Nature of interaction between basic fibroblast growth factor and the antiangiogenic drug 7,7-(carbonyl-bis[imino-N-methyl-4,2- pyrrolecarbonylimino[N-methyl-4,2-pyrrole]-carbonylimino])bis-(1,3- naphthalene disulfonate)

Biophysical Journal

Volumn 75, Issue 2, 1998, Pages 672-682

  Zamai, Moreno ^a,b   Caiolfa, Valeria R ^a   Pines, Dina ^b   Pines, Ehud ^b   Parola, Abraham H ^b  

^a PFIZER INC   (United States)

^b BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

7,7 [CARBONYL BIS[IMINO N METHYL 4,2 PYRROLECARBONYLIMINO (N METHYL 4,2 PYRROLE)CARBONYLIMINO]] BIS(1,3 NAPHTHALENE DISULFONATE); UNCLASSIFIED DRUG;

AFFINITY CHROMATOGRAPHY; ANGIOGENESIS; ANISOTROPY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; DRUG MECHANISM; DRUG PROTEIN BINDING; HYDROGEN BOND; MOLECULAR INTERACTION;

EID: 0031871605     PISSN: 00063495     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-3495(98)77557-5     Document Type: Article

References (51)

1. Abraham, M. H., P. L. Greller, J. M. Abboud, R. M. Doherty, and R. W. Taft. 1988. Solvent effects in organic chemistry - recent developments. Can. J. Chem. 66:2673-2686 and references therein.
2. Alfahel, A., A. Korngreen, A. H. Parola, and Z. Priel. 1996. Purinergically induced membrane fluidization in ciliary cells: characterization and control by calcium and membrane potential. Biophys. J. 70:1045-1053.
3. Auerbach, W., and R. Auerbach. 1994. Angiogenesis inhibitors: a review. Pharmacol. Ther. 63:265-311.
4. Aviezer, D., E. Levy, M. Safran, C. Svahn, E. Buddecke, A. Schmidt, G. David, I. Vlodavsky, and A. Yayon. 1994. Differential structural requirements of heparin and heparan sulfate proteoglycans that promote binding of basic fibroblast growth factor to its receptor. J. Biol. Chem. 269:114-121.
5. Baird, A., D. Schubert, N. Ling, and R. Guillemin. 1988. Receptor- and heparin-binding domains of basic fibroblast growth factor. Proc. Natl. Acad. Sci. USA. 85:2324-2328.
6. Basilico, C., and D. Moscatelli. 1992. The FGF family of growth factors and oncogenes. Adv. Cancer Res. 59:115-165.
7. Biasoli, G., M. Botta, M. Ciomei, F. Corelli, M. Grandi, F. Manetti, N. Mongelli, and A. Paio. 1993. New heterocyclic analogs of suramin with bFGF inhibiting activity. Synthesis, sar and possible mode of action. Med. Chem. Res. 4:202-210.
8. Blood, C. H., and B. R. Zetter. 1990. Tumor interaction with the vasculature: angiogenesis and tumor metastasis. Biochim. Biophys. Acta. 1032:89-118.
9. Burgess, W. H., and T. Maciag. 1989. The heparin-binding (fibroblast) growth factor family of proteins. Annu. Rev. Biochem. 58:575-606.
10. Burke, T. G., and Z. Mi. 1994. The structural basis of camptothecin interactions with human serum albumin: impact on drug stability. J. Med. Chem. 37:40-46.
11. Caccia, P., G. Nitti, O. Cletini, P. Pucci, M. Ruoppolo, F. Bertolero, B. Valsasina, F. Roletto, C. Cristiani, G. Cauet, P Sarmientos, A. Malorni, and G. Marino. 1992. Stabilization of recombinant human basic fibroblast growth factor by chemical modifications of cysteine residues. Eur. J. Biochem. 204:649-655.
12. Ciomei, M., W. Pastori, M. Mariani, F. Sola, M. Grandi, N. Mongelli. 1993. New sulfonated distamycin A derivatives with bFGF complexing activity. Biochem. Pharmacol. 47:295-302.
