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The screening and characterization of 6-aminopurine-based xanthine oxidase inhibitors.
Bioorg Med Chem. 2007 May 15; 15(10):3450-6.BM

Abstract

Xanthine oxidase (XO) is a key enzyme which can catalyze xanthine to uric acid causing hyperuricemia in humans. By using the fractionation technique and inhibitory activity assay, an active compound that prevents XO from reacting with xanthine was isolated from wheat leaf. It was identified by the Mass and NMR as 6-aminopurine (adenine). A structure-activity study based on 6-aminopurine was conducted. The inhibition of XO activity by 6-aminopurine (IC(50)=10.89+/-0.13 microM) and its analogues was compared with that by allopurinol (IC(50)=7.82+/-0.12 microM). Among these analogues, 2-chloro-6(methylamino)purine (IC(50)=10.19+/-0.10 microM) and 4-aminopyrazolo[3,4-d] pyrimidine (IC(50)=30.26+/-0.23 microM) were found to be potent inhibitors of XO. Kinetics study showed that 2-chloro-6(methylamino)purine is non-competitive, while 4-aminopyrazolo[3,4-d]pyrimidine is competitive against XO.

Authors+Show Affiliations

Institute of Biological Chemistry and the Genomics Research Center, Academia Sinica, Nankang, Taipei 115, Taiwan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17379526

Citation

Hsieh, Jung-Feng, et al. "The Screening and Characterization of 6-aminopurine-based Xanthine Oxidase Inhibitors." Bioorganic & Medicinal Chemistry, vol. 15, no. 10, 2007, pp. 3450-6.
Hsieh JF, Wu SH, Yang YL, et al. The screening and characterization of 6-aminopurine-based xanthine oxidase inhibitors. Bioorg Med Chem. 2007;15(10):3450-6.
Hsieh, J. F., Wu, S. H., Yang, Y. L., Choong, K. F., & Chen, S. T. (2007). The screening and characterization of 6-aminopurine-based xanthine oxidase inhibitors. Bioorganic & Medicinal Chemistry, 15(10), 3450-6.
Hsieh JF, et al. The Screening and Characterization of 6-aminopurine-based Xanthine Oxidase Inhibitors. Bioorg Med Chem. 2007 May 15;15(10):3450-6. PubMed PMID: 17379526.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The screening and characterization of 6-aminopurine-based xanthine oxidase inhibitors. AU - Hsieh,Jung-Feng, AU - Wu,Shih-Hsiung, AU - Yang,Yu-Liang, AU - Choong,Kee-Fong, AU - Chen,Shui-Tein, Y1 - 2007/03/12/ PY - 2007/02/01/received PY - 2007/03/05/revised PY - 2007/03/05/accepted PY - 2007/3/24/pubmed PY - 2007/6/28/medline PY - 2007/3/24/entrez SP - 3450 EP - 6 JF - Bioorganic & medicinal chemistry JO - Bioorg. Med. Chem. VL - 15 IS - 10 N2 - Xanthine oxidase (XO) is a key enzyme which can catalyze xanthine to uric acid causing hyperuricemia in humans. By using the fractionation technique and inhibitory activity assay, an active compound that prevents XO from reacting with xanthine was isolated from wheat leaf. It was identified by the Mass and NMR as 6-aminopurine (adenine). A structure-activity study based on 6-aminopurine was conducted. The inhibition of XO activity by 6-aminopurine (IC(50)=10.89+/-0.13 microM) and its analogues was compared with that by allopurinol (IC(50)=7.82+/-0.12 microM). Among these analogues, 2-chloro-6(methylamino)purine (IC(50)=10.19+/-0.10 microM) and 4-aminopyrazolo[3,4-d] pyrimidine (IC(50)=30.26+/-0.23 microM) were found to be potent inhibitors of XO. Kinetics study showed that 2-chloro-6(methylamino)purine is non-competitive, while 4-aminopyrazolo[3,4-d]pyrimidine is competitive against XO. SN - 0968-0896 UR - https://www.unboundmedicine.com/medline/citation/17379526/The_screening_and_characterization_of_6_aminopurine_based_xanthine_oxidase_inhibitors_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(07)00197-6 DB - PRIME DP - Unbound Medicine ER -