Selective reduction of methylsulfinyl-containing compounds by mammalian MsrA suggests a strategy for improved drug efficacy

ACS Chemical Biology

Volumn 6, Issue 10, 2011, Pages 1029-1035

  Lee, Byung Cheon ^a   Fomenko, Dmitri E ^b   Gladyshev, Vadim N ^a  

^a BRIGHAM AND WOMEN S HOSPITAL   (United States)

^b UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL PROTEIN; GREEN FLUORESCENT PROTEIN; HYBRID PROTEIN; MESORIDAZINE; METHIONINE; METHIONINE SULFOXIDE REDUCTASE; METHIONINE SULFOXIDE REDUCTASE A; NATURAL PRODUCT; SIGNAL PEPTIDE; SULFIDE; SULFORAPHANE; SULMAZOLE; THIORIDAZINE; TRICLABENDAZOLE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CELL STRAIN HEK293; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYTOSOLIC FRACTION; DRUG EFFICACY; DRUG METABOLISM; ENANTIOMER; ENZYME ACTIVITY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; KNOCKOUT MOUSE; LIVER; LIVER MICROSOME; MAMMAL CELL; MASS SPECTROMETRY; MOUSE; NONHUMAN; OXIDATION; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; PROTEIN EXPRESSION; STEREOCHEMISTRY; STEREOISOMERISM; TOXICITY TESTING; YEAST;

ANIMALS; HEK293 CELLS; HUMANS; LIVER; METHIONINE SULFOXIDE REDUCTASES; MICE; MICE, INBRED C57BL; OXIDATION-REDUCTION; PHARMACEUTICAL PREPARATIONS; SULFIDES;

MAMMALIA;

EID: 80055017121     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb2001395     Document Type: Article

References (29)

