An orally active selenium-based antihypertensive agent with restricted CNS permeability

Journal of Pharmacology and Experimental Therapeutics

Volumn 283, Issue 2, 1997, Pages 470-477

  May, Sheldon W ^a,b   Wang, Lanqing ^a   Gill Woznichak, Michelle M ^a   Browner, Richard F ^a   Ogonowski, Alison A ^a   Smith, James B ^a   Pollock, Stanley H ^a  

^a MERCER UNIVERSITY   (United States)

^b GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXY ALPHA METHYL PHENYL 2 AMINOETHYL SELENIDE; ANTIHYPERTENSIVE AGENT; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL MODEL; ANTIHYPERTENSIVE THERAPY; ARTICLE; ATOMIC EMISSION SPECTROMETRY; BLOOD PRESSURE REGULATION; CENTRAL NERVOUS SYSTEM; CHRONIC DISEASE; CONTROLLED STUDY; DOSE RESPONSE; DRUG EFFECT; DRUG PENETRATION; DRUG STRUCTURE; HYPERTENSION; MALE; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; RAT; TISSUE DISTRIBUTION;

ADMINISTRATION, ORAL; ANIMALS; ANTIHYPERTENSIVE AGENTS; BLOOD PRESSURE; BRAIN; MALE; MICE; ORGANOSELENIUM COMPOUNDS; PERMEABILITY; RATS; RATS, SPRAGUE-DAWLEY; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030832816     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (37)

