메뉴 건너뛰기




Volumn 9, Issue 28, 2003, Pages 2323-2335

Synthetic oligosaccharides as heparin-mimetics displaying anticoagulant properties

Author keywords

Anticoagulant; Antithrombin III; Antithrombotic; Bis aldonic acid amides; Factor Xa; Heparin; Heparin pentasaccharide; PI 88; Thrombin

Indexed keywords

ANTICOAGULANT AGENT; ANTITHROMBIN; APROSULATE; BLOOD CLOTTING FACTOR 10A INHIBITOR; CARBOHYDRATE DERIVATIVE; FONDAPARINUX; GLUCONIC ACID; GLUCOSE DERIVATIVE; GLUCURONIC ACID; HEMATOLOGIC AGENT; HEPARIN; IDURONIC ACID; LACTOBIONIC ACID; LOW MOLECULAR WEIGHT HEPARIN; LW 10114; LW 10121; LW 10125; LW 10168; LW 10244; MALTOHEPTAOSE; MALTOHEXAOSE; MALTOPENTAOSE; MALTOSE; MALTOTRIOSE; N (2 NAPHTHYLSULFONYL)GLYCYL 4 AMIDINOPHENYLALANINE PIPERIDIDE; OLIGOSACCHARIDE; PENTASACCHARIDE; PI 88; THROMBIN INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 0141886345     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/1381612033453929     Document Type: Review
Times cited : (42)

References (66)
  • 1
    • 0141965374 scopus 로고    scopus 로고
    • Carbohydrates with anticoagulant and antithrombotic properties
    • Witczak, ZJ, Nieforth, KA, editors. New York: Marcel Dekker, INC
    • Susanne A. Carbohydrates with anticoagulant and antithrombotic properties. In: Witczak, ZJ, Nieforth, KA, editors. Carbohydrates in drug design. New York: Marcel Dekker, INC. 1997,
    • (1997) Carbohydrates in Drug Design
    • Susanne, A.1
  • 2
    • 0008350024 scopus 로고
    • The purification of heparin and its chemical and physiological reactions
    • Howell HW. The purification of heparin and its chemical and physiological reactions. Bull Johns Hopkins Hosp 1928; 42: 199,
    • (1928) Bull. Johns Hopkins Hosp. , vol.42 , pp. 199
    • Howell, H.W.1
  • 3
    • 0001582868 scopus 로고
    • A proton magnetic resonance spectral study of heparin. L-Iduronic acid residues in commercial heparins
    • Perlin AS, Mazurek M, Jaques LB. and Kavanaugh LW. A proton magnetic resonance spectral study of heparin. L-Iduronic acid residues in commercial heparins. Carbohydr Res 1968; 7: 369-379.
    • (1968) Carbohydr. Res. , vol.7 , pp. 369-379
    • Perlin, A.S.1    Mazurek, M.2    Jaques, L.B.3    Kavanaugh, L.W.4
  • 4
    • 0001668795 scopus 로고
    • Evidence for a 3-O-sulfated D-Glucosamine residue in the antithrombin-binding sequence of heparin
    • Lindahl U, Bäckström G, Thunberg L. and Leder IG, Evidence for a 3-O-sulfated D-Glucosamine residue in the antithrombin-binding sequence of heparin. Proc Natl Acad Sci 1980; 77: 6551-6555.
    • (1980) Proc. Natl. Acad. Sci. , vol.77 , pp. 6551-6555
    • Lindahl, U.1    Bäckström, G.2    Thunberg, L.3    Leder, I.G.4
  • 5
    • 0022368634 scopus 로고
    • Contribution of monosaccharide residues in heparin binding to antithrombin III
    • Atha DH, Lormeau J-C, Petitou M, Rosenberg RD. and Choay J. Contribution of monosaccharide residues in heparin binding to antithrombin III. Biochem 1985; 24: 6723-6729.
