Plasmodium serine hydroxymethyltransferase as a potential anti-malarial target: Inhibition studies using improved methods for enzyme production and assay

Malaria Journal

Volumn 11, Issue , 2012, Pages

  Sopitthummakhun, Kittipat ^a   Thongpanchang, Chawanee ^b   Vilaivan, Tirayut ^c   Yuthavong, Yongyuth ^b   Chaiyen, Pimchai ^a   Leartsakulpanich, Ubolsree ^b  

^a MAHIDOL UNIVERSITY   (Thailand)

^b NATIONAL SCIENCE AND TECHNOLOGY DEVELOPMENT AGENCY   (Thailand)

^c CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

Plasmodium falciparum; Plasmodium vivax; Pyridoxal 5 phosphate dependent enzyme; Serine hydroxymethyltransferase; Thiosemicarbazide

Indexed keywords

5,10 METHYLENETETRAHYDROFOLATE REDUCTASE (FADH2); AMINO ACID; ENZYME INHIBITOR; FOLIC ACID; GALACTOSIDE; GLYCINE HYDROXYMETHYLTRANSFERASE; ISOPROPYL THIO BETA DEXTRO GALACTOSIDE; THIOSEMICARBAZIDE; THIOSEMICARBAZONE; UNCLASSIFIED DRUG; ANTIMALARIAL AGENT; METHYLENETETRAHYDROFOLATE DEHYDROGENASE;

ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; ENZYME KINETICS; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PLASMODIUM; PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PROTEIN EXPRESSION; SPECTROPHOTOMETRY; DRUG ANTAGONISM; ENZYMOLOGY; HUMAN; ISOLATION AND PURIFICATION; KINETICS; METABOLISM; METHODOLOGY;

ANTIMALARIALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYME INHIBITORS; GLYCINE HYDROXYMETHYLTRANSFERASE; HUMANS; KINETICS; MASS SPECTROMETRY; METHYLENETETRAHYDROFOLATE DEHYDROGENASE (NADP); PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; SPECTROPHOTOMETRY;

EID: 84861990472     PISSN: None     EISSN: 14752875     Source Type: Journal    
DOI: 10.1186/1475-2875-11-194     Document Type: Article

References (34)

