhA, leading to its inactivation. After inactivation of InhA by isoniazid, one mol. of isoniazid per InhA is covalently bound to the enzyme. Mapping studies suggest that Cys243 is the residue modified in the course of the inactivation. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/3593ee77-bc8d-47eb-be57-321c700887c2

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Kai Johnsson
1995
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/3593ee77-bc8d-47eb-be57-321c700887c2

About this result

Related concepts (21)

Mycobacterium tuberculosis

Mycobacterium tuberculosis (M. tb), also known as Koch's bacillus, is a species of pathogenic bacteria in the family Mycobacteriaceae and the causative agent of tuberculosis. First discovered in 1882 by Robert Koch, M. tuberculosis has an unusual, waxy coating on its cell surface primarily due to the presence of mycolic acid. This coating makes the cells impervious to Gram staining, and as a result, M. tuberculosis can appear weakly Gram-positive. Acid-fast stains such as Ziehl–Neelsen, or fluorescent stains such as auramine are used instead to identify M.

Nucleophilic substitution

In chemistry, a nucleophilic substitution is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The molecule that contains the electrophile and the leaving functional group is called the substrate.R. A. Rossi, R. H. de Rossi, Aromatic Substitution by the SRN1 Mechanism, ACS Monograph Series No. 178, American Chemical Society, 1983. .

Nucleophilic aromatic substitution

A nucleophilic aromatic substitution is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring. Aromatic rings are usually nucleophilic, but some aromatic compounds do undergo nucleophilic substitution. Just as normally nucleophilic alkenes can be made to undergo conjugate substitution if they carry electron-withdrawing substituents, so normally nucleophilic aromatic rings also become electrophilic if they have the right substituents.

Related publications (1)

Studies on the Mechanism of Action of Isoniazid and Ethionamide in the Chemotherapy of Tuberculosis

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