    • (1985) Biochem. , vol.24 , pp. 6723-6729
    • Atha, D.H.1    Lormeau, J.-C.2    Petitou, M.3    Rosenberg, R.D.4    Choay, J.5
  • 7
    • 0025759637 scopus 로고
    • Heparin: An important drug enters its seventh decade
    • Linhardt RJ. Heparin: an important drug enters its seventh decade. Chem Indust 1991; 2: 45-50.
    • (1991) Chem. Indust. , vol.2 , pp. 45-50
    • Linhardt, R.J.1
  • 8
    • 0003024732 scopus 로고
    • Biosynthesis and related polysaccharides
    • Lane, DA, Lindahl U. editors. London: Edward Arnold
    • Lindahl U. Biosynthesis and related polysaccharides. In: Lane, DA, Lindahl U. editors. Heparin - chemical and biological properties, clinical applications. London: Edward Arnold; 1989; p. 159-189.
    • (1989) Heparin - Chemical and Biological Properties, Clinical Applications , pp. 159-189
    • Lindahl, U.1
  • 9
  • 10
    • 0029918642 scopus 로고    scopus 로고
    • Clinical applications of new antithrombotic agents
    • Beijering RJR, Cate H. and Cate JW. Clinical applications of new antithrombotic agents. Ann Hematol 1996; 72: 177-183.
    • (1996) Ann. Hematol. , vol.72 , pp. 177-183
    • Beijering, R.J.R.1    Cate, H.2    Cate, J.W.3
  • 11
    • 33748233635 scopus 로고
    • The unique antithrombin III binding domain of heparin: A lead to new synthetic antithrombotics
    • van Boeckel CAA and Petitou M. The unique antithrombin III binding domain of heparin: A lead to new synthetic antithrombotics. Angew Chem Int Ed Engl 1993; 32: 1671-1690.
    • (1993) Angew Chem. Int. Ed. Engl. , vol.32 , pp. 1671-1690
    • van Boeckel, C.A.A.1    Petitou, M.2
  • 12
    • 0142000162 scopus 로고    scopus 로고
    • Synthetic heparin-like antithrombotics
    • van Boeckel CAA. Synthetic heparin-like antithrombotics. Pure & Appl Chem 1997; 69: 389-394.
    • (1997) Pure & Appl. Chem. , vol.69 , pp. 389-394
    • van Boeckel, C.A.A.1
  • 13
    • 0030952743 scopus 로고    scopus 로고
    • Biochemical and pharmacologic rationale for the development of a synthetic heparin pentasaccharide
    • Walenga JM, Jeske W, Bara L, Samama MM. and Fareed J. Biochemical and pharmacologic rationale for the development of a synthetic heparin pentasaccharide. Thromb Res 1997; 86: 1-36.
    • (1997) Thromb. Res. , vol.86 , pp. 1-36
    • Walenga, J.M.1    Jeske, W.2    Bara, L.3    Samama, M.M.4    Fareed, J.5
  • 14
  • 15
    • 0019391466 scopus 로고
    • Structural studies on a biologically active hexasaccharide obtained from heparin
    • Choay J, Lormeau J-C, Petitou M, Sinaÿ P. and Fareed J. Structural studies on a biologically active hexasaccharide obtained from heparin. Anti NY Acad Sci 1981; 370: 644-649.
    • (1981) Ann. NY Acad. Sci. , vol.370 , pp. 644-649
    • Choay, J.1    Lormeau, J.-C.2    Petitou, M.3    Sinaÿ, P.4    Fareed, J.5
  • 16
    • 0020108082 scopus 로고
    • Further characterization of the antithrombin-binding sequence in heparin
    • Thumberg L, Bäckström G. and Lindahl U. Further characterization of the antithrombin-binding sequence in heparin. Carbohydr Res 1982; 100: 393-410.
    • (1982) Carbohydr. Res. , vol.100 , pp. 393-410
    • Thumberg, L.1    Bäckström, G.2    Lindahl, U.3
  • 17
    • 0020544564 scopus 로고
    • The antithrombin-binding sequence in heparin. Identification of an essential 6-O-sulfate group
    • Lindahl U, Bäckström G. and Thunberg L. The antithrombin-binding sequence in heparin. Identification of an essential 6-O-sulfate group. J Biol Chem 1983; 258: 9826-9830.
