Poly(n-acryl amino acids): A new class of biologically active polyanions

Journal of Medicinal Chemistry

Volumn 43, Issue 13, 2000, Pages 2591-2600

  Bentolila, Alfonso ^a   Vlodavsky, Israel ^b   Ishai Michaeli, Rivka ^b   Kovalchuk, Olga ^b   Haloun, Christine ^a   Domb, Abraham J ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b HADASSAH HEBREW UNIVERSITY MEDICAL CENTER   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BASIC FIBROBLAST GROWTH FACTOR; GLYCINE DERIVATIVE; HEPARIN; HEPARIN LYASE; PHENYLALANINE DERIVATIVE; POLYANION; PROLINE DERIVATIVE; SERINE DERIVATIVE;

ANIMAL CELL; ANTICOAGULATION; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; NONHUMAN; POLYMERIZATION; REACTION ANALYSIS; SPECTRAL SENSITIVITY; STEREOCHEMISTRY;

ACRYLIC RESINS; AMINO ACIDS; ANIMALS; ANIONS; ANTICOAGULANTS; CATTLE; CELL DIVISION; CELLS, CULTURED; ENZYME INHIBITORS; EXTRACELLULAR MATRIX; FIBROBLAST GROWTH FACTOR 2; HEPARIN; HEPARIN LYASE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR WEIGHT; MUSCLE, SMOOTH, VASCULAR; SPECTROPHOTOMETRY, INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034729774     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000089j     Document Type: Article

References (41)