1. BECK, M. A., SHI, Q., MORRIS, V. C. AND LEVANDER, O. A.: Rapid genomic evolution of a non-virulent Coxsackievirus B3 in selenium-deficient mice results in selection of identical virulent isolates. Nature Med. 1: 433-436, 1995.
2. BEHNE, D., WEISS-NOWAK, C., KALCKLOSCH, M., WESTPHAL, C., GESSNER, H. AND KYRIAKOPOULOS, A.: Studies on the distribution and characteristics of new mammalian selenium-containing proteins. Analyst 120: 823-825, 1995.
3. CALDWELL, K. A. AND TAPPEL, A. L.: Reactions of seleno-and sulfoamino acids with hydroperoxides. Biochemistry 3: 1643-1647, 1964.
4. CLARK, L. C., COMBS, G. F., JR., TURNBULL, B. W., SLATE, E. H., CHALKER, D. K., CHOW, J., DAVIS, L. S., GLOVER, R. A., GRAHAM, G. F., GROSS, E. G., KRONGRAD, A., LESHER, J. L., JR., PARK, H. K., SANDERS, B. B., JR., SMITH, C. L. AND TAYLAR, R.: Effect of selenium supplementation for cancer prevention in patients with carcinoma of the skin. J. Am. Med. Assoc. 276: 1957-1963, 1996.
5. FOSTER, D. G. AND BROWN, S. F.: Organic selenium compounds. Some derivatives of aromatic seleno-ethers. J. Am. Chem. Soc. 50: 1182-1188, 1928.
6. Fox, J. M.: Selenium: Nutritional implications and prospects for therapeutic medicine. Meth. Find. Exp. Clin. Pharmacol. 14(4): 275-287, 1992.
7. GIBALDI, M. AND PERRIER, D.: Multicompartment Models in Pharmacokinetics, 2nd ed.: pp. 45-109, Marcel Dekker, Inc. New York, 1982.
8. GILMAN, A. G., RALL, T. W., NIES, A. S. AND TAYLOR, P.: Goodman and Gilman's Pharmacological Basis of Therapeutics. 8th ed.: pp. 159, McGraw-Hill, Inc., New York, 1990.
9. GRIECO, P. A., NISHIZAWA, M., OGURI, T., BURKE, S. D. AND MARINOVIC, N.: Sesquiterpene lacones: Total synthesis of (±)-vernolepin and (±)-vernomenin. J. Am. Chem. Soc. 99: 5773-5780, 1977.
10. HERMAN, H. H., WIMALASENA, K., FOWLER, L. C. AND MAY, S. W.: Demonstration of the ascorbate dependence of membrane-bound dopamine β-monooxygenase in adrenal chromaffin granule ghosts. J. Biol. Chem. 263: 666-672, 1988a.
11. HERMAN, H. H., POLLOCK, S. H., FOWLER, L. C. AND MAY, S. W.: Demonstration of the potent antihypertensive activity of phenyl-2-aminoethyl Sulfides. J. Cardiovasc. Pharmacol. 11: 501-510, 1988b.
12. HERMAN, H. H., HUSAIN, P. A., COLBERT, J. E., SCHWERI, M. M., POLLOCK, S. H., FOWLER, L. C. AND MAY, S. W.: The enantiomeric specificity of the antihypertensive activity of 1-(phenylthio)-2-aminopropane, a synthetic substrate analogue for dopamine β-monooxygenase. J. Med. Chem. 34:1082-1085, 1991.
13. HOFFMAN, B. B. AND LEFKOWITZ, R. J.: Catecholamines and sympathomimetic drugs. In The Pharmacological Basis of Therapeutics, 8th ed., ed. by A. G. Goodman, T. W. Rall, A. S. Nies and P. Taylor, pp. 187-220, Pergamon Press, New York, 1990.
14. JANGHORBANI, M. AND TING, B, T. G.: Comparison of pneumatic nebulization and hydride generation inductively coupled plasma mass spectrometry for isotopic analysis for selenium. Anal. Chem. 61: 701-708, 1989.
15. JUDY, W. V., WATANABE, A. M., HENRY, D. P., BESCH, H. R., MURPHY, W. R. AND HOCKEL, G. M.: Sympathetic nerve activity: Role in regulation of blood pressure in the spontaneously hypertensive rat. Circ. Res. 38: 21-29, 1976.
16. KRUSE, L. I., KAISER, C., DEWOLF, W. E., JR., FRAZEE, J. S., ERICKSON, R. W., EZEKIEL, M., OHLSTEIN, E. H., RUFFOLO, R. R. J. AND BERKOWITZ, B. A.: Substituted 1-benzylimidazole-2-thiols as potent and orally active inhibitors of dopamine β-hydroxylase. J. Med. Chem. 29: 887-889, 1986.
17. KRUSE, L. I., KAISER, C., DEWOLF, W. E., JR., FRAZEE, J. S., Ross, S. T., WAWRO, J., WISE, M., FIAIM, K. E., SAWYER, J. L., EZEKIEL, M., OHLSTEIN, E. H. AND BERKOWITZ, B. A.: Multisubstrate inhibitors of dopamine beta-hydroxylase. 2. Structure-activity relationships at the phenethylamine binding site. J. Med. Chem. 30: 486-494, 1987.
