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Chemical Compound Review

CHEMBL309499     2-hydroxyguanidine

Synonyms: CHEBI:43089, NSC-529357, CTK0H5440, NSC529357, AR-1C4060, ...
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Disease relevance of N-HYDROXYGUANIDINE


High impact information on N-HYDROXYGUANIDINE


Biological context of N-HYDROXYGUANIDINE

  • The formation and decay kinetics of the Fe(III)NO complex did not vary greatly as a function of the N-hydroxyguanidine structure, but the formation of Fe(III)NO was substoichiometric in the cases of BuNOHG and FPhNOHG [9].
  • QSAR studies using molecular connectivity and van der Waal volume have been performed on a new series of hydroxyguanidine derivatives and a series of isoindolediones [10].
  • These data indicate that a key factor for efficient oxidation of a guanidine by iNOS to NO is the ability of the corresponding N-hydroxyguanidine to bind to the active site without being too rapidly released before its further oxidation [11].

Anatomical context of N-HYDROXYGUANIDINE

  • We investigated the effects of NG-hydroxy-L-arginine (L-HOArg) and hydroxyguanidine (HOG) on the synthesis and vasorelaxant activity of endothelium-derived relaxing factor (NO) released from the rabbit aortic endothelium [12].
  • The novel guanidine N-(3,4-dimethoxy-2-chlorobenzylideneamino)-guanidine [ME10092; a metabolite to the strongly cardioprotective hydroxyguanidine N-(3,4-dimethoxy-2-chlorobenzylideneamino)-N'-hydroxyguanidine (PR5)] was administered intravenously to rats subjected to left coronary artery clamping followed by reperfusion [13].
  • The free-radical intermediates and the stable products formed on one-electron oxidation of hydroxyguanidine (HOG) were investigated in order to suggest a mechanistic basis for HOG-induced cytotoxicity and cytostasis in leukaemia HL60 cells [14].

Associations of N-HYDROXYGUANIDINE with other chemical compounds



  • This work demonstrates that N-alkyl substituted hydroxyguanidine compounds are novel NOS substrates which 'short-circuit' the first oxidation step of NOS, and N-aryl substituted hydroxyguanidine compounds are isoform selective NOS substrate [16].

Analytical, diagnostic and therapeutic context of N-HYDROXYGUANIDINE

  • The conformation of sulfonyl-N-hydroxyguanidine derivatives, such as N-(4-chlorophenyl)-N'-[(benzo[2,1,3]thiadiazol-4-yl)sulfonyl]-N"- hydroxyguanidine (4g), investigated utilizing HMBC NMR, theoretical calculations, and X-ray crystallography, indicated stacking of the two aromatic rings [6].
  • Cardioprotective effects of N-hydroxyguanidine PR5 in myocardial ischaemia and reperfusion in rats [2].


