Pharmacophore modeling and virtual screening for novel acidic inhibitors of microsomal prostaglandin E2 synthase-1 (mPGES-1)

Journal of Medicinal Chemistry

Volumn 54, Issue 9, 2011, Pages 3163-3174

  Waltenberger, Birgit ^a   Wiechmann, Katja ^b   Bauer, Julia ^b   Markt, Patrick ^a   Noha, Stefan M ^a   Wolber, Gerhard ^a,d   Rollinger, Judith M ^a   Werz, Oliver ^b,c   Schuster, Daniela ^a   Stuppner, Hermann ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

^b UNIVERSITY OF TÜBINGEN   (Germany)

^c FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^d FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

5 LIPOOXYGENASE; LIPOXYGENASE; PROSTAGLANDIN E SYNTHASE 1; PROSTAGLANDIN E2 SYNTHASE 1; PROSTAGLANDIN E2 SYNTHASE 1 INHIBITOR; PROSTAGLANDIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; IC 50; MOLECULAR DOCKING; PHARMACOPHORE; THEORETICAL MODEL;

ANTI-INFLAMMATORY AGENTS; BINDING SITES; CARBOXYLIC ACIDS; CELL LINE; CELL SURVIVAL; CELL-FREE SYSTEM; DATABASES, FACTUAL; HUMANS; IMIDAZOLES; INTRAMOLECULAR OXIDOREDUCTASES; LIPOXYGENASE INHIBITORS; MICROSOMES; MODELS, MOLECULAR; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79955876178     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101309g     Document Type: Article

References (30)

