Differential substrate behaviours of ethylene oxide and propylene oxide towards human glutathione transferase theta hGSTT1-1

Thier, Ricarda, Wiebel, Frederike A., & Bolt, Hermann M. (1999) Differential substrate behaviours of ethylene oxide and propylene oxide towards human glutathione transferase theta hGSTT1-1. Archives of Toxicology, 73(8-9), pp. 489-492.

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The transformation of ethylene oxide (EO), propylene oxide (PO) and 1- butylene oxide (1-BuO) by human glutathione transferase theta (hGSTT1-1) was studied comparatively using 'conjugator' (GSTT1 + individuals) erythrocyte lysates. The relative sequence of velocity of enzymic transformation was PO > EO >> 1-BuO. The faster transformation of PO compared to EO was corroborated in studies with human and rat GSTT1-1 (hGSTT1-1 and rGSTT1-1, respectively) expressed by Salmonella typhimurium TA1535. This sequence of reactivities of homologous epoxides towards GSTT1-1 contrasts to the sequence observed in homologous alkyl halides (methyl bromide, MBr; ethyl bromide, EtBr; n-propyl bromide, PrBr) where the relative sequence MeBr >> EtBr > PrBr is observed. The higher reactivity towards GSTT1-1 of propylene oxide compared to ethylene oxide is consistent with a higher chemical reactivity. This is corroborated by experimental data of acid-catalysed hydrolysis of a number of aliphatic epoxides, including ethylene oxide and propylene oxide and consistent with semi-empirical molecular orbital modelings.

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7 citations in Web of Science®
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ID Code: 77495
Item Type: Journal Article
Refereed: Yes
Keywords: Butylene oxide, Ethylene oxide, Glutathione transferase theta, Methyl bromide, Propylene oxide, glutathione transferase, isoenzyme, organobromine derivative, recombinant enzyme, article, chemoreactivity, controlled study, degradation, hemolysate, human, human cell, nonhuman, priority journal, protein expression, reaction analysis, toxicokinetics, Animals, Carcinogens, Epoxy Compounds, Erythrocytes, Glutathione, Humans, Kinetics, Rats, Salmonella typhimurium
DOI: 10.1007/s002040050640
ISSN: 0340-5761
Divisions: Current > QUT Faculties and Divisions > Faculty of Health
Copyright Owner: Copyright 1999 Springer
Deposited On: 16 Oct 2014 01:58
Last Modified: 22 Jun 2017 23:01

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