The marine cyanobacterial metabolite gallinamide a is a potent and selective inhibitor of human cathepsin L

Journal of Natural Products

Volumn 77, Issue 1, 2014, Pages 92-99

  Miller, Bailey ^a   Friedman, Aaron J ^b   Choi, Hyukjae ^a   Hogan, James ^c   Andrew McCammon, J ^b,d   Hook, Vivian ^c   Gerwick, William H ^a,c  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^d San Diego   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATHEPSIN B; CATHEPSIN H; CATHEPSIN L; CATHEPSIN V; CYSTEINE PROTEINASE INHIBITOR; GALLINAMIDE A; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYANOBACTERIUM; DILUTION; DRUG STRUCTURE; ENZYME INHIBITION; HYDROGEN BOND; IC 50; MICHAEL ADDITION; MOLECULAR DOCKING; MOLECULAR DYNAMICS;

AMINO ACID SEQUENCE; CATALYTIC DOMAIN; CATHEPSIN L; CYANOBACTERIA; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; MARINE BIOLOGY; MOLECULAR STRUCTURE; PEPTIDES; PROTEASE INHIBITORS;

EID: 84893049327     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np400727r     Document Type: Article

References (41)

1. Nunnery, J. K.; Mevers, E.; Gerwick, W. H. Curr. Opin. Biotechnol. 2010, 21, 787-793
2. Pettit, G. R.; Kamano, Y.; Herald, C. L.; Tuinman, A. A.; Boettner, F. E.; Kizu, H.; Schmidt, J. M.; Baczynskyj, L.; Tomer, K. B.; Bontems, R. J. J. Am. Chem. Soc. 1987, 109, 6883-6885
3. Luesch, H.; Moore, R. E.; Paul, V. J.; Mooberry, S. L.; Corbett, T. H. J. Nat. Prod. 2001, 64, 907-910
4. Villa, F. A.; Gerwick, L. Immunopharmacol. Immunotoxicol. 2010, 32, 228-237
5. Linington, R. G.; Edwards, D. J.; Shuman, C. F.; McPhail, K. L.; Matainaho, T.; Gerwick, W. H. J. Nat. Prod. 2008, 71, 22-27
6. Gunasekera, S. P.; Miller, M. W.; Kwan, J. C.; Luesch, H.; Paul, V. J. J. Nat. Prod. 2010, 73, 459-462
7. Gondi, C. S.; Rao, J. S. Expert Opin. Ther. Targets 2013, 17, 281-291
8. Lankelma, J. M.; Voorend, D. M.; Barwari, T.; Koetsveld, J.; Van der Spek, A. H.; De Porto, A. P. N. A.; Van Rooijen, G.; Van Noorden, C. J. F. Life Sci. 2010, 86, 225-233
9. Hook, V. Y. H.; Kindy, M.; Hook, G. J. Biol. Chem. 2008, 283, 7745-7753
10. Sathya, M.; Premkumar, P.; Karthick, C.; Moorthi, P.; Jayachandran, K. S.; Anusuyadevi, M. Clin. Chim. Acta 2012, 414, 171-178
11. Rosenthal, P. J. Emerg. Infect. Dis. 1998, 4, 49-57
12. Kwan, J. C.; Eksioglu, E. A.; Liu, C.; Paul, V. J.; Luesch, H. J. Med. Chem. 2009, 52, 5732-5747
13. Pereira, A. R.; Kale, A. J.; Fenley, A. T.; Byrum, T.; Debonsi, H. M.; Gilson, M. K.; Valeriote, F. A.; Moore, B. S.; Gerwick, W. H. ChemBioChem 2012, 13, 810-817
14. Leto, G.; Sepporta, M. V.; Crescimanno, M.; Flandina, C.; Tumminello, F. M. Biol. Chem. 2010, 391, 655-664
15. Rosenthal, P. J. In Cysteine Proteases of Pathogenic Organisms; Robinson, M. W.; Dalton, J. P., Eds.; Advances in Experimental Medicine and Biology; Springer US, 2011; pp 30-48.
16. Funkelstein, L.; Toneff, T.; Hwang, S.-R.; Reinkeckel, T.; Peters, C.; Hook, V. J. Neurochem. 2008, 106, 384-391
17. Minokadeh, A.; Funkelstein, L.; Toneff, T.; Hwang, S.-R.; Beinfeld, M.; Reinkeckel, T.; Peters, C.; Zadina, J.; Hook, V. Mol. Cell. Neurosci. 2010, 43, 98-107
18. Gallinamide A is also known as symplostatin 4 in the literature; see: Taori, M.; Liu, Y.; Paul, V.; Luesch, H. ChemBioChem 2009, 10, 1634-1639
19. Linington, R. G.; Clark, B. R.; Trimble, E. E.; Almanza, A.; Ureña, L.-D.; Kyle, D. E.; Gerwick, W. H. J. Nat. Prod. 2009, 72, 14-17
