Microbial Models of Mammalian Metabolism: Production of 3'-Hydroxywarfarin, a New Metabolite of Warfarin Using Cunninghamella elegans

Wong, Yiu Wai; Davis, Patrick J.

doi:10.1002/jps.2600800402

Cited by 5 publications

(6 citation statements)

References 32 publications

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“…Trager et al (1970) reported 2 diastereoisomers of warfarin alcohol. Each warfarin alcohol isomer has 2 enantiomers: RSand SR-alcohols, and RR-and SS-alcohols (Chan et al, 1972;Wong and Davis, 1989;Thijssen, 1989, 1992). Interestingly, the rate of formation of each warfarin alcohol diastereoisomer in the cytosol showed drastic interspecies differences.…”

Section: Discussionmentioning

confidence: 98%

Comparative metabolism of warfarin in rats and chickens

et al. 2011

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Warfarin, a coumarin rodenticide, is commonly used worldwide for rodent control, and is often reported as the cause for poisoning accidents in nontarget animals, in particular bird species. However, the metabolism of warfarin in birds is still unclear. In a previous study, we found an unknown warfarin metabolite in chicken cytosolic fractions. In the present study, we aimed to clarify the cytosolic warfarin metabolites in chickens compared with those in rats. The cytosol fractions of both chicken and rat livers showed the metabolic activity of 2 diastereomers and 2 enantiomers of warfarin alcohol. In chicken cytosol, we found that the production level of (S)-warfarin-(S)-alcohol was markedly higher (32-fold) than that in rat cytosol. From the results of the inhibition assay, we finally suggest that aldehyde oxidase may mainly contribute to the warfarin alcohol products in chicken cytosol.

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Section: Discussionmentioning

confidence: 98%

Comparative metabolism of warfarin in rats and chickens

et al. 2011

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“…NMR analysis (Fig. 8) Metabolite I (4'-hydroxywarfarin) is a known mammalian (Park 1988;Kaminsky 1989) and fungal (Rizzo and Davis 1989;Wong and Davis 1989) metabolite of warfarin. Metabolite B (warfarin alpha-diketone) has also been reported as a minor mammalian (Thonnart et al 1977) and microbial (Rizzo and Davis 1988) metabolite.…”

Section: Figure 3 Shows a Tlc Autoradiograph And An Hplc Chromatogrammentioning

confidence: 99%

“…Kaminsky 1989;Park 1988) and also in some fungi (e.g. Rizzo and Davis 1989;Wong and Davis 1991) and thus useful comparisons can be made.…”

Section: Introductionmentioning

confidence: 99%

“…This reaction in C. bainieri was shown to be accompanied by the so-called NIH-shift and was inhibited by carbon monoxide, both strongly implicating acytochrome-P-450-mediated reaction similar to that in mammalian systems (Rizzo and Davis 1989). In a further study, aromatic hydroxylation and ketone reduction of warfarin by C. elegans was investigated and both reactions were found to be stereoselective for R-warfarin (Wong and Davis 1989). The same organism has also been recently shown to produce the novel metabolite 3'-hydroxywarfarin (Wong and Davis 1991).…”

Section: Introductionmentioning

confidence: 99%

“…In a further study, aromatic hydroxylation and ketone reduction of warfarin by C. elegans was investigated and both reactions were found to be stereoselective for R-warfarin (Wong and Davis 1989). The same organism has also been recently shown to produce the novel metabolite 3'-hydroxywarfarin (Wong and Davis 1991).…”

Section: Introductionmentioning

confidence: 99%

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Biotransformation of warfarin by the fungus Beauveria bassiana

Griffiths

Brown

Jezequel

1992

Appl Microbiol Biotechnol

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Biotransformation of racemic warfarin by the fungus Beauveria bassiana IMI 12939 was studied as part of an investigation into alternative methods for the production of drug metabolites. Resting cell suspensions in buffer were able to biotransform warfarin. High activity occurred within a broad pH range (6.0-9.0) with an optimum at 7.0. The major metabolites were 4'-hydroxywarfarin (metabolite I), warfarin alphadiketone (metabolite B) and diastereomers of novel tautomeric ring-cleaved warfarin (metabolites E and F). The exact quantitative metabolite profile obtained following warfarin metabolism was shown to be highly dependent upon the cell concentration. Kinetic evidence suggested the operation of multiple enzyme activities.

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Microbial Models for Drug Metabolism

Azerad

1999

Advances in Biochemical Engineering/Biotechnology

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Microbial Models of Mammalian Metabolism: Production of 3'-Hydroxywarfarin, a New Metabolite of Warfarin Using Cunninghamella elegans

Cited by 5 publications

References 32 publications

Comparative metabolism of warfarin in rats and chickens

Comparative metabolism of warfarin in rats and chickens

Biotransformation of warfarin by the fungus Beauveria bassiana

Microbial Models for Drug Metabolism

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