Probing the interactions of phosphosulfomannans with angiogenic growth factors by surface plasmon resonance

Journal of Medicinal Chemistry

Volumn 46, Issue 21, 2003, Pages 4601-4608

  Cochran, Siska ^a   Li, Caiping ^a   Fairweather, Jon K ^a   Kett, Warren C ^b   Coombe, Deirdre R ^b   Ferro, Vito ^a  

^a Progen Pharmaceuticals Limited   (Australia)

^b CURTIN UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOGENIC FACTOR; ANTINEOPLASTIC AGENT; FIBROBLAST GROWTH FACTOR 2; HEPARIN; MANNAN; PENTASACCHARIDE; PHOSPHORUS DERIVATIVE; PI 88; UNCLASSIFIED DRUG; VASCULOTROPIN;

ARTICLE; BINDING AFFINITY; BIOSENSOR; DEPHOSPHORYLATION; DEVICE; DRUG STRUCTURE; PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SURFACE PLASMON RESONANCE;

ANGIOGENESIS INDUCING AGENTS; BIOSENSING TECHNIQUES; CHEMISTRY, PHYSICAL; ENDOTHELIAL GROWTH FACTORS; FIBROBLAST GROWTH FACTOR 1; FIBROBLAST GROWTH FACTOR 2; HEPARIN; INTERCELLULAR SIGNALING PEPTIDES AND PROTEINS; KINETICS; LYMPHOKINES; MANNANS; OLIGOSACCHARIDES; PICHIA; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SULFATES; SURFACE PLASMON RESONANCE; VASCULAR ENDOTHELIAL GROWTH FACTOR A; VASCULAR ENDOTHELIAL GROWTH FACTORS;

EID: 0141992781     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030180y     Document Type: Article

References (47)

