Localizing antithrombotic and vasodilatory activity with a novel, ultrafast nitric oxide donor

Journal of Medicinal Chemistry

Volumn 39, Issue 22, 1996, Pages 4361-4365

  Saavedra, Joseph E ^a   Southan, Garry J ^a   Davies, Keith M ^b   Lundell, Anders ^c   Markou, Chris ^c   Hanson, Stephen R ^c   Adrie, Christophe ^d   Hurford, William E ^d   Zapol, Warren M ^d   Keefer, Larry K ^e  

^a SAIC FREDERICK INC   (United States)

^b GEORGE MASON UNIVERSITY   (United States)

^c EMORY UNIVERSITY   (United States)

^d MASSACHUSETTS GENERAL HOSPITAL   (United States)

^e NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

15 HYDROXY 11ALPHA,9ALPHA EPOXYMETHANOPROSTA 5,13 DIENOIC ACID; ANTICOAGULANT AGENT; NITRIC OXIDE; NITRIC OXIDE DONOR; PROLINE; VASODILATOR AGENT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICOAGULATION; ARTERIAL PRESSURE; ARTICLE; BABOON; BLOOD VESSEL GRAFT; CONTROLLED STUDY; DOSE RESPONSE; INHALATIONAL DRUG ADMINISTRATION; INTRAVENOUS DRUG ADMINISTRATION; LUNG ARTERY PRESSURE; LUNG BLOOD VESSEL; MALE; NONHUMAN; PULMONARY HYPERTENSION; REACTION ANALYSIS; VASODILATATION;

15-HYDROXY-11 ALPHA,9 ALPHA-(EPOXYMETHANO)PROSTA-5,13-DIENOIC ACID; ANIMALS; DRUG DELIVERY SYSTEMS; FIBRINOLYTIC AGENTS; HYDROGEN-ION CONCENTRATION; MALE; NITRIC OXIDE; NITROGEN OXIDES; NITROPRUSSIDE; PAPIO; PLATELET ADHESIVENESS; POLYMERS; PROLINE; PROSTAGLANDIN ENDOPEROXIDES, SYNTHETIC; PULMONARY CIRCULATION; SHEEP; THROMBOXANE A2; VASOCONSTRICTOR AGENTS; VASODILATOR AGENTS;

EID: 10244255122     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960616s     Document Type: Article

References (23)

