Computational designing of new inhibitors against COX-2 involved in human diseases based on binding energy calculations

International Journal of Integrative Biology

Volumn 2, Issue 3, 2008, Pages 182-189

  Sekhar, P Nataraj ^a   Kavi Kishor, P B ^a   Sunita, M S L ^a   Premkumar, E ^a   Reddy, Ananda Lakkireddy ^a  

^a OSMANIA UNIVERSITY   (India)

Author keywords

Complexation energy; Cyclooxygenase 2; Docking; Interaction energies; Molecular mechanics; Nonsteroidal anti inflammatory drugs

Indexed keywords

1,3 OXAZOLE; 4 (2 PHENYL 1 H PYRROL 3 YL) BENZENE SULFONAMIDE; 4 (2 PHENYL 3 THIENYL) BENZENE SULFONAMIDE; 4 (2 PHENYLTETRAHYDROFURAN 3 YL) BENZENE SULFONAMIDE; 4 (5 PHENYL 1 H IMIDAZOL 4 YL) BENZENE SULFONAMIDE; 4 (5 PHENYL 1, 3 OXAZOL 4 YL) BENZENE SULFONAMIDE; 4 (5 PHENYL 1, 3 THIAZOL 4 YL) BENZENE SULFONAMIDE; BENZENE; CELECOXIB; CYCLOOXYGENASE 2 INHIBITOR; FURAN; IMIDAZOLE; NONSTEROID ANTIINFLAMMATORY AGENT; OXAZOLE DERIVATIVE; PYRROLE; THIAZOLE; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BIOLOGICAL ACTIVITY; CRYSTAL STRUCTURE; DRUG BINDING; DRUG DESIGN; EC50; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME STRUCTURE; HYDROGEN BOND; IC50; MATHEMATICAL ANALYSIS; MOLECULAR DOCKING; MOLECULAR WEIGHT; STRUCTURE ACTIVITY RELATION;

EID: 78650720652     PISSN: 09738363     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. Smith et al. (1996) Prostaglandin endoperoxide H synthases-1 and-2. Adv. Immunol. 62:167-215.
2. Fu, JY et al. (1990) The induction and suppression of prostaglandin H2 synthase (cyclooxygenase) in Human monocytes. J. Biol. Chem. 265: 16737-16740.
3. Xie, W et al. (1991) Expression of a mitogen-responsive gene encoding prostaglandin synthase is regulated by mRNA splicing. Proc. Natl. Acad. Sci. U.S.A. 88: 1692-1696.
4. Herchsman et al. (1996) Prostaglandin synthase 2. Biochim. Biophys. Acta. 1299(1996):125-140.
5. Dubois et al. (1998) Cyclooxygenase in biology and disease. FASEB J.12:1063-1073.
6. Subbaramaiah K et al. (2003) Cyclooxygenase 2: a molecular target for cancer prevention and treatment. Trends Pharmacol. Sci. 24: 96-102
7. Iniguez MA et al. (2003) Cyclooxygenase-2: a therapeutic target for angiogenesis.Trends Mol. Med. 9:73-78.
8. Xiang Z et al. (2002) Cyclooxygenase (COX)-2 and cell cycle activity in a transgenic mouse model of Alzheimer's disease neuropathology. Neurobiol. Aging 23:327-334.
9. Feng ZH et al. (2002) Cyclooxygenase-2-deficient mice are resistant to 1-methyl-4-phenyl1, 2, 3, 6-tetrahydropyridine-induced damage of dopaminergic neurons in the substantia nigra. Neurosci. Lett. 329:354-358.
10. Parente L et al. (2003) Advances in the pathophysiology of constitutive and inducible cyclooxygenases: two enzymes in the spotlight. Biochem. Pharmacol. 65: 153-159
11. Breder CD et al. (1995) Characterization of inducible cyclooxygenase in rat brainComp. Neurol. 355: 296-315.
12. Hogestatt ED et al. (2005) Conversion of Acetaminophen to the Bioactive N-Acylphenolamine AM404 via Fatty Acid Amide Hydrolase-dependent Arachidonic Acid Conjugation in the Nervous System J. Biol. Chem. 280:31405-3141
13. Futaki N et al. (1993) NS-398, a novel non-steroidal antiinflammatory drug with potent analgesic and antipyretic effects, which causes minimal stomach lesions. Gen. Pharmacol. 24:105-110.
14. Gans et al. (1990) Antiinflammatory and safety profile of DuP 697, a novel orally effective prostaglandin synthesis inhibitor. J. Pharmacol. Exp. Ther. 254:180-187.
15. Copeland et al. (1994) Mechanism of selective Inhibition of the inducible isoform of prostaglandin G/H synthase. Proc. Natl. Acad. Sci. U.S.A. 91:11202-11206.
16. Futaki N et al. (1994) NS-398, a new antiinflammatory agent, selectively inhibits prostaglandin G/H synthase/ cyclooxygenase (COX-2) activity in vitro. Prostaglandins 47:55-59.
17. Chan et al (1995) Pharmacology of a selective cyclooxygenase-2 inhibitor, L-745, 337: a novel nonsteroidal antiinflammatory agent with an ulcerogenic sparing effect in rat and nonhuman primate stomach. J. Pharmacol. Exp. Ther. 274:1531-1537.
18. Klein T et al. (1996) Mechanistic studies on the selective inhibition of cyclooxygenase-2 by indanone derivatives. Biochem. Pharmacol. 51:285-290.
19. Ehrich et al. (1999) Characterization of rofecoxib as a cyclooxygenase-2 isoform inhibitor and demonstation of analgesia in the dental pain model. Clin. Pharmacol. Ther. 65:33-347.
20. Penning, T et al. (1997) Synthesis and biological evaluation of the 1, 5-diarylpyrazole class of cyclooxygenase inhibitors: identification of 4-(5-(4-Methylphenyl)-3-(trifluoromethyl)-1Hpyrazol-1-yl)benzenesulfonamide (SC-58635, Celecoxib). J. Med. Chem. 40:1347-1365
21. Kurumbail RG et al. (1996) Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 384:644-648.
22. Engelhardt G et al (1995). Anti-inflammatory, analgesic, antipyretic and related properties of meloxicam, a new non-steroidal anti-inflammatory agent with favourable gastrointestinal tolerance. Inflamm. Res. 44:423-433
23. Jiuxiang Zhu et al. (2002) Using cyclooxygenase-2 inhibitors as molecular platforms to develop a new class of apoptosis-inducing agents. Journal of the National Cancer Institute, 94:23, 4.
24. G. Jones P et al. (1997) Development and validation of a genetic algorithm for flexible docking, J. Mol. Biol. 267:727-748.
25. Lipinski CA et al. (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Del. Rev., 46: 3-26.
26. Ertl P et al. (2000) Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem. 43:3714-3717.
27. Veber D et al. (2002) Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 45:2615-2623
28. Steinbach G et al. (2000) The effect of celecoxib, a cyclooxygenase-2 inhibitor, in familial adenomatous polyposis. N Engl J Med. 342:1946-52.
29. Mitchell, J et al. (1994) Selectivity of nonsteroidal anti-inflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc. Natl. Acad. Sci. USA 90:11693-11697.
30. Ravi G et al. (1996) Structural basis for selective inhibition of cyclooxygenase-2by anti-inflammatory agents. NATURE 384:19-26.