    • (1983) J. Biol. Chem. , vol.258 , pp. 9826-9830
    • Lindahl, U.1    Bäckström, G.2    Thunberg, L.3
  • 20
    • 0023049220 scopus 로고
    • Synthesis of heparin fragments. A chemical synthesis of the pentasaccharide
    • Petitou M, Duchaussoy P, Lederman I, Choay J, Sinaÿ P, Jacquinet J-C, et al. Synthesis of heparin fragments. A chemical synthesis of the pentasaccharide O-(2-deoxy-2-sulfamido-6-O-sulfo-α-D-glucopyranosyl)-(1 → 4)-O-(β-D-glucopyranosyluronic acid)-(1 → 4)-O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-α-D-glucopyranosyl)-(1 → 4)-O-(2-O-sulfo-α-L-idopyranosyluronic acid)-(1→)-2-deoxy-2-sulfamido-6-O-sulfo-D-glucopyranose decasodium salt, a heparin fragment having high affinity for antithrombin III. Carbohydr Res 1986; 147: 221-236.
    • (1986) Carbohydr. Res. , vol.147 , pp. 221-236
    • Petitou, M.1    Duchaussoy, P.2    Lederman, I.3    Choay, J.4    Sinaÿ, P.5    Jacquinet, J.-C.6
  • 21
    • 0022632131 scopus 로고
    • Synthesis of a heparin pentasaccharide fragment with a high affinity for antithrombin III employing cellobiose as a key starting material
    • Ichikawa Y, Monden R and Kuzuhara H. Synthesis of a heparin pentasaccharide fragment with a high affinity for antithrombin III employing cellobiose as a key starting material. Tetrahedron Lett 1986; 27: 611-614.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 611-614
    • Ichikawa, Y.1    Monden, R.2    Kuzuhara, H.3
  • 22
    • 0023656036 scopus 로고
    • Synthesis of heparin fragments: A methyl alpha-pentaoside with high affinity for antithrombin III
    • Petitou M, Duchaussoy P. and Lederman I. Synthesis of heparin fragments: a methyl alpha-pentaoside with high affinity for antithrombin III. Carbohydr Res 1987; 167: 67-75.
    • (1987) Carbohydr. Res. , vol.167 , pp. 67-75
    • Petitou, M.1    Duchaussoy, P.2    Lederman, I.3
  • 23
    • 0025770037 scopus 로고
    • Antifactor Xa activity and antithrombotic activity in rats of structural analogues of the minimum antithrombin III binding sequence: Discovery of compounds with a longer duration of action than of the natural pentasaccharide
    • Meuleman DG, Hobbelen PMJ, van Dinther TG, vogel GMT, van Boeckel CAA. and Moelker HCT. Antifactor Xa activity and antithrombotic activity in rats of structural analogues of the minimum antithrombin III binding sequence: discovery of compounds with a longer duration of action than of the natural pentasaccharide. Semin Thromb Hemostasis 1991; 17: 112-117.
    • (1991) Semin. Thromb. Hemostasis , vol.17 , pp. 112-117
    • Meuleman, D.G.1    Hobbelen, P.M.J.2    van Dinther, T.G.3    vogel, G.M.T.4    van Boeckel, C.A.A.5    Moelker, H.C.T.6
  • 24
    • 0031034272 scopus 로고    scopus 로고
    • Determination of the anti-factor Xa activity of the synthetic pentasaccharide SR 90107A/ORG 31540 and of two structural analogs
    • Lormeau J-C, Hérault J-P, Gaich C, Barzu T, van Dinther TG, Visser A, et al. Determination of the anti-factor Xa activity of the synthetic pentasaccharide SR 90107A/ORG 31540 and of two structural analogs. Thromb Res 1997; 85: 67-75.