1. Ottenbrite, R. M. Structure and Biological activities of some polyanionic polymers. In Anionic Polymeric Drugs; Donaruma, L. G., Ottenbrite, R. M., Vogl, O., Eds.; John Wiley and Sons: New York, 1980; pp 21-48 and references therein.
2. Morahan, P. S.; Regelson, W.; Munson, A. E. Pyran and polyribonucleotides: differences in biological activities. Antimicrob. Agents Chemother. 1972, 2, 16-22.
3. Mohr, S. J.; Chirigos, M. A.; Fuhrman, F. S.; Pryor, J. W. Pyran copolymer as an effective adjuvant to chemotherapy against a murine leukemia and solid tumor. Cancer Res. 1975, 35, 3750-3754.
4. Munson, A. E.; Regelson, W.; Lawrence, W.; Wooles, W. R. Biphasic response of the reticuloendothelial system (RES) induced by pyran copolymer. J. Reticuloendothel. Soc. 1970, 7, 375-385.
5. Hodnett, E. M. Synthetic Polymeric Inducers of Interferon. In Polymeric Materials in Medication; Gebelin, C. G., Carraher, C. E., Eds.; Plenum Press: New York, 1984; pp 211-226.
6. Hatanaka, K.; Yoshida, T.; Miyahara, S.; Sato, T.; Ono, F.; Uryu, T.; Kuzuhara, H. Synthesis of new heparinoids with high anticoagulant activiy. J. Med. Chem. 1987, 30, 810-814.
7. Butler, G. B. Synthesis, Characterization and Biological Activity of Pyran Copolymers. In Anionic Polymeric Drugs; Donaruma, L. G., Ottenbrite, R. M., Vogl, O., Eds.; John Wiley and Sons: New York, 1980; pp 49-210.
8. Lindahl, U. Biosynthesis of heparin and related polysaccharides. In Heparin: Chemical and biological properties, clinical applications; Lane, D. A., Lindahl, U., Eds.; Edward Arnold: London; pp 159-189.
9. Helting, T.; Lindahl, U. Occurrence and biosynthesis of beta-glucuronidic linkages in heparin. J. Biol. Chem. 1971, 246, 5442-5447.
10. Casu, B. Structure of heparin and heparin fragments. Ann. N. Y. Acad. Sci. 1989, 556, 1-17.
11. Martindale. The Extra Pharmacopoeia, 30th ed.; The Pharmaceutical Press: London, 1993; pp 227-232.
12. Claes, P.; Billiau, A.; De Clercq, E.; Desmyter, J.; Schonne, E.; Vanderhaeghe, H.; De Somer, P. Polyacetal Carboxylic Acids: A new group of Antiviral Polyanion. J. Virol. 1970, 5, 313-320.
13. Alban, S.; Kraus, J.; Franz, G. Synthesis of Laminarin Sulfates with Anticoagulant Activity. Arzneim. Forach. / Drug Res. 1992, 42, 1005-1008.
14. Ottenbrite, R. M. The Antitumor and Antiviral Effects of Polycarboxylic Acid Polymers. In Biological Activities of Polymers; Carraher, C. E., Gebelin, C. G., Eds.; ACS Symposium Series 186; ACS: Washington, DC, 1982; pp 205-220 and references therein.
15. Muck, K. F.; Rolly, H.; Burg, K. Herstellung und antivirale wirksamkeit von polyacrylsaure und polymethacrylsaure. Macromol. Chem. 1977, 178, 2773-2784.
16. Gonzalez, R. G.; Blackburn, B. J.; Schleich, T. Fractionation and structural elucidation of the active components of aurintricarboxylic acid, a potent inhibitor of protein nucleic acid interactions. Biochim. Biophys. Acta 1979, 562, 534-545.
17. Cushman, M.; Kanamathareddy, S.; De-Clercq, E.; Schols, D.; Goldman, M. E.; Bowen, J. A. Synthesis and anti-HIV activities of low molecular weight aurintricarboxylic acid fragments and related compounds. J. Med. Chem. 1991, 34, 337-342.
18. Gan, Y. X.; Weaver, J. L.; Pine, P. S.; Zoon, K. C.; Aszalos, A. Aurin tricarboxylic acid, the anti-AIDS compound, prevents the binding of interferon-alpha to its receptor. Biochem. Biophys. Res. Commun. 1990, 172, 1298-303.
19. Moudgil, V. K.; Caradonna, V. M. Modulation of DNA binding of glucocorticoid receptor by aurintricarboxylic acid. J. Steroid Biochem. 1985, 23, 125-132.
20. Regan, J.; Ben-Sasson, S. A.; Sabatino, R.; Eilat, D.; Bruno, J. G.; D'Alisa, R.; Chang, M. N. Mimicry of Biological Macromolecules by Polyaromatic Anionic Compounds. J. Bioact. Compat. Polym. 1993, 8, 317-337.
21. Benezra, M.; Vlodavsky, I.; Yayon, A.; Bar-Shavit, R.; Regan, J.; Chang, M.; Ben-Sasson, S. A. Reversal of basic fibroblast growth factor-mediated autocrine cell transformation by aromatic anionic compounds. Cancer Res. 1992, 52, 5656-5662.
22. Miao, H.-Q.; Ornitz, D. M.; Eingorn, E.; Ben-Sasson, S. A.; Vlodavsky, I. Modulation of fibroblast growth factor-2 receptor binding, dimerization, signaling, and angiogenic activity by a synthetic heparin-mimicking polyanionic compound. J. Clin. Invest. 1997, 99, 1565-1575.
