Cationic derivatives of dextran and hydroxypropylcellulose as novel potential heparin antagonists

Journal of Medicinal Chemistry

Volumn 54, Issue 19, 2011, Pages 6586-6596

  Kamiński, Kamil ^a   Płonka, Monika ^a   Ciejka, Justyna ^a   Szczubiałka, Krzysztof ^a   Nowakowska, Maria ^a   Lorkowska, Barbara ^b   Korbut, Ryszard ^b   Lach, Radosław ^c  

^a JAGIELLONIAN UNIVERSITY   (Poland)

^b JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

^c AGH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; DEXTRAN DERIVATIVE; HEPARIN; HEPARIN ANTAGONIST; HYDROXYPROPYLCELLULOSE; POLYCATION; POLYSACCHARIDE;

ANTICOAGULATION; ARTICLE; CHEMICAL MODIFICATION; DRUG BINDING; DRUG MECHANISM; ERYTHROCYTE AGGREGATION; HEMOLYSIS; HUMAN; IN VITRO STUDY; TEMPERATURE;

CATIONS; CELLULOSE; DEXTRANS; ERYTHROCYTE AGGREGATION; HEMOLYSIS; HEPARIN; HEPARIN ANTAGONISTS; HUMANS; LIGHT; QUATERNARY AMMONIUM COMPOUNDS; SCATTERING, RADIATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80053902063     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200380w     Document Type: Article

References (59)