    • (1997) Thromb. Res. , vol.85 , pp. 67-75
    • Lormeau, J.-C.1    Hérault, J.-P.2    Gaich, C.3    Barzu, T.4    van Dinther, T.G.5    Visser, A.6
  • 25
    • 0023832125 scopus 로고
    • Synthesis of a potent antithrombin activating pentasaccharide. A new heparin-like fragment containing two-3-O-sulfated glucosamines
    • van Boeckel CAA, Beetz T and van Aelst SF. Synthesis of a potent antithrombin activating pentasaccharide. A new heparin-like fragment containing two-3-O-sulfated glucosamines. Tetrahedron Lett 1988; 29: 803-806.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 803-806
    • van Boeckel, C.A.A.1    Beetz, T.2    van Aelst, S.F.3
  • 27
    • 0006181555 scopus 로고
    • 220 MHz spectra of heparin, chondroitins and other mucopolysaccharides
    • Perlin AS, Casu B, Sanderson GR and Johnson LF. 220 MHz spectra of heparin, chondroitins and other mucopolysaccharides. Can J Chem 1970; 48: 2260-2268.
    • (1970) Can. J. Chem. , vol.48 , pp. 2260-2268
    • Perlin, A.S.1    Casu, B.2    Sanderson, G.R.3    Johnson, L.F.4
  • 28
    • 0018120359 scopus 로고
    • Conformations of the major residues in heparin. Proton NMR spectroscopic studies
    • Gatti G, Casu B. and Perlin AS. Conformations of the major residues in heparin. Proton NMR spectroscopic studies. Biochem Biophys Res Commun 1978; 85: 14-20.
    • (1978) Biochem. Biophys. Res. Commun. , vol.85 , pp. 14-20
    • Gatti, G.1    Casu, B.2    Perlin, A.S.3
  • 30
    • 0022394350 scopus 로고
    • Mono- and bidimensional 500 MHz proton NMR spectra of a synthetic pentasaccharide corresponding to the binding sequence of heparin to antithrombin-III: Evidence for conformational peculiarity of the sulfated iduronate residue
    • Torri G, Casu B, Gatti G, Petitou M, Choay J, Jacquinet J-C, et al. Mono- and bidimensional 500 MHz proton NMR spectra of a synthetic pentasaccharide corresponding to the binding sequence of heparin to antithrombin-III: evidence for conformational peculiarity of the sulfated iduronate residue. Biochem Biophys Res Commun 1985; 128: 134-140.
    • (1985) Biochem. Biophys. Res. Commun. , vol.128 , pp. 134-140
    • Torri, G.1    Casu, B.2    Gatti, G.3    Petitou, M.4    Choay, J.5    Jacquinet, J.-C.6
  • 31
    • 84988141308 scopus 로고
    • A force-field study of the conformational characteristics of the iduronate ring
    • Ragazzi M, Ferro DR and Provasoli A. A force-field study of the conformational characteristics of the iduronate ring. J Comput Chem 1986; 7: 105-112.
    • (1986) J. Comput. Chem. , vol.7 , pp. 105-112
    • Ragazzi, M.1    Ferro, D.R.2    Provasoli, A.3
  • 32
    • 0022443619 scopus 로고
    • Evidence for conformational equilibrium of the sulfated L-iduronate residue in heparin and in synthetic heparin mono- and oligo-saccharides: NMR and force-field studies
    • Ferro DR, Provasoli A, Ragazzi M, Torri G, Casu B, Gatti G, et al. Evidence for conformational equilibrium of the sulfated L-iduronate residue in heparin and in synthetic heparin mono- and oligo-saccharides: NMR and force-field studies. J Am Chem Soc 1986; 108: 6773-6778.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 6773-6778
    • Ferro, D.R.1    Provasoli, A.2    Ragazzi, M.3    Torri, G.4    Casu, B.5    Gatti, G.6
  • 36
    • 0036899481 scopus 로고    scopus 로고
    • Probing the heparin-antithrombin III interaction using synthetic pentasaccharide bearing positively charged groups
    • 2002
    • Codée JDC, van der Marel GA, van Boeckel CAA. and van Boom JH. Probing the heparin-antithrombin III interaction using synthetic pentasaccharide bearing positively charged groups. Eur J Org Chem 2002; 2002: 3954-3965.
