Bioactivity screening of partially desulfated low-molecular-weight heparins: A structure/activity relationship study

Glycobiology

Volumn 21, Issue 9, 2011, Pages 1194-1205

  Roy, Sucharita ^a   Lai, Hsuanchi ^a   Zouaoui, Radouane ^a   Duffner, Jay ^a   Zhou, He ^a   P Jayaraman, Lakshmi ^a   Zhao, Ganlin ^a   Ganguly, Tanmoy ^a   Kishimoto, Takashi K ^a   Venkataraman, Ganesh ^a  

^a Momenta Pharmaceuticals Inc   (United States)

Author keywords

Angiogenic growth factors; anti tumor efficacy; P selectin; partially desulfated heparins; SAX HPLC

Indexed keywords

FIBROBLAST GROWTH FACTOR 2; LOW MOLECULAR WEIGHT HEPARIN; POLYSACCHARIDE; PROTEOHEPARAN SULFATE; STROMAL CELL DERIVED FACTOR 1ALPHA;

ACETYLATION; AMINO TERMINAL SEQUENCE; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CHEMICAL MODIFICATION; DESULFATION; DOSE RESPONSE; DRUG DESIGN; DRUG EFFICACY; DRUG PROTEIN BINDING; FEMALE; IN VITRO STUDY; IN VIVO STUDY; LOW DRUG DOSE; MELANOMA B16; METASTASIS INHIBITION; MOUSE; NONHUMAN; PRIORITY JOURNAL; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING SITES; CHEMOKINE CXCL12; DRUG DESIGN; FEMALE; FIBROBLAST GROWTH FACTOR 2; HEPARIN, LOW-MOLECULAR-WEIGHT; HIGH-THROUGHPUT SCREENING ASSAYS; HYDROLYSIS; LUNG NEOPLASMS; MELANOMA, EXPERIMENTAL; MEMBRANE GLYCOPROTEINS; MICE; MICE, INBRED C57BL; NEOPLASM TRANSPLANTATION; NEOVASCULARIZATION, PATHOLOGIC; P-SELECTIN; PROTEIN BINDING; SMALL MOLECULE LIBRARIES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFATES; SURFACE PLASMON RESONANCE; VASCULAR ENDOTHELIAL GROWTH FACTOR A;

MURINAE;

EID: 79959220996     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cwr053     Document Type: Article

References (34)

