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Indolequinone antitumor agents: correlation between quinone structure and rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase. Part 2.

Abstract：

:A series of indolequinones bearing various functional groups has been synthesized, and the effects of substituents on the metabolism of the quinones by recombinant human NAD(P)H:quinone oxidoreductase (NQO1) were studied. Indolequinones were selected for study on the basis of the X-ray crystal structure of the human enzyme, and were designed to probe the effect of substituents particularly at N-1. Metabolism of the quinones by NQO1 revealed that, in general, compounds with electron-withdrawing groups at the indole 3-position were among the best substrates, and that groups larger than methyl at N-1 are clearly tolerated. Compounds with a leaving group at the 3-indolyl methyl position generally inactivated the enzyme. The toxicity toward human colon carcinoma cells with either no detectable activity (BE-WT) or high NQO1 activity (BE-NQ) was also studied in representative quinones. The most toxic compounds were those with a leaving group at the C-3 position; these compounds were 1.1-5.3-fold more toxic to the BE-NQ than the BE-WT cells.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Swann E,Barraja P,Oberlander AM,Gardipee WT,Hudnott AR,Beall HD,Moody CJ

doi

10.1021/jm010884c

keywords:

subject

Has Abstract

pub_date

2001-09-27 00:00:00

pages

3311-9

issue

20

eissn

0022-2623

issn

1520-4804

pii

jm010884c

journal_volume

44

pub_type

杂志文章

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