A basic compositional requirement of agents having heparin-like cell-modulating activities

Biochemical Pharmacology

Volumn 54, Issue 1, 1997, Pages 149-157

  Weisz, Paul B ^a,b,d   Joullié, Madeleine M ^a   Hunter, Cathrine M ^b   Kumor, Kathleen M ^b   Zhang, Zhongda ^a   Levine, Elliot ^c   Macarak, Edward ^a   Weiner, David ^a   Barnathan, Elliot S ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

^c WISTAR INSTITUTE   (United States)

^d NONE   (United States)

Author keywords

Cell modulation activity; Cyclodextrin sulfate; Heparin; Structural requirement

Indexed keywords

BETA CYCLODEXTRIN; CYCLODEXTRIN; CYCLODEXTRIN DERIVATIVE; HEPARIN;

ANGIOGENESIS; ANIMAL CELL; ARTICLE; CELL GROWTH; CELL PROLIFERATION; CELL PROTECTION; COMPLEX FORMATION; CONTROLLED STUDY; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN T CELL LEUKEMIA VIRUS; MOLECULAR WEIGHT; NONHUMAN; PRIORITY JOURNAL; SMOOTH MUSCLE; STRUCTURE ACTIVITY RELATION; SULFATION; VIRUS INFECTION;

ALCIAN BLUE; ANTI-HIV AGENTS; CELL DIVISION; CELL MEMBRANE; CELLS, CULTURED; CYCLODEXTRINS; DEXTRAN SULFATE; DRUG DESIGN; ENDOTHELIUM, VASCULAR; FIBROBLAST GROWTH FACTORS; HEPARIN; HUMANS; MUSCLE, SMOOTH, VASCULAR; NEOVASCULARIZATION, PHYSIOLOGIC; PROTAMINES; SULFATES;

EID: 0030813917     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)00157-3     Document Type: Article

References (52)