13. Eriksson, A. E., L. S. Cousens, and B. W. Matthews. 1993. Refinement of the structure of human basic fibroblast growth factor at 1.6 Å resolution and analysis of presumed heparin binding sites by selenate substitution. Protein Sci. 2:1274-1284.
14. Faham, S., R. E. Hileman, J. R. Fromm, R. J. Linhardt, and D. C. Rees. 1996. Heparin structure and interactions with basic fibroblast growth factor. Science. 271:1116-1120.
15. Fassina, G., and I. M. Chaiken. 1987. Analytical high performance affinity chromatography. In Advances in Chromatography, Vol. 27. J. C. Giddings, E. Grushka, and P. R. Brown, editors. Marcel Dekker, New York and Basel. 247-297.
16. Fernig, D. G., and J. T. Gallagher. 1994. Fibroblast growth factors and their receptors: an information network controlling tissue growth, morphogenesis and repair. Prog. Growth Factor Res. 5:353-377.
17. Folkman, J. 1971. Tumor angiogenesis: therapeutic implications. N. Engl. J. Med. 285:1182-1186.
18. Folkman, J. 1985. Tumor angiogenesis. Adv. Cancer Res. 43:175-203.
19. Folkman, J., and M. Klagsbrun. 1987. Angiogenetic factors. Science. 235:442-447.
20. Glikberg, S., and Y. Markus. 1983. Relation of the Gibbs free energy of transfer of ions from water to polar solvents to the properties of the solvents and the ions. J. Solution Chem. 12:255-270.
21. Gullino, P. M. 1978. Angiogenesis and oncogenesis. J. Natl. Cancer Inst. 61:639-643.
22. Gutmann, V. 1968. Coordination Chemistry in Non-aqueous Solvents. Springer Verlag, Vienna and New York.
23. Hazan, S., I. Fishov, M. Zamai, V. R. Caiolfa, and A. H. Parola. 1995. Fluorescence polarization assay for endothelin converting enzymes. Peptides. 60:333-336.
24. Herblin, W. F., S. Brem, T. P. Fan, and J. L. Gross. 1994. Recent advances in angiogenesis inhibitors. Exp. Opin. Ther. Patents. 4:641-654.
25. Hulme, E. C., and N. J. M. Birdsall. 1992. Strategy and tactics in receptor-binding studies. In Receptor-Ligand Interactions. A Practical Approach. E. C. Hulme, editor. Oxford University Press, New York. 63-176.
26. Klagsbrun, M., and A. Baird. 1991. A dual receptor system is required for basic fibroblast growth factor activity. Cell. 67:229-231.
27. Klagsbrun, M., and P. A. D'Amore. 1991. Regulators of angiogenesis. Annu. Rev. Physiol. 53:17-39.
28. Kohler, K., J. Trepel, and W. Linehan. 1992. Suramin: a novel growth factor antagonist with activity in hormone-refractory metastatic cancer. J. Clin. Oncol. 10:881-889.
29. Kosower, E. M. 1968. An Introduction to Physical Organic Chemistry. Wiley, New York. 293.
30. Krygowski, T. M., and W. R. Fawcett. 1975. Complementary Lewis acid-base description of solvent effects. I. Ion-ion and ion-dipole interactions. J. Am. Chem. Soc. 97:2143-2148.
31. La Rocca, R. V., C. A. Stein, and C. E. Meyers. 1990. Suramin: prototype of a new generation of antitumor compounds. Cancer Cell. 2:106-115.
32. Lindahl, U., K. Lidholt, D. Spillmann, and L. Kjellen. 1994. More to heparin than anticoagulation. Thromb. Res. 75:1-32.
33. Liotta, L. A., P. S. Steeg, and W. G. Stetler-Stevenson. 1991. Cancer metastasis and angiogenesis: an imbalance of positive and negative regulation. Cell. 64:327-336.
34. Middaugh, C. R., H. Mach, C. J. Burke, D. B. Volking, J. M. Dabora, P. K. Tsai, M. W. Bruner, J. A. Ryan, and K. E. Marfia. 1992. Nature of the interaction of growth factors with suramin. Biochemistry. 31: 9016-9024.
