Dickinson, Ronald G. (2011) Iso-glucuronides. Current Drug Metabolism, 12 3: 222-228. doi:10.2174/138920011795101796

Author Dickinson, Ronald G.
Title Iso-glucuronides
Formatted title
Journal name Current Drug Metabolism   Check publisher's open access policy
ISSN 1389-2002
Publication date 2011-03-01
Sub-type Article (original research)
DOI 10.2174/138920011795101796
Volume 12
Issue 3
Start page 222
End page 228
Total pages 7
Place of publication Bussum, Netherlands
Publisher Bentham Science Publishers
Language eng
Subject 3004 Pharmacology
1308 Clinical Biochemistry
Formatted abstract
This review on isomers or acyl glucuronides (iso-glucuronides) updates earlier reviews, and attempts to place in context the advances that have been made, especially over the last 15 years. The essential chemistry behind the intramolecular acyl migration and anomerization reactions of acyl glucuronides has been appreciated for 30 years. The great advances in the past 15 years have been in understanding the dynamics and kinetics of these processes in vitro, using highly sophisticated modern technology, e.g. LC-NMR, LCMS/ MS. In this way, earlier assumptions on kinetics and identification of migration isomers and anomers have come under intense review and update. Extensive structure-activity relationships, involving electronic and steric characteristics of an acyl glucuronide and its possible 7 isomers (excluding transient open-chain species) have been delineated. The covalent modification of endogenous proteins and other macromolecules has been further explored, though direct linkage between such modification and toxic sequelae remains elusive. An alternative view of acyl glucuronides and iso-glucuronides as just xenobiotics has perhaps added the dimension that acyl glucuronidation (and attendant formation of iso-glucuronides) does not necessarily mean that glucuronidation of the aglycone has ended metabolic sequences in vivo.
Keyword Acyl glucuronides
Acyl migration
Chemical reactivity
Carboxylate drugs
Covalent binding
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Medicine Publications
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Citation counts: TR Web of Science Citation Count  Cited 6 times in Thomson Reuters Web of Science Article | Citations
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