BIOLOGICAL AND TOXICOLOGICAL CONSEQUENCES OF QUINONE METHIDE FORMATION

被引：150

作者：

THOMPSON, DC

THOMPSON, JA

SUGUMARAN, M

MOLDEUS, P

机构：

[1] UNIV COLORADO, HLTH SCI CTR, SCH PHARM, MOLEC & ENVIRONM TOXICOL PROGRAM, DENVER, CO 80262 USA

[2] UNIV MASSACHUSETTS, DEPT BIOL, BOSTON, MA 02125 USA

[3] KAROLINSKA INST, DEPT TOXICOL, S-10401 STOCKHOLM 60, SWEDEN

来源：

CHEMICO-BIOLOGICAL INTERACTIONS | 1993年 / 86卷 / 02期

关键词：

QUINONE METHIDE; REVIEW; TOXICITY; BIOCHEMISTRY;

D O I：

10.1016/0009-2797(93)90117-H

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Quinone methides are a class of reactive, electrophilic compounds which are capable of alkylating cellular macromolecules. They are formed during xenobiotic biotransformation reactions and are hypothesized to mediate the toxicity of a large number of quinone antitumor drugs as well as several alkylphenols. In addition, oxidation of specific endogenous alkylphenols (e.g. coniferyl alcohol) and alkylcatechols (e.g. N-acetyldopamine, dopa) to quinone methides plays an important role in the synthesis of several complex plant and animal polymers, including lignin, cuticle and melanin. The role of quinone methides in these various processes is reviewed.

引用

收藏

页码：129 / 162

页数：34

相关论文

共 199 条

[1] A CHEMICAL PERSPECTIVE ON THE ANTHRACYCLINE ANTITUMOR ANTIBIOTICS [J].

ABDELLA, BRJ ;

FISHER, J .

ENVIRONMENTAL HEALTH PERSPECTIVES, 1985, 64 :3-18

[2]

ADAMSON IYR, 1977, LAB INVEST, V36, P26

[3] THE ROLE OF ALTERED MITOCHONDRIAL-FUNCTION IN CITRININ-INDUCED TOXICITY TO RAT RENAL PROXIMAL TUBULE SUSPENSIONS [J].

ALEO, MD ;

WYATT, RD ;

SCHNELLMANN, RG .

TOXICOLOGY AND APPLIED PHARMACOLOGY, 1991, 109 (03) :455-463

[4] SCLEROTIZATION OF INSECT CUTICLE .3. AN UNSATURATED DERIVATIVE OF N-ACETYLDOPAMINE AND ITS ROLE IN SCLEROTIZATION [J].

ANDERSEN, SO ;

ROEPSTORFF, P .

INSECT BIOCHEMISTRY, 1982, 12 (03) :269-276

[5]

ANDERSEN SO, 1985, COMPREHENSIVE INSECT, V3, P59

[6] 2-METHYL-1 AND 6-METHYL-1,4-NAPHTHOQUINONE DERIVATIVES AS POTENTIAL BIOREDUCTIVE ALKYLATING-AGENTS [J].

ANTONINI, I ;

LIN, TS ;

COSBY, LA ;

DAI, YR ;

SARTORELLI, AC .

JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (06) :730-735

[7] REGULATION OF MAMMALIAN MELANOGENESIS .1. PARTIAL-PURIFICATION AND CHARACTERIZATION OF A DOPACHROME CONVERTING FACTOR - DOPACHROME TAUTOMERASE [J].

AROCA, P ;

GARCIABORRON, JC ;

SOLANO, F ;

LOZANO, JA .

BIOCHIMICA ET BIOPHYSICA ACTA, 1990, 1035 (03) :266-275

[8] FURTHER-STUDIES ON DOPA QUINONE IMINE CONVERSION FACTOR FROM CUTICLES OF MANDUCA-SEXTA (L) [J].

ASO, Y ;

IMAMURA, Y ;

YAMASAKI, N .

INSECT BIOCHEMISTRY, 1989, 19 (04) :401-407

[9] EXPERIMENTAL CHEMOTHERAPY-INDUCED SKIN NECROSIS IN SWINE - MECHANISTIC STUDIES OF ANTHRACYCLINE ANTIBIOTIC TOXICITY AND PROTECTION WITH A RADICAL DIMER COMPOUND [J].

AVERBUCH, SD ;

BOLDT, M ;

GAUDIANO, G ;

STERN, JB ;

KOCH, TH ;

BACHUR, NR .

JOURNAL OF CLINICAL INVESTIGATION, 1988, 81 (01) :142-148

[10] QUINONE DEHYDROGENATION .I. OXIDATION OF MONOHYDRIC PHENOLS [J].

BECKER, HD .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (04) :982-&

← 1 2 3 4 5 6 7 8 9 10 →