18. LEIBOVITZ, B., HU, M. AND TAPPEL, A. L.: Dietary supplements of vitamin E, b-carotene, coenzyme Q10, and selenium protect tissue against lipid peroxidation in rat tissue slices. J. Nutr. 120: 97-104, 1990.
19. MAY, S. W., HERMAN, H. H., ROBERTS, S. F. AND CICCARELLO, M. C.: Ascorbate depletion as a consequence of product recycling during dopamine β-monooxygenase catalyzed selenoxidation. Biochemistry 26: 1626-1632, 1987.
20. MAY, S. W., WIMALASENA, K., HERMAN, H. H., FOWLER, L. C., CICCARELLO, M. C. AND POLLOCK, S. H.: Novel antihypertensives targeted at dopamine β-monooxygenase: Turnover-dependent cofactor depletion by phenyl aminoethyl selenide. J. Med. Chem. 31: 1066-1068, 1988.
21. MAY, S. W., YOUNG, F. K., POWERS, J. L. AND GILL-WOZNICHAK, M. M.: Mechanism-based inactivation of dopamine beta-monooxygenase in adrenal chromaffin cells. Biochem. Biophys. Res. Commun. 228: 278-284, 1996.
22. NADELMANN, J. AND FRISHMAN, W. H.: Clinical use of beta-adrenoceptor blockade in systemic hypertension. Drugs 39: 862-876, 1990.
23. PADGETTE, S. R., HERMAN, H. H., HAN, J. H., POLLOCK, S. H. AND MAY, S. W.: Antihypertensive activities of phenyl aminoethyl Sulfides, a class of synthetic substrate for dopamine β-hydroxylase. J. Med. Chem. 27: 1354-1357, 1984.
24. PARNHAM, M. J. AND GRAF, E.: Seleno-organic compounds and the therapy of hydroperoxide-linked pathological conditions. Biochem. Pharmacol. 36: 3095-3102, 1987.
25. PARNHAM, M. J. AND GRAF, E.: Pharmacology of synthetic organic selenium compounds. Prog. Drug Res. 36: 9-47, 1991.
26. POLLOCK, S. H., HERMAN, H. H., FOWLER, L. C., EDWARDS, A. S., EVANS, C. AND MAY, S. W.: Demonstration of the antihypertensive activity of phenyl-2-aminoethyl selenide. J. Pharmacol. Exp. Ther. 246: 227-234, 1988.
27. POLLOCK, S. H., REICHBAUM, M. I., COLBERT, J. C., HUSAIN, P. A., HOLBROOK, J. M., OGONOWSKI, A. A., KHLIEF, J. S. AND MAY, S. W.: The oral antihypertensive activity of the methylated derivatives of phenyl-2-aminoethyl sulfide. J. Pharmacol. Exp. Ther. 265: 1113-1117, 1993.
28. PRINSSEN, E. P., KLEVEN, M. S., VIGNON, J., KAMENKA, J. M. AND KOEK, W.: Effects of repeated administration of N-[1-(2-benzo(b)-thiophenyl)cyclohexyl]piperidine and cocaine on locomotor activity in C57BL/6 mice. J. Pharmacol. Exp. Ther. 276: 904-911, 1996.
29. REJHOLEC, V.: Selenofen. Drugs of the Future 10: 572, 1985.
30. RIMMER, S. J. AND CHURCH, M. K.: The pharmacology and mechanism of actions of histamine H1-antagonists. Clin. Exper. Allergy 20: suppl. 2, 3-17, 1990.
31. SMITH, J. B.: Situational specificity of tolerance to effects of phencyclidine on responding of rats under fixed-ratio and spaced-responding schedules. Psychopharmacology 103: 121-128, 1991.
32. SPALLHOLZ, J. E.: On the nature of selenium toxicity and carcinostatic activity. Free Rad. Biol. Med. 17: 45-64, 1994.
33. STADTMAN, T. C.: Selenocysteine. Ann. Rev. Biochem. 65: 83-100, 1996.
34. URSINI, F. AND BINDOLI, A.: The role of selenium peroxidases in the protection against oxidative damage of membranes. Chem. Phys. Lipids 44: 255-276, 1987.
35. WALTER, R., SCHWARTZ, I. L. AND ROY, J.: Can selenoamino acids act as reversible biological antioxidants? Ann. N. Y. Acad. Sci. 192: 175-180, 1972.
36. WEHRMEISTER, H. L.: N-(arylmercaptoalkyl) amides by reaction of thiols with amino alcohols and carboxylic acids. J. Org. Chem, 28: 2589-2592, 1963.
37. WIMALASENA, K., HERMAN, H. H. AND MAY, S. W.: Effects of dopamine β-monooxygenase substrate analogs on ascorbate levels and norepinephrine synthesis in adrenal chromaffin granule ghosts. J. Biol. Chem. 264: 124-130, 1989.