23. Benezra, M.; Ben-Sasson, S. A.; Regan, J.; Bar-Shavit, R.; Vlodavsky, I. Antiproliferative activity to vascular smooth muscle cells and receptor binding of heparin-mimicking polyaroamatic anionic compounds. Arterioscler. Thromb. 1994, 14, 1992-1999.
24. Burgess, W. H.; Maciag, T. The heparin-binding fibroblast growth factor family of proteins. Annu. Rev. Biochem. 1989, 58, 575-606.
25. Vlodavsky, I.; Bar-Shavit, R.; Ishai-Michaeli, R.; Bashkin, P.; Fuks, Z. Extracellular sequestration and release of fibroblast growth factor: a regulatory mechanism? TIBS 1991, 16, 268-271.
26. Bashkin, P. M.; Doctrow, S.; Svahn, C. M.; Folkman, J.; Vlodavsky, I. Basic fibroblast growth factor binds to subendothelial extracellular matrix and is released by heparanase and heparin like molecules. Biochemistry 1989, 28, 1737-1743.
27. Sandback-Pikas, D.; Li, J.-P.; Vlodavsky, I.; Lindahl, U. Substrate specificity of heparanases from human hepatoma and platelets. J. Biol. Chem. 1998, 273, 18770-18777.
28. Nakajima, M.; Irimura, T.; Nicolson, G. L. Heparanases and tumor metastasis. J. Cell Biochem. 1988, 36, 157-167.
29. Vlodavsky, I.; Eldor, A.; Haimovitz-Friedman, A.; Matzner, Y.; Ishai-Michaeli, R.; Levi, E.; Bashkin, P.; Lider, O.; Naparstek, Y.; Cohen, I. R.; Fuks, Z. Expression of heparanase by platelets and circulating cells of the immune system: Possible involvement in diapedesis and extravasation. Invasion Metastasis. 1992, 12, 112-127.
30. Vlodavsky, I.; Mohsen M.; Lider, O.; Svahn, C. M.; Ekre, H. P.; Vigoda, M.; Ishai-Michaeli, R.; Peretz, T. Inhibition of tumor metastasis by heparanase inhibiting species of heparin. Invasion Metastasis 1995, 14, 290-302.
31. Vlodavsky, I.; Friedmann, Y.; Elkin, M.; Aingorn, H.; Atzmon, A.; Ishai-Michaeli, R.; Bitan, M.; Pappo, O.; Peretz, T.; Michal, I.; Spector, L.; Pecker, I. Mammalian heparanase: a novel gene involved in tumor progression and metastasis. Nat. Med. 1999, 5, 793-802.
32. Hulett, M. D.; Freeman, C.; Hamdorf, B. J.; Baker, R. T.; Harris, M. J.; Parish, C. Cloning of mammalian heparanase, an important enzyme in tumor invasion and metastasis. Nat. Med. 1999, 5, 803-809.
33. Parish, C. R.; Coombe, D. R.; Jakobsen, K. B.; Underwood, P. A. Evidence that sulphated polysaccharides inhibit tumor metastasis by blocking tumor cell-derived heparanase. Int. J. Cancer. 1987, 40, 511-517.
34. Lider, O.; Baharav, E.; Mekori, Y.; Miller, T.; Naparstek, Y.; Vlodavsky, I. Cohen, I. R. Suppression of experimental autoimmune diseases and prolongation of allograft survival by treatment of animals with heparinoid inhibitors of T lymphocyte heparanase. J. Clin. Invest. 1989, 83, 752-756.
35. Wolfrom, M. L.; Shen Han, T. M. The sulfonation of chitosan. J. Am. Chem. Soc. 1959, 81, 1764-1766.
36. Vlodavsky, I. Preparation of extracellular matrixes produced by cultured corneal endothelial and PF-HR9 cells. Current Protocols in Cell Biology; John Wiley & Sons: New York, 1999; pp 10.4.1-10.4.14 (Suppl. 1).
37. Goshen, R.; Hochberg, A.; Korner, G.; Levi, E.; Ishai-Michaeli, R.; Elkin, M.; de Grot, N.; Vlodavsky, I. Purification and characterization of placental heparanase and its expresion by cultured cytotrophoblast. Mol. Hum. Reprod. 1996, 2, 679-684.
38. Bar-Ner, M.; Kramer, M.; Schirrmacher, V.; Ishai-Michaeli, R.; Fuks, Z.; Vlodavsky, I. Sequential degradation of heparan sulfate in the subendothelial extracellular matrix by highly metastatic lymphoma cells. Int. J. Cancer. 1985, 35, 483-491.
39. Ishai-Michaeli, R.; Svahn, C. M.; Weber, M.; Chajek-Shaul, T.; Korner, G.; Ekre, H. P.; Vlodavsky, I. Importance of size and sulfation of heparin in release of bFGF from the vascular endothelium and extracellular matrix. Biochemistry 1992, 31, 2080-2088.
40. Shapiro, G. A.; Huntzinger, S. W.; Wilson, J. E. Variation among commercial activated partial thromboplastin time reagents in response to heparin. Am. J. Clin. Pathol. 1977, 67, 477-480.
41. Finkel, E. Potential target found for antimetastasis drugs. Science 1999, 285, 33-34.