Tumor Suppression by a Rationally Designed Reversible Inhibitor of Methionine Aminopeptidase-2

Cancer Research

Volumn 63, Issue 22, 2003, Pages 7861-7869

  Wang, Jieyi ^a   Sheppard, George S ^a   Lou, Pingping ^a   Kawai, Megumi ^a   BaMaung, Nwe ^a   Erickson, Scott A ^a   Tucker Garcia, Lora ^a   Park, Chang ^a   Bouska, Jennifer ^a   Wang, Yi Chun ^a   Frost, David ^a   Tapang, Paul ^a   Albert, Daniel H ^a   Morgan, Sherry J ^a   Morowitz, Michael ^b   Shusterman, Suzanne ^b   Maris, John M ^b   Lesniewski, Rick ^a   Henkin, Jack ^a  

^a ABBOTT LABORATORIES   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

A 357300; ANTINEOPLASTIC AGENT; BESTATIN; ENZYME INHIBITOR; FUMAGILLOL CHLOROACETYLCARBAMATE; METHIONYL AMINOPEPTIDASE;

ANGIOGENESIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CARCINOMA; CELL CYCLE G1 PHASE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG EFFECT; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MITOSIS INHIBITION; MOUSE; NEUROBLASTOMA; NONHUMAN; PRIORITY JOURNAL; SARCOMA; TOXICITY;

AMINOPEPTIDASES; ANIMALS; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL CYCLE; CELL DIVISION; CHLOROBENZENES; CORNEA; CYCLOHEXANES; DRUG DESIGN; ENDOTHELIUM, VASCULAR; FEMALE; FIBROSARCOMA; HUMANS; METALLOENDOPEPTIDASES; MICE; MICE, SCID; MODELS, MOLECULAR; NEOVASCULARIZATION, PHYSIOLOGIC; NEUROBLASTOMA; PROTEASE INHIBITORS; SESQUITERPENES; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 10744229380     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (48)

