Antiangiogenic and apoptotic properties of a novel amphiphilic folate-heparin-lithocholate derivative having cellular internality for cancer therapy

Pharmaceutical Research

Volumn 24, Issue 4, 2007, Pages 705-714

  Yu, Mi Kyung ^a   Lee, Dong Yun ^b   Kim, Yoo Shin ^c   Park, Kyeongsoon ^d   Park, Soo Ah ^e   Son, Dai Hyun ^e   Lee, Gee Young ^a   Nam, Jong Hee ^f   Kim, Sang Yoon ^e   Kim, In San ^c   Park, Rang Woon ^c   Byun, Youngro ^b  

^a Gwangju Institute of Science and Technology (GIST)   (South Korea)

^b Seoul National University   (South Korea)

^c Kyungpook National University School of Medicine   (South Korea)

^d Korea Institute of Science and Technology   (South Korea)

^e University of Ulsan College of Medicine   (South Korea)

^f Chonnam National University Medical School   (South Korea)

Author keywords

Antiangiogenesis; Apoptosis; Folate heparin lithocholate; Tumor growth

Indexed keywords

AMPHOPHILE; FOLATE HEPARIN LITHOCHOLATE CONJUGATE; FOLATE RECEPTOR; HEPARIN; HEPARIN DERIVATIVE; HEPARIN LITHOCHOLATE CONJUGATE; MATRIGEL; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIANGIOGENIC ACTIVITY; ANTICOAGULATION; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER INHIBITION; CANCER THERAPY; CONTROLLED STUDY; COVALENT BOND; DRUG CONJUGATION; DRUG EFFECT; DRUG INHIBITION; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; INTERNALIZATION; MOUSE; NASOPHARYNX CARCINOMA; NONHUMAN; PRIORITY JOURNAL; TUMOR GROWTH;

ANGIOGENESIS INHIBITORS; ANIMALS; ANTICOAGULANTS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CARRIER PROTEINS; CELL LINE, TUMOR; CELL SURVIVAL; COLLAGEN; DISEASE MODELS, ANIMAL; DRUG COMBINATIONS; ENDOCYTOSIS; FEMALE; HEPARIN; HUMANS; LAMININ; LITHOCHOLIC ACID; MALE; MICE; MICE, INBRED BALB C; MICE, INBRED C57BL; MICE, NUDE; NEOPLASMS, EXPERIMENTAL; NEOVASCULARIZATION, PATHOLOGIC; PROTEOGLYCANS; RECEPTORS, CELL SURFACE; TIME FACTORS; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 33947098035     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-006-9190-3     Document Type: Article

References (34)

