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Catalysis and structural properties of Leishmania infantum glyoxalase II: trypanothione specificity and phylogeny.

Silva MS, Barata L, Ferreira AE, Romão S, Tomás AM, Freire AP, Cordeiro C
Biochemistry 47 195-204 (2008)
Cited: 25 times
EuropePMC logo PMID: 18052346

Abstract

The glyoxalase pathway catalyzes the formation of d-lactate from methylglyoxal, a toxic byproduct of glycolysis. In trypanosomatids, trypanothione replaces glutathione in this pathway, making it a potential drug target, since its selective inhibition might increase methylglyoxal concentration in the parasites. Two glyoxalase II structures were solved. One with a bound spermidine molecule (1.8 A) and the other with d-lactate at the active site (1.9 A). The second structure was obtained by crystal soaking with the enzyme substrate (S)-d-lactoyltrypanothione. The overall structure of Leishmania infantum glyoxalase II is very similar to its human counterpart, with important differences at the substrate binding site. The crystal structure of L. infantum glyoxalase II is the first structure of this enzyme from trypanosomatids. The differential specificity of glyoxalase II toward glutathione and trypanothione moieties was revealed by differential substrate binding. Evolutionary analysis shows that trypanosomatid glyoxalases II diverged early from eukaryotic enzymes, being unrelated to prokaryotic proteins.

Reviews - 2p1e mentioned but not cited (2)

  1. Thioesterases: a new perspective based on their primary and tertiary structures. Cantu DC, Chen Y, Reilly PJ. Protein Sci 19 1281-1295 (2010)
  2. The Potential of Secondary Metabolites from Plants as Drugs or Leads against Protozoan Neglected Diseases-Part III: In-Silico Molecular Docking Investigations. Ogungbe IV, Setzer WN. Molecules 21 E1389 (2016)

Articles - 2p1e mentioned but not cited (1)

  1. In-silico Leishmania target selectivity of antiparasitic terpenoids. Ogungbe IV, Setzer WN. Molecules 18 7761-7847 (2013)


Reviews citing this publication (8)

  1. Glutathione catalysis and the reaction mechanisms of glutathione-dependent enzymes. Deponte M. Biochim Biophys Acta 1830 3217-3266 (2013)
  2. The glyoxalase pathway: the first hundred years... and beyond. Sousa Silva M, Gomes RA, Ferreira AE, Ponces Freire A, Cordeiro C. Biochem J 453 1-15 (2013)
  3. Methylglyoxal metabolism in trypanosomes and leishmania. Wyllie S, Fairlamb AH. Semin Cell Dev Biol 22 271-277 (2011)
  4. Polyamine-Based Thiols in Trypanosomatids: Evolution, Protein Structural Adaptations, and Biological Functions. Manta B, Bonilla M, Fiestas L, Sturlese M, Salinas G, Bellanda M, Comini MA. Antioxid Redox Signal 28 463-486 (2018)
  5. Characteristic Variations and Similarities in Biochemical, Molecular, and Functional Properties of Glyoxalases across Prokaryotes and Eukaryotes. Kaur C, Sharma S, Hasan MR, Pareek A, Singla-Pareek SL, Sopory SK. Int J Mol Sci 18 E250 (2017)
  6. Glycobiology of the Leishmania parasite and emerging targets for antileishmanial drug discovery. Chandra S, Ruhela D, Deb A, Vishwakarma RA. Expert Opin Ther Targets 14 739-757 (2010)
  7. Glyoxalase diversity in parasitic protists. Deponte M. Biochem Soc Trans 42 473-478 (2014)
  8. Glyoxalase 2: Towards a Broader View of the Second Player of the Glyoxalase System. Scirè A, Cianfruglia L, Minnelli C, Romaldi B, Laudadio E, Galeazzi R, Antognelli C, Armeni T. Antioxidants (Basel) 11 2131 (2022)

Articles citing this publication (14)

