Hydrophilic ester-bearing chlorogenic acid binds to a novel domain to inhibit xanthine oxidase

Planta Medica

Volumn 75, Issue 11, 2009, Pages 1237-1240

  Wang, Shwu Huey ^a   Chen, Chien Shu ^b   Huang, Shih Hao ^c   Yu, Szu Hsu ^a   Lai, Zhi Yang ^d,f   Huang, Sheng Tung ^e   Lin, Chun Mao ^d,f  

^a TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^b CHINA MEDICAL UNIVERSITY   (Taiwan)

^c Taipei College of Maritime Technology   (Taiwan)

^d TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^e NATIONAL TAIPEI UNIVERSITY OF TECHNOLOGY   (Taiwan)

^f TAIPEI MEDICAL UNIVERSITY HOSPITAL   (Taiwan)

Author keywords

Caffeic acid; Chlorogenic acid; FAD; Molecular modeling; Olybdopterin; Xanthine oxidase

Indexed keywords

ALLOPURINOL; CAFFEIC ACID; CAFFEIC ACID PHENETHYL ESTER; CHLOROGENIC ACID; ESTER; FLAVINE ADENINE NUCLEOTIDE; MOLYBDOPTERIN; XANTHINE OXIDASE INHIBITOR;

ARTICLE; COMPARATIVE STUDY; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG BINDING; DRUG POTENCY; DRUG STRUCTURE; HYDROPHILICITY; HYDROPHOBICITY; MOLECULAR DOCKING; MOLECULAR MODEL;

BINDING SITES; CAFFEIC ACIDS; CHLOROGENIC ACID; ENZYME INHIBITORS; ESTERIFICATION; MODELS, MOLECULAR; PROTEIN STRUCTURE, TERTIARY; XANTHINE OXIDASE;

EID: 70350755575     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0029-1185521     Document Type: Article

References (25)

1. Harrison R. Physiological roles of xanthine oxidoreductase. DrugMetab Rev 2004; 36: 363-375
2. Okamoto K, Matsumoto K, Hille R, Eger BT, Pai EF, Nishino T. The crystal structure of xanthine oxidoreductase during catalysis: implications for reaction mechanism and enzyme inhibition. Proc Natl Acad Sci USA 2004; 101: 7931-7936
3. Enroth C, Eger BT, Okamoto K, Nishino T, Pai EF. Crystal structures of bovine milk xanthine dehydrogenase and xanthine oxidase: structurebased mechanism of conversion. Proc Natl Acad Sci USA 2000; 97: 10723-10728
4. Wu Y, Hu S. Direct electron transfer of xanthine oxidase and its catalytic reduction to nitrate. Anal Chim Acta 2007; 602: 181-186
5. Godber BL, Doel JJ, Sapkota GP, Blake DR, Stevens CR, Eisenthal R, Harrison R. Reduction of nitrite to nitric oxide catalyzed by xanthine oxidoreductase. J Biol Chem 2000; 275: 7757-7763
6. Schroder K, Vecchione C, Jung O, Schreiber JG, Shiri-Sverdlov R, van Gorp PJ, Busse R, Brandes RP. Xanthine oxidase inhibitor tungsten prevents the development of atherosclerosis in ApoE knockout mice fed aWestern-type diet. Free Radic Biol Med 2006; 41: 1353-1360
7. Pacher P, Nivorozhkin A, Szabo C. Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev 2006; 58: 87-114
8. Feig DI, Soletsky B, Johnson RJ. Effect of allopurinol on blood pressure of adolescents with newly diagnosed essential hypertension: a randomized trial. JAMA 2008; 300: 924-932
9. George J, Struthers AD. The role of urate and xanthine oxidase inhibitors in cardiovascular disease. Cardiovasc Ther 2008; 26: 59-64
10. Bomalaski JS, Clark MA. Serum uric acid-lowering therapies: where are we heading in management of hyperuricemia and the potential role of uricase. Curr Rheumatol Rep 2004; 6: 240-247
11. Lin CM, Chen CT, Lee HH, Lin JK. Prevention of cellular ROS damage by isovitexin and related flavonoids. Planta Med 2002; 68: 365-367
12. Lin HC, Tsai SH, Chen CS, Chang YC, Lee CM, Lai ZY, Lin CM. Structure-activity relationship of coumarin derivatives on xanthine oxidase-inhibiting and free radical-scavenging activities. Biochem Pharmacol 2008; 75: 1416-1425
13. Lin CM, Chen CS, Chen CT, Liang YC, Lin JK. Molecular modeling of flavonoids that inhibits xanthine oxidase. Biochem Biophys Res Commun 2002; 294: 167-172
14. Okamoto K, Eger BT, Nishino T, Kondo S, Pai EF. An extremely potent inhibitor of xanthine oxidoreductase. Crystal structure of the enzymeinhibitor complex and mechanism of inhibition. J Biol Chem 2003; 278: 1848-1855
15. Fukunari A, Okamoto K, Nishino T, Eger BT, Pai EF, Kamezawa M, Yamada I, Kato N. Y-700 [1-[3-Cyano-4-(2, 2-dimethylpropoxy)phenyl]-1Hpyrazole-4- carboxylic acid]: a potent xanthine oxidoreductase inhibitor with hepatic excretion. J Pharmacol Exp Ther 2004; 311: 519-528
16. Chang YC, Lee FW, Chen CS, Huang ST, Tsai SH, Huang SH, Lin CM. Structure-activity relationship of C6-C3 phenylpropanoids on xanthine oxidase-inhibiting and free radical-scavenging activities. Free Radic Biol Med 2007; 43: 1541-1551
17. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 1998; 19: 1639-1662
18. Gasteiger J, Marsili M. Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges. Tetrahedron 1980; 36: 3219-3228
19. Bonita JS, Mandarano M, Shuta D, Vinson J. Coffee and cardiovascular disease: in vitro, cellular, animal, and human studies. Pharmacol Res 2007; 55: 187-198
20. Bose JS, Gangan V, Jain SK, Manna SK. Novel caffeic acid ester derivative induces apoptosis by expressing fasl and downregulating NF-KappaB: potentiation of cell death mediated by chemotherapeutic agents. J Cell Physiol 2009; 218: 653-662
21. McCord JM. Oxygen-derived free radicals in postischemic tissue injury. N Engl J Med 1985; 312: 159-163
22. Hille R, Nishino T. Flavoprotein structure and mechanism. 4. Xanthine oxidase and xanthine dehydrogenase. FASEB J 1995; 9: 995-1003
23. Okamoto K, Nishino T. Crystal structures of mammalian xanthine oxidoreductase bound with various inhibitors: allopurinol, febuxostat, and FYX-051. J Nippon Med Sch 2008; 75: 2-3
24. Pauff JM, Zhang J, Bell CE, Hille R. Substrate orientation in xanthine oxidase:crystal structure of enzyme in reaction with 2-hydroxy-6-methylpurine. J Biol Chem 2008; 283: 4818-4824
25. Porter DJ. Xanthine oxidase-catalyzed reductive debromination of 6- (bromomethyl)-9H-purine with concomitant covalent modification of the FAD prosthetic group. J Biol Chem 1990; 265: 13540-13546