1. R. Sasisekharan, Z. Shriver, G. Venkataraman, and U. Narayanasami. Roles of heparan-sulphate glycosaminoglycans in cancer. Nat. Rev., Cancer 2:521-528 (2002).
2. S. M. Smorenburg and C. J. NoordenVan. The complex effects of heparins on cancer progression and metastasis in experimental studies. Pharmacol. Rev. 53:93-105 (2001).
3. M. Hejna, M. Raderer, and C. C. Zielinski. Inhibition of metastases by anticoagulants. J. Natl. Cancer Inst. 91:22-36 (1999).
4. L. R. Zacharski and D. L. Ornstein. Heparin and cancer. Thromb. Haemost. 80:10-23 (1998).
5. E. Erduran, Y. Tekelioglu, Y. Gedik, and A. Yildiran. Apoptotic effects of heparin on lymphoblasts, neutrophils, and mononuclear cells: results of a preliminary in vitro study. Am. J. Hematol. 61:90-93 (1999).
6. H. L. Li, K. H. Ye, H. W. Zhang, Y. R. Luo, X. D. Ren, A. H. Xiong, and R. Situ. Effect of heparin on apoptosis in human nasopharyngeal carcinoma CNE2 cells. Cell Res. 11:311-315 (2001).
7. S. J. Busch, G. A. Martin, R. L. Barnhart, and R. L. Jackson. Trans-repressor activity of nuclear glycosaminoglycans on Fos and Jun/AP-1 oncoprotein-mediated transcription. J. Cell Biol. 116:31-42 (1992).
8. D. Berry, D. M. Lynn, R. Sasisekharan, and R. Langer. Poly(beta-amino ester)s promote cellular uptake of heparin and cancer cell death. Chem. Biol. 11:487-498 (2004).
9. J. Hasan, S. D. Shnyder, A. R. Clamp, A. T. McGown, R. Bicknell, M. Presta, M. Bibby, J. Double, S. Craig, D. Leeming, K. Stevenson, J. T. Gallagher, and G. C. Jayson. Heparin octasaccharides inhibit angiogenesis in vivo. Clin. Cancer Res. 11:8172-8179 (2005).
10. H. Engelberg. Actions of heparin that may affect the malignant process. Cancer 85:257-272 (1999).
11. C. R. Parsish, C. Freeman, K. J. Brown, D. J. Francis, and W. B. Cowden. Identification of sulfated oligosaccharide-based inhibitors of tumor growth and metastasis using novel in vitro assays for angiogenesis and heparanase activity. Cancer Res. 59:3433-3441 (1999).
12. K. Ono, M. Ishihara, K. Ishikawa, Y. Ozeki, H. Deguchi, M. Sato, H. Hashimoto, Y. Saito, H. Yura, A. Kurita, and T. Maehara. Periodate-treated, non-anticoagulant heparin-carrying polystyrene (NAC-HCPS) affects angiogenesis and inhibits subcutaneous induced tumour growth and metastasis to the lung. Br. J. Cancer 86:1803-1812 (2002).
13. P. E. Thorpe, E. J. Derbyshire, S. P. Andrade, N. Press, P. P. Knowles, S. King, G. J. Watson, Y. C. Yang, and M. Rao-Bette. Heparin-steroid conjugates: new angiogenesis inhibitors with antitumor activity in mice. Cancer Res. 53:3000-3007 (1993).
14. M. Gohda, T. Magoshi, S. Kato, T. Noguchi, S. Yasuda, H. Nonogi, and T. Matsuda. Terminally alkylated heparin. 2. Potent antiproliferative agent for vascular smooth muscle cells. Biomacromolecules 2:1178-1183 (2001).
15. S. Miotti, S. Canevari, S. Menard, D. Mezzanzanica, G. Porro, S. M. Pupa, M. Regazzoni, E. Tagliabue, and M. I. Colnaghi. Characterization of human ovarian carcinoma-associated antigens defined by novel monoclonal antibodies with tumor-restricted specificity. Int. J. Cancer 39:297-303 (1987).
16. L. R. Coney, A. Tomassetti, L. Carayannopoulos, V. Frasca, B. A. Kamen, M. I. Colnaghi, and V. R. Zurawski Jr.. Cloning of a tumor-associated antigen: MOv18 and MOv19 antibodies recognize a folate-binding protein. Cancer Res. 51:6125-6132 (1991).
17. S. D. Weitman, R. H. Lark, L. R. Coney, D. W. Fort, V. Frasca, V. R. Zurawski Jr, and B. A. Kamen. Distribution of the folate receptor GP38 in normal and malignant cell lines and tissues. Cancer Res. 52:3396-3401 (1992).
18. G. Toffoli, C. Cernigoi, A. Russo, A. Gallo, M. Bagnoli, and M. Boiocchi. Overexpression of folate binding protein in ovarian cancers. Int. J. Cancer 74:193-198 (1997).
19. N. Parker, M. J. Turk, E. Westrick, J. D. Lewis, P. S. Low, and C. P. Leamon. Folate receptor expression in carcinomas and normal tissues determined by a quantitative radioligand binding assay. Anal. Biochem. 338:284-293 (2005).
20. C. P. Leamon and P. S. Low. Folate-mediated targeting: from diagnostics to drug and gene delivery. Drug Discov. Today 6:44-51 (2001).
21. J. Sudimack and R. J. Lee. Targeted drug delivery via the folate receptor. Adv. Drug Deliv. Rev. 41:147-162 (2000).
22. K. Park, K. Kim, I. C. Kwon, S. K. Kim, S. Lee, D. Y. Lee, and Y. Byun. Preparation and characterization of self-assembled nanoparticles of heparin-deoxycholic acid conjugates. Langmuir 20:11726-11731 (2004).
23. 67Gadeferoxamine-folate, a potential radiopharmaceutical for tumor imaging. Bioconjug. Chem. 7:56-62 (1996).
24. 67Ga-deferoxamine-folate to folate-receptor-positive human KB tumor xenografts. Nucl. Med. Biol. 26:23-25 (1999).
25. T. Chandy, G. S. Das, R. F. Wilson, and G. H. Rao. Use of plasma glow for surface-engineering biomolecules to enhance blood compatibility of Dacron and PTFE vascular prosthesis. Biomaterials 21:699-712 (2000).
26. Y. Lee, H. T. Moon, and Y. Byun. Preparation of slightly hydrophobic heparin derivatives which can be used for solvent casting in polymeric formulation. Thromb. Res. 92:149-156 (1998).
27. J. O. Nam, J. E. Kim, H. W. Jeong, S. J. Lee, B. H. Lee, J. Y. Choi, R. W. Park, J. Y. Park, and I. S. Kim. Identification of the ανβ3 integrin-interacting motif of ßig-h3 and its anti-angiogenic effect. J. Biol. Chem. 278:25902-25909 (2003).
28. T. Barzu, J. L. RijnVan, M. Petitou, P. Molho, G. Tobelem, and J. P. Caen. Endothelial binding sites for heparin. Specificity and role in heparin neutralization. Biochem. J. 238:847-854 (1986).
29. P. A. Raj, E. Marcus, and R. Rein. Conformational requirements of suramin to target angiogenic growth factors. Angiogenesis 2:183-199 (1998).
30. R. J. Linhardt. Heparin-induced cancer cell death. Chem. Biol. 11:420-422 (2004).
31. O. Filhol, C. Cochet, and E. M. Chambaz. DNA binding activity of casein kinase II. Biochem. Biophys. Res. Commun. 173:862-871 (1990).
32. E. Beutler, T. Gelbart, and W. Kuhl. Interference of heparin with the polymerase chain reaction. Biotechniques 9:166-170 (1990).
33. K. Park, G. Y. Lee, Y. S. Kim, M. Yu, R. W. Park, I. S. Kim, S. Y. Kim, and Y. Byun. Heparin-deoxycholic acid chemical conjugate as an anticancer drug carrier and its antitumor activity. J. Control. Release 114:300-306 (2006).
34. K. Park, Y. S. Kim, G. Y. Lee, J. O. Nam, S. K. Lee, R. W. Park, S. Y. Kim, I. S. Kim, and Y. Byun. Antiangiogenic effect of bile acid acylatedfs heparin derivative. Pharm. Res. 24:176-185 (2007).