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Chemical Compound Review:

Betoxan 2-naphthalen-2-ylethanoic acid

Synonyms: CHEMBL948, NSC-301, N4002_ALDRICH, NSC301, SureCN238445, ...

Beebe, L.E. et al., Emudianughe, T.S. et al., Roberts, E.S. et al., Hamar-Hansen, C. et al., Roberts, E.S. et al.

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Disease relevance of beta-Naphthaleneacetate

Truncated 2B4 lacking amino acids 2-27, 2B4 (Delta2-27), was expressed in Escherichia coli, purified, and found to catalyze the oxidation of 2EN to 2-naphthylacetic acid (2NA) [1].

High impact information on beta-Naphthaleneacetate

2-EN was a 5- to 10-fold less potent inhibitor of mouse P4502b, as compared with the rat, even though it was shown to bind to the active site of the mouse isoform as demonstrated by its metabolism to 2-naphthylacetic acid [2].
Liquid chromatographic and GC-MS analyses of the organic extracts from these incubations showed that the major metabolite was 2-naphthylacetic acid, and a partition ratio of 4-5 mol of acid produced per mole of cytochrome P450 2B1 inactivated was determined [3].
A general method for the assay of UDP-glucuronosyltransferase activity towards arylcarboxylic acids (clofibric acid, 1- and 2-naphthylacetic acid) using UDP-[U-14C] glucuronic acid in liver microsomes is described [4].
1. The influence of dose size upon the metabolic conjugation of 2-naphthylacetic acid with various amino acids and glucuronic acid has been studied in the guinea pig, mouse and hamster [5].
3. Mice conjugated 2-naphthylacetic acid with glycine, taurine and glucuronic acid [5].

References

A role for threonine 302 in the mechanism-based inactivation of P450 2B4 by 2-ethynylnaphthalene. Roberts, E.S., Pernecky, S.J., Alworth, W.L., Hollenberg, P.F. Arch. Biochem. Biophys. (1996) [Pubmed]
Mechanism-based inhibition of mouse P4502b-10 by selected arylalkynes. Beebe, L.E., Roberts, E.S., Fornwald, L.W., Hollenberg, P.F., Alworth, W.L. Biochem. Pharmacol. (1996) [Pubmed]
Mechanism-based inactivation of cytochrome P450 2B1 by 2-ethynylnaphthalene: identification of an active-site peptide. Roberts, E.S., Hopkins, N.E., Alworth, W.L., Hollenberg, P.F. Chem. Res. Toxicol. (1993) [Pubmed]
Liquid chromatographic assay for the measurement of glucuronidation of arylcarboxylic acids using uridine diphospho-[U-14C] glucuronic acid. Hamar-Hansen, C., Fournel, S., Magdalou, J., Boutin, J.A., Siest, G. J. Chromatogr. (1986) [Pubmed]
Studies on the metabolism of arylacetic acids. 7. The influence of varying dose size upon the conjugation pattern of 2-naphthylacetic acid in the guinea pig, mouse and hamster. Emudianughe, T.S., Caldwell, J., Smith, R.L. Xenobiotica (1987) [Pubmed]

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