1,3-Dimethyluric acid

1,3-二甲基尿酸（1,3-Dimethyluric acid）是一种氧嘌呤，它是 7,9-二氢-1H-嘌呤-2,6,8(3H)-三酮，在 N-1 和 N-3 被甲基取代。是人体茶碱代谢的产物。1,3-二甲基尿酸是尿路结石中的嘌呤成分之一。

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Background

1,3-Dimethyluric acid is an active metabolite of the methylxanthine alkaloids caffeine and theophylline .¹ It is formed from caffeine and theophylline by the cytochrome P450 (CYP) isoforms CYP1A2 and CYP2E1.^2,3 1,3-Dimethyluric acid (500 ?M) scavenges hydroxyl radicals in a cell-free assay and inhibits t-butyl hydroperoxide-induced lipid peroxidation by 77% in isolated human erythrocyte membranes.⁴ It induces contractions in isolated rabbit duodenal, jejunal, and ileal preparations, but induces relaxation in isolated rabbit ascending colon preparations, in a concentration-dependent manner.⁵ Intracerebral administration of 1,3-dimethyluric acid induces clonic convulsions in mice (ED₅₀ = 360 nmol/animal).⁶ It has been found in urinary caliculi.⁷

1.Cornish, H.H., and Christman, A.A.A study of the metabolism of theobromine, theophylline, and caffeine in manJ. Biol. Chem.228(1)315-323(1957) 2.Caubet, M.-S., Elbast, W., Dubuc, M.-C., et al.Analysis of urinary caffeine metabolites by HPLC-DAD: The use of metabolic ratios to assess CYP1A2 enzyme activityJ. Pharm. Biomed. Anal.27(1-2)261-270(2002) 3.Fuhr, U., Doehmer, J., Battula, N., et al.Biotransformation of methylxanthines in mammalian cell lines genetically engineered for expression of single cytochrome P450 isoforms. Allocation of metabolic pathways to isoforms and inhibitory effects of quinolonesToxicology82(1-3)169-189(1993) 4.Bhat, V.B., Sridhar, G.R., and Madyastha, K.M.Efficient scavenging of hydroxyl radicals and inhibition of lipid peroxidation by novel analogues of 1,3,7-trimethyluric acidLife Sci.70(4)381-393(2001) 5.Psarra, T.A., Batzias, G.C., Peeters, T.L., et al.Theophylline and its metabolites produce a stimulating cholinergic effect on the small intestine and a nonadrenergic noncholinergic relaxing effect on the colon: A comparative study in the rabbit intestineJ. Vet. Pharmacol. Ther.30(6)541-519(2007) 6.Yamamoto, K., Toyama, E., Kawakami, J., et al.Neurotoxic convulsions induced by theophylline and its metabolites in miceBiol. Pharm. Bull.19(6)869-872(1996) 7.Safranow, K., and Machoy, Z.Methylated purines in urinary stonesClin. Chem.51(8)1493-1498(2005)