Chemically induced dimerization of human nonpancreatic secretory phospholipase A2 by bis-indole derivatives

Journal of Medicinal Chemistry

Volumn 51, Issue 12, 2008, Pages 3360-3366

  Zhou, Lu ^a   Fang, Chao ^a   Wei, Ping ^a   Liu, Shiyong ^a,b   Liu, Ying ^a   Lai, Luhua ^a,b  

^a PEKING UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 BIS[[(3 ACETAMINO 5 METHOXY 2 METHYLINDOLE) 2 METHYLENE]PHENOXY]PENTANE; DIVALENT CATION; INDOLE DERIVATIVE; PHOSPHOLIPASE A2;

ARTICLE; CHEMICAL MODIFICATION; CORRELATION ANALYSIS; DIMERIZATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; LIGAND BINDING; MOLECULAR INTERACTION; MOLECULAR MODEL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRACENTRIFUGATION;

DIMERIZATION; GROUP II PHOSPHOLIPASES A2; HUMANS; INDOLES; LIGANDS; MODELS, MOLECULAR;

EID: 45749116608     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm7010707     Document Type: Article

References (31)

1. Ullrich, A.; Schlessinger, J. Signal transduction by receptors with tyrosine kinase-activity. Cell 1990, 61, 203-212.
2. Spencer, D. M.; Wandless, T. J.; Schreiber, S. L.; Crabtree, G. R. Controlling signal-transduction with synthetic ligands. Science 1993, 262, 1019-1024.
3. Ho, S. N.; Biggar, S. R.; Spencer, D. M.; Schreiber, S. L.; Crabtree, G. R. Dimeric ligands define a role for transcriptional activation domains in reinitiation. Nature 1996, 382, 822-826.
4. Belshaw, P. J.; Ho, S. N.; Crabtree, G. R.; Schreiber, S. L. Controlling protein association and subcellular localization with a synthetic ligand that induces heterodimerization of proteins. Proc. Natl Acad. Sci. U.S.A. 1996, 93, 4604-4607.
5. Rivera, V. M.; Clackson, T.; Natesan, S.; Pollock, R.; Amara, J. F.; Keenan, T.; Magari, S. R.; Phillips, T.; Courage, N. L.; Cerasoli, F.; Holt, D. A.; Gilman, M. A humanized system for pharmacologic control of gene expression. Nat. Med. 1996, 2, 1028-1032.
6. Farrar, M. A.; Alberol, I.; Perlmutter, R. M. Activation of the Raf-1 kinase cascade by coumermycin-induced dimerization. Nature 1996, 383, 178-181.
7. Kopytek, S. J.; Standaert, R. F.; Dyer, J. C. D.; Hu, J. C. Chemically induced dimerization of dihydrofolate reductase by a homobifunctional dimer of methotrexate. Chem. Biol. 2000, 7, 313-321.
8. Harvey, I.; Garneau, P.; Pelletier, J. Forced engagement of a RNA/protein complex by a chemical inducer of dimerization to modulate gene expression. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 1882-1887.
9. Liu, J. Y.; Zhang, Z. S.; Tan, X. J.; Hol, W. G. J.; Verlinde, C. L. M. J.; Fan, E. K. Protein heterodimerization through ligand-bridged multivalent pre-organization: enhancing ligand binding toward both protein targets. J. Am. Chem. Soc. 2005, 127, 2044-2045.
10. Tachedjian, G.; Orlova, M.; Sarafianos, S. G.; Arnold, E.; Goff, S. P. Nonnucleoside reverse transcriptase inhibitors are chemical enhancers of dimerization of the HIV type 1 reverse transcriptase. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 7188-7193.
11. Berg, T. Modulation of protein-protein interactions with small organic molecules. Angew. Chem., Int. Ed. 2003, 42, 2462-2481.
12. Nevalainen, T. Serum phospholipases A2 in inflammatory diseases. J. Clin. Chem. 1993, 39, 2453-2457.
13. Pruzanski, W.; Vadas, P.; Browning, J. Secretory non-pancreatic group II phospholipase A2: role in physiologic and inflammatory processes. J. Lipid Mediators 1993, 8, 161-167.
14. Gelb, M. H.; Min, J. H.; Jain, M. K. Do membrane-bound enzymes access their substrates from the membrane or aqueous phase: interfacial versus non-interfacial enzymes. Biochim. Biophys. Acta 2000, 1488, 20-27.
