Relationship between structure and inhibitory effect of arginine analogues on neuronal nitric oxide synthase activity

Neurochemical Research

Volumn 21, Issue 10, 1996, Pages 1187-1192

  Yokoi, Isao ^a   Namba, Yukiko ^a   Kabuto, Hideaki ^a   Inada, Kazunori ^a   Iida, Motoyuki ^a   Mori, Akitane ^a   Ogawa, Norio ^a  

^a OKAYAMA UNIVERSITY MEDICAL SCHOOL   (Japan)

Author keywords

diamidinocystamine; guanethidine; guanidino compounds; Nitric oxide synthase inhibitor

Indexed keywords

DIAMIDINOCYSTAMINE; GLUTAMATE RECEPTOR; GUANETHIDINE; GUANIDINE DERIVATIVE; HIRUDONINE; N(G) METHYLARGININE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ANIMAL TISSUE; ARTICLE; DRUG CONFORMATION; DRUG RECEPTOR BINDING; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX; NONHUMAN; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; ARGININE; MALE; MOLECULAR STRUCTURE; NEURONS; NITRIC OXIDE SYNTHASE; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA;

EID: 0029859559     PISSN: 03643190     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02532394     Document Type: Article

References (26)

1. Garthwaite, J., Charles, S. L., and Chess-Williams, R. 1988. Endothelium-derived relaxing factor release on activation of NMDA receptors suggests role as intercellular messenger in the brain. Nature 336:385-388.
2. Knowles, R. G., Palacios, M., Palmer, R. M. J., and Moncada, S. 1989. Formation of nitric oxide from L-arginine in the central nervous system: A transduction mechanism for stimulation of the soluble guanylate cyclase. Proc. Natl. Acad. Sci. USA 86:5159-5162.
3. Hu, J., and El-Fakahany, E. 1993. Role of intercellular and intracellular communication by nitric oxide in coupling of muscarinic receptors to activation of guanylate cyclase in neuronal cells. J. Neurochem. 61:578-585.
4. Tanaka, K., Fukuuchi, Y., Gomi, S., Mihara, B., Shirai, T., Nogawa, S., Nozaki, H., and Nagata, E. 1993. Inhibition of nitric oxide synthesis impairs autoregulation of local cerebral blood flow in the rat. Neuroreport 4:267-270.
5. Dawson, V. L., Dawson, T. M., Bartley, D. A., Uhl, G. R., and Snyder, S. H. 1993. Mechanisms of nitric oxide-mediated neurotoxicity in primary brain cultures. J. Neurosci. 13:2651-2661.
6. Shibuki, K., and Okada, D. 1991. Endogenous nitric oxide release required for long-term synaptic depression in the cerebellum. Nature 349:326-328.
7. Snyder, S. H., and Bret, D. S. 1992. Biological roles of nitric oxide. Scientific American May: 28-35.
8. Yokoi, I., Kabuto, H., Habu, H., and Mori, A. 1994. α-Guanidinoglutaric acid, an endogenous convulsant, as a novel nitric oxide synthase inhibitor. J. Neurochem. 63:1565-1567.
9. Kabuto, H., Yokoi, I., Habu, H., Asahara, H., and Mori, A. 1995. Inhibitory effect of arcaine on nitric oxide synthase in the rat brain. Neuroreport 6:554-556.
10. Asahara, H., Abut, H., Yokoi, I., Habu, H., and Mori, A. 1995. Nitric oxide synthase inhibited by audouine in the rat brain. Neuroreport 6:1143-1148.
11. Ohkusu, H., and Mori, A. 1969. Isolation of α-N-acetyl-L-arginine from cattle brain. J. Neurochem. 16:1485-1486.
12. Mori, A., Ichimura, T., and Matsumoto, H. 1978. Gas chromatography-mass spectrometry of guanidino compounds in brain. Anal. Biochem. 89:393-399.
13. Mori, A., Akagi, M., Katayama, Y., and Watanabe, Y. 1980. αGuanidinoglutaric acid in cobalt-induced epileptogenic cerebral cortex of cats. J. Neurochem. 35:603-605.
14. Yokoi, I., Tsuruta, K., Shiraga, H., and Mori, A. 1987. δ-Guanidinovaleric acid as an endogenous and specific GABA-receptor antagonist: electroencephalographic study. Epilepsy Res. 1:114-120.
15. Watanabe, Y., Yokoi, I., Watanabe, S., Sugi, H., and Mori, A. 1988. Formation of 2-guanidinoethanol by a transamidination reaction from arginine and ethanolamine by the rat kidney and pancreas. Life Sci. 43:295-302.
16. Yokoi, I., Kabuto, H., Habu, H., Inada, K., Toma, J., and Mori, A. 1994. Structure-activity relationships of arginine analogues on nitric oxide synthase activity in the rat brain. Neuropharmacol. 33: 1261-1265.
17. Habu, H., Yokoi, I., Kabuto, H., and Mori, A. 1994. Application of automated flow injection analysis to determine nitrite and nitrate in mouse brain. Neuroreport 5:1571-1573.
18. Lowry, O. J., Rosenbrought, N. J., Farr, A. L., and Randall, R. J. 1951. Protein measurement with folin-phenol reagent. J. Biol. Chem. 193:265-275.
19. Segel, I. H. 1976. Biochemical Calculations [second edition], Pages 246-266. John Wiley & Sons, New York.
20. Misko, T. P., Moore, W. M., Kasten, T. P., Nickols, G. A., Gorbertt, J. A., Tilton, R. G., McDaniel, M. L., Williamson, J. R., and Currie, M. G. 1993. Selective inhibition of the inducible nitric oxide synthase by aminoguanidine. Eur. J. Pharmacol. 233:119-125.
21. Ranson, R. W., and Deschenes, N. L. 1990. Polyamines regulate glycine interaction with the N-methyl-D-aspartate receptor. Synapse 5:294-298.
22. Reynolds, I. J. 1990. Arcaine is a competitive antagonist of the polyamine site of the NMDA receptor. Eur. J. Pharmacol. 177: 215-216.
23. Moncada, S., Palmer, R. M. J., and Higgs, E. A. 1991. Nitric oxide: physiology, pathology and pharmacology. Pharmacol. Rev. 43:109-142.
24. Maxwell, R. A., Plummer, A. J., Schneider, F., Povalski, H., and Daniel, A. I. 1960. Pharmacology of [2 (octahydro-1-azocinyl)ethyl]-guanidine sulfate (SU-5864). J. Pharmacol. Exp. Ther. 128: 22-29.
25. Kuntzman, R., Costa, E., Gessa, G. L., and Brodie, B. B. 1962. Reserpine and guanethidine action on peripheral stores of catecholamines. Life Sci. 1:65-74.
26. Rahn, K. H. and Goldberg, L. I. 1969. Comparison of antihypertensive efficacy, intestinal absorption, and excretion of guanethidine in hypertensive patient. Clin. Pharmacol. Ther. 10:858-866.