A nitric oxide-releasing heparin conjugate for delivery of a combined antiplatelet/anticoagulant agent

Molecular Pharmaceutics

Volumn 11, Issue 2, 2014, Pages 645-650

  Suchyta, Dakota J ^a   Handa, Hitesh ^b   Meyerhoff, Mark E ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF MICHIGAN HEALTH SYSTEM   (United States)

Author keywords

combined antiplatelet anticoagulant agent; diazeniumdiolated heparin; nitric oxide release

Indexed keywords

ADENOSINE DIPHOSPHATE; ANTICOAGULANT AGENT; ANTITHROMBOCYTIC AGENT; CALCIUM; CYCLIC GMP; HEPARIN; NITRIC OXIDE; SPERMINE; SPERMINE DERIVATIVE;

ARTICLE; CONJUGATE; PRIORITY JOURNAL; THROMBOCYTE; THROMBOCYTE ACTIVATION; THROMBOCYTE AGGREGATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS;

ANTICOAGULANTS; HEPARIN; MOLECULAR STRUCTURE; NITRIC OXIDE; PLATELET AGGREGATION; PLATELET AGGREGATION INHIBITORS; SPERMINE;

EID: 84893240300     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp400501c     Document Type: Article

References (30)

1. Lloyd-Jones, D. Heart disease and stroke statistics-2009 update Circulation 2009, 119, 480-486
2. Homer, K. L.; Wanstall, J. C. Inhibition of rat platelet aggregation by the diazeniumdiolate nitric oxide donor MAHMA NONOate Br. J. Pharmacol. 2002, 137, 1071-1081 (Pubitemid 35440748)
3. Radomski, M. W.; Palmer, R.; Moncada, S. An L-arginine/nitric oxide pathway present in human platelets regulates aggregation Proc. Natl. Acad. Sci. 1990, 87, 5193-5197
4. Gries, A.; Bode, C.; Peter, K.; Herr, S. A.; Böhrer, H.; Motsch, J.; Martin, E. Inhaled nitric oxide inhibits human platelet aggregation, p-selectin expression, and fibrinogen binding in vitro and in vivo Circulation 1998, 97, 1481-1487 (Pubitemid 28191304)
5. Isenberg, J. S. Thrombospondin-1 stimulates platelet aggregation by blocking the antithrombotic activity of nitric oxide/cGMP signaling Blood 2008, 111, 613-623
6. Rosenberg, R. D. Heparin action Circulation 1974, 49, 603-605
7. Wilson, J. W. Heparin sodium- a review J. Extra-Corp. Tech. 1974, 4, 207-213
8. Schneider, D. J.; Sobel, B. E. Conundrums in the combined use of anticoagulants and antiplatelet drugs Circulation 2007, 116, 305-315 (Pubitemid 47196567)
9. Mowery, K. A.; Schoenfisch, M. H.; Saavedra, J. E.; Keefer, L. K.; Meyerhoff, M. E. Preparation and characterization of hydrophobic polymeric films that are thromboresistant via nitric oxide release Biomaterials 2000, 21, 9-21
10. Saavedra, J. E.; Mooradian, D. L.; Mowery, K. A.; Schoenfisch, M. H.; Citro, M. L.; Davies, K. M.; Meyerhoff, M. E.; Keefer, L. K. Conversion of a polysaccharide to nitric oxide-releasing form. Dual-mechanism anticoagulant activity of diazeniumdiolated heparin Bioorg. Med. Chem. Lett. 2000, 10, 751-753 (Pubitemid 30215876)
11. Grabarek, Z.; Gergely, J. Zero-length crosslinking procedure with the use of active esters Anal. Biochem. 1990, 185, 131-135 (Pubitemid 20082102)
12. Wissink, M. J. B.; Beernink, R.; Pieper, J. S.; Poot, A. A.; Engbers, G. H. M.; Beugeling, T.; van Aken, W. G.; Feijen, J. Immobilization of heparin to EDC/NHS-crosslinked collagen. Characterization and in vitro evaluation Biomaterials 2001, 22, 151-163