1. Kerwin, J. F., Jr.; Lancaster, J. R., Jr.; Feldman, P. L. Nitric Oxide: A New Paradigm for Second Messengers. J. Med. Chem. 1995, 38, 4343-4362.
2. Moncada, S.; Higgs, E. A. Molecular Mechanisms and Therapeutic Strategies Related to Nitric Oxide. FASEB J. 1995, 9, 1319-1330.
3. Kröncke, K.-D.; Fehsel, K.; Kolb-Bachofen, V. Inducible Nitric Oxide Synthase and its Product Nitric Oxide, a Small Molecule with Complex Biological Activities. Biol. Chem. Hoppe-Seyler 1995, 376, 327-343.
4. Hanson, S. R.; Hutsell, T. C.; Keefer, L. K.; Mooradian, D. L.; Smith, D. J. Nitric Oxide Donors: A Continuing Opportunity in Drug Design. Adv. Pharmacol. 1995, 34, 383-398.
5. Keefer, L. K.; Nims, R. W.; Davies, K. M.; Wink, D. A. "NON-Oates" (1-Substituted Diazen-1-ium-1,2-diolates) as Nitric Oxide Donors: Convenient Nitric Oxide Dosage Forms. Methods Enzymol. 1996, 268, 281-294.
6. Hanson, S. R. Intralumenal Drug Delivery for Experimental Thrombosis and Restenosis. Restenosis Summit V. 1993, 296-300.
7. Scott, N. A.; Nunes, G. L.; King, S. B., III; Harker, L. A.; Hanson, S. R. Local Delivery of an Antithrombin Inhibits Platelet-dependent Thrombosis. Circulation 1994, 90, 1951-1955.
8. Zapol, W. M.; Hurford, W. E. Inhaled Nitric Oxide in the Adult Respiratory Distress Syndrome and Other Lung Diseases. New Horizons 1993, 1, 638-650.
9. Torres, A.; Kimball, W. R.; Qvist, J.; Stanek, K.; Kacmarek, R. M.; Whyte, R. I.; Montalescot, G.; Zapol, W. M. Sonomicrometric Regional Diaphragmatic Shortening in Awake Sheep after Thoracic Surgery. J. Appl. Physiol. 1989, 67, 2357-2368.
10. - Group. J. Med. Chem. 1996, 39, 1148-1156.
11. Ragsdale, R. O.; Karstetter, B. R.; Drago, R. S. Decomposition of the Adducts of Diethylamine and Isopropylamine with Nitrogen(II) Oxide. Inorg. Chem. 1965, 4, 420-422.
12. Greenblatt, M.; Lijinsky, W. Failure to Induce Tumors in Swiss Mice after Concurrent Administration of Amino Acids and Sodium Nitrite. J. Natl. Cancer Inst. 1972, 48, 1389-1392.
13. Nagasawa, H. T.; Fraser, P. S.; Yuzon, D. L. New Method for Nitrosation of Proline and Related Sec-α-Amino Acids to N-Nitrosamino Acids with Possible Oncogenic Activity. J. Med. Chem. 1973, 16, 583-585.
14. Garcia, H.; Lijinsky, W. Studies of the Tumorigenic Effect in Feeding of Nitrosamino Acids and of Low Doses of Amines and Nitrite to Rats. Z. Krebsforsch. 1973, 79, 141-144.
15. Nixon, J. E.; Wales, J. H.; Scanlan, R. A.; Bills, D. D.; Sinnhuber, R. O. Null Carcinogenic Effect of Large Doses of Nitrosoproline and Nitrosohydroxyproline in Wistar Rats. Food Cosmet. Toxicol. 1976, 14, 133-135.
16. Mirvish, S. S.; Bulay, O.; Runge, R. G.; Patil, K. Study of the Carcinogenicity of Large Doses of Dimethylnitramine, N-Nitroso-L-proline, and Sodium Nitrite Administered in Drinking Water to Rats. J. Natl. Cancer Inst. 1980, 64, 1435-1442.
17. Lijinsky, W.; Reuber, M. D. Transnitrosation by Nitrosamines In Vivo. In N-Nitroso Compounds: Occurrence and Biological Effects; Bartsch, H., O'Neill, I. K., Castegnaro, M., Okada, M., Eds.; International Agency for Research on Cancer (IARC Scientific Publications No. 41): Lyon, 1982; pp 625-631.
18. Hecht, S. S.; Abbaspour, A.; Hoffman, D. A Study of Tobacco Carcinogenesis XLII. Bioassay in A/J Mice of Some Structural Analogs of Tobacco-Specific Nitrosamines. Cancer Lett. (Shannon, Irel) 1988, 42, 141-145.
19. Hrabie, J. A.; Klose, J. R.; Wink, D. A.; Keefer, L. K. New Nitric Oxide-releasing Zwitterions Derived from Polyamines. J. Org. Chem. 1993, 58, 1472-1476.
20. Maragos, C. M.; Morley, D.; Wink, D. A.; Dunams, T. M.; Saavedra, J. E.; Hoffman, A.; Bove, A. A.; Isaac, L.; Hrabie, J. A.; Keefer, L. K. Complexes of ·NO with Nucleophiles as Agents for the Controlled Biological Release of Nitric Oxide. Vasorelaxant Effects. J. Med. Chem. 1991, 34, 3242-3247.
21. Hanson, S. R.; Ku, D. N. Efficiency of Boundary Layer Drug Delivery for Antithrombotic Therapy. Thromb. Haemostasia 1993, 69, 1240 (abstract 2489).
22. Hanson, S. R.; Kotze, H. F.; Savage, B.; Harker, L. A. Platelet Interactions with Dacron Vascular Grafts. A Model of Acute Thrombosis in Baboons. Arteriosclerosis (Dallas) 1985, 5, 595-603.
23. Adrie, C.; Hirani, W. M.; Holzmann, A.; Keefer, L.; Zapol, W. M.; Hurford, W. E. Selective Pulmonary Vasodilation by Intravenous Infusion of an Ultrashort Half-life Nucleophile/Nitric Oxide Adduct. Unpublished work.