Modeling of COX-2 inhibotory activity of flavonoids

International Journal of Pharmacy and Pharmaceutical Sciences

Volumn 3, Issue 4, 2011, Pages 33-40

  D'mello, Priscilla ^a   Gadhwal, Manoj Kumar ^a   Joshi, Urmila ^a   Shetgiri, Preetam ^a  

^a PRIN K M KUNDNANI COLLEGE OF PHARMACY   (India)

Author keywords

Anti inflammatory activity; Cyclooxygenase(COX); Docking studies; Flavonoids; Structure Activity Relationship

Indexed keywords

4 [5 (4 BROMOPHENYL) 3 TRIFLUOROMETHYL 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; 5 (4 FLUOROPHENYL) 1 [(4 METHYLSULFONYL)PHENYL] 3 TRIFLUOROMETHYLPYRAZOLE; 6 (2,4 DIFLUOROPHENYLTHIO) 5 METHANESULFONAMIDO 1 INDANONE; ALIZARIN; ALOE EMODIN; APIGENIN; BAICALEIN; CELECOXIB; CHRYSIN; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; EMODIN; FLAVANONE; FLAVONE; FLAVONOID; FLAVONOL; FLOSULIDE; GENISTEIN; HESPERETIN; ISOFLAVONE; KAEMPFEROL; LUTEOLIN; MORIN; MYRICETIN; NARINGENIN; PYRROLE DERIVATIVE; QUERCETIN; ROFECOXIB; TERPHENYL DERIVATIVE; ZOMEPIRAC;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; DRUG ACTIVITY; DRUG PROTEIN BINDING; ENZYME INHIBITION; IC 50; MOLECULAR DOCKING;

EID: 80054874680     PISSN: None     EISSN: 09751491     Source Type: Journal    
DOI: None     Document Type: Article

References (24)

1. Smith RM, DeWitt DL, Garavito RM: Cyclooxygenases: structural, cellular and molecular biology, Ann Rev Biochem, 2000;69:145-182.
2. Vane JR, Bakhle YS, Botting RM: Cyclooxygenases 1 and 2, Annu Rev Pharmacol Toxicol, 1998;38:97-120.
3. Smith CJ, Morrow JD, Roberts LJI, Marnett LJ: Differentiation of monocytoid THP-1 cells with phorbol ester induces expression of prostaglandin endoperoxide synthase-1 (COX-1), Biochem Biophys Res Commun, 1993;192:787-793.
4. Kurumbail RG, Stevens AM, Gierse JK, McDonald JJ, Stegeman RA, Pak JY, Gildehaus D, Miyashiro JM, Penning TO, Seibert K, Isakson PC, Stallings WC: Structural Basis for Selective Inhibition of cyclooxygenase 2 by antiinflammatory agents, Nature, 1996;384:644.
5. Herschman HR: Prostaglandin synthase 2, Biochim. Biophys. Acta Lipids Lipid Metab., 1996;1299:125-140.
6. Kujubu DA, Fletcher B, Varnum BC, Lim RW, Herschman HR: TIS10, a phorbol ester tumor promoter-inducible mRNA from Swiss 3T3 cells, encodes a novel prostaglandin synthase/cyclooxygenase homologue, J. Biol. Chem., 1991;266:12866.
7. Dewitt DL, Meade EA, Smith WL: PGH synthase isoenzyme selectivity: the potential for safer nonsteroidal anti-inflammatory drugs, Am J Med,1993;95:2A405-2A44S.
8. Xie W, Robertson DL, Simmons DL: Mitogen-inducible prostaglandin G/H synthase: a new target for nonsteroidal antiinflammatory drugs, Drug Dev Res, 1992;25:249-265.
9. Marnett LJ, Kalgutkar A: Cyclooxygenase 2 Inhibitors: Discovery, Selectivity and the future, Trends Pharmacol. Sci., 1999;20:465.
10. Prescott MA, Fitzpatrick FA: Cyclooxygenase and Carcinogenesis, Biochim Biophys Acta, 2000; 1470: M69-M78.
11. Chan AT, Giovannucci EL, Meyerhardt JA, Schernhammer ES, Curhan GC & Fuchs CS: Long-term use of aspirin and nonsteroidal anti-inflammatory drugs and risk of colorectal cancer, JAMA, 2005;294:914-923.
12. Vaughan TL, Dong LM, Blount PL, Ayub K, Odze RD, Sanchez CA, Rabinovitch PS, Reid BJ: Non-steroidal anti-inflammatory drugs and risk of neoplastic progression in Barrett's oesophagus: a prospective study, Lancet Oncol, 2005;6:945-952.
13. Cheong E, Ivory K, Doleman J, Parker ML, Rhodes M, Johnson IT: Synthetic and naturally occurring COX-2 inhibitors suppress proliferation in a human oesophageal adenocarcinoma cell line (OE33) by inducing apoptosis and cell cycle arrest, Carcinogenesis, 2004;25(10):1945-1952.
14. Atsushi T, Kazuhiro M, Yoko S, Katya G, Taku T, Teruyuki K, Yuh Y, Yuichi S, Akira T, Takashi T, Choitsu S: Cyclooxygenase-2 expression correlates with angiogenesis and apoptosis in gastric cancer tissue, Human pathology, 2004;35:488-495.
15. Ren W, Qiao Z, Wang H, Zhu L, Zhang L: Flavonoids: Promising Anticancer Agents, Medicinal Research Reviews, 2003;23(4):519-534.
16. Comalada, M, Camuesco D, Sierra S, Ballester I, Xaus J, Galvez J, Zarzuelo A: In vivo quercitrin anti-inflammatory effect involves release of quercetin, which inhibits inflammation through down-regulation of the NF-kappaB pathway, For. J. Immunol., 2005;35:584-592.
17. O'Leary KA, de Pascual-Tereasa S, Needs PW, Bao YP, O'Brien NM, Williamson G: Effect of flavonoid and vitamin E on cyclooxygenase-2 (COX-2) transcription, Mutat. Res, 2004;551:245-254.
18. Price MLP, Jorgensen WL: Rationale for the observed COX-2/COX-1 selectivity of celecoxib from Monte Carlo simulations, Bioorg. Med. Chem. Lett., 2001;11:1541-1544.
19. Kiefer JR, Pawlitz JL, Moreland KT, Stageman RA, Hood WF, Gierse JK, Stevens AM, Goodwin DC, Rowilson SW, Marnett LJ, Stallings WC, Kurumbail RG: Structural insights into the stereochemistry of the cyclooxygenase reaction, Nature, 2000;405:97-101.
20. Llorens O, Perez J, Palomer A and Mauleon D: Differential binding mode of Diverse cyclooxygenase inhibitors, Journal of Molecular Graphics and Modelling, 2002; 20:359-371.
21. Xin Feng Zhang, Tran Manh Hung, Phuong Thien Phuong, et al: Anti-inflammatory activity of flavonoids from Populus davidiana, Arch Pharm Res, 2006;29(12):1102-1108.
22. Moore and Simmons: COX-2 inhibition, apoptosis, and chemoprevention by nonsteroidal anti-inflammatory drugs, Current Med Chem, 2000;7:1131-1144.
23. Jia Qi, Timothy C., Rhoden, Eric E., Waite, Scott: Identification of free-B-ring flavonoids as potent COX-2 inhibitors, United States Patent 7192611.
24. Cheong E., Ivory K., Doleman J., et al: Synthetic and naturally occurring COX-2 inhibitors suppress proliferation in a human oesophageal adenocarcinoma cell line (0E33) by inducing apoptosis and cell cycle, Carcinogenesis, 2004;25(10):1945-1952.