Targeting tissue factor-expressing tumor angiogenesis and tumors with EF24 conjugated to factor VIIa

Journal of Drug Targeting

Volumn 16, Issue 3, 2008, Pages 185-197

  Shoji, Mamoru ^a   Sun, Aiming ^a   Kisiel, Walter ^b   Lu, Yang J ^a   Shim, Hyunsuk ^a   McCarey, Bernard E ^c   Nichols, Christopher ^a   Parker, Ernest T ^a   Pohl, Jan ^a   Mosley, Cara A ^a   Alizadeh, Aaron R ^a   Liotta, Dennis C ^a   Snyder, James P ^a  

^a EMORY UNIVERSITY   (United States)

^b UNIVERSITY OF NEW MEXICO HEALTH SCIENCES CENTER   (United States)

^c EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Curcumin analog; EF24; Factor VIIa inhibitor; Targeted drug delivery; Tissue factor

Indexed keywords

BLOOD CLOTTING FACTOR 7A; CURCUMIN; CURCUMIN DERIVATIVE; DRUG CARRIER; EF 24; MATRIGEL; PEPTIDE CHLOROMETHYL KETONE; THROMBOPLASTIN; UNCLASSIFIED DRUG; VASCULOTROPIN;

ANGIOGENESIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIANGIOGENIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CANCER INHIBITION; CONTROLLED STUDY; CORNEA TUMOR; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG TARGETING; ENDOCYTOSIS; FEMALE; HUMAN; HUMAN CELL; MICROMETASTASIS; MOUSE; NONHUMAN; NUDE MOUSE; PRIORITY JOURNAL; RABBIT; STRUCTURE ANALYSIS; TUMOR VASCULARIZATION; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZYLIDENE COMPOUNDS; CELL LINE, TUMOR; ENDOCYTOSIS; FACTOR VIIA; HUMANS; MICE; NEOPLASMS, EXPERIMENTAL; NEOVASCULARIZATION, PATHOLOGIC; PIPERIDONES; RABBITS; THROMBOPLASTIN; VASCULAR ENDOTHELIAL GROWTH FACTOR A; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 41549086576     PISSN: 1061186X     EISSN: 10292330     Source Type: Journal    
DOI: 10.1080/10611860801890093     Document Type: Article

References (53)

