Design and synthesis of a novel synthetic NAPAP-pentasaccharide conjugate displaying a dual antithrombotic action

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 14, 1999, Pages 2013-2018

  Buijsman, Rogier C ^a   Basten, Jan E M ^b   Van Dinther, Theo G ^b   Van der Marel, Gijsbert A ^a   Van Boeckel, Constant A A ^b   Van Boom, Jacques H ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b NV ORGANON   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; HEPARIN DERIVATIVE; N (2 NAPHTHALENESULFONYL) GLYCYL DEXTRO 4 AMINOPHENYLALANYLPIPERIDINE; PIPERIDINE DERIVATIVE; THROMBIN INHIBITOR; UNCLASSIFIED DRUG;

ANTICOAGULANT THERAPY; ARTICLE; CONJUGATION; DRUG CONFORMATION; DRUG HALF LIFE; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION; REACTION ANALYSIS;

ANIMALS; ANTITHROMBINS; CARBOHYDRATE SEQUENCE; DIPEPTIDES; DRUG DESIGN; FACTOR XA; HALF-LIFE; HEPARIN; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; PIPERIDINES; RATS; SOLUBILITY; THROMBIN;

EID: 0033584213     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00320-0     Document Type: Article

References (20)

1. Lane, D.A.; Lindahl, U. In Heparin: Chemical and Biological Properties; Clinical Applications, Edward Arnold: London, 1989;
2. Choay, J.; Petitou, M.; Lormeau, J.-C.; Sinaÿ, P.; Casu, B.; Gatti, G.; Biochem. Biophys. Res. Comm. 1983, 116, 492.
3. Tunberg, T.; Bäckström, G.; Lindahl, U.; Carbohydrate Res. 1982, 100, 393.
4. (a) Grootenhuis, P.D.; Westerduin, P.; Meulenman, D.; Petitou, M.; Van Boeckel, C.A.A.; Nature Struct. Biol. 1995, 2, 736.
5. (b) Westerduin, P.; Basten, J.; Broekhoven, M.; De Kimpe, V.; Kuijpers, W.; Van Boeckel, C.A.A.; Angew. Chem. Int. Ed. Engl. 1996, 35, 331.
6. (c) Basten, J.E.M.; Dreef-Tromp, C.M.; De Wijs, B.; Van Boeckel, C.A.A.; Bioorg. Med. Chem. Lett. 1998, 8, 1201.
7. (d) Buijsman, R.C.; Kuijpers, W.H.A.; Basten, J.E.M.; Kuyl-Yeheskiely, E.; Van der Marel, G.A.; Van Boeckel, C.A.A.; Van Boom, J.H.; Chem. Eur. J. 1996, 2, 1572;
8. (e) Buijsman, R.C.; Basten, J.E.M., Dreef-Tromp, C.M.; Van der Marel, G.A., Van Boeckel, C.A.A.; Van Boom, J.H.; Abstract of papers 9th European Carbohydrate Symposium Utrecht 1997, Abstract A150.
9. (a) Van Boeckel, C.A.A., Petitou, M.; Angew. Chem. Int. Ed. Engl. 1993, 32, 1671.
10. (b) Westerduin, P.; Van Boeckel, C.A.A.; Basten, J.E.M.; Broekhoven, M.A.; Lucas, H.; Rood, A.; Van der Heijden, H.; Van Amsterdam, R.G.M.; Van Dinter, T.G.; Bioorg. Med. Chem. 1994, 2, 1267;
11. Stürzebecher, J.; Markwardt, F.; Voigt, B.; Wagner, G.; Walsmann, P.; Thromb. Res. 1983, 29, 635.
12. Vogel, G.M.T.; Van Dinther, Th.G.; Visser, A.; Buiting, M.T.; Van Amsterdam, R.G.M.; Meuleman, D.G.; Thromb. Haemostas. 1991, 65, 930.
13. Various pentasaccharide analogs have been prepared (see ref 5b), which display half-lives between 1 to 11 hrs (in rat). Since there is a direct correlation between the binding affinity of a pentasaccharide domain with ATIII and its half-life in circulation (see ref 7), various conjugates could be prepared with different PS analogs, thus tuning the half-lives of these conjugates.
14. (a) Stüber, W.; Koschinsky, R.; Kolar, C.; Reers, M.; Dickneite, G.; Hoffmann, D.; Czech, J.; Diehl, K.-H.; Pâques, E.-P. In Peptides-Chemistry; Hodges, R.S. and Smith, J.A., Ed.; Escom: Leiden, 1994; pp 643.
15. (b) Stüber, W.; Koschinsky, R.; Reers, M.; Hoffmann, D.; Czech, J.; Dickneite, G.; Peptide Res. 1995, 8, 78.
16. Hermanson, G.T. In Bioconjugate Techniques; Academic Press: San Diego, 1996; pp 237-242.
17. Harrison, J.G.; Balasubramanian, S.; Bioorg. Med. Chem. Lett. 1997, 7, 1041.
18. - 2680.6.
19. Teien, A.N.; Lie, M.; Thromb. Res. 1977, 10, 339.
20. Vogel, G.M.T.; Van Amsterdam, R.G.M.; Zandberg, P.; Van Houwelingen, P.; Kop, W.J.; Van Mensvoort, F.W.J.; Meuleman, D.G.; Thromb. Haemostas. 1997, 77, 183.