1. Anderson, W. F. Human gene therapy Science 1992, 256, 808-813
2. Hunter, A. C.; Moghimi, S. M. Cationic carriers of genetic material and cell death: a mitochondrial tale Biochim. Biophys. Acta, Bioenerg. 2010, 1797, 1203-1209
3. Mintzer, M. A.; Simanek, E. E. Nonviral vectors for gene delivery Chem. Rev. 2009, 109, 259-302
4. Pietersz, G. A.; Tang, C.; Apostolopoulos, V. Structure and design of polycationic carriers for gene delivery Mini-Rev. Med. Chem. 2006, 6, 1285-1298 (Pubitemid 44890536)
5. El-Aneed, A. An overview of current delivery systems in cancer gene therapy J. Controlled Release 2004, 94, 1-14 (Pubitemid 37542373)
6. Dash, P. R.; Toncheva, V.; Schacht, E.; Seymour, L. W. Synthetic polymers for vectorial delivery of DNA: characterisation of polymer-DNA complexes by photon correlation spectroscopy and stability to nuclease degradation and disruption by polyanions in vitro J. Controlled Release 1997, 48, 269-276 (Pubitemid 27401984)
7. Yavari, M.; Becker, R. C. Anticoagulant therapy during cardiopulmonary bypass J. Thromb. Thrombolysis 2008, 26, 218-228
8. Rosamond, W.; Flegal, K.; Friday, G.; Furie, K.; Go, A.; Greenlund, K.; Haase, N.; Ho, M.; Howard, V.; Kissela, B.; Kittner, S.; Lloyd-Jones, D.; McDermott, M.; Meigs, J.; Moy, C.; Nichol, G.; O'Donnell, C. J.; Roger, V.; Rumsfeld, J.; Sorlie, P.; Steinberger, J.; Thom, T.; Wasserthiel-Smoller, S.; Hong, Y. Heart disease and stroke statistics-2007 update: a report from the American Heart Association Statistics Committee and Stroke Statistics Subcommittee Circulation 2007, 115, e69-e171
9. Park, K. W. Protamine and protamine reactions Int. Anesthesiol. Clin. 2004, 42, 135-145 (Pubitemid 38963099)
10. Carr, J. A.; Silverman, N. The heparin-protamine interaction. A review J.Cardiovasc.Surg. 1999, 40, 659-666
11. Kitani, T.; Nagarajan, S. C.; Shanberge, J. N. Effect of protamine on heparin-antithrombin III complexes. In vivo studies Thromb. Res. 1980, 17, 375-382 (Pubitemid 10129026)
12. Vincentelli, A.; Jude, B.; Belisle, S. Antithrombotic therapy in cardiac surgery Can. J. Anaesth. 2006, 53, S89-S102
13. Maurer, J.; Haselbach, S.; Klein, O.; Baykut, D.; Vogel, V.; Mäntele, W. Analysis of the complex formation of heparin with protamine by light scattering and analytical ultracentrifugation: implications for blood coagulation management J. Am. Chem. Soc. 2011, 133, 1134-1140
14. Weitz, J. I. Low-molecular-weight heparins N. Engl. J. Med. 1997, 337, 688-698 (Pubitemid 27375477)
15. Schulman, S.; Bijsterveld, N. R. Anticoagulants and their reversal Transfus. Med. Rev. 2007, 21, 37-48 (Pubitemid 44881256)
16. Thompson, W. H. Z. Physiol. Chem. 1900, 29, 1-19
17. Khan, N. U.; Wayne, C. K.; Barker, J.; Strang, T. The effects of protamine overdose on coagulation parameters as measured by the thrombelastograph Eur. J. Anaesthesiol. 2010, 27, 624-627
18. Horrow, J. C. Protamine allergy J. Cardiothorac. Vasc. Anesth. 1988, 2, 225-242 (Pubitemid 19041514)
19. Lowenstein, E.; Johnston, W. E.; Lappas, D. G.; D'Ambra, M. N.; Schneider, R. C.; Daggett, W. M.; Akins, C. W.; Philbin, D. M. Catastrophic pulmonary vasoconstriction associated with protamine reversal of heparin Anesthesiology 1983, 59, 470-473 (Pubitemid 14227526)
20. Collins, C; O'Donnell, A. Does an allergy to fish pre-empt an adverse protamine reaction? A case report and a literature review Perfusion 2008, 23, 369-372
21. Nybo, M.; Madsen, J. S. Serious anaphylactic reactions due to protamine sulfate: a systematic literature review Basic Clin. Pharmacol. Toxicol. 2008, 103, 192-196 (Pubitemid 352019729)
22. Chu, Y.; Cai, L.; Jiang, D.; Jia, D.; Yan, S.; Wang, Y. Allergic shock and death associated with protamine administration in a diabetic patient Clin. Ther. 2010, 32, 1729-1732