1. Abe, K., Shoji, M., Chen, J., Bierhaus, A., Danave, I., Micko, C., Casper, K., Dillehay, DL, Nawroth, PP and Rickles, FR (1999) Regulation of vascular endothelial growth factor and angiogenesis by the cytoplasmic tail of tissue factor. Proc Natl Acad Sci USA, 96:15, pp. 8663-8668.
2. Adams, BK, Ferstl, EM, Davis, MC, Herold, M., Kurtkaya, S., Camalier, RF, Hollingshead, MG, Kaur, G., Sausville, EA, Rickles, FR, Snyder, JP, Liotta, DC and Shoji, M. (2004) Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents. Bioorg Med Chem, 12:14, pp. 3871-3883.
3. Adams, BK, Cai, J., Armstrong, J., Herold, M., Lu, YJ, Sun, A., Snyder, JP, Liotta, DC, Jones, DP and Shoji, M. (2005) EF24, a novel synthetic curcumin analog, induces apoptosis in cancer cells via a redox-dependent mechanism. Anticancer Drugs, 16:3, pp. 263-275.
4. Aggarwal, BB, Kumar, A. and Bharti, AC (2003) Anticancer potential of curcumin: Preclinical and clinical studies. Anticancer Res, 23:1, pp. 363-398.
5. Armesilla, AL, Lorenzo, E., Arco, P Gomez del, Martinez-Martinez, S., Alfranca, A. and Redondo, JM (1999) Vascular endothelial growth factor activates nuclear factor of activated T cells in human endothelial cells: A role for tissue factor gene expression. Mol Cell Biol, 19:3, pp. 2032-2043.
6. Awasthi, S., Pandya, U., Singhal, SS, Lin, JT, Thiviyanathan, V., Seifert Jr., WE, Awasthi, YC and Ansari, GA (2000) Curcumin-glutathione interactions and the role of human glutathione S-transferase P1-1. Chem Biol Interact, 128:1, pp. 19-38.
7. Callander, NS, Varki, N. and Rao, LV (1992) Immunohistochemical identification of tissue factor in solid tumors. Cancer, 70:5, pp. 1194-1201.
8. Chattopadhyay, I., Biswas, K., Bandyopadhyay, U. and Banerjee, RK (2004) Turmeric and curcumin: Biological actions and medicinal applications. Curr Sci, 87:1, pp. 44-53.
9. Chen, J., Bierhaus, A., Schiekofer, S., Andrassy, M., Chen, B., Stern, DM and Nawroth, PP (2001) Tissue factor - a receptor involved in the control of cellular properties, including angiogenesis. Thromb Haemost, 86:1, pp. 334-345.
10. Clauss, M., Gerlach, M., Gerlach, H., Brett, J., Wang, F., Familletti, PC, Pan, YC, Olander, JV, Connolly, DT and Stern, D. (1990) Vascular permeability factor: A tumor-derived polypeptide that induces endothelial cell and monocyte procoagulant activity and promotes monocyte migration. J Exp Med, 172:6, pp. 1535-1545.
11. Contrino, J., Hair, GA, Schmeizl, MA, Rickles, FR and Kreutzer, DL (1994) In situ characterization of antigenic and functional tissue factor expression in human tumors utilizing monoclonal antibodies and recombinant factor VIIa as probes. Am J Pathol, 145:6, pp. 1315-1322.
12. Contrino, J., Hair, G., Kreutzer, DL and Rickles, FR (1996) In situ detection of tissue factor in vascular endothelial cells: Correlation with the malignant phenotype of human breast disease. Nat Med, 2:2, pp. 209-215.
13. Dickinson, CD, Kelly, CR and Ruf, W. (1996) Identification of surface residues mediating tissue factor binding and catalytic function of the serine protease factor VIIa. Proc Natl Acad Sci USA, 93:25, pp. 14379-14384.
14. Drake, TA, Morrissey, JH and Edgington, TS (1989) Selective cellular expression of tissue factor in human tissues. Implications for disorders of hemostasis and thrombosis. Am J Pathol, 134:5, pp. 1087-1097.
15. Elvira, C., Gallardo, A., Roman, JS and Cifuentes, A. (2005) Covalent plolymer-drug conjugates. Molecules, 10:1, pp. 114-125.
16. Flossel, C., Luther, T., Muller, M., Albrecht, S. and Kasper, M. (1994) Immunohistochemical detection of tissue factor (TF) on paraffin sections of routinely fixed human tissue. Histochem, 101:6, pp. 449-453.
17. Folkman, J. (2001) Angiogenesis. Harrison's principles of internal medicine, pp. 517-530. McGraw Hill, New York, USA
18. Folkman, J. (2007) Angiogenesis: An organizing principle for drug discovery. Nat Rev Drug Discov, 6:4, pp. 273-286.
19. Forster, Y., Meye, A., Albrecht, S. and Schwenzer, B. (2006) Tissue factor and tumor: Clinical and laboratory aspects. Clin Chim Acta, 364:1, pp. 12-21.