1. Lindahl U, Heparin: Chemical and biological properties, clinical applications. In: Heparin (Eds. Lane DA and Lindahl U), pp. 159-189. Edward Arnold, London, 1989.
2. van Boeckel CAA and Petitou P, The unique antithrombin III binding domain of heparin: A lead to new synthetic antithrombics. Angew Chem Int Ed Engl 32: 1671-1690, 1993.
3. Jaques LB, Heparin - Anionic polyelectrolyte drugs. Pharmacol Rev 31: 99-166, 1980.
4. Jaques LB, Heparin: An old drug with a new paradigm. Science 206: 528-533, 1979.
5. Lindahl U, Lindhold K, Spillmann D and Kjellen L, More to heparin than anticoagulation. Thromb Res 75: 1-32, 1994.
6. Hasdai D, Blumber N and Battler A, The non-antithrombic therapeutic potential of heparin and related heparinoids in cardiovascular diseases. Coron Artery Dis 5: 81-91, 1994.
7. Folkman J, Langer R, Linhardt RJ, Haudenschild C and Taylor S, Angiogenesis inhibition and tumor regression caused by heparin or heparin fragment in the presence of cortisone. Science 221: 719-725, 1983.
8. Folkman J, Weisz PB, Joullié MM, Li WW and Ewing WR, Control of angiogenesis with synthetic heparin substitutes. Science 243: 1490-1493, 1989.
9. Weisz PB, Herrmann HC, Joullié MM, Kumor K, Levine EM, Macarak EJ and Weiner D, Angiogenesis and GAG-mimics. In: Angiogenesis - Key Principles-Science-Technology-Medicine (Eds. Steiner R and Weisz PB), pp. 107-117, Langer R. Birkhaeuser, Basel, 1992.
10. Gilbert EE, The reaction of sulfur trioxide, and its adducts, with organic compounds. Chem Rev 62: 549-581, 1962.
11. Shing Y, Folkman J, Weisz PB, Joullie MM and Ewing WR, Affinity of fibroblast growth factors for β-cyclodextrin tetradecasulfate. Anal Biochem 185: 108-111, 1990.
12. Crum R, Szabo S and Folkman J, A new class of steroids inhibits angiogenesis in the presence of heparin or heparin fragments. Science 230: 1375-1378, 1985.
13. Taylor S and Folkman J, Protamine is an inhibitor of angiogenesis. Nature 297: 307-312, 1982.
14. Thornton SC, Mueller SN and Levine EM, Human endothelial cells: Use of heparin in cloning and long-term serial cultivation. Science 222: 623-625, 1983.
15. Herrmann HC, Okada SS, Hozakowska E, LeVeen RF, Golden MA, Tomaszewski JE, Weisz PB and Barnathan ES, Inhibition of smooth muscle cell proliferation and experimental angioplasty restenosis by β-cyclodextrin tetradecasulfate. Arterioscler Thromb 13: 924-931, 1993.
16. Okada SS, Kuo A, Muttreja MR, Hozakowska E, Weisz PB and Bamathan ES, Inhibition of human vascular smooth muscle cell migration and proliferation by β-cyclodextrin tetradecasulfate. J Pharmacol Exp Ther 273: 948-954, 1995.
17. Weiner DB, Williams WV, Weisz PB and Greene MI, Synthetic cyclodextrin derivatives inhibit HIV infection in vitro. Pathobiology 60: 206-212, 1992.
18. Grant AC, Linhardt RJ, Fitzgerald GL, Park JJ and Langer R, Metachromatic activity of heparin and heparin fragments. Anal Biochem 137: 25-32, 1984.
19. Bachinsky WB, Barnathan ES, Liu H, Okada SS, Kuo A, Raghunath PN, Muttreja M, Caron RJ, Tomaszewski JE, Weisz PB and Golden MA, Sustained inhibition of intimai thickening. In vitro and in vivo effects of polymeric β-cyclodextrin sulfate. J Clin Invest 96: 2583-2592, 1995.
20. Gimbrone MA, Cotran RS, Leapman SB and Folkman J, Tumor growth and neovascularization: An experimental model using the rabbit cornea. J Natl Cancer Inst 52: 413-427, 1974.
21. Clowes AW and Karnovsky MJ, Suppression by heparin of smooth muscle cell proliferation in injured arteries. Nature 265: 625-626, 1977.
22. Ito M, Baba M, Sato A, Pauwels R, DeClercq E and Shigeta S, Inhibitory effect of dextran sulfate and heparin on the replication of human immunodeficiency virus (HIV) in vitro. Antiviral Res 7: 361-367, 1987.
23. Flexner C, Barditch-Crovo PA, Kornhauser DM, Farzadegan H, Nerhood LJ, Chaisson RE, Bell KM, Lorentsen KJ, Hendrix CW, Petty BG and Lietman PS, Pharmacokinetics, toxicity, and activity of intravenous dextran sulfate in human immunodeficiency virus infection. Antimicrob Agents Chemother 35: 2544-2550, 1991.
24. Scott JE and Dorling J, Differential staining of acid glycosaminoglycans (mucopolysaccharides) by Alcian Blue in salt solutions. Histochemie 5: 221-225, 1965.
25. Snow AD, Willmer J and Kisilevsky R, Sulfated glycosaminoglycans: A common constituent of all amyloids. Lab Invest 56: 120-123, 1987.
26. Klein MD, Drongowsi RA, Linhardt RL and Langer RS, A colorimetric assay for chemical heparin in plasma. Anal Biochem 124: 59-64, 1982.
