Chitosan derivatives as novel potential heparin reversal agents

Journal of Medicinal Chemistry

Volumn 53, Issue 10, 2010, Pages 4141-4147

  Kamiński, Kamil ^a   Szczubiałka, Krzysztof ^a   Zazakowny, Karolina ^a   Lach, Radosław ^b   Nowakowska, Maria ^a  

^a JAGIELLONIAN UNIVERSITY   (Poland)

^b AGH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CHITOSAN DERIVATIVE; HEPARIN; LOW MOLECULAR WEIGHT HEPARIN; N (2 HYDROXYPROPYL) 3 TRIMETHYLAMMONIUM CHITOSAN CHLORIDE; PROTAMINE SULFATE; UNCLASSIFIED DRUG;

ANTICOAGULATION; ARTICLE; BINDING AFFINITY; DRUG EFFICACY; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; LIGHT SCATTERING; PH;

ANTICOAGULANTS; CHITOSAN; CONDUCTOMETRY; HEPARIN; HEPARIN, LOW-MOLECULAR-WEIGHT; HYDROGEN-ION CONCENTRATION; LIGHT; NANOPARTICLES; PROTAMINES; QUATERNARY AMMONIUM COMPOUNDS; SCATTERING, RADIATION;

EID: 77952728995     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1001666     Document Type: Article

References (41)