20. Hansen, CB, Pyke, C., Petersen, LC and Rao, LV (2001) Tissue factor-mediated endocytosis, recycling and degradation of factor VIIa by a clathrin-independent mechanism not requiring the cytoplasmic domain of tissue factor. Blood, 97:6, pp. 1712-1720.
21. Hu, Z., Sun, Y. and Garen, A. (1999) Targeting tumor vasculature endothelial cells and tumor cells for immunotherapy of human melanoma in a mouse xenograft model. Proc Natl Acad Sci USA, 96:14, pp. 8161-8166.
22. Huang, X., Molema, G., King, S., Watkins, L., Edgington, TS and Thorpe, PE (1997) Tumor infarction in mice by antibody-directed targeting of tissue factor to tumor vasculature. Science, 275:5299, pp. 547-550.
23. Iakhiaev, A., Pendurthi, UR, Voigt, J. and Ezban, M. (1999) Catabolism of factor VIIa bound to tissue factor in fibroblasts in the presence and absence of tissue factor pathway inhibitor. J Biol Chem, 274:52, pp. 36995-37003.
24. Jilma, B., Marsik, C., Mayr, F., Graninger, MT, Taylor Jr., FB and Ribel, MC (2002) Pharmacodynamics of active site-inhibited factor VIIa in endotoxin-induced coagulation in humans. Clin Pharm Therap, 72:4, pp. 403-410.
25. Kakkar, AK, Lemoine, NR, Scully, MF, Tebbutt, S. and Williamson, RC (1995) Tissue factor expression correlates with histological grade in human pancreatic cancer. Br J Surg, 82:8, pp. 1101-1104.
26. Lev, EI, Marmur, JD, Zdravkovic, M., Osende, JI, Robbins, J. and Delfin, JA (2002) Antithrombotic effect of tissue factor inhibition by inactivated factor VIIa: An ex vivo human study. Arterioscler Thromb Vasc Biol, 22:6, pp. 1036-1041.
27. Mechtcheriakova, D., Wlachos, A., Holzmuller, H., Binder, BR and Hofer, E. (1999) Vascular endothelial cell growth factor-induced tissue factor expression in endothelial cells is mediated by EGR-1. Blood, 93:11, pp. 3811-3823.
28. Morphy, R., Kay, C. and Rankovic, Z. (2004) From magic bullets to designed multiple ligands. Drug Discov Today, 9:15, pp. 641-651.
29. Nemerson, Y. (1988) Tissue factor and hemostasis. Blood, 71:1, pp. 1-8.
30. Nicholson, DW, Ali, A., Thornberry, NA, Vaillancourt, JP, Ding, CK, Gallant, M., Gareau, Y., Griffin, PR, Labelle, M. and Lazebnik, YA (1995) Identification and inhibition of the ICE/CED-3 protease necessary for mammalian apoptosis. Nature, 376:6535, pp. 37-43.
31. Nicolaisen, EM, Kristensen, H., Kristensen, A. and Hedner, U. (2002) Evaluation of potential antigenicity of active-site-inhibited recombinant human FVIIa (FFR-rFVIIa) in an immune-tolerant rat model. Thromb Haemost, 87:5, pp. 836-839.
32. O'Reilly, MS, Holmgren, L., Shing, Y., Chen, C., Rosenthal, RA, Moses, M., Lane, WS, Cao, Y., Sage, EH and Folkman, J. (1994) Angiostatin: A novel angiogenesis inhibitor that mediates the suppression of metastases by a Lewis lung carcinoma. Cell, 79:2, pp. 315-328.
33. Passaniti, A., Taylor, RM, Pili, R., Guo, Y., Long, PV, Haney, JA, Pauly, RR, Grant, DS and Martin, GR (1992) A simple, quantitative method for assessing angiogenesis and antiangiogenic agents using reconstituted basement membrane, heparin and fibroblast growth factor. Lab Invest, 67:4, pp. 519-528.
34. Rubinstein, LV, Shoemaker, RH, Paull, KD, Simon, RM, Tosini, S., Skehan, P., Scudiero, DA, Monks, A. and Boyd, MR (1990) Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines. J Natl Cancer Inst, 82:13, pp. 1113-1118.
35. Sevinsky, JR, Rao, LV and Ruf, W. (1996) Ligand-induced protease receptor translocation into caveolae: A mechanism for regulating cell surface proteolysis of the tissue factor-dependent coagulation pathway. J Cell Biol, 133:2, pp. 293-304.
36. Shan, S., Lockhart, AC, Saito, WY, Knapp, AM, Laderoute, KR and Dewhirst, MW (2001) The novel tubulin-binding drug BTO-956 inhibits R3230AC mammary carcinoma growth and angiogenesis in Fischer 344 rats. Clin Cancer Res, 7:8, pp. 2590-2596.
37. Sharma, RA, McLelland, HR, Hill, KA, Ireson, CR, Euden, SA, Manson, MM, Pirmohamed, M., Marnett, LJ, Andreas, J., Gescher, AJ and Steward, WP (2001) Pharmacodynamic and pharmacokinetic study of oral curcuma extract in patients with colorectal cancer. Clin Cancer Res, 7:7, pp. 1894-1900.
