Literature DB >> 20306345

Cysteine S-conjugate β-lyases: important roles in the metabolism of naturally occurring sulfur and selenium-containing compounds, xenobiotics and anticancer agents.

Arthur J L Cooper1, Boris F Krasnikov, Zoya V Niatsetskaya, John T Pinto, Patrick S Callery, Maria T Villar, Antonio Artigues, Sam A Bruschi.   

Abstract

Cysteine S-conjugate β-lyases are pyridoxal 5'-phosphate-containing enzymes that catalyze β-elimination reactions with cysteine S-conjugates that possess a good leaving group in the β-position. The end products are aminoacrylate and a sulfur-containing fragment. The aminoacrylate tautomerizes and hydrolyzes to pyruvate and ammonia. The mammalian cysteine S-conjugate β-lyases thus far identified are enzymes involved in amino acid metabolism that catalyze β-lyase reactions as non-physiological side reactions. Most are aminotransferases. In some cases the lyase is inactivated by reaction products. The cysteine S-conjugate β-lyases are of much interest to toxicologists because they play an important key role in the bioactivation (toxication) of halogenated alkenes, some of which are produced on an industrial scale and are environmental contaminants. The cysteine S-conjugate β-lyases have been reviewed in this journal previously (Cooper and Pinto in Amino Acids 30:1-15, 2006). Here, we focus on more recent findings regarding: (1) the identification of enzymes associated with high-M(r) cysteine S-conjugate β-lyases in the cytosolic and mitochondrial fractions of rat liver and kidney; (2) the mechanism of syncatalytic inactivation of rat liver mitochondrial aspartate aminotransferase by the nephrotoxic β-lyase substrate S-(1,1,2,2-tetrafluoroethyl)-L-cysteine (the cysteine S-conjugate of tetrafluoroethylene); (3) toxicant channeling of reactive fragments from the active site of mitochondrial aspartate aminotransferase to susceptible proteins in the mitochondria; (4) the involvement of cysteine S-conjugate β-lyases in the metabolism/bioactivation of drugs and natural products; and (5) the role of cysteine S-conjugate β-lyases in the metabolism of selenocysteine Se-conjugates. This review emphasizes the fact that the cysteine S-conjugate β-lyases are biologically more important than hitherto appreciated.

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Year:  2010        PMID: 20306345      PMCID: PMC2898922          DOI: 10.1007/s00726-010-0552-0

Source DB:  PubMed          Journal:  Amino Acids        ISSN: 0939-4451            Impact factor:   3.520


  119 in total

1.  In vitro effects of Se-allylselenocysteine and Se-propylselenocysteine on cell growth, DNA integrity, and apoptosis.

Authors:  Z Zhu; W Jiang; H E Ganther; C Ip; H J Thompson
Journal:  Biochem Pharmacol       Date:  2000-11-15       Impact factor: 5.858

2.  Chemoprevention of mammary cancer with Se-allylselenocysteine and other selenoamino acids in the rat.

Authors:  C Ip; Z Zhu; H J Thompson; D Lisk; H E Ganther
Journal:  Anticancer Res       Date:  1999 Jul-Aug       Impact factor: 2.480

3.  Purification and characterisation of a novel cysteine conjugate beta-lyase from the tapeworm Moniezia expansa.

Authors:  H J Adcock; P M Brophy; P H Teesdale-Spittle; L D Buckberry
Journal:  Int J Parasitol       Date:  2000-04-24       Impact factor: 3.981

4.  In vitro and in vivo studies of methylseleninic acid: evidence that a monomethylated selenium metabolite is critical for cancer chemoprevention.

Authors:  C Ip; H J Thompson; Z Zhu; H E Ganther
Journal:  Cancer Res       Date:  2000-06-01       Impact factor: 12.701

5.  Cysteine conjugate of methazolamide is metabolized by beta-lyase.

Authors:  K Kishida; N Saida; N Yamamura; Y Iwai; T Sasabe
Journal:  J Pharm Sci       Date:  2001-02       Impact factor: 3.534

6.  Evaluation of the kinetics of beta-elimination reactions of selenocysteine Se-conjugates in human renal cytosol: possible implications for the use as kidney selective prodrugs.

Authors:  M Rooseboom; N P Vermeulen; I Andreadou; J N Commandeur
Journal:  J Pharmacol Exp Ther       Date:  2000-08       Impact factor: 4.030

7.  Bioactivation of selenocysteine Se-conjugates by a highly purified rat renal cysteine conjugate beta-lyase/glutamine transaminase K.