1. Stadtman, E. R., Moskovitz, J., and Levine, R. L. (2003) Oxidation of Methionine Residues of Proteins: Biological Consequences Antioxid. Redox Signaling 5, 577-582 (Pubitemid 37315145)
2. Weissbach, H., Resnick, L., and Brot, N. (2005) Methionine Sulfoxide Reductases: History and Cellular Role in Protecting against Oxidative Damage Biochim. Biophys. Acta 1703, 203-212 (Pubitemid 40170443)
3. Imlay, J. A. (2008) Cellular Defenses against Superoxide and Hydrogen Peroxide Annu. Rev. Biochem. 77, 755-776
4. Stadtman, E. R. (2004) Cyclic Oxidation and Reduction of Methionine Residues of Proteins in Antioxidant Defense and Cellular Regulation Arch. Biochem. Biophys. 423, 2-5 (Pubitemid 38198207)
5. Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., and Lowther, W. T. (2007) Free Methionine-(R)-Sulfoxide Reductase from Escherichia coli Reveals a New GAF Domain Function Proc. Natl. Acad. Sci. U.S.A. 104, 9597-9602 (Pubitemid 47175312)
6. Lee, B. C., Le, D. T., and Gladyshev, V. N. (2008) Mammals Reduce Methionine- S -Sulfoxide with MsrA and Are Unable to Reduce Methionine- R -Sulfoxide, and This Function can be Restored with a Yeast Reductase J. Biol. Chem. 283, 28361-28369
7. Kim, H. Y. and Gladyshev, V. N. (2007) Methionine Sulfoxide Reductases: Selenoprotein Forms and Roles in Antioxidant Protein Repair in Mammals Biochem. J. 407, 321-329 (Pubitemid 350058466)
8. Lynch, T. and Price, A. (2007) The Effect of Cytochrome P450 Metabolism on Drug Response, Interactions, and Adverse Effects Am. Fam. Physician 76, 391-396 (Pubitemid 47219454)
9. Beedham, C. (1997) The Role of Non-P450 Enzymes in Drug Oxidation Pharm. World Sci. 19, 255-263 (Pubitemid 27511692)
10. Bentley, R. (2005) Role of Sulfur Chirality in the Chemical Processes of Biology Chem. Soc. Rev. 34, 609-624 (Pubitemid 40992748)
11. Etienne, F., Resnick, L., Sagher, D., Brot, N., and Weissbach, H. (2003) Reduction of Sulindac to its Active Metabolite, Sulindac Sulfide: Assay and Role of the Methionine Sulfoxide Reductase System Biochem. Biophys. Res. Commun. 312, 1005-1010 (Pubitemid 37490915)
12. Sagher, D., Brunell, D., Hejtmancik, J. F., Kantorow, M., Brot, N., and Weissbach, H. (2006) Thionein Can Serve as a Reducing Agent for the Methionine Sulfoxide Reductases Proc. Natl. Acad. Sci. U.S.A. 103, 8656-8661 (Pubitemid 43878076)
13. Grimaud, R., Ezraty, B., Mitchell, J. K., Lafitte, D., Briand, C., Derrick, P. J., and Barras, F. (2001) Repair of Oxidized Proteins. Identification of a New Methionine Sulfoxide Reductase J. Biol. Chem. 276, 48915-48920
14. Lee, B. C. and Gladyshev, V. N. (2011) The Biological Significance of Methionine Sulfoxide Stereochemistry Free Radical Biol. Med. 50, 221-227
15. Lee, B. C., Dikiy, A., Kim, H. Y., and Gladyshev, V. N. (2009) Functions and Evolution of Selenoprotein Methionine Sulfoxide Reductases Biochim. Biophys. Acta 1790, 1471-1477
16. Gruez, A., Libiad, M., Boschi-Muller, S., and Branlant, G. (2010) Structural and Biochemical Characterization of Free Methionine- R -Sulfoxide Reductase from Neisseria meningitidis J. Biol. Chem. 285, 25033-25043
17. Boschi-Muller, S., Gand, A., and Branlant, G. (2008) The Methionine Sulfoxide Reductases: Catalysis and Substrate Specificities Arch. Biochem. Biophys. 474, 266-273
18. Neiers, F., Sonkaria, S., Olry, A., Boschi-Muller, S., and Branlant, G. (2007) Characterization of the Amino Acids from Neisseria meningitidis Methionine Sulfoxide Reductase B Involved in the Chemical Catalysis and Substrate Specificity of the Reductase Step J. Biol. Chem. 282, 32397-32405 (Pubitemid 350106432)
19. Ranaivoson, F. M., Antoine, M., Kauffmann, B., Boschi-Muller, S., Aubry, A., Branlant, G., and Favier, F. (2008) A Structural Analysis of the Catalytic Mechanism of Methionine Sulfoxide Reductase A from Neisseria meningitidis J. Mol. Biol. 377, 268-280
20. Brunell, D., Sagher, D., Kesaraju, S., Brot, N., and Weissbach, H. (2011) Studies on the Metabolism and Biological Activity of the Epimers of Sulindac Drug Metab. Dispos. 39, 1014-1021
21. Bylund, D. B. (1981) Interactions of Neuroleptic Metabolites with Dopaminergic, Alpha Adrenergic and Muscarinic Cholinergic Receptors J. Pharmacol. Exp. Ther. 217, 81-86 (Pubitemid 11103826)
22. Alvarez, L. I., Solana, H. D., Mottier, M. L., Virkel, G. L., Fairweather, I., and Lanusse, C. E. (2005) Altered Drug influx/efflux and Enhanced Metabolic Activity in Triclabendazole-Resistant Liver Flukes Parasitology 131, 501-510 (Pubitemid 43329682)
23. Brennan, G. P., Fairweather, I., Trudgett, A., Hoey, E., McCoy, McConville, M., Meaney, M., Robinson, M., McFerran, N., Ryan, L., Lanusse, C., Mottier, L., Alvarez, L., Solana, H., Virkel, G., and Brophy, P. M. (2007) Understanding Triclabendazole Resistance Exp. Mol. Pathol. 82, 104-109 (Pubitemid 46505133)
24. Ahn, Y. H., Hwang, Y., Liu, H., Wang, X. J., Zhang, Y., Stephenson, K. K., Boronina, T. N., Cole, R. N., Dinkova-Kostova, A. T., Talalay, P., and Cole, P. A. (2010) Electrophilic Tuning of the Chemoprotective Natural Product Sulforaphane Proc. Natl. Acad. Sci. U.S.A. 107, 9590-9595
25. Kim, H. Y. and Gladyshev, V. N. (2005) Different Catalytic Mechanisms in Mammalian Selenocysteine- and Cysteine-Containing Methionine- R -Sulfoxide Reductases PLoS Biol. 3, e375
26. Kim, H. Y. and Gladyshev, V. N. (2005) Role of Structural and Functional Elements of Mouse Methionine- S -Sulfoxide Reductase in its Subcellular Distribution Biochemistry 44, 8059-8067 (Pubitemid 40776667)
27. Le, D. T., Lee, B. C., Marino, S. M., Zhang, Y., Fomenko, D. E., Kaya, A., Hacioglu, E., Kwak, G. H., Koc, A., Kim, H. Y., and Gladyshev, V. N. (2009) Functional Analysis of Free Methionine- R -Sulfoxide Reductase from Saccharomyces cerevisiae J. Biol. Chem. 284, 4354-4364
28. Novoselov, S. V., Kim, H. Y., Hua, D., Lee, B. C., Astle, C. M., Harrison, D. E., Friguet, B., Moustafa, M. E., Carlson, B. A., Hatfield, D. L., and Gladyshev, V. N. (2010) Regulation of Selenoproteins and Methionine Sulfoxide Reductases A and B1 by Age, Calorie Restriction, and Dietary Selenium in Mice Antioxid. Redox Signal. 12, 829-838
29. Kim, H. Y. and Gladyshev, V. N. (2004) Methionine Sulfoxide Reduction in Mammals: Characterization of Methionine- R -Sulfoxide Reductases Mol. Biol. Cell 15, 1055-1064 (Pubitemid 38316216)