23. Grobler, C.; Callum, J.; McCluskey, S. A. Reversal of vitamin K antagonists prior to urgent surgery Can. J. Anesth. 2010, 57, 458-467
24. Ansell, J.; Hirsh, J.; Poller, L.; Bussey, H.; Jacobson, A.; Hijlek, E. The pharmacology and management of the vitamin K antagonists: the seventh ACCP conference on antithrombotic and thrombolytic therapy Chest 2004, 126, 204S-233S (Pubitemid 39297955)
25. Franchini, M.; Lippi, G. Prothrombin complex concentrates: an update Blood Transfus. 2010, 8, 149-154
26. Lewis, B.; O'Leary, M.; Vinh, T. Successful use of rVIIa (NovoSeven) to reverse enoxaparin (Lovenox) overdose in an adult patient with intracranial bleeding Thromb. Haemostasis 2001, Suppl.) 2633
27. Morris, T. A. New synthetic antithrombotic agents for venous thromboembolism: pentasaccharides, direct thrombin inhibitors, direct Xa inhibitors Clin. Chest Med. 2010, 31, 707-718
28. Walenga, J. M.; Jeske, W. P.; Fareed, J. Short- and long-acting synthetic pentasaccharides as antithrombotic agents Expert Opin. Invest. Drugs 2005, 14, 847-858 (Pubitemid 41038404)
29. Nijkeuter, M.; Huisman, M. V. Pentasaccharides in the prophylaxis and treatment of venous thromboembolism: a systematic review Curr. Opin. Pulm. Med. 2004, 10, 338-344 (Pubitemid 39099927)
30. Turpie, A. G. G. Pentasaccharides Semin. Hematol. 2002, 39, 158-171 (Pubitemid 34793037)
31. Schaden, E.; Kozek-Langenecker, S. A. Direct thrombin inhibitors: pharmacology and application in intensive care medicine Intensive Care Med. 2010, 36, 1127-1137
32. Kuliczkowski, W.; Floyd, J.; Malinin, A.; Serebruany, V. Aptamers: the emerging class of future anticoagulation for vascular disease Expert Rev. Cardiovasc. Ther. 2010, 8, 503-507
33. Becker, R. C.; Povsic, T.; Cohen, M. G.; Rusconi, C. P.; Sullenger, B. Nucleic acid aptamers as antithrombotic agents: opportunities in extracellular therapeutics Thromb. Haemostasis 2010, 103, 586-595
34. Lewis, B.; O'Leary, M.; Vinh, T. Successful use of rVIIa (NovoSeven) to reverse enoxaparin (Lovenox) overdose in an adult patient with intracranial bleeding Thromb. Haemostasis 2001, Suppl.) 2633
35. Stafford-Smith, M.; Lefrak, E. A.; Qazi, A. G.; Welsby, I. J.; Barber, L.; Hoeft, A.; Dorenbaum, A.; Mathias, J.; Rochon, J. J.; Newman, M. F. Efficacy and safety of heparinase I versus protamine in patients undergoing coronary artery bypass grafting with and without cardiopulmonary bypass Anesthesiology 2005, 103 (2) 229-240 (Pubitemid 41076719)
36. Schick, B. P.; Maslow, D.; Moshinski, A.; San Antonio, J. D. Novel concatameric heparin-binding peptides reverse heparin and low-molecular-weight heparin anticoagulant activities in patient plasma in vitro and in rats in vivo Blood 2004, 103 (4) 1356-1363 (Pubitemid 38168648)
37. Cushing, D. J.; Cooper, W. D.; Cohen, M. L.; McVoy, J,R,S; Sobel, M.; Harris, R. B. Reversal of heparin-induced increases in aPTT in the rat by PM102, a novel heparin antagonist Eur. J. Pharmacol. 2010, 635 (1-3) 165-170
38. Shenoy, S.; Sobel, M.; Harris, R. B. Development of heparin antagonists with focused biological activity Curr. Pharm. Des. 1999, 5 (12) 965-986 (Pubitemid 30014006)
39. Mixon, T. A.; Dehmer, G. J. Recombinant platelet factor 4 for heparin neutralization Semin. Thromb. Hemostasis 2004, 30, 369-377 (Pubitemid 39037631)
40. Kamiński, K.; Zazakowny, K.; Szczubiałka, K.; Nowakowska, M. pH-sensitive genipin-cross-linked chitosan microspheres for heparin removal Biomacromolecules 2008, 9, 3127-3132
41. Kamiński, K.; Szczubiałka, K.; Zazakowny, K.; Lach, R.; Nowakowska, M. Chitosan derivatives as novel potential heparin reversal agents J. Med. Chem. 2010, 53, 4141-4147
42. Choksakulnimitr, S.; Masuda, S.; Tokuda, H.; Takakura, Y.; Hashida, M. In vitro cytotoxicity of macromolecules in different cell culture systems J. Controlled Release 1995, 34, 233-241