  1. Mechanism of the quorum-quenching lactonase (AiiA) from Bacillus thuringiensis. 1. Product-bound structures. Liu D, Momb J, Thomas PW, Moulin A, Petsko GA, Fast W, Ringe D. Biochemistry 47 7706-7714 (2008)
  2. A glutathione responsive rice glyoxalase II, OsGLYII-2, functions in salinity adaptation by maintaining better photosynthesis efficiency and anti-oxidant pool. Ghosh A, Pareek A, Sopory SK, Singla-Pareek SL. Plant J 80 93-105 (2014)
  3. Antileishmanial phytochemical phenolics: molecular docking to potential protein targets. Ogungbe IV, Erwin WR, Setzer WN. J Mol Graph Model 48 105-117 (2014)
  4. Glyoxalase II does not support methylglyoxal detoxification but serves as a general trypanothione thioesterase in African trypanosomes. Wendler A, Irsch T, Rabbani N, Thornalley PJ, Krauth-Siegel RL. Mol Biochem Parasitol 163 19-27 (2009)
  5. Glyoxalase I activity and immunoreactivity in the aging human lens. Mailankot M, Padmanabha S, Pasupuleti N, Major D, Howell S, Nagaraj RH. Biogerontology 10 711-720 (2009)
  6. Structural and functional characterization of Salmonella enterica serovar Typhimurium YcbL: an unusual Type II glyoxalase. Stamp AL, Owen P, El Omari K, Nichols CE, Lockyer M, Lamb HK, Charles IG, Hawkins AR, Stammers DK. Protein Sci 19 1897-1905 (2010)
  7. Human glyoxalase II contains an Fe(II)Zn(II) center but is active as a mononuclear Zn(II) enzyme. Limphong P, McKinney RM, Adams NE, Bennett B, Makaroff CA, Gunasekera T, Crowder MW. Biochemistry 48 5426-5434 (2009)
  8. Plasmodium falciparum glyoxalase II: Theorell-Chance product inhibition patterns, rate-limiting substrate binding via Arg(257)/Lys(260), and unmasking of acid-base catalysis. Urscher M, Deponte M. Biol Chem 390 1171-1183 (2009)
  9. Reaction mechanism of the binuclear zinc enzyme glyoxalase II - A theoretical study. Chen SL, Fang WH, Himo F. J Inorg Biochem 103 274-281 (2009)
  10. Intracellular zinc flux causes reactive oxygen species mediated mitochondrial dysfunction leading to cell death in Leishmania donovani. Kumari A, Singh KP, Mandal A, Paswan RK, Sinha P, Das P, Ali V, Bimal S, Lal CS. PLoS One 12 e0178800 (2017)
  11. Enlightening the molecular basis of trypanothione specificity in trypanosomatids: mutagenesis of Leishmania infantum glyoxalase II. Barata L, Sousa Silva M, Schuldt L, Ferreira AE, Gomes RA, Tomás AM, Weiss MS, Ponces Freire A, Cordeiro C. Exp Parasitol 129 402-408 (2011)
  12. The crystal structure of a homodimeric Pseudomonas glyoxalase I enzyme reveals asymmetric metallation commensurate with half-of-sites activity. Bythell-Douglas R, Suttisansanee U, Flematti GR, Challenor M, Lee M, Panjikar S, Honek JF, Bond CS. Chemistry 21 541-544 (2015)
  13. Hunting down zinc(II)-binding sites in proteins with distance matrices. Laveglia V, Bazayeva M, Andreini C, Rosato A. Bioinformatics 39 btad653 (2023)
  14. Loss of glyoxalase 2 alters the glucose metabolism in zebrafish. Tabler CT, Lodd E, Bennewitz K, Middel CS, Erben V, Ott H, Poth T, Fleming T, Morgenstern J, Hausser I, Sticht C, Poschet G, Szendroedi J, Nawroth PP, Kroll J. Redox Biol 59 102576 (2023)


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