1. Sin, N., Meng, L., Wang, M. Q., Wen, J. J., Bornmann, W. G., and Crews, C. M. The anti-angiogenic agent fumagillin covalently binds and inhibits the methionine aminopeptidase, MetAP-2. Proc. Natl. Acad. Sci. USA, 94: 6099-6103, 1997.
2. Griffith, E. C., Su, Z., Turk, B. E., Chen, S., Chang, Y. H., Wu, Z., Biemann, K., and Liu, J. O. Methionine aminopeptidase (type 2) is the common target for angiogenesis inhibitors AGM-1470 and ovalicin. Chem. Biol., 4: 461-467, 1997.
3. Liu, S., Widom, J., Kemp, C. W., Crews, C. M., and Clardy, J. Structure of human methionine aminopeptidase-2 complexed with fumagillin. Science (Wash. DC), 282: 1324-1327, 1998.
4. Griffith, E. C., Su, Z., Niwayama, S., Ramsay, C. A., Chang, Y. H., and Liu, J. O. Molecular recognition of angiogenesis inhibitors fumagillin and ovalicin by methionine aminopeptidase 2. Proc. Natl. Acad. Sci. USA, 95: 15183-15188, 1998.
5. Kusaka, M., Sudo, K., Matsutani, E., Kozai, Y., Marui, S., Fujita, T., Ingber, D., and Folkman, J. Cytostatic inhibition of endothelial cell growth by the angiogenesis inhibitor TNP-470 (AGM-1470). Br. J. Cancer, 69: 212-216, 1994.
6. 1 phase of the cell cycle. Cancer Res., 54: 2073-2076, 1994.
7. Wang, J., Lou, P., and Henkin, J. Selective inhibition of endothelial cell proliferation by fumagillin is not due to differential expression of methionine aminopeptidases. J. Cell. Biochem., 77: 465-473, 2000.
8. Yeh, J. R., Mohan, R., and Crews, C. M. The antiangiogenic agent TNP-470 requires p53 and p21CIP/WAF for endothelial cell growth arrest. Proc. Natl. Acad. Sci. USA, 97: 12782-12787, 2000.
9. Turk, B. E., Griffith, E. C., Wolf, S., Biemann, K., Chang, Y. H., and Liu, J. O. Selective inhibition of amino-terminal methionine processing by TNP-470 and ovalicin in endothelial cells. Chem. Biol., 6: 823-833, 1999.
10. Bergers, G., Javaherian, K., Lo, K. M., Folkman, J., and Hanahan, D. Effects of angiogenesis inhibitors on multistage carcinogenesis in mice. Science (Wash. DC), 284: 808-812, 1999.
11. Liekens, S., Verbeken, E., Vandeputte, M., De Clercq, E., and Neyts, J. A. novel animal model for hemangiomas: inhibition of hemangioma development by the angiogenesis inhibitor TNP-470. Cancer Res., 59: 2376-2383, 1999.
12. Ikebe, T., Yamamoto, T., Kubo, S., Hirohashi, K., Kinoshita, H., Kaneda, K., and Sakurai, M. Suppressive effect of the angiogenesis inhibitor TNP-470 on the development of carcinogen-induced hepatic nodules in rats. Jpn. J. Cancer Res., 89: 143-149, 1998.
13. Ingber, D., Fujita, T., Kishimoto, S., Sudo, K., Kanamaru, T., Brem, H., and Folkman, J. Synthetic analogues of fumagillin that inhibit and suppress tumour growth. Nature (Lond.), 348: 555-557, 1990.
14. Castronovo, V., and Belotti, D. TNP-470 (AGM-1470): mechanisms of action and early clinical development. Eur. J. Cancer. 32A: 2520-2527, 1996.
15. Shusterman, S., Grupp, S. A., Barr, R., Carpentieri, D., Zhao, H., and Maris, J. M. The angiogenesis inhibitor TNP-470 effectively inhibits human neuroblastoma xenograft growth, especially in the setting of subclinical disease. Clin. Cancer Res., 7: 977-984, 2001.
16. Yamaoka, M., Yamamoto, T., Masaki, T., Ikeyama, S., Sudo, K., and Fujita, T. Inhibition of tumor growth and metastasis of rodent tumors by the angiogenesis inhibitor O-(chloroacetyl-carbamoyl)fumagillol (TNP-470: AGM-1470). Cancer Res., 53: 4262-4267, 1993.
17. Yoshizawa, J., Mizuno, R., Yoshida, T., Hara, A., Ashizuka, S., Kanai, M., Kuwashima, N., Kurobe, M., and Yamazaki, Y. Inhibitory effect of TNP-470 on hepatic metastasis of mouse neuroblastoma. J. Surg. Res., 93: 82-87, 2000.