  1. Optimization of the Schiff bases of N-hydroxy-N'-aminoguanidine as anticancer and antiviral agents. T'ang, A., Lien, E.J., Lai, M.M. J. Med. Chem. (1985) [Pubmed]
  2. Cardioprotective effects of N-hydroxyguanidine PR5 in myocardial ischaemia and reperfusion in rats. Veveris, M., Dambrova, M., Cirule, H., Meirena, D., Kalvinsh, I., Wikberg, J.E. Br. J. Pharmacol. (1999) [Pubmed]
  3. Inhibition of murine coronavirus RNA synthesis by hydroxyguanidine derivatives. Keck, J.G., Wang, P.H., Lien, E.J., Lai, M.M. Virus Res. (1989) [Pubmed]
  4. The novel binding mode of N-alkyl-N'-hydroxyguanidine to neuronal nitric oxide synthase provides mechanistic insights into NO biosynthesis. Li, H., Shimizu, H., Flinspach, M., Jamal, J., Yang, W., Xian, M., Cai, T., Wen, E.Z., Jia, Q., Wang, P.G., Poulos, T.L. Biochemistry (2002) [Pubmed]
  5. Efficient formation of nitric oxide from selective oxidation of N-aryl N'-hydroxyguanidines by inducible nitric oxide synthase. Renodon-Cornière, A., Boucher, J.L., Dijols, S., Stuehr, D.J., Mansuy, D. Biochemistry (1999) [Pubmed]
  6. Synthesis and cytotoxic evaluation of substituted sulfonyl-N-hydroxyguanidine derivatives as potential antitumor agents. Chern, J.W., Leu, Y.L., Wang, S.S., Jou, R., Lee, C.F., Tsou, P.C., Hsu, S.C., Liaw, Y.C., Lin, H.M. J. Med. Chem. (1997) [Pubmed]
  7. Analysis of substrate-induced electronic, catalytic, and structural changes in inducible NO synthase. Sennequier, N., Stuehr, D.J. Biochemistry (1996) [Pubmed]
  8. Characterization of the enzymatic activity for biphasic competition by guanoxabenz (1-(2,6-dichlorobenzylidene-amino)-3-hydroxyguanidine) at alpha2-adrenoceptors. I. Description of an enzymatic activity in spleen membranes. Uhlén, S., Dambrova, M., Tiger, G., Oliver, D.W., Wikberg, J.E. Biochem. Pharmacol. (1998) [Pubmed]
  9. Reactivity of the heme-dioxygen complex of the inducible nitric oxide synthase in the presence of alternative substrates. Lefèvre-Groboillot, D., Boucher, J.L., Mansuy, D., Stuehr, D.J. FEBS J. (2006) [Pubmed]
  10. Quantitative structure-activity relationship studies on some anticancerous, antiviral and cytostatic agents. Pandey, C., Dwivedi, K.P., Yadava, G.D., Singh, V.K., Srivastava, A.K., Agrawal, V.K. Indian J. Biochem. Biophys. (1989) [Pubmed]
  11. Relationship between the structure of guanidines and N-hydroxyguanidines, their binding to inducible nitric oxide synthase (iNOS) and their iNOS-catalysed oxidation to NO. Lefèvre-Groboillot, D., Boucher, J.L., Stuehr, D.J., Mansuy, D. FEBS J. (2005) [Pubmed]
  12. NG-hydroxy-L-arginine and hydroxyguanidine potentiate the biological activity of endothelium-derived relaxing factor released from the rabbit aorta. Zembowicz, A., Chłopicki, S., Radziszewski, W., Vane, J.R., Gryglewski, R.J. Biochem. Biophys. Res. Commun. (1992) [Pubmed]
  13. The novel guanidine ME10092 protects the heart during ischemia-reperfusion. Dambrova, M., Veveris, M., Cirule, H., Pugovichs, O., Post, C., Lundstedt, T., Kalvinsh, I., Skottner, A., Wikberg, J.E. Eur. J. Pharmacol. (2002) [Pubmed]
  14. Nitric oxide involvement in the toxicity of hydroxyguanidine in leukaemia HL60 cells. Everett, S.A., Smith, K.A., Patel, K.B., Dennis, M.F., Stratford, M.R., Wardman, P. Br. J. Cancer Suppl. (1996) [Pubmed]
  15. Conversion of canavanine to alpha-keto-gamma-guanidinooxybutyrate and to vinylglyoxylate and 2-hydroxyguanidine. Hollander, M.M., Reiter, A.J., Horner, W.H., Cooper, A.J. Arch. Biochem. Biophys. (1989) [Pubmed]
  16. Novel substrates for nitric oxide synthases. Xian, M., Fujiwara, N., Wen, Z., Cai, T., Kazuma, S., Janczuk, A.J., Tang, X., Telyatnikov, V.V., Zhang, Y., Chen, X., Miyamoto, Y., Taniguchi, N., Wang, P.G. Bioorg. Med. Chem. (2002) [Pubmed]
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