Inhibition of cathepsin D by tripeptides containing statine analogs

Biochemical Pharmacology

Volumn 58, Issue 2, 1999, Pages 329-333

  Bessodes, Michel ^a   Antonakis, Kostas ^a   Herscovici, Jean ^a   Garcia, Marcel ^b   Rochefort, Henri ^b   Capony, Françoise ^c   Lelièvre, Yves ^d   Scherman, Daniel ^d  

^a CNRS   (France)

^b INSERM   (France)

^c HÔPITAL ARNAUD DE VILLENEUVE   (France)

^d SANOFI   (France)

Author keywords

Cathepsin D; Cell proliferation; Inhibitor; Protease; Statine; Tripeptide

Indexed keywords

CATHEPSIN D; PEPSTATIN DERIVATIVE; PROTEINASE;

ANIMAL CELL; ARTICLE; CANCER; CELL PROLIFERATION; DRUG ACTIVITY; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL;

AMINO ACIDS; CATHEPSIN D; HIV PROTEASE INHIBITORS; HUMANS; OLIGOPEPTIDES; PEPSTATINS; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0033566269     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(99)00103-3     Document Type: Article

References (23)

1. Alexander D.S., Aimes R.T., Quigley J.P. What structure and function of avian plasminogen activator and matrix metalloproteinase-2 reveal about their counterpart mammalian enzymes, their regulation and their role in tumor invasion. Enzyme Protein. 49:1996;38-58.
2. Wilson C.L., Matrisian L.M. Matrilysin An epithelial matrix metalloproteinase with potentially novel functions . Int J Biochem Cell Biol. 28:1996;123-136.
3. Stetler-Stevenson W.G., Hewitt R., Corcoran M. Matrix metalloproteinases and tumor invasion From correlation and causality to the clinic . Semin Cancer Biol. 7:1996;147-154.
4. Schwartz G.K. Invasion and metastases in gastric cancer In vitro and in vivo models with clinical correlations . Semin Oncol. 23:1996;316-324.
5. Rochefort H. Cathepsin D in breast cancer A tissue marker associated with metastasis . Eur J Cancer. 28A:1992;1780-1783.
6. Ferrandina G., Scambia G., Bardelli F., et al. Relationship between cathepsin D content and disease-free survival in node-negative breast cancer patients: A meta-analysis . Br J Cancer. 76:1997;661-666.
7. Foekens J.A., Look M.P., Bolt-de Vries J. Cathepsin D in primary breast cancer Prognostic evaluation involving 2810 patients . Br J Cancer. 79:1999;300-307.
8. Liaudet E., Garcia M., Rochefort H. Cathepsin D maturation and its stimulatory effect on metastasis are prevented by addition of KDEL retention signal. Oncogene. 9:1994;1145-1154.
9. Liaudet E., Derocq D., Rochefort H., Garcia M. Transfected cathepsin D stimulates high density cancer cell growth by inactivating secreted growth inhibitors. Cell Growth Differ. 6:1995;1045-1052.
10. Vignon F., Capony F., Chambon M., Freiss G., Garcia M., Rochefort H. Autocrine growth stimulation of the MCF7 breast cancer cells by the estrogen-regulated 52KD protein. Endocrinology. 118:1986;1537-1545.
11. Fusek M., Vetvicka V. Mitogenic function of the human procathepsin D The role of the propeptide . Biochem J. 303:1994;775-780.
12. Laurent-Matha V., Farnoud M.R., Lucas C., Garcia M., Rochefort H. Endocytosis of procathepsin D in breast cancer cells is mostly independent of mannose-6-phosphate receptors. J Cell Sci. 111:1998;2539-2549.
13. Umezawa H., Aoyagi T., Morishima H., Matsuzaki M., Hamada H., Takeuchi T. Pepstatin, a new pepsin inhibitor produced by Actinomycetes. J Antibiot. 23:1970;259-262.
14. Kunimoto S., Aoyagi T., Nishizawa R., Komai T., Takeuchi T., Umezawa H. Mechanism of inhibition of pepsin by pepstatin. J Antibiot. 27:1974;413-418.
15. Subramanian E., Swan I.D.A., Davies D.R. The crystal at 5.5A resolution of an acid-protease from Rhizopus chinensis. Biochem Biophys Res Commun. 68:1976;875.
16. Saïah M., Bessodes M., Antonakis K. An enantiospecific and versatile synthesis of statine. Tetrahedron Asymm. 2:1991;111-112.
17. Bessodes M., Saïah M., Antonakis K. A new, versatile and stereospecific route to unusual amino acids The enantiospecific total synthesis of statine amide and its three stereoisomers . J Org Chem. 57:1992;4441-4444.
18. Katsuki T., Sharpless K.B. The first practical method for asymmetric epoxidation. J Am Chem Soc. 102:1980;5974-5976.
19. Martin V.S., Woodard S.S., Katsuki T., Yamada Y., Ikeda M., Sharpless K.B. Kinetic resolution of racemic allylic alcohols by enantioselective epoxidation. A route to substances of absolute enantiomeric purity. J Am Chem Soc. 103:1981;6237-6240.
20. Rich D.H., Sun E.T., Singh J. Synthesis of dideoxy-pepstatin. Mechanism of inhibition of porcine pepsin. Biochem Biophys Res Commun. 74:1977;762-767.
21. Loibner H., Zbiral E. Reaktionen mit phosphororganischen verbindungen. XLI[1]. Neuartige synthetische aspekte des systems triphenylphosphin-azodicarbon-saüreester hydroxyverbindung. Helv Chim Acta. 59:1976;2100.
22. Liu W.S., Smith S.C., Glover G.I. Synthesis of all the stereoisomers of statine (4-amino-3-hydroxy-6-methylheptanoic acid). Inhibition of pepsin activity by N-carbobenzoxy-L-valyl-L-valyl-statine derived from the four stereoisomers. J Med Chem. 22:1979;577.
23. Capony F., Morisset M., Barrett A.J., Capony J.P., Broquet P., Vignon F., Chambon M., Louisot P., Rochefort H. Phosphorylation, glycosylation, and proteolytic activity of the 52-kD estrogen-induced protein secreted by MCF7 cells. J Cell Biol. 104:1987;253-262.