20. Conroy, T.; Guo, J. T.; Linington, R. G.; Hunt, N. H.; Payne, R. J. Chem. Weinh. Bergstr. Ger. 2011, 17, 13544-13552
21. Yasothornsrikul, S.; Greenbaum, D.; Medzihradszky, K. F.; Toneff, T.; Bundey, R.; Miller, R.; Schilling, B.; Petermann, I.; Dehnert, J.; Logvinova, A.; Goldsmith, P.; Neveu, J. M.; Lane, W. S.; Gibson, B.; Reinheckel, T.; Peters, C.; Bogyo, M.; Hook, V. Proc. Natl. Acad. Sci. 2003, 100, 9590-9595
22. Copeland, R. A. Methods Biochem. Anal. 2005, 46, 1-265
23. Stolze, S. C.; Deu, E.; Kaschani, F.; Li, N.; Florea, B. I.; Richau, K. H.; Colby, T.; van der Hoorn, R. A. L.; Overkleeft, H. S.; Bogyo, M.; Kaiser, M. Chem. Biol. 2012, 19, 1546-1555
24. Tian, W. X.; Tsou, C. L. Biochemistry (Moscow) 1982, 21, 1028-1032
25. Leytus, S. P.; Toledo, D. L.; Mangel, W. F. Biochim. Biophys. Acta, Protein Struct. Mol. Enzym. 1984, 788, 74-86
26. Warren, G. L.; Andrews, C. W.; Capelli, A.-M.; Clarke, B.; LaLonde, J.; Lambert, M. H.; Lindvall, M.; Nevins, N.; Semus, S. F.; Senger, S.; Tedesco, G.; Wall, I. D.; Woolven, J. M.; Peishoff, C. E.; Head, M. S. J. Med. Chem. 2006, 49, 5912-5931
27. Hardegger, L. A.; Kuhn, B.; Spinnler, B.; Anselm, L.; Ecabert, R.; Stihle, M.; Gsell, B.; Thoma, R.; Diez, J.; Benz, J.; Plancher, J.-M.; Hartmann, G.; Banner, D. W.; Haap, W.; Diederich, F. Angew. Chem., Int. Ed. 2011, 50, 314-318
28. Hook, V.; Funkelstein, L.; Lu, D.; Bark, S.; Wegrzyn, J.; Hwang, S.-R. Annu. Rev. Pharmacol. Toxicol. 2008, 48, 393-423
29. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. Nucleic Acids Res. 2000, 28, 235-242
30. Bas, D. C.; Rogers, D. M.; Jensen, J. H. Proteins 2008, 73, 765-783
31. Li, H.; Robertson, A. D.; Jensen, J. H. Proteins 2005, 61, 704-721
32. Søndergaard, C. R.; Olsson, M. H. M.; Rostkowski, M.; Jensen, J. H. J. Chem. Theory Comput. 2011, 7, 2284-2295
33. Olsson, M. H. M.; Søndergaard, C. R.; Rostkowski, M.; Jensen, J. H. J. Chem. Theory Comput. 2011, 7, 525-537
34. Dolinsky, T. J.; Nielsen, J. E.; McCammon, J. A.; Baker, N. A. Nucleic Acids Res. 2004, 32, W665-667
35. Sherman, W.; Day, T.; Jacobson, M. P.; Friesner, R. A.; Farid, R. J. Med. Chem. 2006, 49, 534-553
36. Horn, H. W.; Swope, W. C.; Pitera, J. W.; Madura, J. D.; Dick, T. J.; Hura, G. L.; Head-Gordon, T. J. Chem. Phys. 2004, 120, 9665-9678
37. Sinko, W.; de Oliveira, C.; Williams, S.; Van Wynsberghe, A.; Durrant, J. D.; Cao, R.; Oldfield, E.; McCammon, J. A. Chem. Biol. Drug Des. 2011, 77, 412-420
38. Lippert, R. A.; Bowers, K. J.; Dror, R. O.; Eastwood, M. P.; Gregersen, B. A.; Klepeis, J. L.; Kolossvary, I.; Shaw, D. E. J. Chem. Phys. 2007, 126, 046101
39. Darden, T.; York, D.; Pedersen, L. J. Chem. Phys. 1993, 98, 10089-10092
40. Case, D. A.; Darden, T. A.; Cheatham, T. E.; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Walker, R. C; Zhang, W.; Merz, K. M.; Roberts, B.; Hayik, S.; Roitberg, A.; Seabra, G.; Swails, J.; Goetz, A. W.; Kolossváry, I.; Wong, K. F.; Paesani, F.; Vanicek, J.; Wolf, R. M.; Liu, J.; Wu, X.; Brozell, S. R.; Steinbrecher, T.; Gohlke, H.; Cai, Q.; Ye, X.; Wang, J.; Hsieh, M. J.; Cui, G.; Roe, D. R.; Mathews, D. H.; Seetin, M. G.; Salomon-Ferrer, R.; Sagui, C.; Babin, V.; Luchko, T.; Gusarov, S.; Kovalenko, A.; Kollman, P. A. AMBER 12; University of California: San Francisco, 2012.
41. Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graph. 1996, 14 (33-38) 27-28