Characterisation of the decomposition behaviour of S-nitrosoglutathione and a new class of analogues: S-Nitrosophytochelatins

Dasgupta, 2005, Transfer of nitric oxide from nitrovasodilators to free thiols—evidence of two distinct stages, Biochemical and Biophysical Research Communications, 335, 730, 10.1016/j.bbrc.2005.07.126 Gross, 2001, Vascular biology. Targeted delivery of nitric oxide, Nature, 409, 577, 10.1038/35054661 Condorelli, 2001, In vivo control of soluble guanylate cyclase activation by nitric oxide: a kinetic analysis, Biophysical Journal, 80, 2110, 10.1016/S0006-3495(01)76184-X Donzelli, 2006, The activation of metabolites of nitric oxide synthase by metals is both redox and oxygen dependent: a new feature of nitrogen oxide signaling, Antioxidants and Redox Signaling, 8, 1363, 10.1089/ars.2006.8.1363 Al-Sa’doni, 2000, S-Nitrosothiols: a class of nitric oxide-donor drugs, Clinical Science, 98, 507, 10.1042/CS19990267 Kohen, 2002, Oxidation of biological systems: oxidative stress phenomena, antioxidants, redox reactions, and methods for their quantification, Toxicologic Pathology, 30, 620, 10.1080/01926230290166724 Hall, 2004, Peroxynitrite-mediated protein nitration and lipid peroxidation in a mouse model of traumatic brain injury, Journal of Neurotrauma, 21, 9, 10.1089/089771504772695904 Cai, 2005, Nitric oxide and nitric oxide donors, 1 Wang, 2003, Inhaled nitric oxide in 2003: a review of its mechanisms of action, Canadian Journal of Anaesthesia, 50, 839, 10.1007/BF03019384 de Oliveira, 2002, Thermal stability of primary S-nitrosothiols: roles of autocatalysis and structural effects on the rate of nitric oxide release, Journal of Physical Chemistry A, 106, 8963, 10.1021/jp025756u Noble, 1999, Nitric oxide release from S-nitrosoglutathione (GSNO), Chemical Communications, 2317, 10.1039/a907891f Zhang, 2004, The mechanism of transmembrane S-nitrosothiol transport, Proceedings of the National Academy of Sciences of the United States of America, 101, 7891, 10.1073/pnas.0401167101 Fang, 2000, S-Nitrosoglutathione breakdown prevents airway smooth muscle relaxation in the guinea pig, American Journal of Physiology-Lung Cellular and Molecular Physiology, 279, L716, 10.1152/ajplung.2000.279.4.L716 Hogg, 2000, Biological chemistry and clinical potential of S-nitrosothiols, Free Radical Biology and Medicine, 28, 1478, 10.1016/S0891-5849(00)00248-3 Singh, 1996, The chemistry of the S-nitrosoglutathione glutathione system, Proceedings of the National Academy of Sciences of the United States of America, 93, 14428, 10.1073/pnas.93.25.14428 Chen, 2001, Fluorophore-labeled S-nitrosothiols, Journal of Organic Chemistry, 66, 6064, 10.1021/jo015658p Richardson, 2002, Potential therapeutic uses for S-nitrosothiols, Clinical Science, 102, 99, 10.1042/CS20010207 Gaston, 1998, Bronchodilator S-nitrosothiol deficiency in asthmatic respiratory failure, Lancet, 351, 1317, 10.1016/S0140-6736(97)07485-0 Butcher, 2001, S-Nitrosothiols—lots of deep breaths required, Lancet, 358, 897, 10.1016/S0140-6736(01)06085-8 Maxwell, 1999, S-Nitrosothiols for nitrate tolerance, Lancet, 354, 338, 10.1016/S0140-6736(05)75246-6 Zhao, 2005, Nitrosonium-catalyzed decomposition of S-nitrosothiols in solution: a theoretical and experimental study, Journal of the American Chemical Society, 127, 10917, 10.1021/ja050018f Lucente, 1998, Design and synthesis of glutathione analogues, Farmaco, 53, 721, 10.1016/S0014-827X(98)00098-6 Godoy, 2006, S-Nitrosogluthathione reductase activity of amphioxus ADH3: insights into the nitric oxide metabolism, International Journal of Biological Sciences, 2, 117, 10.7150/ijbs.2.117 Munro, 1999, Reactivity of nitrogen nucleophiles towards S-nitrosopenicillamine, Journal of the Chemical Society-Perkin Transactions, 2, 1989, 10.1039/a905901f Inouhe, 2005, Phytochelatins, Brazilian Journal of Plant Physiology, 17, 65, 10.1590/S1677-04202005000100006 Cobbett, 2000, Phytochelatins and their roles in heavy metal detoxification, Plant Physiology, 123, 825, 