The Metabolism Of <u>N</u>-Heterocycles

Stubley, C.; Subryan, L.; Stell, J. G. P.; Perrett, R. H.; Ingle, P.B.H.; Mathieson, D. W.

doi:10.1111/j.2042-7158.1977.tb11545.x

Cited by 11 publications

(2 citation statements)

References 4 publications

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“…Except with cinnoline, in all cases with aldehyde oxidase, but not with cytochrome P450, the hydroxylation occurred at the carbon adjacent to an N-atom. The study indicates that the conversions by aldehyde oxidase may be more efficient than those by cytochrome P450 (Stubley et al, 1977).…”

Section: Candidate Substancesmentioning

confidence: 86%

Flavouring Group Evaluation 17, Revision 1 (FGE.17Rev1): Pyrazine derivatives from chemical group 24 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)

2008

EFSA Journal

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Section: Candidate Substancesmentioning

confidence: 86%

Flavouring Group Evaluation 17, Revision 1 (FGE.17Rev1): Pyrazine derivatives from chemical group 24 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)

2008

EFSA Journal

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“…Except with cinnoline, in all cases with aldehyde oxidase, but not with cytochrome P-450, the hydroxylation occurred at the carbon adjacent to an N atom. The study indicates that the conversions by aldehyde oxidase may be more efficient than those by cytochrome P-450 (Stubley et al, 1977).…”

Section: Candidate Substancesmentioning

confidence: 92%

Scientific Opinion on Flavouring Group Evaluation 17, Revision 3 (FGE.17Rev3): Pyrazine derivatives from chemical group 24

Flavourings¹

2011

EFS2

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Oxidation of quinazoline and quinoxaline by xanthine oxidase and aldehyde oxidase

McCormack

Allen

Hodnett

1978

Journal of Heterocyclic Chem

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Quinazoline is oxidized by xanthine oxidase initially (and rapidly) to 4‐hydroxyquinazoline which subsequently is oxidized more slowly to 2,4‐dihydroxyquinazoline. Both oxidative reactions are inhibited strongly by allopurinol. Quinazoline is oxidized by aldehyde oxidase to 4‐hydroxyquinazoline but within a short time (3–5 minutes) the reaction ceases; the proposal that cessation of reaction is due to product inhibition is rendered untenable by our observation that 4‐hydroxyquinazoline is rapidly oxidized by aldehyde oxidase to 2,4‐dihydroxyquinazoline. Preincubation of aldehyde oxidase with quinazoline results in complete inhibition of the ability of the enzyme to oxidize 4‐hydroxyquinazoline and the standard substrate N‐methylnicotinamide. It appears therefore that quinazoline is able to react with aldehyde oxidase and inactivate it. Quinoxaline and 2‐hydroxyquinoxaline are not oxidized by xanthine oxidase but are converted by aldehyde oxidase to 2,3‐dihydroxyquinoxaline; all oxidations mediated by aldehyde oxidase are inhibited completely by menadione.

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The Metabolism Of N-Heterocycles

Cited by 11 publications

References 4 publications

Flavouring Group Evaluation 17, Revision 1 (FGE.17Rev1): Pyrazine derivatives from chemical group 24 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)

Flavouring Group Evaluation 17, Revision 1 (FGE.17Rev1): Pyrazine derivatives from chemical group 24 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)

Scientific Opinion on Flavouring Group Evaluation 17, Revision 3 (FGE.17Rev3): Pyrazine derivatives from chemical group 24

Oxidation of quinazoline and quinoxaline by xanthine oxidase and aldehyde oxidase

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