35. Ornitz, D. M., A. B. Herr, M. Nilsson, J. Westman, C. M. Svahn, and G. Waksman. 1995. FGF binding and FGF receptor activation by synthetic heparan-derived di- and trisaccharides. Science. 268:432-436.
36. Ornitz, D. M., A. Yayon, J. G. Flanagan, C. M. Svahn, E. Levi, E., and P. Leder. 1992. Cell surface, heparin-like molecules are required for binding of basic fibroblast growth factor to its high affinity receptor. Mol. Cell. Biol. 12:240-247.
37. Presta, M., M. Rusnati, A. Gualandris, P. Dell'Era, C. Urbinati, D. Coltrini, E. Tanghetti, and M. Belleri. 1994. Human basic fibroblast growth factor: structure-function relationship of an angiogeneic molecule. In Angiogenesis: Molecular Biology, Clinical Aspects. Series A: Life Sciences. 263. M. E. Maragoudakis, P. M. Gullino, and P. I. Lelkes, editors. Plenum Press, New York. 39-50.
38. Reichardt, C. 1990. Solvent and Solvent Effects in Organic Chemistry. VCH, Weinhein, Germany.
39. Reichardt, C. 1994. "Solvatocromic dyes" as solvent polarity indicators. Chem. Rev. 94:2319-2358.
40. Seed, M. P. 1996. Angiogenesis inhibition as a drug target for diseases: an update. Exp. Opin. Invest. Drugs. 5:1617-1637.
41. Sola, F., M. Farao, E. Pesenti, A. Marsilio, N. Mongelli, and M. Grandi. 1995. Antitumoral activity of FCE26644, a new growth-factor complexing molecule. Cancer Chemother. Pharmacol. 36:217-222.
42. Springer, B. A., M. W. Pantoliano, F. A. Barbera, P. L. Gunyuzlu, L. D. Thompson, W. F. Herblin, S. A. Rosenfeld, and G. W. Book. 1994. Identification and concerted function of two receptor binding surfaces on basic fibroblast growth factor required for mitogenesis. J. Biol. Chem. 269:26869-26884.
43. Terano, H., Y. Shibata, and T. Otsuka. 1993. Angiogenesis inhibitors of microbial origin. Drugs Future. 18:239-247.
44. Thompson, L. D., M. W. Pantoliano, and B. A. Springer. 1994. Energetic characterization of the basic fibroblast growth factor-heparin interaction: identification of the heparin binding domain. Biochemistry. 33: 3831-3840.
45. Vlodavsky, I., R. Bar-Shavit, R. Ishai-Michaeli, P. Bashkin, and Z. Fuks. 1991. Extracellular sequestration and release of fibroblast growth factor: a regulatory mechanism. Trends Biochem. Sci. 16:268-271.
46. Yayon. A., M. Klagsbrun, J. D. Esko, P. Leder, and D. M. Ornitz. 1991. Cell surface, heparin-like molecules are required for binding of basic fibroblast growth factor to its high affinity receptor. Cell. 64:841-848.
47. Zamai, M., and G. Fassina. 1991. Mobile phase effects in the high-performance affinity purification of thermolysin. J. Chromatogr. 549: 195-205.
48. Zamai, M., A. H. Parola, N. Mongelli, M. Grandi, and V. R. Caiolfa. 1997. Naphthalene sulfonic distamycin-A derivatives: interaction with human basic fibroblast growth factor. Med. Chem. Res. 7:36-44.
49. Zhong-yuan, Z., S. Cheng-e, and H. Te-kang. 1985. Solvent effects on the rate of the reaction of 2,4-dinitrofluorobenzene with the ethyl ester of tyrosine. J. Chem. Soc. Perkin Trans. 11:929-934.
50. Zhu, H., K. Ramnarayan, J. Anchin, W. Y. Miao, A. Sereno, L. Millman, J. Zheng, V. N. Balaji, and M. E. Wolff. 1995. Glu-96 of basic fibroblast growth factor is essential for high affinity receptor binding. J. Biol. Chem. 270:21869-21874.
51. Zhu, X., H. Komiya, A. Chirino, S. Faham, G. M. Fox, T. Arakawa, B. T. Hsu, and D. C. Rees. 1990. Three-dimensional structure of acidic and basic fibroblast growth factors. Science. 251:90-93.