1. Crafoord, C. Preliminary report on postoperative treatment with heparin as a preventive of thrombosis Acta Chir. Scand. 1937, 79, 407-426
2. Björk, I.; Lindahl, U. Mechanism of the anticoagulant action of heparin Mol. Cell. Biochem. 1982, 48, 161-182
3. Weitz, J. I.; Hudoba, M.; Massel, D.; Maraganore, J.; Hirsh, J. Clot-bound thrombin is protected from inhibition by heparin-antithrombin III but is susceptible to inactivation by antithrombin III-independent inhibitors J. Clin. Invest. 1990, 86, 385-391
4. Clowes, A. W.; Karnowsky, M. J. Suppression by heparin of smooth muscle cell proliferation in injured arteries Nature 1977, 265, 625-626
5. Laghi Pasini, F.; Pasqui, A. L.; Ceccatelli, L. Heparin inhibition of polymorphonuclear leukocyte activation in vitro. A possible pharmacological approach to granulocyte-mediated vascular damage Thromb. Res. 1984, 35, 527-537
6. Friedrichs, G. S.; Kilgore, K. S.; Manley, P. J.; Gralinski, M. R.; Lucchesi, B. R. Effects of heparin and N-acetyl heparin on ischemia/reperfusion- induced alterations in myocardial function in the rabbit isolated heart Circ. Res. 1994, 75, 701-710
7. Ludwig, R. J. Therapeutic use of heparin beyond anticoagulation Curr. Drug Discovery Technol. 2009, 6, 281-289
8. Ejiri, M.; Fujita, M.; Miwa, K.; Hirai, T.; Yamanishi, K.; Sakai, O.; Ishizaka, S.; Sasayama, S. Effects of heparin treatment on collateral development and regional myocardial function in acute myocardial infarction Am. Heart J. 1990, 119, 248-253
9. Linhardt, R. J. 2003 Claude S. Hudson Award Address in Carbohydrate Chemistry. Heparin: structure and activity J. Med. Chem. 2003, 46, 2551-2564
10. Jorpes, E. The chemistry of heparin Biochem. J. 1935, 29, 1817-1830
11. Leone-Bay, A.; Paton, D. R.; Freeman, J.; Lercara, C.; OToole, D.; Gschneidner, D.; Wang, E.; Harris, E.; Rosado, C.; Rivera, T.; DeVincent, A.; Tai, M.; Mercogliano, F.; Agarwal, R.; Leipold, H.; Baughman, R. A. Synthesis and evaluation of compounds that facilitate the gastrointestinal absorption of heparin J. Med. Chem. 1998, 41, 1163-1171
12. Nishizawa, E. E.; Wynalda, D. J.; Harmon, R. E.; De, K. K.; Gupta, S. K. Preparation and anticoagulant activity of trimethylsilyl heparin in Carbowax J. Med. Chem. 1975, 18, 250-253
13. Granger, C. B.; Hirsh, J.; Califf, R. M.; Col, J.; White, H. D.; Betriu, A.; Woodlief, L.; Lee, K. L.; Bovill, E.; Simes, R. J.; Topol, E. J. Activated partial thromboplastin time and outcome after thrombolytic therapy for acute myocardial infarction results from the GUSTO-I trial Circulation 1996, 93, 870-878
14. Greinacher, A. Heparin-induced thrombocytopenia J. Thromb. Haemostasis 2009, 7, 9-12
15. Ambrus, J. L.; Mahafzah, M.; Hague, M.; Tjota, A.; Ambrus, C. M. Comparative study of the osteoporosis inducing effect of unfractionated heparin and a low molecular weight heparin preparation (dalteparin-fragmin) J. Med. 2005, 36, 127-133
16. Boneu, B. Low molecular weight heparins: are they superior to unfractionated heparins to prevent and to treat deep vein thrombosis? Thromb. Res. 2000, 100, V113-V120
17. Hirsh, J.; Warkentin, T. E.; Raschke, R.; Granger, C.; Olman, E. M.; Dalen, J. E. Heparin and low-molecular-weight heparin: Mechanisms of action, pharmacokinetics, dosing considerations, monitoring, efficacy, and safety Chest 1998, 114, 489S-510S
18. Warkentin, T. E.; Levine, M. N.; Hirsh, J.; Horsewood, P.; Roberts, R. S.; Gent, M.; Kelton, J. G. Heparin-induced thrombocytopenia in patients treated with low-molecular-weight heparin or unfractionated heparin N. Engl. J. Med. 1995, 332, 1330-1335
19. Matzch, T.; Bergqvist, D.; Hedner, U.; Nilsson, B.; Ostergaard, P. Effects of low molecular weight heparin and unfragmented heparin on induction of osteoporosis in rats Thromb. Haemostasis 1990, 63, 505-509
20. Carr, J. A.; Silverman, N. The heparin-protamine interaction. A review J. Cardiovasc. Surg. 1999, 40, 659-666
21. Horrow, J. C. Protamine: a review of its toxicity Anesth. Analg. 1985, 64, 348-361
22. Lindblad, B. Protamine sulphate: a review of its effects: hypersensitivity and toxicity Eur. J. Vasc. Surg. 1989, 3, 195-201
23. Çetinel, Ş.; Ercan, F.; Şirvanci, S.; Şehirli, Ö.; Ersoy, Y.; Şan, T.; Şener, G. The ameliorating effect of melatonin on protamine sulfate induced bladder injury and its relationship to interstitial cystitis J. Urol. 2003, 169, 1564-1568
24. Pugsley, M. K.; Kalra, V.; Froebel-Wilson, S. Protamine is a low molecular weight polycationic amine that produces actions on cardiac muscle Life Sci. 2002, 72, 293-305
25. Kurtz, A. B.; Gray, R. S.; Markand, S.; Nabarro, J. D. Circulating IgG antibody to protamine in patients treated with protamine-insulins Diabetologia 1983, 25, 322-324
26. Samama, M. M.; Gerotziafas, G. T. Newer anticoagulants in 2009 J. Thromb. Thrombolysis 2010, 29, 92-104
27. Karewicz, A.; Zasada, K.; Szczubiałka, K.; Zapotoczny, S.; Lach, R.; Nowakowska, M. Smart alginate-hydroxypropylcellulose microbeads for controlled release of heparin Int. J. Pharm. 2010, 385, 163-169
28. Kamiński, K.; Zazakowny, K.; Szczubiałka, K.; Nowakowska, M. pH-sensitive genipin-cross-linked chitosan microspheres Biomacromolecules 2008, 9, 3127-3132
29. Sandri, G.; Rossi, S.; Bonferoni, M. C.; Ferrari, F.; Zambito, Y.; Colo, G. D.; Caramella, C. Buccal penetration enhancement properties of N-trimethyl chitosan: influence of quaternization degree on absorption of a high molecular weight molecule Int. J. Pharm. 2005, 297 (1-2) 146-55
30. Kotzé, A. F.; Luessen, H. L.; Leeuw, B. J.; Boer, B. G.; Verhoef, J. C.; Junginger, H. E. N-trimethyl chitosan chloride as a potential absorption enhancer across mucosal surfaces: in vitro evaluation in intestinal epithelial cells (Caco-2) Pharm. Res. 1997, 14 (9) 1197-1202
31. Lim, H. L.; Hudson, S. M. Synthesis and antimicrobial activity of a water-soluble chitosan derivative with a fiber-reactive group Carbohydr. Res. 2004, 339 (2) 313-319
32. Gastaud, J.-M.; Senelar, R.; Pujol, H. In vitro antiproliferative effect of halogenic quarternary ammonium on tumor cells C. R. Acad. Sci., Ser. III 1993, 316, 1363-1367
33. Ji, Q. X.; Zhong, D. Y.; Lü, R.; Zhang, W. Q.; Deng, J.; Chen, X. G. In vitro evaluation of the biomedical properties of chitosan and quaternized chitosan for dental applications Carbohydr. Res. 2009, 344, 1297-1302
34. Wu, J.; Su, Z. G.; Ma, G. H. A thermo- and pH-sensitive hydrogel composed of quaternized chitosan/glycerophosphate Int. J. Pharm. 2006, 315, 1-11
35. Lim, S.; Hudson, S. M. Application of a fiber-reactive chitosan derivative to cotton fabric as an antimicrobial textile finish Carbohydr. Res. 2004, 339, 313-319
36. Qin, C.; Ciao, Q.; Li, H.; Fanga, M.; Liu, Y. Calorimetric studies of the action of chitosan-N-2-hydroxypropyl trimethyl ammonium chloride on the growth of microorganisms Int. J. Biol. Macromol. 2004, 34, 121-126
37. Gupta, K. C.; Jabrail, F. H. Effects of degree of deacetylation and cross-linking on physical characteristics, swelling and release behavior of chitosan microspheres Carbohydr. Polym. 2006, 66, 43-54
38. Hirsh, J.; Bauer, K. A.; Donati, M. B.; Gould, M.; Samama, M. M.; Weitz, J. I. Parenteral anticoagulants: American College of Chest Physicians Evidence-Based Clinical Practice Guidelines (8 th ed.). Chest 2008, 133, 141S - 159S. (Pubitemid 351892966)
39. Weitz, D. S.; Weitz, J. I. Update on heparin: what do we need to know? J. Thromb. Thrombolysis 2010, 29, 1-9
40. Cho, J.; Grant, J.; Piquette-Miller, M.; Allen, C. Synthesis and physicochemical and dynamic mechanical properties of a water-soluble chitosan derivative as a biomaterial Biomacromolecules 2006, 7, 2845-2855
41. Nemcova, I.; Rychlovsky, P.; Havelcova, M.; Brabcova, M. Determination of heparin using flow injection analysis with spectrophotometric detection Anal. Chim. Acta 1999, 401, 223-228 (Pubitemid 29516583)