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Selective depletion of mitochondrial glutathione concentrations by (R,S)-3-hydroxy-4-pentenoate potentiates oxidative cell death.
The critical role of mitochondrial glutathione in cytoprotection is established and (R,S)-3-hydroxy-4-pentenoate may find utility in exploring mitochondrial glutATHione homeostasis. Expand
Bioactivation mechanism of S-(3-oxopropyl)-N-acetyl-L-cysteine, the mercapturic acid of acrolein.
Findings indicate that the cytotoxicity of S-conjugate 1 is associated with a novel bioactivation mechanism that involves sulfoxidation followed by a general-base-catalyzed elimination of acrolein from S-oxide 2. Expand
Bioactivation of [13C]dichloromethane in mouse, rat, and human liver cytosol: 13C nuclear magnetic resonance spectroscopic studies.
The results corroborate the finding that formaldehyde is a reactive intermediate formed during the glutathione-dependent bioactivation of dichloromethane that may be involved in the observed tumorigenicity in susceptible species and indicate that S-(chloromethyl)-N-acetyl-L-cysteine methyl ester is an intermediate in the glutATHione- dependent bioactivation and may also play a role in its mutagenicity and carcinogenicity. Expand
Flavin-containing monooxygenase-dependent stereoselective S-oxygenation and cytotoxicity of cysteine S-conjugates and mercapturates.
The metabolism of cysteine S-conjugates of both cis- and trans-1,3-dichloropropene in the presence of rat kidney microsomes and purified flavin-containing monooxygenase from hog liver was investigated in vitro and indicated that considerable S-oxygenases stereoselectivity and structural selectivity was observed. Expand
Enzymatic reaction of β-N-methylaminoalanine with l-amino acid oxidase
The reaction of β-N-methylaminoalanine (BMAA) with l -amino acid oxidase ( l -AAO) in the presence of catalase yields ammonia and β-N-methylaminopyruvate, which was trapped as itsExpand
Fourier-transform ion cyclotron resonance mass spectrometric evidence for the formation of alpha-chloroenethiolates and thioketenes from chloroalkene-derived, cytotoxic 4-thiaalkanoates.
Observations support the intermediacy of alpha-chloroenethiolates and chlorothioketenes in the bioactivation of cytotoxic, chloroalkene-derived 4-thiaalkanoates and cysteine S-conjugates and demonstrate the utility of Fourier-transform ion cyclotron mass spectrometry in studying the formation of reactive intermediates. Expand
Affinity ligands and related agents for brain muscarinic and nicotinic cholinergic receptors.
DMBAB and its analogues are useful affinity ligands for examining the biochemical and functional characteristics of brain cholinergic receptors, particularly the muscarinic which has an affinity near the nanomolar concentration range. Expand
Enantioselective depletion of mitochondrial glutathione concentrations by (S)- and (R)-3-hydroxy-4-pentenoate.
Results show that (S)-3-Hydroxy-4-pentenoate is a substrate for 3-hydroxy-butanoate dehydrogenase and is converted to the Michael acceptor 3-oxo- 4-pentenosate, which reacts with glutathione and thereby depletes the mitochondrial glutathion pool. Expand
Enzymatic reaction of beta-N-methylaminoalanine with L-amino acid oxidase.
Results indicate that BMAA is converted by L-AAO to the corresponding alpha-imino acid, which undergoes hydrolysis to beta-N-methylaminopyruvate, which is readily oxidized to N-methylglycine by hydrogen peroxide. Expand
Opioid receptor antagonist affinity ligands: 6β-bromoacetamido-6-desoxynaltrexone and 6β-thioglycolamido-6-desoxynaltrexone
The present study, utilizing thioglycolamido as the reactive group, describes the synthesis and pharmacology of a new opioid antagonist affinity ligand, 6β-thioglycolamido-6-desoxynaltrexone (TAN)Expand