1. Folkman, J. Tumor angiogenesis: therapeutic implications. New Engl. J. Med. 1971, 285, 1182-1186.
2. Folkman, J. Angiogenesis in cancer, vascular, rheumatoid and other disease. Nat. Med. 1995, 1, 27-31.
3. Klohs, W. D.; Hamby, J. M. Antiangiogenic agents. Curr. Opin. Biotechnol. 1999, 10, 544-549.
4. Taraboletti, G.; Margosio, B. Antiangiogenic and antivascular therapy for cancer. Curr. Opin. Pharmacol. 2001, 1, 378-384.
5. Madhusudan, S.; Harris, A. L. Drug inhibition of angiogenesis. Curr. Opin. Pharmacol. 2002, 2, 403-414.
6. Boehm, T.; Folkman, J.; Browder, T.; O'Reilly, M. S. Antiangiogenic therapy of experimental cancer does not induce acquired drug resistance. Nature 1997, 390, 404-407.
7. Pluda, J. M. Tumor-associated angiogenesis: mechanisms, clinical implications, and therapeutic strategies. Semin. Oncol. 1997, 24, 203-218.
8. Parish, C. R.; Freeman, C.; Brown, K. J.; Francis, D. J.; Cowden, W. B. Identification of sulfated oligosaccharide-based inhibitors of tumor growth and metastasis using novel in vitro assays for angiogenesis and heparanase activity. Cancer Res. 1999, 59, 3433-3441.
9. Iversen, P. O.; Sorenson, D. R.; Benestad, H. B. Inhibitors of angiogenesis selectively reduce the malignant cell load in rodent models of human myeloid leukemias. Leukemia 2002, 16, 376-381.
10. Ferro, V.; Don, R. The development of the novel angiogenesis inhibitor PI-88 as an anticancer drug. Australas. Biotechnol. 2003, 13, 38-39.
11. Vlodavsky, I.; Friedmann, Y. Molecular properties and involvement of heparanase in cancer metastasis and angiogenesis. J. Clin. Invest. 2001, 108, 341-347.
12. Parish, C. R.; Freeman, C.; Hulett, M. D. Heparanase: a key enzyme involved in cell invasion. Biochim. Biophys. Acta 2001, 1471, M99-M108.
13. Wall, D.; Douglas, S.; Ferro, V.; Cowden, W.; Parish, C. Characterisation of the anticoagulant properties of a range of structurally diverse sulfated oligosaccharides. Thromb. Res. 2001, 103, 325-335.
14. Demir, M.; Iqbal, O.; Hoppensteadt, D. A.; Piccolo, P.; Ahmad, S.; Schultz, C. L.; Linhardt, R. J.; Fareed, J. Anticoagulant and antiprotease profiles of a novel natural heparinomimetic mannopentaose phosphate sulfate (PI-88). Clin. Appl. Thromb. Hemost. 2001, 7, 131-140.
15. Hembrough, T. A.; Ruiz, J. F.; Papathanassiu, A. E.; Green, S. J.; Strickland, D. K. Tissue factor pathway inhibitor inhibits endothelial cell proliferation via association with the very low density lipoprotein receptor. J. Biol. Chem. 2001, 276, 12241-12248.
16. Amirkhosravi, A.; Meyer, T.; Chang, J. Y.; Amaya, M.; Siddiqui, F.; Desai, H.; Francis, J. L. Tissue factor pathway inhibitor reduces experimental lung metastasis of B16 melanoma. Thromb. Haemost. 2002, 87, 930-936.
17. Ferro, V.; Li, C.; Fewings, K.; Palermo, M. C.; Linhardt, R. J.; Toida, T. Determination of the composition of the oligosaccharide phosphate fraction of Pichia (Hansenula) holstii NRRL Y-2448 phosphomannan by capillary electrophoresis and HPLC. Carbohydr. Res. 2002, 337, 139-146.
18. Yu, G.; Gunay, N. S.; Linhardt, R. J.; Toida, T.; Fareed, J.; Hoppensteadt, D. A.; Shadid, H.; Ferro, V.; Li, C.; Fewings, K.; Palermo, M. C. ; Podger, D. Preparation and anticoagulant activity of the phosphosulfomannan PI-88. Eur. J. Med. Chem. 2002, 37, 783-791.
19. Parolis, L. A. S.; Parolis, H.; Kenne, L.; Meldal, M.; Bock, K. The extracellular polysaccharide of Pichia (Hansenula) holstii NRRL Y-2448: the phosphorylated side chains. Carbohydr. Res. 1998, 309, 77-87.
20. Ferro, V.; Fewings, K.; Palermo, M. C.; Li, C. Large-scale preparation of the oligosaccharide phosphate fraction of Pichia holstii NRRL Y-2448 phosphomannan for use in the manufacture of PI-88. Carbohydr. Res. 2001, 332, 183-189.
21. Hileman, R. E.; Siegel, M. M.; Tabei, K.; Balagurunathan, K.; Linhardt, R. J. Isolation and characterization of β-cyclodextrin sulfates by preparative gradient polyacrylamide gel electrophoresis, capillary electrophoresis and electrospray ionization-mass spectrometry. Electrophoresis 1998, 19, 2677-2681.
22. Venkataraman, G.; Shriver, Z.; Raman, R.; Sasisekharan, R. Sequencing complex polysaccharides. Science 1999, 286, 537-542.
23. Juhasz, P.; Biemann, K. Mass spectrometric molecular-weight determination of highly acidic compounds of biological significance via their complexes with basic polypeptides. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4333-4337.
24. Juhasz, P.; Biemann, K. Utility of non-covalent complexes in the matrix-assisted laser desorption ionization mass spectrometry of heparin-derived oligosaccharides. Carbohydr. Res. 1995, 270, 131-147.
25. Siegel, M. M.; Tabei, K.; Kagan, M. Z.; Vlahov, I. R.; Hileman, R. E.; Linhardt, R. J. Polysulfated carbohydrates analyzed as ion-paired complexes with basic peptides and proteins using electrospray negative ionization mass spectrometry. J. Mass Spectrom. 1997, 32, 760-772.
