Isolation, structure, and functional elucidation of a modified pentapeptide, cysteine protease inhibitor (CPI-2081) from streptomyces species 2081 that exhibit inhibitory effect on cancer cell migration

Journal of Medicinal Chemistry

Volumn 53, Issue 14, 2010, Pages 5121-5128

  Singh, Jay Prakash ^a   Tamang, Sudarsan ^a   Rajamohanan, P R ^a   Jima, N C ^a   Chakraborty, Goutam ^b   Kundu, Gopal C ^b   Gaikwad, Sushma M ^a   Khan, Mohamad I ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b NATIONAL CENTRE FOR CELL SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CPI 2081; CYSTEINE PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CELL MIGRATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STREPTOMYCES;

ANTIBIOTICS, ANTINEOPLASTIC; CELL LINE, TUMOR; CELL MOVEMENT; CELL SURVIVAL; CYSTEINE PROTEINASE INHIBITORS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOPEPTIDES; PAPAIN; PROTEIN BINDING; STREPTOMYCES; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 77954737697     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm9014179     Document Type: Article

References (35)

1. Lah, T. T.; Kos, J. Cysteine proteinases in cancer progression and their clinical relevance for prognosis Biol. Chem. 1998, 379, 125-130
2. Premzl, A.; Puizdar, V.; Zavasnik-Bergant, V.; Kopitar-Jerala, N.; Lah, T. T.; Katunuma, N.; Sloane, B. F.; Turk, V.; Kos, J. Invasion of ras-transformed breast epithelial cells depends on the proteolytic activity of cysteine and aspartic proteinases Biol. Chem. 2001, 382, 853-857
3. Sameni, M.; Moin, K.; Sloane, B. F. Imaging proteolysis by living human breast cancer cells Neoplasia 2000, 2, 496-504
4. Wang, B.; Sun, J.; Kitamoto, S.; Yang, M.; Grubb, A.; Chapman, H. A.; Kalluri, R.; Shi, G. P. Cathepsin S controls angiogenesis and tumor growth via matrix-derived angiogenic factors J. Biol. Chem. 2006, 281, 6020-6929
5. Heidtmann, H. H.; Salge, U.; Abrahamson, M.; Bencina, M.; Kastelic, L.; Kopitar-Jerala, N.; Turk, V.; Lah, T. T. Cathepsin B and cysteine proteinase inhibitors in human lung cancer cell lines Clin. Exp. Metastasis 1997, 15, 368-381
6. Sloane, B. F.; Moin, K.; Krepela, E.; Rozhin, J. Cathepsin B and its endogenous inhibitors: the role in tumor malignancy Cancer Metastasis Rev. 1990, 9, 333-352
7. Desai, S. N.; White, D. M.; O'Shea, K, M.; Brown, M. L.; Cywin, C. L.; Spero, D. M.; Panzenbeck, M. J. An orally active reversible inhibitor of cathepsin S inhibits human trans vivo delayed-type hypersensitivity Eur. J. Pharmacol. 2006, 538, 168-174
8. Wang, D.; Li, W.; Pechar, M.; Kopeckova, P.; Bromme, D.; Kopecek, J. Cathepsin K inhibitor-polymer conjugates: potential drugs for the treatment of osteoporosis and rheumatoid arthritis Int. J. Pharm. 2004, 277, 73-79
9. Weidauer, E.; Yasuda, Y.; Biswal, B. K.; Cherny, M.; James, M. N.; Bromme, D. Effects of disease-modifying anti-rheumatic drugs (DMARDs) on the activities of rheumatoid arthritis-associated cathepsins K and S Biol. Chem. 2007, 388, 331-336
10. Costales, J.; Rowland, E. C. A role for protease activity and host-cell permeability during the process of Trypanosoma cruzi egress from infected cells J. Parasitol. 2007, 93, 1350-1359
11. Hernandez, A. A.; Roush, W. R. Recent advances in the synthesis, design and selection of cysteine protease inhibitors Curr. Opin. Chem. Biol. 2002, 6, 459-465
12. Pandey, K. C.; Singh, N.; Arastu-Kapur, S.; Bogyo, M.; Rosenthal, P. J. Falstatin, a cysteine protease inhibitor of Plasmodium falciparum, facilitates erythrocyte invasion PLoS Pathog. 2006, 2, 1031-1041
13. Sajid, M.; McKerrow, J. H. Cysteine proteases of parasitic organisms Mol. Biochem. Parasitol. 2002, 120, 1-21
14. Shenai, B. R.; Sijwali, P. S.; Singh, A.; Rosenthal, P. J. Characterization of native and recombinant falcipain-2, a principal trophozoite cysteine protease and essential hemoglobinase of Plasmodium falciparum J. Biol. Chem. 2000, 275, 29000-29010
15. Sijwali, P. S.; Shenai, B. R.; Gut, J.; Singh, A.; Rosenthal, P. J. Expression and characterization of the Plasmodium falciparum haemoglobinase falcipain-3 Biochem. J. 2001, 360, 481-489
