Irreversible inhibition of CD13/aminopeptidase N by the antiangiogenic agent curcumin

Chemistry and Biology

Volumn 10, Issue 8, 2003, Pages 695-704

  Shim, Joong Sup ^a   Kim, Jin Hee ^a   Cho, Hyun Young ^b   Yum, Young Na ^b   Kim, Seung Hee ^b   Park, Hyun Ju ^c   Shim, Bum Sang ^d   Choi, Seung Hoon ^d   Kwon, Ho Jeong ^a  

^a Sejong University   (South Korea)

^b Korea Food and Drug Administration   (South Korea)

^c Sungkyunkwan University   (South Korea)

^d Kyung Hee University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041914004     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(03)00169-8     Document Type: Article

References (40)

1. Look A.T., Ashmun R.A., Shapiro L.H., Peiper S.C. Human myeloid plasma membrane glycoprotein CD13 (gp150) is identical to aminopeptidase N. J. Clin. Invest. 83:1989;1299-1307.
2. Matsas R., Stephenson S.L., Hryszko J., Kenny A.J., Turner A.J. The metabolism of neuropeptides. Biochem. J. 231:1985;445-449.
3. Fujii H., Nakajima M., Saiki I., Yoneda J., Azuma I., Tsuruo T. Human melanoma invasion and metastasis enhancement by high expression of aminopeptidase N/CD13. Clin. Exp. Metastasis. 13:1995;337-344.
4. Saiki I., Fujii H., Yoneda J., Abe F., Nakajima M., Tsuruo T., Azuma I. Role of aminopeptidase N (CD13) in tumor-cell invasion and extracellular matrix degradation. Int. J. Cancer. 54:1993;137-143.
5. Menrad A., Speicher D., Wacker J., Herlyn M. Biochemical and functional characterization of aminopeptidase N expressed by human melanoma cells. Cancer Res. 53:1993;1450-1455.
6. Pasqualini R., Koivunen E., Kain R., Lahdenranta J., Sakamoto M., Stryhn A., Ashmun R.A., Shapiro L.H., Arap W., Ruoslahti E. Aminopeptidase N is a receptor for tumor-homing peptides and a target for inhibiting angiogenesis. Cancer Res. 60:2000;722-727.
7. Bhagwat S.V., Lahdenranta J., Giordano R., Arap W., Pasqualini R., Shapiro L.H. CD13/APN is activated by angiogenic signals and is essential for capillary tube formation. Blood. 97:2001;652-659.
8. Kwon H.J., Shim J.S., Kim J.H., Cho H.Y., Yum Y.N., Kim S.H., Yu J. Betulinic acid inhibits growth factor-induced in vitro angiogenesis via the modulation of mitochondrial function in endothelial cells. Jpn. J. Cancer Res. 93:2002;417-425.
9. Hashida H., Takabayashi A., Kanai M., Adachi M., Kondo K., Kohno N., Yamaoka Y., Miyake M. Aminopeptidase N is involved in cell motility and angiogenesis. its clinical significance in human colon cancer Gastroenterology. 122:2002;376-386.
10. Huang M.T., Lou Y.R., Ma W., Newmark H.L., Reuhl K.R., Conney A.H. Inhibitory effects of dietary curcumin on forestomach, duodenal, and colon carcinogenesis in mice. Cancer Res. 54:1994;5841-5847.
11. Conney A.H., Lysz T., Ferraro T., Abidi T.F., Manchand P.S., Laskin J.D., Huang M.T. Inhibitory effect of curcumin and some related dietary components on tumor promotion and arachidonic acid metabolism in mouse skin. Adv. Enzyme Regul. 31:1991;385-396.
12. Khar A., Ali A.M., Pardhasaradhi B.V.V., Begum Z., Anjum R. Antitumor activity of curcumin is mediated through the induction of apoptosis in AK-5 tumor cells. FEBS Lett. 445:1999;165-168.
13. Mehta K., Pantazis P., McQueen T., Aggarwal B.B. Antiproliferative effect of curcumin (diferuloylmethane) against human breast tumor cell lines. Anticancer Drugs. 8:1997;470-481.
14. Shim J.S., Lee H.J., Park S.S., Cha B.G., Chang H.R. Curcumin-induced apoptosis of A-431 cells involves caspase-3 activation. J. Biochem. Mol. Biol. 34:2001;189-193.
15. Huang T.S., Lee S.C., Lin J.K. Suppression of c-jun/AP-1 activation by an inhibitor of tumor promotion in mouse fibroblast cells. Proc. Natl. Acad. Sci. USA. 88:1991;5292-5296.
16. Singh S., Aggarwal B.B. Activation of transcription factor NF-kappa B is suppressed by curcumin. J. Biol. Chem. 270:1995;24995-25000.
17. Liu J.Y., Lin S.J., Lin J.K. Inhibitory effects of curcumin on protein kinase C activity induced by 12-O-tetradecanoylphorbol-13-acetate in NIH3T3 cells. Carcinogenesis. 14:1993;857-861.
18. Thaloor D., Singh A.K., Sidhu G.S., Prasad P.V., Kleinman H.K., Maheshwari R.K. Inhibition of angiogenic differentiation of human umbilical vein endothelial cells by curcumin. Cell Growth Differ. 9:1998;305-312.