1. Loeffler, G.; Petrides, P. E. Biochemie and Pathobiochemie, 7th ed.; Springer: Berlin, Heidelberg, New York, 2003.
2. Samuelsson, B.; Morgenstern, R.; Jakobsson, P. J. Membrane prostaglandin E synthase-1: a novel therapeutic target Pharmacol. Rev. 2007, 59, 207-224 (Pubitemid 47481434)
3. Mehrotra, S.; Morimiya, A.; Agarwal, B.; Konger, R.; Badve, S. Microsomal prostaglandin E2 synthase-1 in breast cancer: a potential target for therapy J. Pathol. 2006, 208, 356-363 (Pubitemid 43210522)
4. Friesen, R. W.; Mancini, J. A. Microsomal prostaglandin E2 synthase-1 (mPGES-1): a novel anti-inflammatory therapeutic target J. Med. Chem. 2008, 51, 4059-4067 (Pubitemid 352032432)
5. Thoren, S.; Jakobsson, P. J. Coordinate up- and down-regulation of glutathione-dependent prostaglandin E synthase and cyclooxygenase-2 in A549 cells. Inhibition by NS-398 and leukotriene C4 Eur. J. Biochem. 2000, 267, 6428-6434
6. Quraishi, O.; Mancini, J. A.; Riendeau, D. Inhibition of inducible prostaglandin E(2) synthase by 15-deoxy-delta(12,14)-prostaglandin J(2) and polyunsaturated fatty acids Biochem. Pharmacol. 2002, 63, 1183-1189 (Pubitemid 34267034)
7. Riendeau, D.; Aspiotis, R.; Ethier, D.; Gareau, Y.; Grimm, E. L.; Guay, J.; Guiral, S.; Juteau, H.; Mancini, J. A.; Methot, N.; Rubin, J.; Friesen, R. W. Inhibitors of the inducible microsomal prostaglandin E2 synthase (mPGES-1) derived from MK-886 Bioorg. Med. Chem. Lett. 2005, 15, 3352-3355 (Pubitemid 40835734)
8. AbdulHameed, M. D.; Hamza, A.; Liu, J.; Huang, X.; Zhan, C. G. Human microsomal prostaglandin E synthase-1 (mPGES-1) binding with inhibitors and the quantitative structure-activity correlation J. Chem. Inf. Model. 2008, 48, 179-185 (Pubitemid 351271063)
9. Cote, B.; Boulet, L.; Brideau, C.; Claveau, D.; Ethier, D.; Frenette, R.; Gagnon, M.; Giroux, A.; Guay, J.; Guiral, S.; Mancini, J.; Martins, E.; Masse, F.; Methot, N.; Riendeau, D.; Rubin, J.; Xu, D.; Yu, H.; Ducharme, Y.; Friesen, R. W. Substituted phenanthrene imidazoles as potent, selective, and orally active mPGES-1 inhibitors Bioorg. Med. Chem. Lett. 2007, 17, 6816-6820 (Pubitemid 350061309)
10. Claveau, D.; Sirinyan, M.; Guay, J.; Gordon, R.; Chan, C. C.; Bureau, Y.; Riendeau, D.; Mancini, J. A. Microsomal prostaglandin E synthase-1 is a major terminal synthase that is selectively up-regulated during cyclooxygenase-2- dependent prostaglandin E2 production in the rat adjuvant-induced arthritis model J. Immunol. 2003, 170, 4738-4744 (Pubitemid 36519982)
11. San Juan, A. A.; Cho, S. J. 3D-QSAR study of microsomal prostaglandin E2 synthase (mPGES-1) inhibitors J. Mol. Model. 2007, 13, 601-610 (Pubitemid 46690947)
12. Jakobsson, P. J.; Morgenstern, R.; Mancini, J.; Ford-Hutchinson, A.; Persson, B. Common structural features of MAPEG - a widespread superfamily of membrane associated proteins with highly divergent functions in eicosanoid and glutathione metabolism Protein Sci. 1999, 8, 689-692 (Pubitemid 29117984)
13. Jegerschold, C.; Pawelzik, S. C.; Purhonen, P.; Bhakat, P.; Gheorghe, K. R.; Gyobu, N.; Mitsuoka, K.; Morgenstern, R.; Jakobsson, P. J.; Hebert, H. Structural basis for induced formation of the inflammatory mediator prostaglandin E2 Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 11110-11115
14. Rorsch, F.; Wobst, I.; Zettl, H.; Schubert-Zsilavecz, M.; Grosch, S.; Geisslinger, G.; Schneider, G.; Proschak, E. Nonacidic inhibitors of human microsomal prostaglandin synthase 1 (mPGES 1) identified by a multistep virtual screening protocol J. Med. Chem. 2010, 53, 911-915
15. Koeberle, A.; Zettl, H.; Greiner, C.; Wurglics, M.; Schubert-Zsilavecz, M.; Werz, O. Pirinixic acid derivatives as novel dual inhibitors of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase J. Med. Chem. 2008, 51, 8068-8076
16. Hessler, G.; Baringhaus, K.-H. The scaffold hopping potential of pharmacophores Drug Discovery Today: Technol. 2010, 7, 263-269
17. Köberle, A.; Zettl, H.; Greiner, C.; Wurglics, M.; Schubert-Zsilavecz, M.; Werz, O. Pirinixic acid derivatives as novel dual inhibitors of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase J. Med. Chem. 2008, 51, 8068-8076
18. Olofsson, K.; Suna, A.; Pelcman, B.; Ozola, V.; Katkevics, M.; Kalvins, I. Indoles useful for the treatment of inflammation. Int. Pat. Appl. PCT WO 2005/123673 A1, 29 Dec 2005.
19. Olofsson, K.; Suna, A.; Pelcman, B.; Ozola, V.; Katkevics, M.; Kalvins, I.; Schaal, W. Indoles useful in the treatment of inflammation. Int. Pat. Appl. PCT WO 2005/123675 A1, 29 Dec 2005.
20. Edwards, B. S.; Bologa, C.; Young, S. M.; Balakin, K. V.; Prossnitz, E. R.; Savchuck, N. P.; Sklar, L. A.; Oprea, T. I. Integration of virtual screening with high-throughput flow cytometry to identify novel small molecule formylpeptide receptor antagonists Mol. Pharmacol. 2005, 68, 1301-1310 (Pubitemid 41539986)
21. Rohrer, S. G.; Baumann, K. Maximum unbiased validation (MUV) data sets for virtual screening based on PubChem bioactivity data J. Chem. Inf. Model. 2009, 49, 169-184
22. Chen, C. Y.-C. Pharmacoinformatics approach for mPGES-1 in anti-inflammation by 3D-QSAR pharmacophore mapping J. Taiwan Inst. Chem. Eng. 2009, 40, 155-161
23. Celotti, F.; Laufer, S. Anti-inflammatory drugs: new multitarget compounds to face an old problem. The dual inhibition concept Pharmacol. Res. 2001, 43, 429-436 (Pubitemid 32578858)
24. Koeberle, A.; Siemoneit, U.; Buhring, U.; Northoff, H.; Laufer, S.; Albrecht, W.; Werz, O. Licofelone suppresses prostaglandin E2 formation by interference with the inducible microsomal prostaglandin E2 synthase-1 J. Pharmacol. Exp. Ther. 2008, 326, 975-982
25. Peters-Golden, M.; Henderson, W. R., Jr. Leukotrienes N. Engl. J. Med. 2007, 357, 1841-1854
26. Hopkins, A. L. Network pharmacology: the next paradigm in drug discovery Nature Chem. Biol. 2008, 4, 682-690
27. Fischer, L.; Szellas, D.; Radmark, O.; Steinhilber, D.; Werz, O. Phosphorylation- and stimulus-dependent inhibition of cellular 5-lipoxygenase activity by nonredox-type inhibitors FASEB J. 2003, 17, 949-951
28. Werz, O.; Burkert, E.; Samuelsson, B.; Radmark, O.; Steinhilber, D. Activation of 5-lipoxygenase by cell stress is calcium independent in human polymorphonuclear leukocytes Blood 2002, 99, 1044-1052 (Pubitemid 34527142)
29. Pergola, C.; Dodt, G.; Rossi, A.; Neunhoeffer, E.; Lawrenz, B.; Northoff, H.; Samuelsson, B.; Radmark, O.; Sautebin, L.; Werz, O. ERK-mediated regulation of leukotriene biosynthesis by androgens: a molecular basis for gender differences in inflammation and asthma Proc. Natl. Acad. Sci. U.S.A 2008, 105, 19881-19886
30. Tretiakova, I.; Blaesius, D.; Maxia, L.; Wesselborg, S.; Schulze-Osthoff, K.; Cinatl, J., Jr.; Michaelis, M.; Werz, O. Myrtucommulone from Myrtus communis induces apoptosis in cancer cells via the mitochondrial pathway involving caspase-9 Apoptosis 2008, 13, 119-131