    • (2002) Eur. J. Org. Chem. , pp. 3954-3965
    • Codée, J.D.C.1    van der Marel, G.A.2    van Boeckel, C.A.A.3    van Boom, J.H.4
  • 37
    • 0021344246 scopus 로고
    • Anticoagulant activities of heparin oligosaccharides and their neutralization by platelet factor 4
    • Lane DL, Denton J, Flynn A, Thunberg L. and Lindahl U. Anticoagulant activities of heparin oligosaccharides and their neutralization by platelet factor 4. Biochem J 1984; 218: 732-735.
    • (1984) Biochem. J. , vol.218 , pp. 732-735
    • Lane, D.L.1    Denton, J.2    Flynn, A.3    Thunberg, L.4    Lindahl, U.5
  • 38
    • 0025730441 scopus 로고
    • Quantitative characterization of the thrombin-heparin interaction. Discrimination between specific and nonspecific binding models
    • Olson ST, Halvorson HR. and Björk I. Quantitative characterization of the thrombin-heparin interaction. Discrimination between specific and nonspecific binding models. J Biol Chem 1991; 266: 6342-6352.
    • (1991) J. Biol. Chem. , vol.266 , pp. 6342-6352
    • Olson, S.T.1    Halvorson, H.R.2    Björk, I.3
  • 39
    • 0030668306 scopus 로고    scopus 로고
    • Does low molecular weight heparin cause less bleeding?
    • Thomas DP. Does low molecular weight heparin cause less bleeding? Thromb Haemost 1997; 78: 1422-1425.
    • (1997) Thromb. Haemost. , vol.78 , pp. 1422-1425
    • Thomas, D.P.1
  • 48
    • 0031823306 scopus 로고    scopus 로고
    • The extracellular polysaccharide of Pichia (Hansenula) holstii NRRL Y-2448: The phosphorylated side chains
    • Parolis LA, Parolis H, Kenne L, Meldal M. and Bock K. The extracellular polysaccharide of Pichia (Hansenula) holstii NRRL Y-2448: the phosphorylated side chains. Carbohydr Res 1998; 309 77-87.
    • (1998) Carbohydr. Res. , vol.309 , pp. 77-87
    • Parolis, L.A.1    Parolis, H.2    Kenne, L.3    Meldal, M.4    Bock, K.5
  • 49
    • 0035907101 scopus 로고    scopus 로고
    • Large-scale preparation of the oligosaccharide phosphate fraction of Pichia holstii NRRL Y-2448 phosphomannan for use in the manufacture of P1-88
    • Ferro V, Fewings K, Palermo MC. and Li C. Large-scale preparation of the oligosaccharide phosphate fraction of Pichia holstii NRRL Y-2448 phosphomannan for use in the manufacture of P1-88. Carbohydr Res 2001; 332: 183-189.
    • (2001) Carbohydr. Res. , vol.332 , pp. 183-189
    • Ferro, V.1    Fewings, K.2    Palermo, M.C.3    Li, C.4
  • 51
    • 0033565247 scopus 로고    scopus 로고
    • Identification of sulfated oligosaccharide-based inhibitors of tumor growth and metastasis using novel in vitro assays for angiogenesis and heparanase activity
    • Parish CR, Freeman C, Brown KJ, Francis DJ and Cowden WB. 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.
    • (1999) Cancer Res. , vol.59 , pp. 3433-3441
    • Parish, C.R.1    Freeman, C.2    Brown, K.J.3    Francis, D.J.4    Cowden, W.B.5
  • 52
    • 0142000161 scopus 로고    scopus 로고
    • The effect of the heparanase inhibitor PI-88 on neo-intimal formation following acute arterial injury
    • Brisbane: University of Quinsland
    • McGarry M. The effect of the heparanase inhibitor PI-88 on neo-intimal formation following acute arterial injury. Brisbane: University of Quinsland; 1999.
    • (1999)
    • McGarry, M.1
  • 53
    • 0035880995 scopus 로고    scopus 로고
    • Characterisation of the anticoagulant properties of a range of structurally diverse sulfated oligosaccharides
    • Wall D, Douglas S, Ferro V, Cowden W. and Parish C. Characterisation of the anticoagulant properties of a range of structurally diverse sulfated oligosaccharides. Thromb Res 2001; 103: 325-335.