1. Ahmed T, Gonzalez BJ, Danta I. 1999. Prevention of exercise-induced bronchoconstriction by inhaled low-molecular-weight heparin. Am J Respir Crit Care Med. 160(2):576-581. (Pubitemid 29380675)
2. Bergamaschini L, Donarini C, Rossi E, De Luigi A, Vergani C, De Simon MG. 2002. Heparin attenuates cytotoxic and inflammatory activity of Alzheimer amyloid-β in vitro. Neurobiol Aging. 23(4):531-536. (Pubitemid 34495463)
3. Borsig L. 2007. Antimetastatic activities of modified heparins: Selectin inhibition by heparin attenuates metastasis. Semin Thromb Hemost. 33:540-546. (Pubitemid 47105745)
4. Borsig L, Wong R, Feramisco J, Nadeau DR, Varki NM, Varki A. 2001. Heparin and cancer revisited: Mechanistic connections involving platelets, P-selectin, carcinoma mucins, and tumor metastasis. Proc Natl Acad Sci USA. 98(6):3352-3357. (Pubitemid 32220849)
5. Capila I, Linhardt RJ. 2002. Heparin-protein interactions. Angew Chem Int Ed. 41(3):391-412.
6. Casu B, Guerrini M, Guglieri S, Naggi A, Perez M, Torri G, Cassinelli G, Ribatti D, Carminati P, Giannini G, et al. 2004. Undersulfated and glycol-split heparins endowed with antiangiogenic activity. J Med Chem. 47(4):838-848. (Pubitemid 38176787)
7. Casu B, Naggi A, Torri G. 2002. Chemical derivatization as a strategy to study structure-activity relationships of glycosaminoglycans. Semin Thromb Hemostat. 28(4):335-342. (Pubitemid 34971920)
8. Casu B, Vlodavsky I, Sanderson RD. 2007. Non anti-coagulant heparins and inhibition of cancer. Pathophysiol Haemost Thromb. 36(3-4):195-203.
9. Conrad HE. 1998. Heparin Binding Proteins. San Diego (CA): Academic Press. p. 7-22.
10. Esko JD. 1999. Glycosaminoglycan binding proteins. In: Varki A, editor. Essentials of Glycobiology. Cold Spring Harbor (NY): Cold Spring Harbor Laboratory.
11. Esko JD, Lindahl U. 2001. Molecular diversity of heparan sulfate. J Clin Invest. 108(2):169-173. (Pubitemid 32656238)
12. Foxall C, Holme KR, Liang W, Wei Z. 1995. An enzyme-linked immunosor-bent assay using biotinylated heparan sulfate to evaluate the interactions of heparin-like molecules and basic fibroblast growth factor. Anal Biochem. 231(2):366-373.
13. Garg H, Yu L, Hales CA, Toida T, Islam T, Linhardt RJ. 2003. Sulfation patterns in heparin and heparan sulfate: Effects on the proliferation of bovine pulmonary artery smooth muscle cells. Biochim Biophys Acta. 1639 (3):225-231. (Pubitemid 37421429)
14. Guimond S, Maccarana M, Olwin BB, Lindahl U, Rapraeger AC. 1993. Activating and inhibitory heparin sequences for FGF-2 (basic FGF). J Biol Chem. 268(32):23906-23914.
15. Inoue Y, Nagasawa K. 1976. Selective N-desulfation of heparin with dimethyl sulfoxide containing water or methanol. Carbohydr Res 46 (1):87-95.
16. Jaseja M, Rej RN, Sauriol F, Perlin AS. 1989. Novel regio-and stereo-selective modifications of heparin in alkaline solution. Nuclear magnetic resonance spectroscopic evidence. Can J Chem. 67:1449-1456. (Pubitemid 19248003)
17. Karlsson R. 1994. Real-time competitive kinetic analysis of interactions between low molecular weight ligands in solution and surface immobilized receptors. Anal Biochem. 221:142-151. (Pubitemid 24262784)
18. Kim SK, Vaishali B, Lee E, Lee S, Lee Y-K, Kumar TS, Moon HT, Byun Y. 2006. Oral delivery of chemical conjugates of heparin and deoxycholic acid in aqueous formulation. Thromb Res. 117(4):419-427. (Pubitemid 43197494)
19. Kutteh WH. 1996. Antiphospholipid antibody-associated recurrent pregnancy loss: Treatment with heparin and low-dose aspirin is superior to low-dose aspirin alone. Am J Obstet Gynecol. 174(5):1584-1589. (Pubitemid 26165282)
20. Lever R, Page CP. 2002. Novel drug development opportunities for heparin. Nat Rev Drug Discovery. 1(2):140-148. (Pubitemid 41646521)
21. Levvy GA, McAllan A. 1959. The N-acetylation and estimation of hexosa-mines. Biochem J. 73:127-132.
22. Lin Y-L, Lei H-Y, Lin Y-S, Yeh T-M, Chen S-H, Liu H-S. 2002. Heparin inhibits dengue-2 virus infection of five human liver cell lines. Antiviral Res. 56(1):93-96. (Pubitemid 35248112)
23. Linhardt RJ. 2003. Heparin: Structure and activity. J Med Chem. 46 (13):2551-2564.
24. Ma Q, Cornelli U, Hanin I, Jeske WP, Linhardt RJ, Walenga JM, Fareed J, Lee JM. 2007. Heparin oligosaccharides as potential therapeutic agents in senile dementia. Curr Pharm Des. 13(15):1607-1616. (Pubitemid 46860863)
25. Matsuo M, Takano R, Kamei-Hayashi K, Hara S. 1993. A novel regioselec-tive desulfation of polysaccharide sulfates: Specific 6-O-desulfation with N, O-bis (trimethylsilyl) acetamide. Carbohydr Res. 241:209-215. (Pubitemid 23085632)
26. Naggi A, Torri G, Casu B, Pangrazzi J, Abbadini M, Zametta M, Donati MB, Lansen J, Maffrand JP. 1987. Supersulfated heparin fragments, a new type of low-molecular weight heparin. Biochem Pharm. 36(12): 1895-1900.
27. Presta M, Leali D, Stabile H, Ronca R, Camozzi M, Coco L, Moroni E, Liekens S, Rusnati M. 2003. Heparin derivatives as angiogenesis inhibitors. Curr Pharm Des. 9(7):553-566. (Pubitemid 36221723)
28. Powell AK, Yates EA, Fernig DG, Turnbull JE. 2004. Interactions of heparin/heparan sulfate with proteins: Appraisal of structural factors and experimental approaches. Glycobiology. 14(4):17R-30R. (Pubitemid 38628108)
29. Sasisekharan R, Shriver Z, Sundaram M, Venkataraman G. 2003. Analytical techniques for the characterization and sequencing of glycosaminoglycans. In: Wong C-H, editor. Carbohydrate Based Drug Discovery. Weinheim: Wiley VCH. p. 517-539.
30. Tyrrell DJ, Horne AP, Holme KR, Preuss JM, Page CP. 1999. Heparin in inflammation: Potential therapeutic applications beyond anticoagulation. Adv Pharmacol. 46:151-208.
31. Vogt AM, Pettersson F, Moll K, Jonsson C, Normark J, Ribacke U, Egwang TG, Ekre H-P, Spillmann D, Chen Q, et al. 2006. Release of sequestered malaria parasites upon injection of a glycosaminoglycan. PLoS Pathog. 2 (9):853-863.
32. Volpi N. 2006. Therapeutic applications of glycosaminoglycans. Curr Med Chem. 13(15):1799-1810. (Pubitemid 43871757)
33. Wei M, Gao Y, Tian M, Li N, Hao S, Zeng X. 2005. Selectively desulfated heparin inhibits P-selectin mediated adhesion of human melanoma cells. Cancer Res. 229(1):123-26. (Pubitemid 41262548)
34. Wessel HP, Hosang M, Tschopp TB, Weimann B-J. 1990. Heparin, carboxyl reduced sulfated heparin, and Trestatin A sulfate. Antiproliferative and anticoagulant activities. Carbohydrate Res. 204:131-139.