43. Moreau, E.; Ferrari, I.; Drochon, A.; Chapon, P.; Vert, M.; Domurado, D. Interactions between red blood cells and a lethal, partly quaternized tertiary polyamine J. Controlled Release 2000, 64, 115-128 (Pubitemid 30035312)
44. Karchalsky, A.; Danon, D.; Nevo, A.; de Vries, A. Interaction of basic polyelectrolytes with the red blood cell. II. Agglutination of red blood cells by polymeric bases Biochim. Biophys. Acta 1959, 33, 120-138
45. Wander, A. H. Long-term use of hydroxypropyl cellulose ophthalmic insert to relieve symptoms of dry eye in a contact lens wearer: case-based experience Eye Contact Lens 2011, 37, 39-44
46. Luchs, J. I.; Nelinson, D. S.; Macy, J. I. Efficacy of hydroxypropyl cellulose ophthalmic inserts (LACRISERT) in subsets of patients with dry eye syndrome: findings from a patient registry Cornea 2010, 29, 1417-1427
47. Yamamoto, Y; Dohi, M; Uejima, Y. Effect of polymeric excipients on the nasal absorption of dry powder formulations Oto-Rhino-Laryn. Tokyo 2003, 46 (SUPPL. 1) 24-27 (Pubitemid 37071339)
48. Yamamoto, Y; Dohi, M; Uejima, Y. Enhancement of nasal absorption of a peptidal drug by powder formulations Oto Rhino-Laryn, Tokyo 2003, 46 (Suppl. 1) 20-23 (Pubitemid 37071338)
49. Gao, J.; Haidar, G.; Lu, X.; Hu, Z. Self-association of hydroxypropylcellulose in water Macromolecules 2001, 34, 2242-2247 (Pubitemid 34216796)
50. Nowakowska, M.; Szczubiałka, K.; Grȩbosz, M. Modifying the thermosensitivity of copolymers of sodium styrene sulfonate and N -isopropylacrylamide with dodecyltrimethylammonium chloride Colloid Polym. Sci. 2004, 283, 291-298 (Pubitemid 40069129)
51. Nowakowska, M; Szczubiałka, K; Grȩbosz, M. S. Interactions of temperature-responsive anionic polyelectrolytes with a cationic surfactant J. Colloid Interface Sci. 2003, 265, 214-219 (Pubitemid 36961432)
52. Rosół, K.; Szczubiałka, K.; Jachimska, B.; Zapotoczny, S.; Nowakowska, M. Interactions of a smart cationic polyelectrolyte based on hydroxypropylcellulose with an anionic surfactant J. Appl. Polym. Sci. 2008, 107, 3184-3189 (Pubitemid 351238753)
53. Szczubiałka, K.; Rosół, K.; Nowakowska, M. Smart anionic polyelectrotytes based on natural polymer for complexation of cationic surfactant J. Appl. Polym. Sci. 2006, 102, 2401-2407 (Pubitemid 44619617)
54. Thomas, J. J.; Rekha, M. R.; Sharma, C. P. Dextran- glycidyltrimethylammonium chloride conjugate/DNA nanoplex: a potential non-viral and haemocompatible gene delivery system Int. J. Pharm. 2010, 389, 195-206
55. Venkataraman, S.; Zhang, Y.; Liu, L.; Yang, Y. Design, syntheses and evaluation of hemocompatible pegylated-antimicrobial polymers with well-controlled molecular structures Biomaterials 2010, 31, 1751-1756
56. Kainthan, R. K.; Gnanamani, M.; Ganguli, M.; Ghosh, T.; Brooks, D. E.; Maiti, S.; Kizhakkedathu, J. N. Blood compatibility of novel water soluble hyperbranched polyglycerol-based multivalent cationic polymers and their interaction with DNA Biomaterials 2006, 27, 5377-5390 (Pubitemid 44109897)
57. Dubruel, P.; Dekie, L.; Christiaens, B.; Vanloo, B.; Rosseneu, M.; Van De Kerckhove, J.; Mannisto, M.; Urtti, A.; Schacht, E. Poly- l -glutamic acid derivatives as multifunctional vector for gene delivery. Part B. Biological evaluation Biomacromolecules 2003, 4, 1177-1183 (Pubitemid 37184628)
58. Kuroda, K.; Caputo, G. A.; DeGrado, W. F. The role of hydrophobicity in the antimicrobial and hemolytic activities of polymethacrylate derivatives Chem.-Eur. J. 2009, 15, 1123-1133
59. Ho, F.F.-L.; Kohler, R. R.; Ward, G. A. Determination of molar substitution and degree of substitution of hydroxypropyl cellulose by nuclear magnetic resonance spectrometry Anal. Chem. 1972, 44 (1) 178-181