    • (2001) Thromb. Res. , vol.103 , pp. 325-335
    • Wall, D.1    Douglas, S.2    Ferro, V.3    Cowden, W.4    Parish, C.5
  • 55
    • 0011891160 scopus 로고
    • Lactonization of aldonic acids
    • Whistler, RL, Wolfram, ML,Bemiller, JN, editors. New York: Academic Press
    • Isbell HS. and Frush HL. Lactonization of aldonic acids. In: Whistler, RL, Wolfram, ML,Bemiller, JN, editors. Methods in Carbohydrate Chemistry. New York: Academic Press, 1963. p. 16-18.
    • (1963) Methods in Carbohydrate Chemistry , pp. 16-18
    • Isbell, H.S.1    Frush, H.L.2
  • 56
    • 0027399328 scopus 로고
    • In vivo pharmacology of aprosulate, a new synthetic polyanion with anticoagulant activity
    • Sugidachi A, Asai F. and Koike H. In vivo pharmacology of aprosulate, a new synthetic polyanion with anticoagulant activity. Thromb Res 1993; 69: 71-80.
    • (1993) Thromb. Res. , vol.69 , pp. 71-80
    • Sugidachi, A.1    Asai, F.2    Koike, H.3
  • 57
    • 0026575322 scopus 로고
    • Inhibition of factor X, factor V. and prothrombin activation by the bis (lactobionic acid amide) LW 10082
    • Ofosu FA, Fareed J, Smith LM, Anvari N, Hoppensteadt DA and Blajchman MA. Inhibition of factor X, factor V. and prothrombin activation by the bis (lactobionic acid amide) LW 10082. Eur J Biochem 1992, 203: 121-125.
    • (1992) Eur. J. Biochem. , vol.203 , pp. 121-125
    • Ofosu, F.A.1    Fareed, J.2    Smith, L.M.3    Anvari, N.4    Hoppensteadt, D.A.5    Blajchman, M.A.6
  • 60
    • 0027247501 scopus 로고
    • Antithrombotic activities of aprosulate sodium (LW 10082) and its neutralisation by protamine
    • Raake W, Klauser RJ. and Meinetsberger E. Antithrombotic activities of aprosulate sodium (LW 10082) and its neutralisation by protamine. Semin Thromb Hemostasis 1993; 19: 183-185.
    • (1993) Semin. Thromb. Hemostasis , vol.19 , pp. 183-185
    • Raake, W.1    Klauser, R.J.2    Meinetsberger, E.3
  • 61
    • 0029958147 scopus 로고    scopus 로고
    • In vitro effects of aprosulate sodium, a novel anticoagulant, on platelet activation: Possible mechanism for antiplatelet action
    • Sugidachi A, Breiter N, Ogawa T, Asai F. and Koike H. In vitro effects of aprosulate sodium, a novel anticoagulant, on platelet activation: Possible mechanism for antiplatelet action. Thromb Haemost 1996; 76: 786-790.
    • (1996) Thromb. Haemost. , vol.76 , pp. 786-790
    • Sugidachi, A.1    Breiter, N.2    Ogawa, T.3    Asai, F.4    Koike, H.5
  • 65
    • 0036239004 scopus 로고    scopus 로고
    • Keratinocyte Growth Factor (KGF) in hematology and oncology
    • MacDonald KP, Hill GR. Keratinocyte Growth Factor (KGF) in hematology and oncology. Curr Pharm Design 2002; 8(5): 395-403.
    • (2002) Curr. Pharm. Design , vol.8 , Issue.5 , pp. 395-403
    • MacDonald, K.P.1    Hill, G.R.2
  • 66
    • 0036242405 scopus 로고    scopus 로고
    • Leech thrombin inhibitors
    • Salzet M. Leech thrombin inhibitors. Curr Pharm Design 2002; 8(7): 493-503.
    • (2002) Curr. Pharm. Design , vol.8 , Issue.7 , pp. 493-503
    • Salzet, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.