A new dimethyl ester bisphosphonate inhibits angiogenesis and growth of human epidermoid carcinoma xenograft in nude mice

Anti-Cancer Drugs

Volumn 17, Issue 4, 2006, Pages 479-485

  Ledoux, Dominique ^a,d   Hamma Kourbali, Yamina ^b   Di Benedetto, Mélanie ^a   Foucault Bertaud, Alexandrine ^c   Oudar, Olivier ^a   Sainte Catherine, Odile ^a   Lecouvey, Marc ^a   Kraemer, Michel ^a  

^a UNIVERSITÉ PARIS 13   (France)

^b UNIVERSITÉ PARIS EST CRÉTEIL   (France)

^c INSERM   (France)

^d AVICENNE HOSPITAL   (France)

Author keywords

A431 cells; Angiogenesis; Diesterified bisphosphonate; Tumor growth

Indexed keywords

[1 HYDROXY 1 (HYDROXYMETHOXYPHOSPHORYL) 2 PHENYLETHYL]PHOSPHONIC ACID MONOMETHYL ESTER; BISPHOSPHONIC ACID DERIVATIVE; ENDOTHELIAL CELL GROWTH FACTOR; MATRIGEL; UNCLASSIFIED DRUG;

ANGIOGENESIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CANCER INVASION; CELL DENSITY; CELL PROLIFERATION; CELL STIMULATION; CONTROLLED STUDY; ENDOTHELIUM CELL; ESTERIFICATION; FEMALE; HUMAN; HUMAN CELL; IMMUNOHISTOCHEMISTRY; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; NUDE MOUSE; PRIORITY JOURNAL; SQUAMOUS CELL CARCINOMA; TUMOR GROWTH; TUMOR XENOGRAFT;

ANIMALS; BENZYL ALCOHOLS; CARCINOMA, SQUAMOUS CELL; CELL MOVEMENT; CELL PROLIFERATION; DIPHOSPHONATES; HUMANS; MICE; MICE, NUDE; NEOPLASM TRANSPLANTATION; NEOVASCULARIZATION, PATHOLOGIC; VASCULAR ENDOTHELIAL GROWTH FACTOR A;

EID: 33748190796     PISSN: 09594973     EISSN: None     Source Type: Journal    
DOI: 10.1097/01.cad.0000198909.52701.0f     Document Type: Article

References (29)

