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Structure and activity of NO synthase inhibitors specific to the L-arginine binding site

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Abstract

Synthesis of compounds containing a fragment similar to the guanidine group of L-arginine, which is a substrate of nitric oxide synthase (NOS), is the main direction in creating NOS inhibitors. The inhibitory effect of such compounds is caused not only by their competition with the substrate for the L-arginine-binding site and/or oxidizing center of the enzyme (heme) but also by interaction with peptide motifs of the enzyme that influence its dimerization, affinity for cofactors, and interaction with associated proteins. Structures, activities, and relative in vitro and in vitro specificities of various NOS inhibitors (amino acid and non-amino acid) with linear or cyclic structure and containing guanidine, amidine, or isothiuronium group are considered. These properties are mainly analyzed by comparison with effects of the inhibitors on the inducible NOS.

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Abbreviations

NO⋅ :

nitric oxide

O -2 :

superoxide anion radical

ROS:

reactive oxygen species

LPS:

lipopolysaccharide

NOS:

nitric oxide synthase

nNOS:

neuronal NOS

iNOS:

inducible NOS

eNOS:

endothelial NOS

m-, r-, b-, and h-NOS:

mouse, rat, bovine, and human NOS

CaM:

calmodulin

BH4 :

(6R)5,6,7,8-tetrahydro-L-biopterin

ITU:

isothiourea

1400W:

N[3-(aminomethyl)-benzyl]-acetamidine

AG:

aminoguanidine

2-AP:

2-aminopicoline

7-NI:

7-nitroindazole

L-NA:

Nωnitro-L-arginine

L-NMMA:

Nω-monomethyl-L-arginine

PA:

Nω-propyl-L-arginine

cPA:

Nω-cyclopropyl-L-arginine

L-NIO:

N5-iminoethyl-L-ornithine

L-VNIO:

L-N5-(1-iminobuten-3-yl)-L-ornithine

L-NIL:

N6-iminoethyl-L-lysine

L-TC:

L-thiocitrulline

S-methyl-TC:

S-methyl-L-thiocitrulline

2-ADT:

2-amino-5,6-dihydro-4H-1,3-thiazine

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Authors and Affiliations

  1. Medical Radiological Research Center, Russian Academy of Medical Sciences, ul. Koroleva 4, 249036, Obninsk, Russia

    S. Ya. Proskuryakov, A. G. Konoplyannikov & V. G. Skvortsov

  2. Faculty of Chemistry, Lomonosov Moscow State University, 119992, Moscow, Russia

    A. A. Mandrugin & V. M. Fedoseev

Authors
  1. S. Ya. Proskuryakov
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  2. A. G. Konoplyannikov
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  3. V. G. Skvortsov
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  4. A. A. Mandrugin
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  5. V. M. Fedoseev
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Correspondence to S. Ya. Proskuryakov.

Additional information

Translated from Biokhimiya, Vol. 70, No. 1, 2005, pp. 14–32. Original Russian Text Copyright © 2005 by Proskuryakov, Konoplyannikov, Skvortsov, Mandrugin, Fedoseev.

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Proskuryakov, S.Y., Konoplyannikov, A.G., Skvortsov, V.G. et al. Structure and activity of NO synthase inhibitors specific to the L-arginine binding site. Biochemistry (Moscow) 70, 8–23 (2005). https://doi.org/10.1007/PL00021750

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  • DOI: https://doi.org/10.1007/PL00021750

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