Bioreductive activation of quinones: a mixed blessing.

Bioreductive activation of quinones: a mixed blessing. Research Abstract Details 

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Bioreductive activation of quinones: a mixed blessing. Abstract Text:

Quinones can be metabolized by various routes: substitution or reductive addition with nucleophilic compounds (mainly glutathione and protein thiol groups), one-electron reduction (mainly by NADPH: cytochrome P-450 reductase) and two-electron reduction (by D,T-diaphorase). During reduction semiquinone radicals and hydroquinones are formed, which can transfer electrons to molecular oxygen, resulting in the formation of reactive oxygen intermediates and back-formation of the parent quinone (redox cycling). Reaction of semiquinones and reactive oxygen intermediates with DNA and other macromolecules can lead to acute cytotoxicity and/or to mutagenicity and carcinogenicity. The enhanced DNA-alkylating properties of certain hydroquinones are exploited in the bioreductive alkylating quinones. Acute cytotoxicity of quinones appears to be related to glutathione depletion and to interaction with mitochondria and subsequent disturbance of cellular energy homoeostasis and calcium homoeostasis. These effects can to a certain extent be predicted from the electron-withdrawing and electron-donating effects of the substituents on the quinone nucleus of the molecule. Prediction of cytostatic potential remains much more complicated, because reduction of the quinones and the reactivity of the reduction products with DNA are modulated by the prevailing oxygen tension and by the prevalence of reducing enzymes in tumour cells.

Bioreductive activation of quinones: a mixed blessing. Publishing Authors By Initials

For similar organic chemicals: quinones research abstracts see: organic chemicals: quinones research

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Bioreductive activation of quinones: a mixed blessing. Journal Published:

PUBLICATION TYPE: Review

Journal: Pharmaceutisch weekblad. Scientific edition

VOLUME: 13

Page Numbers: 123-6

Journal Abbreviation:

ISSN: 0167-6555

DAY: 21

MONTH: Jun

YEAR: 1991

Bioreductive activation of quinones: a mixed blessing. Information

Number of References: 27

LANGUAGE: eng

NlmUniqueID: 7907992

Bioreductive activation of quinones: a mixed blessing. Keywords Mesh Terms:

KEYWORDS: Quinones

MESH TERMS: metabolism

Chemical & Substance for Abstract: Bioreductive activation of quinones: a mixed blessing. Information

Substance Name: Quinones

Registry Number: 0

Grant and Affiliation Information for Bioreductive activation of quinones: a mixed blessing.

AFFILIATION: Department of Pharmacology, Faculty of Pharmacy, Utrecht University, The Netherlands.

Country: NETHERLANDS

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MEDLINETA: Pharm Weekbl Sci

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