18. Morishita, T., Mii, Y., Miyauchi, Y., Miura, S., Honoki, K., Aoki, M., Kido, A., Tamai, S., Tsutsumi, M., and Konishi, Y. Efficacy of the angiogenesis inhibitor O-(chloroacetyl-carbamoyl)fumagillol (AGM-1470) on osteosarcoma growth and lung metastasis in rats. Jpn. J. Clin. Oncol., 25: 25-31, 1995.
19. Konno, H., Tanaka, T., Kanai, T., Maruyama, K., Nakamura, S., and Baba, S. Efficacy of an angiogenesis inhibitor, TNP-470, in xenotransplanted human colorectal cancer with high metastatic potential. Cancer (Phila.), 77 (Suppl.): 1736-1740, 1996.
20. Kudelka, A. P., Verschraegen, C. F., and Loyer, E. Complete remission of metastatic cervical cancer with the angiogenesis inhibitor TNP-470. N. Engl. J. Med., 338: 991-992, 1998.
21. Kudelka, A. P., Levy, T., Verschraegen, C. F., Edwards, C. L., Piamsomboon, S., Termrungruanglert, W., Freedman, R. S., Kaplan, A. L., Kieback, D. G., Meyers, C. A., Jaeckle, K. A., Loyer, E., Steger, M., Mante, R., Mavligit, G., Killian, A., Tang, R. A., Gutterman, J. U., and Kavanagh, J. J. A Phase I study of TNP-470 administered to patients with advanced squamous cell cancer of the cervix. Clin. Cancer Res., 3: 1501-1505, 1997.
22. Offodile, R., Walton, T., Lee, M., Stiles, A., and Nguyen, M. Regression of metastatic breast cancer in a patient treated with the anti-angiogenic drug TNP-470. Tumori, 85: 51-53, 1999.
23. Milkowski, D. M., and Weiss, R. A. Antiangiogenic agents. In: B. A. Teicher (ed.), Cancer Therapy, pp. 385-398. Totowa, NJ: Humana Press Inc., 1998.
24. Bhargava, P., Marshall, J. L., Rizvi, N., Dahut, W., Yoe, J., Figuera, M., Phipps, K., Ong, V. S., Kato, A., and Hawkins, M. J. A Phase I and pharmacokinetic study of TNP-470 administered weekly to patients with advanced cancer. Clin. Cancer Res., 5: 1989-1995, 1999.
25. Arfin, S. M., Kendall, R. L., Hall, L., Weaver, L. H., Stewart, A. E., Matthews, B. W., and Bradshaw, R. A. Eukaryotic methionyl aminopeptidases: two classes of cobalt-dependent enzymes. Proc. Natl. Acad. Sci. USA, 92: 7714-7718, 1995.
26. Bradshaw, R. A., Brickey, W. W., and Walker, K. W. N-terminal processing: the methionine aminopeptidase and N α-acetyl transferase families. Trends Biochem. Sci., 23: 263-267, 1998.
27. Lowther, W. T., and Matthews, B. W. Structure and function of the methionine aminopeptidases. Biochim. Biophys. Acta. 1477: 157-167, 2000.
28. Li, X., and Chang, Y. H. Evidence that the human homologue of a rat initiation factor-2 associated protein (p67) is a methionine aminopeptidase. Biochem. Biophys. Res. Commun., 227: 152-159, 1996.
29. Matsuzawa, T., Hatsugai, M., and Moriguchi, K. Increase of methionine aminopeptidase activity in hyperplastic Leydig cells of rat cryptorchid testis: a histochemical study. J. Vet. Med. Sci., 54: 1157-1163, 1992.
30. Kanno, T., Endo, H., Takeuchi, K., Morishita, Y., Fukayama, M., and Mori, S. High expression of methionine aminopeptidase type 2 in germinal center B cells and their neoplastic counterparts. Lab. Investig., 82: 893-901, 2002.
31. Catalano, A., Romano, M., Robuffo, I., Strizzi, L., and Procopio, A. Methionine aminopeptidase-2 regulates human mesothelioma cell survival: role of Bcl-2 expression and telomerase activity. Am. J. Pathol., 159: 721-731, 2001.
32. Datta, B., and Datta, R. Induction of apoptosis due to lowering the level of eukaryotic initiation factor 2-associated protein, p67, from mammalian cells by antisense approach. Exp. Cell Res., 246: 376-383, 1999.
33. Wang, J., Sheppard, G. S., Lou, L., Kawai, M., Park, C., Egan, D., Schneider, A., Bouska, J. Lesniewski, R., and Henkin, J. Physiologically relevant metal cofactor for methionine aminopeptidase-2 is manganese. Biochemistry, 42: 5035-5042, 2003.