38. Shoji, M., Hancock, WW, Abe, K., Micko, C., Casper, KA, Baine, RM, Wilcox, JN, Danave, I., Dillehay, DL, Matthews, E., Contrino, J., Morrissey, JH, Gordon, S., Edgington, TS, Kudryk, B., Kreutzer, DL and Rickles, FR (1998) Activation of coagulation and angiogenesis in cancer: Immunohistochemical localization in situ of clotting proteins and vascular endothelial growth factor in human cancer. Am J Pathol, 152:2, pp. 399-411.
39. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, JT, Bokesch, H., Kenney, S. and Boyd, MR (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst, 82:13, pp. 1107-1112.
40. Sorensen, BB, Persson, E., Freskgard, PO, Kjalke, M., Ezban, M., Williams, T. and Rao, LV (1997) Incorporation of an active site inhibitor in factor VIIa alters the affinity for tissue factor. J Biol Chem, 272:18, pp. 11863-11868.
41. Sun, A., Shoji, M., Lu, YJ, Liotta, DC and Snyder, JP (2006) Synthesis of EF24-tripeptide chloromethyl ketone: A novel curcumin-related anticancer drug delivery system. J Med Chem, 49:11, pp. 3153-3158.
42. Takano, S., Tsuboi, K., Tomono, Y., Mitsui, Y. and Nose, T. (2000) Tissue factor, osteopontin, alphavbeta3 integrin expression in microvasculature of gliomas associated with vascular endothelial growth factor expression. Br J Cancer, 82:12, pp. 1967-1973.
43. Vasey, PA, Kaye, SB, Morrison, R., Twelves, C., Wilson, P. and Duncan, R. (1999) Phase I clinical and pharmacokinetic study of PK1 [N-(2-hydroxypropyl)methacrylamide copolymer doxorubicin]: First member of a new class of chemotherapeutic agents-drug-polymer conjugates. Cancer Res. Campaign Phase I/II Committee. Clin Cancer Res, 5:1, pp. 83-94.
44. Wan, YL, Rong, L., Liu, YC, Yao, HW, Wang, X., Wu, T., Pan, YS and Zhu, J. (2005) [The role of tissue factor in the invasion and metastasis of colorectal carcinoma cells]. Chung-Hua Wai Ko Tsa Chih [Chinese Journal of Surgery], 43:19, pp. 1265-1267.
45. Wilcox, JN, Smith, KM, Schwartz, SM and Gordon, D. (1989) Localization of tissue factor in the normal vessel wall and in the atherosclerotic plaque. Proc Natl Acad Sci USA, 86:8, pp. 2839-2843.
46. Williams, EB, Krishnaswamy, S. and Mann, KG (1989) Zymogen/enzyme discrimination using peptide chloromethyl ketones. J Biol Chem, 264:13, pp. 7536-7545.
47. Zhang, SZ, Lipsky, MM, Trump, BF and Hsu, IC (1990) Neutral red (NR) assay for cell viability and xenobiotic-induced cytotoxicity in primary cultures of human and rat hepatocytes. Cell Biol Toxicicol, 6:2, pp. 219-234.
48. Zhang, Y., Deng, Y., Luther, T., Muller, M., Ziegler, R., Waldherr, R., Stern, DM and Nawroth, PP (1994) Tissue factor controls the balance of angiogenic and antiangiogenic properties of tumor cells in mice. J Clin Invest, 94:3, pp. 1320-1327.
49. Zhang, Y., Deng, Y., Wendt, T., Liliensiek, B., Bierhaus, A., Greten, J., He, W., Chen, B., Hach-Wunderle, V., Waldherr, R., Ziegler, R., Mannel, D., Stern, DM and Nawroth, PP (1996) Intravenous somatic gene transfer with antisense tissue factor restores blood flow by reducing tumor necrosis factor-induced tissue factor expression and fibrin deposition in mouse meth-A sarcoma. J Clin Invest, 97:10, pp. 2213-2224.
50. Zhang, J., Ding, J., Zhang, X., Shao, X. and Hao, Z. (2005) Regulation of vascular endothelial growth factor (VEGF) production and angiogenesis by tissue Factor (TF) in SGC-7901 gastric cancer cells. Cancer Biol Ther, 4:7, pp. 769-772.
51. Zamai, M., vandeVen, M., Farao, M., Gratton, E., Ghiglieri, A. and Castelli, MG (2003) Camptothecin poly[N-(2-hydroxypropyl) methacrylamide] copolymers in antitopoisomerase-I tumor therapy: Intratumor release and antitumor efficacy. Mol Cancer Ther, 2:1, pp. 29-40.
52. Zhou, JN, Ljungdahl, S., Shoshan, MC, Swedenborg, J. and Linder, S. (1998) Activation of tissue-factor gene expression in breast carcinoma cells by stimulation of the RAF-ERK signaling pathway. Mol Carcinog, 21:4, pp. 234-243.
53. Zucker, S., Mirza, H., Conner, CE, Lorenz, AF, Drews, MH, Bahou, WF and Jesty, J. (1998) Vascular endothelial growth factor induces tissue factor and matrix metalloproteinase production in endothelial cells: Conversion of prothrombin to thrombin results in progelatinase A activation and cell proliferation. Int J Cancer, 75:5, pp. 780-786.