1. Clezardin P, Fournier P, Boissier S, Peyruchaud O. In vitro and in vivo antitumor effects of bisphosphonates. Curr Med Chem 2003; 10:173-180.
2. Green JR. Antitumor effects of bisphosphonates. Cancer 2003; 97:840-847.
3. Guenin E, Ledoux D, Oudar O, Lecouvey M, Kraemer M. Structure-activity relationships of a new class of aromatic bisphosphonates that inhibit tumor cell proliferation in vitro. Anticancer Res 2005; 25:1139-1145.
4. Boissier S, Ferreras M, Peyruchaud O, Magnetto S, Ebetino FH, Colombel M, et al. Bisphosphonates inhibit breast and prostate carcinoma cell invasion, an early event in the formation of bone metastases. Cancer Res 2000; 60:2949-2954.
5. Boissier S, Magnetto S, Frappart L, Cuzin B, Ebetino FH, Delmas PD, et al. Bisphosphonates inhibit prostate and breast carcinoma cell adhesion to unmineralized and mineralized bone extracellular matrices. Cancer Res 1997; 57:3890-3894.
6. Hamma-Kourbali Y, Di Benedetto M, Ledoux D, Oudar O, Leroux Y, Lecouvey M, et al. A novel non-containing-nitrogen bisphosphonate inhibits both in vitro and in vivo angiogenesis. Biochem Biophys Res Commun 2003; 310:816-823.
7. Wood J, Bonjean K, Ruetz S, Bellahcene A, Devy L, Foidart JM, et al. Novel antiangiogenic effects of the bisphosphonate compound zoledronic acid. J Pharmacol Exp Ther 2002; 302:1055-1061.
8. Ezra A, Golomb G. Administration routes and delivery systems of bisphosphonates for the treatment of bone resorption. Adv Drug Deliv Rev 2000; 42:175-195.
9. Lin JH. Bisphosphonates: a review of their pharmacokinetic properties. Bone 1996; 18:75-85.
10. Vepsalainen JJ. Bisphosphonate prodrugs. Curr Med Chem 2002; 9:1201-1208.
11. Niemi R, Turhanen P, Vepsalainen J, Taipale H, Jarvinen T. Bisphosphonate prodrugs: synthesis and in vitro evaluation of alkyl and acyloxymethyl esters of etidronic acid as bioreversible prodrugs of etidronate. Eur J Pharm Sci 2000; 11:173-180.
12. Ahlmark M, Vepsalainen J, Taipale H, Niemi R, Jarvinen T. Bisphosphonate prodrugs: synthesis and in vitro evaluation of novel clodronic acid dianhydrides as bioreversible prodrugs of clodronate. J Med Chem 1999; 42:1473-1476.
13. Ezra A, Hoffman A, Breuer E, Alferiev IS, Monkkonen J, El Hanany-Rozen N, et al. A peptide prodrug approach for improving bisphosphonate oral absorption. J Med Chem 2000; 43:3641-3652.
14. Schultz C. Prodrugs of biologically active phosphate esters. Bioorg Med Chem 2003; 11:885-898.
15. Migianu E, Mallard I, Bouchemal N, Lecouvey M. One-pot synthesis of 1-hydroxymethylene-1,1-bisphosphonate partial esters. Tetrahedron Lett 2004; 45:4511-4513.
16. Workman P, Twentyman P, Balkwill F, Balmain A, Chaplin D, Double J, et al. United Kingdom Coordinating Committee on Cancer Research (UKCCCR) Guidelines for the Welfare of Animals in Experimental Neoplasia (second edition). Br J Cancer 1998; 77:1-10.
17. Di Benedetto M, Starzec A, Vassy R, Perret GY, Crepin M, Kraemer M. Inhibition of epidermoid carcinoma A431 cell growth and angiogenesis in nude mice by early and late treatment with a novel dextran derivative. Br J Cancer 2003; 88:1987-1994.
18. Hamma-Kourbali Y, Starzec A, Vassy R, Martin A, Kraemer M, Perret G, et al. Carboxymethyl benzylamide dextran inhibits angiogenesis and growth of VEGF-overexpressing human epidermoid carcinoma xenograft in nude mice. Br J Cancer 2003; 89:215-221.
19. Bagheri-Yarmand R, Kourbali Y, Rath AM, Vassy R, Martin A, Jozefonvicz J, et al. Carboxymethyl benzylamide dextran blocks angiogenesis of MDA-MB435 breast carcinoma xenografted in fat pad and its lung metastases in nude mice. Cancer Res 1999; 59:507-510.
20. Alroy J, Goyal V, Skutelsky E. Lectin histochemistry of mammalian endothelium. Histochemistry 1987; 86:603-607.
21. Passaniti A, Taylor RM, Pili R, Guo Y, Long PV, Haney JA, et al. A simple, quantitative method for assessing angiogenesis and antiangiogenic agents using reconstituted basement membrane, heparin, and fibroblast growth factor. Lab Invest 1992; 67:519-528.
22. Magnetto S, Boissier S, Delmas PD, Clezardin P. Additive antitumor activities of taxoids in combination with the bisphosphonate ibandronate against invasion and adhesion of human breast carcinoma cells to bone. Int J Cancer 1999; 83:263-269.
23. Virtanen SS, Vaananen HK, Harkonen PL, Lakkakorpi PT. Alendronate inhibits invasion of PC-3 prostate cancer cells by affecting the mevalonate pathway. Cancer Res 2002; 62:2708-2714.
24. Inoki I, Shiomi T, Hashimoto G, Enomoto H, Nakamura H, Makino K, et al. Connective tissue growth factor binds vascular endothelial growth factor (VEGF) and inhibits VEGF-induced angiogenesis. FASEB J 2002; 16:219-221.
25. Clezardin P, Ebetino FH, Fournier PG. Bisphosphonates and cancer-induced bone disease: beyond their antiresorptive activity. Cancer Res 2005; 65:4971-4974.
26. Woodward JK, Coleman RE, Holen I. Preclinical evidence for the effect of bisphosphonates and cytotoxic drugs on tumor cell invasion. Anticancer Drugs 2005; 16:11-19.
27. Raiman J, Niemi R, Vepsalainen J, Yritys K, Jarvinen T, Monkkonen J. Effects of calcium and lipophilicity on transport of clodronate and its esters through Caco-2 cells. Int J Pharm 2001; 213:135-142.
28. Niemi R, Taipale H, Ahlmark M, Vepsalainen J, Jarvinen T. Simultaneous determination of clodronate and its partial ester derivatives by ion-pair reversed-phase high-performance liquid chromatography coupled with evaporative light-scattering detection. J Chromatogr B Biomed Sci Appl 1997; 701:97-102.
29. DeLombaert S, Erion MD, Tan J, Blanchard L, el-Chehabi L, Ghai RD, et al. N-Phosphonomethyl dipeptides and their phosphonate prodrugs, a new generation of neutral endopeptidase (NEP, EC 3.4.24.11) inhibitors. J Med Chem 1994; 37:498-511.