16. Sakano, Y.; Shibuya, M.; Matsumoto, A.; Takahashi, Y.; Tomoda, H.; Omura, S.; Ebizuka, Y. Lanopylins A1, B1, A2, and B2, novel lanosterol synthase inhibitors from Streptomyces sp. K99-5041 J. Antibiot. (Tokyo) 2003, 56, 817-826
17. Tani, M.; Gyobu, Y.; Sasaki, T.; Takenouchi, O.; Kawamura, T.; Kamimura, T.; Harada, T. SF2809 compounds, novel chymase inhibitors from Dactylosporangium sp. 1. Taxonomy, fermentation, isolation and biological properties J. Antibiot. (Tokyo) 2004, 57, 83-88
18. Tani, M.; Harimaya, K.; Gyobu, Y.; Sasaki, T.; Takenouchi, O.; Kawamura, T.; Kamimura, T.; Harada, T. SF2809 compounds, novel chymase inhibitors from Dactylosporangium sp. 2. Structural elucidation J. Antibiot. (Tokyo) 2004, 57, 89-96
19. Singh, M. P.; Petersen, P. J.; Weiss, W. J.; Janso, J. E.; Luckman, S. W.; Lenoy, E. B.; Bradford, P. A.; Testa, R. T.; Greenstein, M. Mannopeptimycins, new cyclic glycopeptide antibiotics produced by Streptomyces hygroscopicus LL-AC98: antibacterial and mechanistic activities Antimicrob. Agents Chemother. 2003, 47, 62-69
20. Aoyagi, T.; Takeuchi, T.; Matsuzaki, A.; Kawamura, K.; Kondo, S. Leupeptins, new protease inhibitors from Actinomycetes J. Antibiot. (Tokyo) 1969, 22, 283-286
21. Suda, H.; Aoyagi, T.; Hamada, M.; Takeuchi, T.; Umezawa, H. Antipain, a new protease inhibitor isolated from actinomycetes J. Antibiot. (Tokyo) 1972, 25, 263-266
22. Kadowaki, T.; Kitano, S.; Baba, A.; Takii, R.; Hashimoto, M.; Katunuma, N.; Yamamoto, K. Isolation and characterization of a novel and potent inhibitor of Arg-gingipain from Streptomyces sp. strain FA-70 Biol. Chem. 2003, 384, 911-920
23. Nakamura, H.; Takahashi, Y.; Naganawa, H.; Nakae, K.; Imoto, M.; Shiro, M.; Matsumura, K.; Watanabe, H.; Kitahara, T. Absolute configuration of migrastatin, a novel 14-membered ring macrolide J. Antibiot. (Tokyo) 2002, 55, 442-444
24. Hanada, K.; T., M.; Yamagishi, M. Isolation and charrecterization of E64, a new cysteine protease inhibitor Agric. Biol. Chem. 1978, 42, 523-528
25. Hymes, A. J.; Robinson, D. A.; Canady, W. J. Thermodynamics Of The Solution Process. II. The Use Of An Extraction Model For Enzyme-Inhibitor Complex Formation J. Biol. Chem. 1965, 240, 134-138
26. Gordon, S. R.; DeMoss, J. Exposure to lysosomotropic amines and protease inhibitors retard corneal endothelial cell migration along the natural basement membrane during wound repair Exp. Cell Res. 1999, 246, 233-242
27. Liang, C.-C.; P., A. Y.; Guan., J.-L. In vitro scratch assay: a convenient and inexpensive method for analysis of cell migration in vitro Nature Protoc. 2007, 2, 329-333
28. Li, W.; Henry, G.; Fan, J.; Bandyopadhyay, B.; Pang, K.; Garner, W.; Chen, M.; Woodley, D. T. Signals that initiate, augment, and provide directionality for human keratinocyte motility J. Invest. Dermatol. 2004, 123, 622-633
29. Chevallier, C.; Richardson, A. D.; Edler, M. C.; Hamel, E.; Harper, M. K.; Ireland, C. M. A new cytotoxic and tubulin-interactive milnamide derivative from a marine sponge Cymbastela sp Org. Lett. 2003, 5, 3737-3739
30. Geonseek Ryu, S. M.; Nobuhiro, F. Discodermin E, a cytotoxic and antimicrobial tetradecapeptide, from the marine sponge Discodermia kiiensis Tetrahedron Lett. 1994, 35, 8251-8254
31. Hamel, E. Interactions of antimitotic peptides and depsipeptides with tubulin Biopolymers 2002, 66, 142-160
32. Matsunaga, S.; F., N.; Konosu, S. Bioactive marine metabolites VII. Structures of discodermins B, C, and D, antimicrobial peptides from the marine sponge Discodermia kiiensis Tetrahedron Lett. 1985, 26, 855-856
33. Mujumdar, R. B.; R., A. V. R.; Rathi, S. S.; Venkataraman, K. Swietenone, the first natural-butyl ketone, from Chloroxylon swietenia Tetrahedron Lett. 1975, 16, 867-868
34. Cavallini, D.; Graziani, M. T.; Dupre, S. Determination of disulphide groups in proteins Nature 1966, 212, 294-298
35. Spande, T. F.; Witkop, B. Determination of the tryptophan content of proteins with N -bromosuccinimide Methods Enzymol. 1967, 11, 498-505