27. Eckert G and Gutmann F, Electochemistry of some drug interactions. J Electroanal Chem Interfacial Electrochem 62: 267-272, 1975.
28. Wiedenhof N, Lammers JNJJ and van Panthalon van Eck CL, Cyclodextrin-epichlorhydrin resins. Preparation and analysis. Stärke 21: 119-122, 1969.
29. Höök M, Kjellén L, Johansson S and Robinson J, Cell-surface glycosaminoglycans. Annu Rev Biochem 53: 847-869, 1984.
30. Lubec G, Interactions of N-CAM with heparin-like molecules. Nature 323: 743-744, 1986.
31. Lindahl U and Höök M, Glycosaminoglycans and their binding to biological macromolecules. Annu Rev Biochem 47: 385-417, 1978.
32. Nader HB, Buonassisi V, Colburn P and Dietrich CP, Heparin stimulates the synthesis and modifies the sulfation pattern of heparan sulfate proteoglycan from endothelial cells. J Cell Physiol 140: 305-310, 1989.
33. Mutoh S, Clowes MM and Clowes AW, Heparin increased cell membrane-associated heparan sulfate proteoglycan in balloon-injured rat carotid artery. J Vasc Res 30: 161-168, 1993.
34. Yagon A, Klagsbrun M, Esko JD, Leder P and Ornitz DM, Cell surface, heparin-like molecules are required for binding of basic fibroblast growth factor to its high affinity receptor. Cell 64: 841-848, 1991.
35. Lobb RR, Clinical applications of heparin-binding growth factors. Eur J Clin Invest 18: 321-336, 1988.
36. Castellot JJ, Structural determinants of the capacity of heparin to inhibit the proliferation of vascular smooth muscle cells. J Cell Physiol 120: 315-320, 1984.
37. Sudhalter L, Folkman J, Svahn CM, Bergendahl K and D'Amore PA, Importance of size, sulfation and anticoagulant activity in the potentiation of acidic fibroblast growth factor by heparin. J Biol Chem 264: 6892-6897, 1989.
38. Jaques LB, Glucosaminoglycans as polyelectrolytes: Rejuvenation of original concepts. Semin Thromb Hemost 17 (Suppl 1): 1-4, 1991.
39. Margalit H, Fischer N and Ben-Sasson SA, Comparitive analysis of structurally defined heparin binding sequences reveals distinct spatial distribution of basic residues. J Biol Chem 268: 19228-19231, 1993.
40. Glimelius B, Busch C and Höök M, Binding of heparin on the surface of cultured human endothelial cells. Thromb Res 12: 773-782, 1978.
41. Sommer A and Rifkin DB, Interaction of heparin with human basic FGF: Protection of the angiogenic protein from proteolytic degradation by glycosaminoglycan. J Cell Physiol 138: 215-220, 1989.
42. Mach H, Volkin DB, Burke CJ, Middaugh CR, Linhardt RJ, Fromm JR, Loganathan D and Mattson L, Nature of the interaction of heparin with acidic fibroblast growth factor. Biochemistry 32: 5480-5489, 1993.
43. Danesi R, Del Bianchi S, Soldani P, Campagni A, La Rocca RV, Myers CE, Paparelli A and Del Tacca M, Suramin inhibits bFGF-induced endothelial cell proliferation and angiogenesis in the chick chorioallantoic membrane. Br J Cancer 68: 932-938, 1993.
44. Middaugh CR, Mach H, Burke CJ, Volkin DB, Dabora JM, Tsai PK, Bruner MW, Ryan JA and Marfia KE, Nature of the interaction of growth factors with suramin. Biochemistry 31: 9016-9024, 1992.
45. Swain S, Wellstein A, Parker B, Lippman M, Steakley C and DeLap R, Heparin-binding growth factor blockade with pentosan polysulfate. Ann NY Acad Sci 698: 63-70, 1993.
46. Parker BW, Swain SM, Zugmaier G, Lippman ME and Wellstein A, Detectable inhibition of heparin-binding growth factor activity in sera from patients treated with pentosan polysulfate. J Natl Cancer Inst 85: 1068-1073, 1993.
47. McKee TC, Cardellina JH, Tischler M, Snader KM and Boyd MR, Ibisterol sulfate, a novel HIV-inhibitory sulfated sterol from the deep water sponge Topsentia SP. Tetrahedron Lett 34: 389-393, 1993.
48. Volkin DB, Verticelli AM, Marfia KE, Burke CJ, Mach H and Middaugh CR, Sucralfate and soluble sucrose octasulfate bind and stabilize acidic fibroblast growth factor. Biochim Biophys Acta 1203: 18-26, 1993.
49. Vischer P and Buddeckee E, Different action of heparin and fucoidan on arterial smooth muscle cell proliferation and thrombospondin and fibronectin metabolism. Eur J Cell Biol 56: 407-414, 1991.
50. Hoffman R and Sykes D, Inhibition of binding of basic fibroblast growth factor to low and high affinity receptors by carrageenans. Biochem Pharmacol 45: 2348-2351, 1993.
51. Ogamo A, Nagai A and Nagasawa K, Binding of heparin fractions and other polysulfated polysaccharides to plasma fibronectin: Effects of molecular size and degree of sulfation of polysaccharides. Biochim Biophys Acta 841: 30-41, 1985.
52. Szejtli J, Cyclodextrins and Their Inclusion Complexes. Akademiai Kiado, Budapest, 1982.