26. Katsuraya, K.; Nakashima, H.; Yamamoto, N.; Uryu, T. Synthesis of sulfated oligosaccharide glycosides having high anti-HIV activity and the relationship between activity and chemical structure. Carbohydr. Res. 1999, 315, 234-242.
27. Wessel, H. P. Heparinoid mimetics. Topics Curr. Chem. 1997, 187, 215-239.
28. Karlsson, R. Real-time competitive kinetic analysis of interactions between low-molecular-weight ligands in solution and surface-immobilized receptors. Anal. Biochem. 1994, 221, 142-151.
29. Nieba, L.; Krebber, A.; Plückthun, A. Competition BIAcore for measuring true affinities: large differences from values determined from binding kinetics. Anal. Biochem. 1996, 234, 155-165.
30. Karlsson, R.; Roos, H.; Fägerstam, L.; Persson, B. Kinetics and concentration analysis using BIA technology. Methods: A Companion to Methods Enzymol. 1994, 6, 99-110.
31. Brown, K. J.; Maynes, S. F.; Bezos, A.; Maguire, D. J.; Ford, M. D.; Parish, C. R. A novel in vitro assay for human angiogenesis. Lab. Invest. 1996, 75, 539-555.
32. Pesenti, E.; Sola, F.; Mongelli, N.; Grandi, M.; Spreafico, F. Suramin prevents neovascularisation and tumour growth through blocking of basic fibroblast growth factor activity. Br. J. Cancer 1992, 66, 367-372.
33. Copeland, R. A.; Ji, H.; Halfpenny, A. J.; Williams, R. W.; Thompson, K. C.; Herber, W. K.; Thomas, K. A.; Bruner, M. W.; Ryan, J. A.; Marquis-Omer, D.; Sanyal, G.; Sitrin, R. D.; Yamazaki, S.; Middaugh, C. R. The structure of human acidic fibroblast growth factor and its interaction with heparin. Arch. Biochem. Biophys. 1991, 289, 53-61.
34. DiGabriele, A. D.; Lax, I.; Chen, D. I.; Svahn, C. M.; Jaye, M.; Schlessinger, J.; Hendrickson, W. A. Structure of a heparin-linked biologically active dimer of fibroblast growth factor. Nature 1998, 393, 812-817.
35. Venkataraman, G.; Shriver, Z.; Davis, J. C.; Sasisekharan, R. Fibroblast growth factors 1 and 2 are distinct in oligomerization in the presence of heparin-like glycosaminoglycans. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 1892-1897.
36. Li, L. Y.; Seddon, A. P. Fluorospectrometric analysis of heparin interaction with fibroblast growth factors. Growth Factors 1994, 11, 1-7.
37. Mach, H.; Middaugh, C. R. Probing the affinity of polyanions for acidic fibroblast growth factor by unfolding kinetics. Arch. Biochem. Biophys. 1994, 309, 36-42.
38. Kamei, K.; Wu, X.; Xu, X.; Minami, K.; Huy, N. T.; Takano, R.; Kato, H.; Hara, S. The analysis of heparin-protein interactions using evanescent wave biosensor with regioselectively desulfated heparins as the ligands. Anal. Biochem. 2001, 295, 203-213.
39. Lee, M. K.; Lander, A. D. Analysis of affinity and structural selectivity in the binding of proteins to glycosaminoglycans: development of a sensitive electrophoretic approach. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 2768-2772.
40. Satoh, A.; Matsumoto, I. Ligand-binding properties of annexin from Caenorhabditis elegans (annexin XVI, Nex-1). Anal. Biochem. 1999, 275, 268-270.
41. Cochran, S.; Li, C.; Ferro, V. Unpublished results.
42. After submission of this paper, the Ki for inhibition of FGF-2 binding to immobilized heparin by PI-88 (10.3 nM) was reported: Francis, D. J.; Parish, C. R.; McGarry, M.; Santiago, F. S.; Lowe, H. C.; Brown, K. J.; Bingley, J. A.; Hayward, I. P.; Cowden, W. B.; Campbell, J. H.; Campbell, G. R.; Chesterman, C. N.; Khachigian, L. M. Blockade of vascular smooth muscle cell proliferation and intimal thickening after balloon injury by the sulfated oligosaccharide PI-88: phosphomannopentaose sulfate directly binds FGF-2, blocks cellular signaling, and inhibits proliferation. Circ. Res. 2003, 92, e70-77.
43. Kanyo, Z. F.; Christianson, D. W. Biological recognition of phosphate and sulfate. J. Biol. Chem. 1991, 266, 4264-4268.
44. Luecke, H.; Quiocho, F. A. High specificity of a phosphate transport protein determined by hydrogen bonds. Nature 1990, 347, 402-406.
45. Thatcher, G. R. J.; Cameron, D. R.; Nagelkerke, R.; Schmitke, J. Selective hydrogen bonding as a mechanism for differentiation of sulfate and phosphate at biomolecular receptor sites. J. Chem. Soc., Chem. Commun. 1992, 386-388.
46. Van Boeckel, C. A. A.; Petitou, M. The unique antithrombin III binding domain of heparin: a lead to new synthetic antithrombotics. Angew. Chem., Int. Ed. Engl. 1993, 32, 1671-1818.
47. Foxall, C.; Wei, Z.; Schaefer, M. E.; Casabonne, M.; Fugedi, P.; Peto, C.; Castellot, J. J., Jr; Brandley, B. K. Sulfated malto-oligosaccharides bind to basic FGF, inhibit endothelial cell proliferation, and disrupt endothelial cell tube formation J. Cell. Physiol. 1996, 168, 657-667.