10.1104/pp.123.3.825 Cobbett, 2001, Heavy metal detoxification in plants: phytochelatin biosynthesis and function, IUBMB Life, 51, 183, 10.1080/152165401753544250 Available from: <www.danforthcenter.org/jez/research.htm>. Rauser, 1995, Phytochelatins and related peptides. Structure, biosynthesis, and function, Plant Physiology, 109, 1141, 10.1104/pp.109.4.1141 Rauser, 1990, Phytochelatins, Annual Review of Biochemistry, 59, 61, 10.1146/annurev.bi.59.070190.000425 Smith, 2000, Kinetics and mechanism of the decomposition of S-nitrosoglutathione by l-ascorbic acid and copper ions in aqueous solution to produce nitric oxide, Nitric oxide, 4, 57, 10.1006/niox.2000.0272 Sliskovic, 2005, Characterization of the S-denitrosation activity of protein disulfide isomerase, Journal of Biological Chemistry, 280, 8733, 10.1074/jbc.M408080200 Barnett, 1995, NO-group transfer (transnitrosation) between S-nitrosothiols and thiols. 2, Journal of the Chemical Society-Perkin Transactions, 2, 1279, 10.1039/p29950001279 Bartberger, 2000, Theory, spectroscopy, and crystallographic analysis of S-nitrosothiols: conformational distribution dictates spectroscopic behavior, Journal of the American Chemical Society, 122, 5889, 10.1021/ja994476y Liu, 1998, S-Transnitrosation reactions are involved in the metabolic fate and biological actions of nitric oxide, Journal of Pharmacology and Experimental Therapeutics, 284, 526 Spain, 2003, Characterization of the acid/base and redox chemistry of phytochelatin analogue peptides, Analytical Chemistry, 75, 3712, 10.1021/ac0207426 Kumar, 2004, Protein stiffening and entropic stabilization in the subdenaturing limit of guanidine hydrochloride, Biophysical Journal, 87, 2656, 10.1529/biophysj.104.044701 Dunbar, 1997, The effect of denaturants on protein structure, Protein Science, 6, 1727, 10.1002/pro.5560060813 Sulkowska, 2005, The effect of concentration of guanidine hydrochloride on the sulfasalazine-serum albumin complex, Journal of Molecular Structure, 744, 775, 10.1016/j.molstruc.2004.10.093 Wood, 1996, The mechanism of photochemical release of nitric oxide from S-nitrosoglutathione, Photochemistry and Photobiology, 64, 518, 10.1111/j.1751-1097.1996.tb03099.x Singh, 1995, Photosensitized decomposition of S-nitrosothiols and 2-methyl-2-nitrosopropane. Possible use for site-directed nitric oxide production, FEBS Letters, 360, 47, 10.1016/0014-5793(95)00065-H Hu, 2006, The kinetics of thiol-mediated decomposition of S-nitrosothiols, AAPS Journal, 8, E485, 10.1208/aapsj080357 Ceron, 2001, The relaxation induced by S-nitroso-glutathione and S-nitroso-N-acetylcysteine in rat aorta is not related to nitric oxide production, Journal of Pharmacology and Experimental Therapeutics, 298, 686 Huber, 2005, A selection for mutants that interfere with folding of Escherichia coli thioredoxin-1 in vivo, Proceedings of the National Academy of Sciences of the United States of America, 102, 18872, 10.1073/pnas.0509583102 Dicks, 1998, The reaction of S-nitrosothiols with thiols at high thiol concentration, Canadian Journal of Chemistry-Revue Canadienne De Chimie, 76, 789, 10.1139/v98-062 Simon, 1996, Polynitrosylated proteins: characterization, bioactivity, and functional consequences, Proceedings of the National Academy of Sciences of the United States of America, 93, 4736, 10.1073/pnas.93.10.4736 Gaston, 2003, S-Nitrosylation signaling in cell biology, Molecular Interventions, 3, 253, 10.1124/mi.3.5.253 Wang, 2001, Equilibrium and kinetics studies of transnitrosation between S-nitrosothiols and thiols, Bioorganic and Medicinal Chemistry Letters, 11, 433, 10.1016/S0960-894X(00)00688-0 Rossi, 1997, A method to study kinetics of transnitrosation with nitrosoglutathione: reactions with hemoglobin and other thiols, Analytical Biochemistry, 254, 215, 10.1006/abio.1997.2424 Miersch, 2005, Protein S-nitrosation: biochemistry and characterization of protein thiol–NO interactions as cellular signals, Clinical Biochemistry, 38, 777, 10.1016/j.clinbiochem.2005.05.014