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Chemical Compound Review:

Thiocitrulline (2S)-2-amino-5- (carbamothioylamino)pentano...

Synonyms: CHEMBL93247, BSPBio_001158, KBioGR_000498, KBioSS_000498, CHEBI:252632, ...

Frey, C. et al., Sawyer, T.W., Bodnárová, M. et al., Zassler, B. et al., Salerno, J.C. et al., et al.

Sawyer, Risk,

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Disease relevance of L-thiocitrulline

In vivo, L-thiocitrulline is a potent pressor agent in both normal and endotoxemic rats, the latter finding suggesting utility in treating the hypotension of septic shock [1].
The protective effects of l-thiocitrulline (l-TC) against HD toxicity were also assessed [2].

High impact information on L-thiocitrulline

No inhibition is observed after addition of L-arginine, NG-hydroxy-L-arginine, L-thiocitrulline, and L-NG-monomethyl arginine to activated eNOS [3].
Cells were also treated either with L-thiocitrulline (L-Thio), an irreversible inhibitor of NOS, or with exogenous superoxide dismutase (SOD) and catalase [4].
Characterization by electron paramagnetic resonance of the interactions of L-arginine and L-thiocitrulline with the heme cofactor region of nitric oxide synthase [5].
We report here that L-thiocitrulline (gamma-thioureido-L-norvaline) is a potent, stereospecific inhibitor of the constitutive brain and endothelial isoforms of NOS as well as the isoform induced in vascular smooth muscle cells by lipopolysaccharide and interferon-gamma [1].
Organotypic brain slices of the basal nucleus of Meynert were cultured for 2 weeks in the presence of 1-100 microM urea with or without NGF or other growth factors or with or without 1-10 microM of the NOS inhibitor L-thiocitrulline [6].

Chemical compound and disease context of L-thiocitrulline

Previous studies in this laboratory have shown that the arginine analogues L-thiocitrulline (L-TC) and L-nitroarginine methyl ester (L-NAME) have potent protective activity against sulphur mustard (HD) toxicity that was not related to their nitric oxide synthase inhibiting activities [7].

Associations of L-thiocitrulline with other chemical compounds

S-Ethylisothiourea hydrobromide (5mM), a selective inhibitor of all NOS isoforms, suppressed ApNOS by 85%, l-N6-(1-iminoethyl)lysine dihydrochloride (L-NIL, 5mM), an iNOS inhibitor, by 78% and L-thiocitrulline (5mM) (an inhibitor of nNOS and iNOS) by greater than 95% [8].

Gene context of L-thiocitrulline

L-Thiocitrulline is a known potent inhibitor of several isoforms of nitric oxide synthase (NOS) [9].

References

L-thiocitrulline. A stereospecific, heme-binding inhibitor of nitric-oxide synthases. Frey, C., Narayanan, K., McMillan, K., Spack, L., Gross, S.S., Masters, B.S., Griffith, O.W. J. Biol. Chem. (1994) [Pubmed]
Effects of selected arginine analogues on sulphur mustard toxicity in human and hairless guinea pig skin keratinocytes. Sawyer, T.W., Risk, D. Toxicol. Appl. Pharmacol. (2000) [Pubmed]
Superoxide generation by endothelial nitric oxide synthase: the influence of cofactors. Vásquez-Vivar, J., Kalyanaraman, B., Martásek, P., Hogg, N., Masters, B.S., Karoui, H., Tordo, P., Pritchard, K.A. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
L-arginine increases UVA cytotoxicity in irradiated human keratinocyte cell line: potential role of nitric oxide. Didier, C., Emonet-Piccardi, N., Béani, J.C., Cadet, J., Richard, M.J. FASEB J. (1999) [Pubmed]
Characterization by electron paramagnetic resonance of the interactions of L-arginine and L-thiocitrulline with the heme cofactor region of nitric oxide synthase. Salerno, J.C., Frey, C., McMillan, K., Williams, R.F., Masters, B.S., Griffith, O.W. J. Biol. Chem. (1995) [Pubmed]
Urea enhances the nerve growth factor-induced neuroprotective effect on cholinergic neurons in organotypic rat brain slices. Zassler, B., Dechant, G., Humpel, C. Neuroscience (2005) [Pubmed]
Synergistic protective effects of selected arginine analogues against sulphur mustard toxicity in neuron culture. Sawyer, T.W. Toxicol. Appl. Pharmacol. (1999) [Pubmed]
Calcium/calmodulin-dependent nitric oxide synthase activity in the CNS of Aplysia californica: biochemical characterization and link to cGMP pathways. Bodnárová, M., Martásek, P., Moroz, L.L. J. Inorg. Biochem. (2005) [Pubmed]
Heterocyclic analogues of L-citrulline as inhibitors of the isoforms of nitric oxide synthase (NOS) and identification of N(delta)-(4,5-dihydrothiazol-2-yl)ornithine as a potent inhibitor. Ulhaq, S., Chinje, E.C., Naylor, M.A., Jaffar, M., Stratford, I.J., Threadgill, M.D. Bioorg. Med. Chem. (1999) [Pubmed]

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