Authors:  J N Commandeur; I Andreadou; M Rooseboom; M Out; L J de Leur; E Groot; N P Vermeulen
Journal:  J Pharmacol Exp Ther       Date:  2000-08       Impact factor: 4.030

8.  Determination of tetrahydrothiophene formation as a probe of in vitro busulfan metabolism by human glutathione S-transferase A1-1: use of a highly sensitive gas chromatographic-mass spectrometric method.

Authors:  C A Ritter; F Bohnenstengel; U Hofmann; H K Kroemer; B Sperker
Journal:  J Chromatogr B Biomed Sci Appl       Date:  1999-06-25

9.  Cysteine conjugate beta-lyase activity in three species of parasitic helminth.

Authors:  H J Adcock; P M Brophy; P H Teesdale-Spittle; L D Buckberry
Journal:  Int J Parasitol       Date:  1999-04       Impact factor: 3.981

10.  Acylase-catalyzed deacetylation of haloalkene-derived mercapturates.

Authors:  V Uttamsingh; M W Anders
Journal:  Chem Res Toxicol       Date:  1999-10       Impact factor: 3.739

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  29 in total

1.  Whole genome expression profile in neuroblastoma cells exposed to 1-methyl-4-phenylpyridine.

Authors:  E Mazzio; K F A Soliman
Journal:  Neurotoxicology       Date:  2012-07-07       Impact factor: 4.294

2.  Comparative enzymology of (2S,4R)4-fluoroglutamine and (2S,4R)4-fluoroglutamate.

Authors:  Arthur J L Cooper; Boris F Krasnikov; John T Pinto; Hank F Kung; Jianyong Li; Karl Ploessl
Journal:  Comp Biochem Physiol B Biochem Mol Biol       Date:  2012-05-19       Impact factor: 2.231

3.  Glutathione conjugates of the mercapturic acid pathway and guanine adduct as biomarkers of exposure to CEES, a sulfur mustard analog.

Authors:  Marie Roser; David Béal; Camille Eldin; Leslie Gudimard; Fanny Caffin; Fanny Gros-Désormeaux; Daniel Léonço; François Fenaille; Christophe Junot; Christophe Piérard; Thierry Douki
Journal:  Anal Bioanal Chem       Date:  2021-01-07       Impact factor: 4.142

4.  Kynurenine aminotransferase III and glutamine transaminase L are identical enzymes that have cysteine S-conjugate β-lyase activity and can transaminate L-selenomethionine.

Authors:  John T Pinto; Boris F Krasnikov; Steven Alcutt; Melanie E Jones; Thambi Dorai; Maria T Villar; Antonio Artigues; Jianyong Li; Arthur J L Cooper
Journal:  J Biol Chem       Date:  2014-09-17       Impact factor: 5.157

5.  Site-Specific Incorporation of Selenocysteine Using an Expanded Genetic Code and Palladium-Mediated Chemical Deprotection.

Authors:  Jun Liu; Feng Zheng; Rujin Cheng; Shanshan Li; Sharon Rozovsky; Qian Wang; Lei Wang
Journal:  J Am Chem Soc       Date:  2018-07-09       Impact factor: 15.419

Review 6.  Trichloroethylene biotransformation and its role in mutagenicity, carcinogenicity and target organ toxicity.

Authors:  Lawrence H Lash; Weihsueh A Chiu; Kathryn Z Guyton; Ivan Rusyn
Journal:  Mutat Res Rev Mutat Res       Date:  2014 Oct-Dec       Impact factor: 5.657

Review 7.  α-Ketoglutaramate: an overlooked metabolite of glutamine and a biomarker for hepatic encephalopathy and inborn errors of the urea cycle.

Authors:  Arthur J L Cooper; Tomiko Kuhara
Journal:  Metab Brain Dis       Date:  2013-11-14       Impact factor: 3.584

8.  Dietary supplemented 2-mercaptoethanol prevents spontaneous and delays virally-induced murine mammary tumorigenesis.

Authors:  Robert E Click
Journal:  Cancer Biol Ther       Date:  2013-06       Impact factor: 4.742

9.  A comparison of reversible versus irreversible protein glutathionylation.

Authors:  Danyelle M Townsend; Volodymyr I Lushchak; Arthur J L Cooper
Journal:  Adv Cancer Res       Date:  2014       Impact factor: 6.242

Review 10.  Toxicity mechanism-based prodrugs: glutathione-dependent bioactivation as a strategy for anticancer prodrug design.

Authors:  Xin-Yu Zhang; Adnan A Elfarra
Journal:  Expert Opin Drug Discov       Date:  2018-08-13       Impact factor: 6.098

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