C2-Symmetric azobenzene-amino acid conjugates and their inhibition of Subtilisin Kexin Isozyme-1

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 13, 2010, Pages 3977-3981

  Basak, Amit ^a   Mitra, Debarati ^a   Das, Amit K ^a   Mohottalage, Dayani ^b   Basak, Ajoy ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

^b OTTAWA HOSPITAL RESEARCH INSTITUTE   (Canada)

Author keywords

Amino acid; Azobenzene; C2 Symmetric; Hybrid; Inhibitor; Peptide; SKI 1

Indexed keywords

AMINO ACID DERIVATIVE; AZOBENZENE DERIVATIVE; ISOENZYME; KEXIN; PROTEINASE; SUBTILISIN;

ARTICLE; CHOLESTEROL SYNTHESIS; COMPETITIVE INHIBITION; CONJUGATE; DRUG HALF LIFE; DRUG SYNTHESIS; HYBRID; IN VITRO STUDY; IRRADIATION; ISOMERISM; ISOMERIZATION; LIPID METABOLISM; MAMMAL; OSSIFICATION; PROTEIN FUNCTION; ULTRAVIOLET RADIATION; VIRUS INFECTION;

AMINO ACIDS; ANIMALS; AZO COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; PROPROTEIN CONVERTASES; SERINE ENDOPEPTIDASES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

MAMMALIA;

EID: 77954315502     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.04.101     Document Type: Article

References (22)

1. F.M. Richards, and H.W. Wyckoff The Enzymes 3rd ed. 1971 Academic press New York p 647
2. R.T. Raines Chem. Rev. 98 1998 1045
3. J.W. Fett, D.J. Strydom, R.R. Lobb, E.M. Alderman, J.L. Bethune, J.F. Riordan, and B.L. Vallee Biochemistry 20 1985 5480
4. S. Sorrentino, D.G. Glitz, K.J. Hamann, D.A. Loegering, J.L. Checkel, and G.J. Gleich J. Biol. Chem. 267 1992 14859
5. J. Matousek Comp. Biochem. Phys. C 129 2001 175
6. N.G. Seidah, S. Benjannet, J. Hamelin, A.M. Mamarbachi, A. Basak, J. Marcinkiewicz, M. Mbikay, M. Chrétien, and M. Marcinkiewicz Ann. N.Y. Acad. Sci. 885 1999 57
7. N.G. Seidah, G. Mayer, A. Zaid, E. Rousselet, N. Nassoury, S. Poirier, R. Essalmani, and A. Prat Int. J. Biochem. Cell Biol. 40 2008 1111
8. N.G. Seidah, S.J. Mowla, J. Hamelin, A.M. Mamarbachi, S. Benjannet, B.B. Touré, A. Basak, J.S. Munzer, J. Marcinkiewicz, M. Zhong, J.C. Barale, C. Lazure, R.A. Murphy, M. Chrétien, and M. Marcinkiewicz Proc. Natl. Acad. Sci. U.S.A. 96 1999 1321
9. D. Cheng, P.J. Espenshade, C.A. Slaughter, J.C. Jaen, M.S. Brown, and J.L. Goldstein J. Biol. Chem. 274 1999 22805
10. N.G. Seidah, S. Benjannet, L. Wickham, J. Marcinkiewicz, S.B. Jasmin, S. Stifani, A. Basak, A. Prat, and M. Chretien Proc. Natl. Acad. Sci. U.S.A. 100 2003 928
11. M. Nagahama, T. Taniguchi, E. Hashimoto, A. Imamaki, K. Mori, A. Tsuji, and Y. Matsuda FEBS Lett. 434 1998 155
12. D. Mohottalage, N. Goto, and A. Basak Adv. Exp. Med. Biol. 611 2009 83
13. D. Fan, P.G. Yancey, S. Qiu, L. Ding, E.J. Weeber, M.F. Linton, and S. Fazio Biochemistry 47 2008 1631
14. Y. Bontemps, N. Scamuffa, F. Calvo, and A.M. Khatib Med. Res. Rev. 27 2007 631
15. M. Chrétien, N.G. Seidah, A. Basak, and M. Mbikay Expert Opin. Ther. Targets 12 2008 1289
16. A. Basak, D. Mohottalage, and A. Basak Protein Pept. Lett. 13 2006 863
17. A. Basak, D. Mitra, M. Kar, and K. Biradha Chem. Commun. 2008 3067
18. M. Kar, and A. Basak Chem. Rev. 107 2007 2861
19. I.E. Dreostic, M.J. Wargovich, and C.S. Yang Crit. Rev. Food Sci. 37 1997 761
20. Initially we decided to go with the E-forms only for comparison purpose but other isoform (Z-form) will also be tested in future study.
21. A. Pasquato, P. Pullikotil, M.C. Asselin, M. Vacatello, L. Paolillo, F. Ghezzo, F. Basso, C. Di Bello, M. Dettin, and N.G. Seidah J. Biol. Chem. 281 2006 23471
22. 10 919.3666. Found 919.3670.