15. Berg, O. G.; Yu, B. Z.; Rogers, J.; Jain, M. K. Interfacial catalysis by phospholipase-A2. Determination of the interfacial kinetic rate constants. Biochemistry 1991, 30, 7283-7297.
16. Brunie, S.; Bolin, J.; Gewirth, D.; Sigler, P. B. The refined crystal structure of dimeric phospholipase A2 at 2.5 Å. Access to a shielded catalytic center. J. Biol. Chem. 1985, 260, 9742-9749.
17. Suzuki, A.; Matsueda, E.; Yamane, T.; Ashida, T.; Kihara, H.; Ohno, M. Crystal-structure analysis of phospholipase a(2) from trimeresurusflavoviridis (Habu Snake) venom at 1.5 angstrom resolution. J. Biochem. 1995, 117, 730-740.
18. Pan, Y. H.; Epstein, T. M.; Jain, M. K.; Bahnson, B. J. Five coplanar anion binding sites on one face of phospholipase A(2). Relationship to interface binding. Biochemistry 2001, 40, 609-617.
19. Schevitz, R. W.; Bach, N. J.; Carlson, D. G.; Chirgadze, N. Y.; Clawson, D. K.; Dillard, R. D.: Draheim, S. E.; Hartley, L. W.; Jones, N. D.; Mihelich, E. D.; Olkowski, J. L.; Snyder, D. W.; Sommers, C.; Wery, J. P. Structure-based design of the first potent and selective inhibitor of human nonpancreatic secretory phospholipase-a(2). Nat. Struct. Biol. 1995, 2, 458-465.
20. Dillard, R. D.; Bach, N. J.; Draheim, S. E.; Berry, D. R.; Carlson, D. G.; Chirgadze, N. Y.; Clawson, D. K.; Hartley, L. W.; Johnson, L. M.; Jones, N. D.; McKinney, E. R.; Mihelich, E. D.; Olkowski, J. L.; Schevitz, R. W.; Smith, A. C.; Snyder, D. W.; Sommers, C. D.; Wery, J. P. Indole inhibitors of human nonpancreatic secretory phospholipase A2. 2. Indole-3-acetamides with additional functionality. J. Med. Chem. 1996, 39, 5137-5158.
21. Huang, C. K.; Zhou, L.; Liu, Y.; Lai, L. H. A continuous fluorescence assay for phospholipase A2 with nontagged lipid. Anal. Biochem. 2006, 351, 11-17.
22. Jackson, R. M.; Gabb, H. A.; Sternberg, M. J. E. Rapid refinement of protein interfaces incorporating solvation: application to the docking problem. J. Mol. Biol. 1998, 276, 265-285.
23. Warren, S. C.; DeLano, L. The PyMOL Molecular Graphics System; DeLano Scientific LLC: Palo Alto, CA; http://pymol.sourceforge.net/.
24. Liu, Y.; Han, X. F.; Huang, C. K.; Hao, X.; Lai, L. H. Indole-5-phenylcarbamate derivatives as human non-pancreatic secretory phospholipase A2 inhibitor. Bioorg. Med. Chem. Lett. 2005, 15, 4540-4542.
25. Lebowitz, J.; Lewis, M. S.; Schuck, P. Modern analytical ultracentrifugation in protein science: a tutorial review. Protein Sci. 2002, 11, 2067-2079.
26. Laue, T. M.; Stafford, W. F. Modern applications of analytical ultracentrifugation. Annu. Rev. Biophys. Biomol. Struct. 1999, 28, 75-100.
27. Schuck, P. On the analysis of protein self-association by sedimentation velocity analytical ultracentrifugation. Anal. Biochem. 2003, 320, 104-124.
28. Carlson, J. C. T.; Kanter, A.; Thuduppathy, G. R.; Cody, V.; Pineda, P. E.; McIvor, R. S.; Wagner, C. R. Designing protein dimerizers: the importance of ligand conformational equilibria. J. Am. Chem. Soc. 2003, 125, 1501-1507.
29. Othman, R.; Baker, S.; Li, Y.; Worrall, A. F.; Wilton, D. C. Human non-pancreatic (group II) secreted phospholipase A(2) expressed from a synthetic gene in Escherichia coli: characterisation of N-terminal mutants. Biochim. Biophys. Acta 1996, 2, 92-102.
30. Han, S. K.; Lee, B. I.; Cho, W. H. Bacterial expression and characterization of human pancreatic phospholipase A(2). Biochim. Biophys. Acta 1997, 1346, 185-192.
31. Jain, M. K.; Berg, O. G. Coupling of the i-face and the active site of phospholipase A(2) for interfacial activation. Curr. Opin. Chem. Biol 2006, 10, 473-479.