13. Yang, C. Enhanced physicochemical properties of collagen by using EDC/NHS-crosslinking Bull. Mater. Sci. 2012, 35, 913-918
14. Evans, A. S.; Toscano, J. P. The chemistry of NO- and HNO-producing diazeniumdiolates Patai's Chem. Funct. Groups 2010, 1-16
15. Hrabie, J. A.; Keefer, L. K. Chemistry of the nitric oxide-releasing diazeniumdiolate ("nitrosohydroxylamine") functional group and its oxygen-substituted derivatives Chem. Rev. 2002, 102, 1135-1154 (Pubitemid 35377605)
16. Hetrick, E. M.; Schoenfisch, M. H. Analytical chemistry of nitric oxide Annu. Rev. Anal. Chem. 2009, 2, 409-433
17. Maragos, C. M. Complexes of NO with nucleophiles as agents for the controlled biological release of nitric oxide. Vasorelaxant effects J. Med. Chem. 1991, 34, 3242-3247
18. Siller-Matula, J. M.; Plasenzotti, R.; Spiel, A.; Quehenberger, P.; Jilma, B. Interspecies differences in coagulation profile Thromb. Haemost. 2008, 100, 397-404
19. Saravanababu, M.; Xie, J.; Linhardt, R. J. Immobilization of heparin: approaches and applications Curr. Top. Med. Chem. 2008, 8, 80-100 (Pubitemid 351791033)
20. Soda, K.; Kano, Y.; Sakuragi, M.; Takao, K.; Lefor, A.; Konishi, F. Long-term oral polyamine intake increases blood polyamine concentrations J. Nutr. Sci. Vitaminol. 2009, 55, 361-2009
21. Davis, R. H.; Morris, D. R.; Coffino, P. Sequestered end products and enzyme regulation: the case of ornithine decarboxylase Microbiol. Rev. 1992, 56, 280-290
22. Desser, H.; Höcker, P.; Weiser, M.; Böhnel, J. The content of unbound polyamines in blood plasma and leukocytes of patients with polycythemia vera Clin. Chim. Acta 1975, 63, 243-247
23. Keefer, L. K.; Nims, R. W.; Davies, K. M.; Wink, D. A. "NONOates" (1-substituted diazen-1-ium-1,2-diolates) as nitric oxide donors: convenient nitric oxide dosage forms Methods Enzymol. 1996, 268, 281-293 (Pubitemid 26286370)
24. Seiler, N. Polyamine oxidase, properties and functions Prog. Brain Res. 1995, 106, 333-344 (Pubitemid 26027010)
25. Davies, K. M.; Wink, D. A.; Saavedra, J. E.; Keefer, L. K. Chemistry of the diazeniumdiolates. 2. Kinetics and mechanism of dissociation to nitric oxide in aqueous solution J. Am. Chem. Soc. 2001, 123, 5473-5481 (Pubitemid 32888516)
26. Keefer, L. K. Fifty years of diazeniumdiolate research. From laboratory curiosity to broad-spectrum biomedical advances ACS Chem. Biol. 2011, 6, 1147-1155
27. Seckel, H. Blood volume and circulation time in children Arch. Dis. Child. 1936, 11, 21-30
28. Hemker, H. C.; Béguin, S. Standard and method independent units for heparin anticoagulant activities Thromb. Haemostasis 1993, 70, 724-728 (Pubitemid 23339442)
29. Ersdal-Badju, E.; Lu, A.; Zuo, Y.; Picard, V.; Bock, S. C. Identification of the antithrombin III heparin binding site J. Biol. Chem. 1997, 272, 19393-19400 (Pubitemid 27337735)
30. Gorbet, M. B.; Sefton, M. V. Biomaterial-associated thrombosis: roles of coagulation factors, complement, platelets and leukocytes Biomaterials 2004, 25, 5681-5703