Toxicology of quinone-thioethers

Research output: Contribution to journalArticle

115 Citations (Scopus)

Abstract

Cytotoxivity associated with exposure to quinones has generally been attributed to either redox cycling, and the subsequent development of 'oxidative stress', and/or to their interaction with cellular nucleophiles, such as protein and non-protein sulfhydryls. Glutathione (GSH) is the major non-protein sulfhydryl present in cells, and conjugation of potentially toxic electrophiles with GSH is usually associated with detoxication and excretion. However, this review discusses the biological (re)activity of quinone-thioethers. For example, quinone-thioethers are (1) capable of redox cycling (2) substrates for, and inhibitors of, a variety of enzymes (3) methemoglobinemic (4) potent nephrotoxicants (5) DNA reactive and (6) may contribute to quinone-mediated carcinogenicity and neurotoxicity. The ubiquitous nature of quinones, and the high intracellular concentrations of GSH, ensures that cells and tissues will be exposed to quinone-thioethers. The toxicological importance of quinone-thioethers in quinone-mediated toxicities therefore deserves further attention.

Original languageEnglish (US)
Pages (from-to)243-270
Number of pages28
JournalCritical Reviews in Toxicology
Volume22
Issue number5-6
StatePublished - 1992
Externally publishedYes

Fingerprint

Sulfides
Toxicology
Quinones
Oxidation-Reduction
Substrate Cycling
Nucleophiles
Oxidative stress
Poisons
Glutathione
Toxicity
benzoquinone
Oxidative Stress
Tissue
DNA
Substrates
Enzymes
Proteins

Keywords

  • Glutathione
  • Glutathione conjugates
  • Nephrocarcinogenicity
  • Nephrotoxicity
  • Neurotoxicity
  • Quinone-thioethers
  • Quinones

ASJC Scopus subject areas

  • Toxicology

Cite this

Toxicology of quinone-thioethers. / Monks, Terrence; Lau, Serrine.

In: Critical Reviews in Toxicology, Vol. 22, No. 5-6, 1992, p. 243-270.

Research output: Contribution to journalArticle

@article{3fb9d73f37c24d78a196e97acb0adc33,
title = "Toxicology of quinone-thioethers",
abstract = "Cytotoxivity associated with exposure to quinones has generally been attributed to either redox cycling, and the subsequent development of 'oxidative stress', and/or to their interaction with cellular nucleophiles, such as protein and non-protein sulfhydryls. Glutathione (GSH) is the major non-protein sulfhydryl present in cells, and conjugation of potentially toxic electrophiles with GSH is usually associated with detoxication and excretion. However, this review discusses the biological (re)activity of quinone-thioethers. For example, quinone-thioethers are (1) capable of redox cycling (2) substrates for, and inhibitors of, a variety of enzymes (3) methemoglobinemic (4) potent nephrotoxicants (5) DNA reactive and (6) may contribute to quinone-mediated carcinogenicity and neurotoxicity. The ubiquitous nature of quinones, and the high intracellular concentrations of GSH, ensures that cells and tissues will be exposed to quinone-thioethers. The toxicological importance of quinone-thioethers in quinone-mediated toxicities therefore deserves further attention.",
keywords = "Glutathione, Glutathione conjugates, Nephrocarcinogenicity, Nephrotoxicity, Neurotoxicity, Quinone-thioethers, Quinones",
author = "Terrence Monks and Serrine Lau",
year = "1992",
language = "English (US)",
volume = "22",
pages = "243--270",
journal = "Critical Reviews in Toxicology",
issn = "1040-8444",
publisher = "Informa Healthcare",
number = "5-6",

}

TY - JOUR

T1 - Toxicology of quinone-thioethers

AU - Monks, Terrence

AU - Lau, Serrine

PY - 1992

Y1 - 1992

N2 - Cytotoxivity associated with exposure to quinones has generally been attributed to either redox cycling, and the subsequent development of 'oxidative stress', and/or to their interaction with cellular nucleophiles, such as protein and non-protein sulfhydryls. Glutathione (GSH) is the major non-protein sulfhydryl present in cells, and conjugation of potentially toxic electrophiles with GSH is usually associated with detoxication and excretion. However, this review discusses the biological (re)activity of quinone-thioethers. For example, quinone-thioethers are (1) capable of redox cycling (2) substrates for, and inhibitors of, a variety of enzymes (3) methemoglobinemic (4) potent nephrotoxicants (5) DNA reactive and (6) may contribute to quinone-mediated carcinogenicity and neurotoxicity. The ubiquitous nature of quinones, and the high intracellular concentrations of GSH, ensures that cells and tissues will be exposed to quinone-thioethers. The toxicological importance of quinone-thioethers in quinone-mediated toxicities therefore deserves further attention.

AB - Cytotoxivity associated with exposure to quinones has generally been attributed to either redox cycling, and the subsequent development of 'oxidative stress', and/or to their interaction with cellular nucleophiles, such as protein and non-protein sulfhydryls. Glutathione (GSH) is the major non-protein sulfhydryl present in cells, and conjugation of potentially toxic electrophiles with GSH is usually associated with detoxication and excretion. However, this review discusses the biological (re)activity of quinone-thioethers. For example, quinone-thioethers are (1) capable of redox cycling (2) substrates for, and inhibitors of, a variety of enzymes (3) methemoglobinemic (4) potent nephrotoxicants (5) DNA reactive and (6) may contribute to quinone-mediated carcinogenicity and neurotoxicity. The ubiquitous nature of quinones, and the high intracellular concentrations of GSH, ensures that cells and tissues will be exposed to quinone-thioethers. The toxicological importance of quinone-thioethers in quinone-mediated toxicities therefore deserves further attention.

KW - Glutathione

KW - Glutathione conjugates

KW - Nephrocarcinogenicity

KW - Nephrotoxicity

KW - Neurotoxicity

KW - Quinone-thioethers

KW - Quinones

UR - http://www.scopus.com/inward/record.url?scp=0027102766&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027102766&partnerID=8YFLogxK

M3 - Article

C2 - 1489507

AN - SCOPUS:0027102766

VL - 22

SP - 243

EP - 270

JO - Critical Reviews in Toxicology

JF - Critical Reviews in Toxicology

SN - 1040-8444

IS - 5-6

ER -