34. Craig, R. A., Kawai, M., Lynch, L. M., Patel, J. R., Sheppard, G. S., Wang, J., Yang, F., and BaMaung, N. Y. Hydrazide and Alkoxyamide Angiogenesis Inhibitors. PCT International Publication Number WO 01/79157. US Patent Application US2002002152, 2002.
35. Lin, Y., Weisdorf, D. J., Solovey, A., and Hebbel, R. P. Origins of circulating endothelial cells and endothelial outgrowth from blood. J. Clin. Investig., 105: 71-77, 2000.
36. Montesano, R., Pepper, M. S., Mohle-Steinlein, U., Risau, W., Wagner, E. T., and Ordi, L. Increased proteolytic activity is responsible for the aberrant morphogenetic behavior of endothelial cells expressing the middle T oncogene. Cell, 62: 435-445, 1990.
37. Nehls, V., and Drenckhahn, D. A novel, microcarrier-based in vitro assay for rapid and reliable quantification of three-dimensional cell migration and angiogenesis. Microvas. Res., 50: 311-322, 1995.
38. Wang, J., Lou, P., Lesniewski, R., and Henkin, J. Paclitaxel at ultra low concentrations inhibits angiogenesis without affecting cellular microtubule assembly. Anti-Cancer Drugs, 14: 13-19, 2003.
39. Tomayko, M. M., and Reynolds, C. P. Determination of subcutaneous tumor size in athymic (nude) mice. Cancer Chemother. Pharmacol., 24: 148-154, 1989.
40. Umezawa, H., Ishizuka, M., Aoyagi, T., and Takeuchi, T. Enhancement of delayed-type hypersensitivity by bestatin, an inhibitor of aminopeptidase B and leucine aminopeptidase. J. Antibiot. (Tokyo), 29: 857-859, 1976.
41. Peichev, M., Naiyer, A. J., Pereira, D., Zhu, Z., Lane, W. J., Williams, M., Oz, M. C., Hicklin, D. J., Witte, L., Moore, M. A., and Rafii, S. Expression of VEGFR-2 and AC133 by circulating human CD34(+) cells identifies a population of functional endothelial precursors. Blood, 95: 952-958, 2001.
42. Zhang, Y., Griffith, E. C., Sage, J., Jacks, T., and Liu, J. O. Cell cycle inhibition by the anti-angiogenic agent TNP-470 is mediated by p53 and p21WAF1/CIP1. Proc. Natl. Acad. Sci. USA, 97: 6427-6432, 2000.
43. Phillips, P. E., Towbin, H., Stolz, B., Wood, J., and Decaprio, J. A novel biomarker for methionine aminopeptidase inhibitors: NH2-terminal changes in 14-3-3γ and detection in in vitro and in vivo samples treated with NVP-LAF389. Proc. Am. Assoc. Cancer Res., Abstract 4723, 2002.
44. Resh, M. D. Fatty acylation of proteins: new insights into membrane targeting of myristoylated and palmitoylated proteins. Biochim. Biophys. Acta, 1451: 1-16, 1999.
45. Varshavsky, A., Turner, G., Du, F., and Xie, Y. Felix Hoppe-Seyler Lecture 2000. The ubiquitin system and the N-end rule pathway. Biol. Chem., 381: 779-789, 2000.
46. Kwon, Y. T., Kashina, A. S., Davydov, I. V., Hu, R. G., An, J. Y., Seo, J. W., Du, F., and Varshavsky, A. An essential role of N-terminal arginylation in cardiovascular development. Science (Wash. DC), 297: 96-99, 2002.
47. Yamaoka, M., Yamamoto, T., Ikeyama, S., Sudo, K., and Fujita, T. Angiogenesis inhibitor TNP-470 (AGM-1470) potently inhibits the tumor growth of hormone-independet human breast and prostate carcinoma cell lines. Cancer Res., 53: 5233-5236, 1993.
48. Herbst, R. S., Madden, T. L., Tran, H. T., Blumenschein, G. R., Jr., Meyers, C. A., Seabrooke, L. F., Khuri, F. R., Puduvalli, V. K., Allgood, V., Fritsche, H. A., Jr., Hinton, L., Newman, R. A., Crane, E. A., Fossella, F. V., Dordal, M., Goodin, T., and Hong, W. K. Safety and pharmacokinetic effects of TNP-470, an angiogenesis inhibitor, combined with paclitaxel in patients with solid tumors: evidence for activity in non-small-cell lung cancer. J. Clin. Oncol., 20: 4440-4447, 2002.