A simple assay for detection of small-molecule redox activity

Journal of Biomolecular Screening

Volumn 12, Issue 6, 2007, Pages 881-890

  Lor, Leng A ^a   Schneck, Jessica ^a   McNulty, Dean E ^a   Diaz, Elsie ^a   Brandt, Martin ^a   Thrall, Sara H ^a   Schwartz, Benjamin ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

Caspase 8; Cathepsin L; Cysteine phosphatases; Cysteine proteases; Iron enzymes; Nuisance hits; Redox cofactors

Indexed keywords

CASPASE 8 INHIBITOR; CATHEPSIN L INHIBITOR; CYSTEINE; CYSTEINE PROTEINASE; CYSTEINE PROTEINASE INHIBITOR; OXYGENASE INHIBITOR; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; TAURINE DIOXYGENASE INHIBITOR; UNCLASSIFIED DRUG;

ACYLATION; ALKYLATION; ARTICLE; ENZYME METABOLISM; HIGH THROUGHPUT SCREENING; LIQUID CHROMATOGRAPHY; OXIDATION; OXIDATION REDUCTION REACTION; PREDICTION; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

CATHEPSINS; CHROMATOGRAPHY, LIQUID; CYSTEINE ENDOPEPTIDASES; DRUG EVALUATION, PRECLINICAL; INHIBITORY CONCENTRATION 50; MODELS, BIOLOGICAL; OXIDANTS; OXIDATION-REDUCTION; PROTEIN PROCESSING, POST-TRANSLATIONAL; TANDEM MASS SPECTROMETRY;

EID: 34548351239     PISSN: 10870571     EISSN: 1552454X     Source Type: Journal    
DOI: 10.1177/1087057107304113     Document Type: Article

References (27)

1. Rishton GM: Nonleadlikeness and leadlikeness in biochemical screening. Drug Discov Today 2003 ; 8: 86-96.
2. Schoichet BK: Screening in a spirit haunted world. Drug Discov Today 2006 ; 11: 607-615.
3. Huth JR, Mendoza R., Olejniczak ET, Johnson RW, Cothron DA, Liu Y.,, et al. ALARM NMR: a rapid and robust experimental method to detect reactive false positives in biochemical screens. J Am Chem Soc 2005 ; 127: 217-224.
4. Copeland RA: Evaluation of Enzyme Inhibitors in Drug Discovery: A Guide for Medicinal Chemists and Pharmacologists. New York: John Wiley, 2005.
5. McGovern SL, Caselli E., Grigorieff N., Shoichet BK: A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. J Med Chem 2002 ; 45: 1712-1722.
6. Seidler J., McGovern SL, Doman TN, Shoichet BK: Identification and prediction of promiscuous aggregating inhibitors among known drugs. J Med Chem 2003 ; 46: 4477-4486.
7. Feng BY, Shelat A., Doman TN, Guy RK, Shoichet BK: High-throughput assays for promiscuous inhibitors. Nat Chem Biol 2005 ; 1: 146-148.
8. Ryan AJ, Gray NM, Lowe PN, Chung C.: Effect of detergent on "promiscuous" inhibitors. J Med Chem 2003 ; 46: 3448-3451.
9. Kaiserova K., Srivastava S., Hoetker JD, Awe SO, Tand XL, Cai J.,, et al. Redox activation of aldose reductase in the ischemic heart. J Biol Chem 2006 ; 281: 15110-15120.
10. Seth D., Rudolph J.: Redox regulation of MAP kinase phosphatase 3. Biochemistry 2006 ; 45: 8476-8487.
11. Smith GK, Barrett DG, Blackburn K., Cory M., Dallas WS, Davis R.,, et al. Expression, preparation, and high-throughput screening of caspase-8: discovery of redox-based and steroid diacid inhibition. Arch Biochem Biophys 2002 ; 399: 195-205.
12. Percival MD, Ouellet M., Campagnolo C., Claveau D., Li C.: Inhibition of cathepsin K by nitric oxide donors: evidence for formation of mixed disulfides and a sulfenic acid. Biochemistry 1999 ; 38: 13574-13583.
13. Conway ME, Poole LB, Hutson SM: Roles for cysteine residues in the regulatory CXXC motif of human mitochondrial branched chain aminotransferase enzyme. Biochemistry 2004 ; 43: 7356-7364.
14. Sohn J., Rudolph J.: Catalytic and chemical competence of regulation of Cdc25 by phosphatase by oxidation/reduction. Biochemistry 2003 ; 42: 10060-10070.
15. Reinheckel T., Deussing J., Roth W., Peters C.: Towards specific functions of lysosomal cysteine peptidases: phenotypes of mice deficient for cathepsin B or cathepsin L. Biol Chem 2001 ; 382: 735-741.
16. Mann M., Steen H.: The ABC's (and XYZ's) of peptide sequencing. Nat Mol Cell Biol 2004 ; 5: 699-711.
17. Guertin KR, Grimsby J.: Small molecule glucokinase activators as glucose lowering agents: a new paradigm for diabetes therapy. Curr Med Chem 2006 ; 13: 1839-1843.
18. Lal M., Rao R., Fang X., Schuchmann HP, von Sonntag C.: Radical-induced oxidation of dithiothreitol in acidic oxygenated aqueous solution: a chain reaction. J Am Chem Soc 1997 ; 119: 5735-5739.
19. Ballou D., Palmer G., Massey V.: Direct demonstration of superoxide anion production during the oxidation of reduced flavin and of its catalytic decomposition by erythrocuprein. Biochem Biophys Res Comm 1969 ; 36: 898-904.
20. Muller F.: Flavin radicals: chemistry and biochemistry. Free Radical Biol Med 1987 ; 3: 215-230.
21. Prutz WA, Butler J., Land EJ: Photocatalytic and free radical interactions of the heterocyclic N-oxide resazurin with NADH, GSH, and DOPA. Arch Biochem Biophys 1996 ; 327: 239-248.
22. Costas M., Mehn MP, Jensen MP, Que L. Jr: Dioxygen activation at mononuclear nonheme iron active sites: enzymes, modelas, and intermediates. Chem Rev 2004 ; 104: 939-986.
23. Polgar L.: Mechanisms of Protease Action. Vol. 1. Boca Raton, FL: CRC Press, 1989.
24. Salmeen A., Andersen JN, Myers MP, Meng T., Hinks JA, Tonks NK,, et al. Redox regulation of protein tyrosine phosphatase 1B involves a sulphenylamide intermediate. Nature 2003 ; 423: 769-773.
25. van Montfort RL, Congreve M., Tisi D., Carr R., Jhotl H.: Oxidation state of the active site cysteine in protein tyrosine phosphatase 1B. Nature 2003 ; 423: 773-777.
26. Bleasdale JE, Ogg D., Palazuk BJ, Jacob CS, Swanson ML, Wang X.,, et al. Small molecule peptidomimetics containing a novel phosphotyrosine bioisostere inhibit protein phosphatase 1B and augment insulin action. Biochemistry 2001 ; 40: 5642-5654.
27. Kivirikko KI, Myllyharju J.: Prolyl 4-hydroxylases and their protein disulfide isomerase subunit. Matrix Biol 1998 ; 16: 357-368.