19. Mohan R., Sivak J., Ashton P., Russo L.A., Pham B.Q., Kasahara N., Raizman M.B., Fini M.E. Curcuminoids inhibit the angiogenic response stimulated by fibroblast growth factor-2, including expression of matrix metalloproteinase gelatinase B. J. Biol. Chem. 275:2000;10405-10412.
20. Arbiser J.L., Klauber N., Rohan R., van Leeuwen R., Huang M.T., Fisher C., Flynn E., Byers H.R. Curcumin is an in vivo inhibitor of angiogenesis. Mol. Med. 4:1998;376-383.
21. Ashmun R.A., Look A.T. Metalloprotease activity of CD13/aminopeptidase N on the surface of human myeloid cells. Blood. 75:1990;462-469.
22. Kijima M., Yoshida M., Sugita K., Horinouchi S., Beppu T. Trapoxin, an antitumor cyclic tetrapeptide, is an irreversible inhibitor of mammalian histone deacetylase. J. Biol. Chem. 268:1993;22429-22435.
23. Bradstock K.F., Favaloro E.J., Kabral A., Kerr A., Hughes W.G., Musgrove E. Myeloid progenitor surface antigen identified by monoclonal antibody. Br. J. Haematol. 61:1985;11-20.
24. Yoneda J., Saiki I., Fujii H., Abe F., Kojima Y., Azuma I. Inhibition of tumor invasion and extracellular matrix degradation by ubenimex (bestatin). Clin. Exp. Metastasis. 10:1992;49-59.
25. Kagechika H., Komoda M., Fujimoto Y., Koiso Y., Takayama H., Kadoya S., Miyata K., Kato F., Kato M., Hashimoto Y. Potent homophthalimide-type inhibitors of B16F10/L5 mouse melanoma cell invasion. Biol. Pharm. Bull. 22:1999;1010-1012.
26. Benbow U., Schoenermark M.P., Orndorff K.A., Givan A.L., Brinckerhoff C.E. Human breast cancer cells activate procollagenase-1 and invade type I collagen. invasion is inhibited by all-trans retinoic acid Clin. Exp. Metastasis. 17:1999;231-238.
27. Kelloff G.J., Crowell J.A., Hawk E.T., Steele V.E., Lubet R.A., Boone C.W., Covey J.M., Doody L.A., Omenn G.S., Greenwald P.et al. Strategy and planning for chemopreventive drug development. clinical development plans II J. Cell. Biochem. 26(suppl.):1996;54-71.
28. Sharma R.A., McLelland H.R., Hill K.A., Ireson C.R., Euden S.A., Manson M.M., Pirmohamed M., Marnett L.J., Gescher A.J., Steward W.P. Pharmacodynamic and pharmacokinetic study of oral Curcuma extract in patients with colorectal cancer. Clin. Cancer Res. 7:2001;1894-1900.
29. Cheng A.L., Hsu C.H., Lin J.K., Hsu M.M., Ho Y.F., Shen T.S., Ko J.Y., Lin J.T., Lin B.R., Ming-Shiang W.et al. Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res. 21:2001;2895-2900.
30. Aggarwal B.B., Kumar A., Bharti A.C. Anticancer potential of curcumin. preclinical and clinical studies Anticancer Res. 23:2003;363-398.
31. Folkman J. What is the evidence that tumors are angiogenesis dependent? J. Natl. Cancer Inst. 82:1989;4-6.
32. van Iersel M.L.P.S., Ploemen J.H.T.M., Bello M.L., Federici G., van Bladeren P.J. Interaction of α, β-unsaturated aldehydes and ketones with human glutathione S-transferase P1-1. Chem. Biol. Interact. 108:1997;67-78.
33. 350 as a critical residue involved in the N-terminal amine binding site of aminopeptidase N (EC 3.4.11.2). insights into its mechanism of action Biochemistry. 37:1998;686-692.
34. Burley S.K., David P.R., Sweet R.M., Taylor A., Lipscomb W.N. Structure determination and refinement of bovine lens leucine aminopeptidase and its complex with bestatin. J. Mol. Biol. 224:1992;113-140.
35. 2+. J. Biol. Chem. 276:2001;46905-46911.
36. Kim J.H., Shim J.S., Lee S.K., Kim K.W., Rah S.Y., Chung H.C., Kwon H.J. Microarray-based analysis of anti-angiogenic activity of demethoxycurcumin on human umbilical vein endothelial cells. crucial involvement of the down-regulation of matrix metalloproteinase Jpn. J. Cancer Res. 93:2002;1378-1385.
37. Zhang F., Altorki N.K., Mestre J.R., Subbaramaiah K., Dannenberg A.J. Curcumin inhibits cyclooxygenase-2 transcription in bile acid- and phorbol ester-treated human gastrointestinal epithelial cells. Carcinogenesis. 20:1999;445-451.
38. Shim J.S., Kim D.H., Jung H.J., Kim J.H., Lim D.Y., Lee S.K., Kim K.W., Ahn J.W., Yoo J.S., Rho J.R.et al. Hydrazinocurcumin, a novel synthetic curcumin derivative, is a potent inhibitor of endothelial cell proliferation. Bioorg. Med. Chem. 10:2002;2439-2444.
39. Kwon H.J., Kim M.S., Kim M.J., Nakajima H., Kim K.W. Histone deacetylase inhibitor FK228 inhibits tumor angiogenesis. Int. J. Cancer. 97:2002;290-296.
40. Jeong J.W., Sohn T.K., Yu D.Y., Kim K.W. Membrane-type matrix metalloproteinase-1 induced invasive and angiogenic activities in chick chorioallantoic membrane (CAM) model. J. Korean Cancer Assoc. 33:2001;49-55.