N-Hydroxyguanidines oxidation by a N3S copper-complex mimicking the reactivity of Dopamine β-Hydroxylase

作者: Patrick Slama , Jean-Luc Boucher , Marius Réglier , None

DOI: 10.1016/J.JINORGBIO.2008.12.012

关键词:

摘要: Abstract N -Aryl- ′-hydroxyguanidines are compounds that display interesting pharmacological properties but their chemical reactivity remains poorly investigated. Some of these substrates for the heme-containing enzymes nitric-oxide synthases (NOS) and act as reducing co-substrates copper-containing enzyme Dopamine β-Hydroxylase (DBH) [P. Slama, J.L. Boucher, M. Reglier, Biochem. Biophys. Res. Commun. 316 (2004) 1081–1087]. DBH catalyses hydroxylation important neurotransmitter dopamine into norepinephrine in presence both molecular oxygen a co-substrate. Although many molecules have been used DBH, interaction at active site role mechanism not clearly characterized. In present paper, we water-soluble copper-N 3 S complex mimics Cu B aromatic -hydroxyguanidines reducers to address this question. readily reduced copper(II) Cu(I) were oxidized nitrosoamidine previously observed reactions performed with purified DBH. These data describe first time -aryl- help understand copper

参考文章(45)
D J Stuehr, N S Kwon, C F Nathan, O W Griffith, P L Feldman, J Wiseman, N omega-hydroxy-L-arginine is an intermediate in the biosynthesis of nitric oxide from L-arginine. Journal of Biological Chemistry. ,vol. 266, pp. 6259- 6263 ,(1991) , 10.1016/S0021-9258(18)38112-2
R��my Ricoux, Jean-Luc Boucher, Dominique Mandon, Yves-Michel Frapart, Yann Henry, Daniel Mansuy, Jean-Pierre Mahy, Microperoxidase 8 catalysed nitrogen oxides formation from oxidation of N‐hydroxyguanidines by hydrogen peroxide FEBS Journal. ,vol. 270, pp. 47- 55 ,(2002) , 10.1046/J.1432-1033.2003.03358.X
Garry J. Southan, Andrew L. Salzman, Csaba Szabó, Hydroxyguanidines inhibit peroxynitrite-induced oxidation Free Radical Biology and Medicine. ,vol. 25, pp. 914- 925 ,(1998) , 10.1016/S0891-5849(98)00120-8
Denis M. Bailey, C. George DeGrazia, Harlan E. Lape, Richard Frering, Dorothy Fort, Thomas Skulan, Hydroxyguanidines. A new class of antihypertensive agents. Journal of Medicinal Chemistry. ,vol. 16, pp. 151- 156 ,(1973) , 10.1021/JM00260A015
Sean T Prigge, Betty A Eipper, Richard E Mains, L Mario Amzel, Dioxygen Binds End-On to Mononuclear Copper in a Precatalytic Enzyme Complex Science. ,vol. 304, pp. 864- 867 ,(2004) , 10.1126/SCIENCE.1094583
Judith P. Klinman, Mechanisms Whereby Mononuclear Copper Proteins Functionalize Organic Substrates. Chemical Reviews. ,vol. 96, pp. 2541- 2562 ,(1996) , 10.1021/CR950047G
Jean-Luc Boucher, Sandrine Vadon, Alain Tomas, Bernard Viossat, Daniel Mansuy, Oxidation of arylamidoximes by hydrogen peroxide and horseradish peroxidase in water: Easy preparation and X-ray structure of O-(arylimidoyl)arylamidoximes Tetrahedron Letters. ,vol. 37, pp. 3113- 3116 ,(1996) , 10.1016/0040-4039(96)00504-7
Jon M. Fukuto, Dennis J. Stuehr, Paul L. Feldman, Michael P. Bova, Patrick Wong, Peracid oxidation of an N-hydroxyguanidine compound: A chemical model for the oxidation of Nω-hydroxy-L-arginine by nitric oxide synthase Journal of Medicinal Chemistry. ,vol. 36, pp. 2666- 2670 ,(1993) , 10.1021/JM00070A010