1. Discovery of potent small-molecule inhibitors of multidrug- resistantPlasmodium falciparumusing a novel miniaturized high-throughput luciferase-based assay. Lucumi E, Darling C, Jo H, Napper AD, Chandramohanadas R, Fisher N, Shone AE, Jing H, Ward SA, Biagini GA, DeGrado WF, Diamond SL, Greenbaum DC, Antimicrob Agents Chemother 2010 54 3597 3604 10.1128/AAC.00431-10 20547797
2. Structure-guided lead optimization of triazolopyrimidine-ring substituents identifies potent Plasmodium falciparum dihydroorotate dehydrogenase inhibitors with clinical candidate potential. Coteron JM, Marco M, Esquivias J, Deng X, White KL, White J, Koltun M, El Mazouni F, Kokkonda S, Katneni K, Bhamidipati R, Shackleford DM, Angulo- Barturen I, Ferrer SB, Jiménez-Díaz MB, Gamo FJ, Goldsmith EJ, Charman WN, Bathurst I, Floyd D, Matthews D, Burrows JN, Rathod PK, Charman SA, Phillips MA, J Med Chem 2011 54 5540 5561 10.1021/jm200592f 21696174
3. An overview of chemotherapeutic targets for antimalarial drug discovery. Olliaro P, Yuthavong V, Pharmacol Ther 1999 89 91 110
4. Pyridoxal phosphate enzymes: mechanistic, structural, and evolutionary considerations. Eliot AC, Kirsch JF, Annu Rev Biochem 2004 73 383 415 10.1146/annurev.biochem.73.011303.074021 15189147
5. Folates in serine and glycine metabolism. Schirch V, Folate and pterins New York: Wiley, Blankley RL, Benkovic SJ, 1984 399 431
6. Characterization ofPlasmodium falciparumserine hydroxymethyltransferase-A potential antimalarial target. Maenpuen S, Sopitthummakhun K, Yuthavong Y, Chaiyen P, Leartsakulpanich U, Mol Biochem Parasitol 2009 168 63 73 10.1016/j.molbiopara.2009.06.010 19591881
7. Serine hydroxymethyltransferase fromPlasmodium vivaxis different in substrate specificity from its homologues. Sopitthummakhun K, Maenpuen S, Yuthavong Y, Leartsakulpanich U, Chaiyen P, FEBS J 2009 276 4023 4036 10.1111/j.1742-4658.2009.07111.x 19549189
8. Transcriptional analysis of genes encoding enzymes of the folate pathway. Nirmalan N, Wang P, Sims P, H J, Mol Microbiol 2002 46 179 190 10.1046/j.1365-2958.2002.03148.x 12366841
9. Purification, physicochemical and regulatory properties of serine hydroxymethyltransferase from sheep liver. Manohar R, Ramesh KS, Rao NA, J Biosci 1982 4 31 50 10.1007/BF02702579
10. The crystal structure of human cytosolic serine hydroxymethyltransferase: a target for cancer chemotherapy. Renwick SB, Snell K, Baumann U, Structure 1998 6 1105 1116 10.1016/S0969-2126(98)00112-9 9753690
11. In silico andin vitrovalidation of serine hydroxymethyltransferase as a chemotherapeutic target of the antifolate drug pemetrexed. Daidone F, Florio R, Rinaldo S, Contestabile R, di Salvo M, Cutruzzolà F, Bossa F, Paiardini A, Eur J Med Chem 2011 46 1616 1621 10.1016/j.ejmech.2011.02.009 21371789
12. A three-dimensional structure ofPlasmodium falciparumserine hydroxymethyltransferase in complex with glycine and 5-formyl-tetrahydrofolate. Homology modeling and molecular dynamics. Franca TC, Pascutti PG, Ramalho TC, Figueroa-Villar JD, Biophys Chem 2005 115 1 10 10.1016/j.bpc.2004.12.002 15848278
13. Characterization of three genes encoding enzymes of the folate biosynthetic pathway inPlasmodium falciparum. Lee CS, Salcedo E, Wang Q, Wang P, Sims PF, Hyde JE, Parasitology 2001 122 1 13 10.1017/S0031182000006946 11197757
14. Catalytic and ligand-binding characteristics ofPlasmodium falciparumserine hydroxymethyltransferase. Pang CK, Hunter JH, Gujjar R, Podutoori R, Bowman J, Mudeppa DG, Rathod PK, Mol Biochem Parasitol 2009 168 74 83 10.1016/j.molbiopara.2009.06.011 19591883
15. Sirichaiwat C, Target guided synthesis of 5-benzyl-2,4-diaminopyrimidine antimalarials.PhD thesis Mahidol University: Chemistry Department 2003
16. Target guided synthesis of 5-benzyl-2,4-diaminopyrimidines: their antimalarial activities and binding affinities to wild type and mutant dihydrofolate reductases fromPlasmodium falciparum. Sirichaiwat C, Intaraudom C, Kamchonwongpaisan S, Vanichtanankul J, Thebtaranonth Y, Yuthavong Y, J Med Chem 2004 47 345 354 10.1021/jm0303352 14711307
17. Antimalarial compounds with flexible side-chains. US patent application no. 20090099220. Yuthavong Y, Vilaian T, Kamchonwongpaisan S, Tarnchompoo B, Thongpanchang C, Chitnumsub P, Yuvaniyama J, Matthews D, Charman W, Charman S, Vivas L, Katiyar SB, Medicines for Malaria Venture 2009
18. Protein production by auto-induction in high density shaking cultures. Studier FW, Protein Expr Purif 2005 41 207 234 10.1016/j.pep.2005.01.016 15915565
19. Enzymatic determination of homocysteine in cell extracts. Fu TF, di Salvo M, Schirch V, Anal Biochem 2001 290 359 365 10.1006/abio.2001.4994 11237340
20. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein dye binding. Bradford M, Anal Biochem 1976 72 245 248
21. SIB Bioinformatics Resource Portal [ http://web.expasy.org/protparam/ ]
22. Expression, purification and crystallization of native and selenomethionine labeledMycobacterium tuberculosisFGD1 (Rv0407) using aMycobacterium smegmatisexpression system. Bashiri G, Squire CJ, Baker EN, Moreland NJ, Protein Expr Purif 2007 54 38 44 10.1016/j.pep.2007.01.014 17376702
23. Expression of membrane proteins fromMycobacterium tuberculosisinEscherichia colias fusions with maltose binding protein. Korepanova A, Moore JD, Nguyen HB, Hua Y, Cross TA, Gao F, Protein Expr Purif 2007 53 24 30 10.1016/j.pep.2006.11.022 17275326
24. Expression of G-protein coupled receptors inEscherichia colifor structural studies. Petrovskaya LE, Shulga AA, Bocharova OV, Ermolyuk YS, Kryukova EA, Chupin VV, Blommers MJ, Arseniev AS, Kirpichnikov MP, Biochemistry (Mosc) 2010 75 881 891 10.1134/S0006297910070102
25. Characterisation of the bifunctional dihydrofolate synthase- folylpolyglutamate synthase fromPlasmodium falciparum; a potential novel target for antimalarial antifolate inhibition. Wang P, Wang Q, Yang Y, Coward JK, Nzila A, Sims PF, Hyde JE, Mol Biochem Parasitol 2010 172 41 51 10.1016/j.molbiopara. 2010.03.012 20350571
26. Radioactive assay for serine transhydroxymethylase. Taylor RT, Weissbach H, Anal Biochem 1965 13 80 84 10.1016/0003-2697(65)90120-X
27. Interactions of pig liver serine hydroxymethyltransferase with methyltetrahydropteroylpolyglutamate inhibitors and with tetrahydropteroylpolyglutamate substrates. Matthews RG, Ross J, Baugh CM, Cook JD, Davis L, Biochemistry 1982 21 1230 1238 10.1021/bi00535a019 7074079
28. Purification and characterization of recombinant rabbit cytosolic serine hydroxymethyltransferase. di Salvo ML, Delle Fratte S, De Biase D, Bossa F, Schirch V, Protein Expr Purif 1998 13 177 183 10.1006/prep.1998.0890 9675060
29. Expression, purification, and characterization of human cytosolic serine hydroxymethyltransferase. Kruschwitz H, Ren S, Di Salvo M, Schirch V, Protein Expr Purif 1995 6 411 416 10.1006/prep.1995.1055 8527925
30. A novel intermediate in the interaction of thiosemicarbazide with sheep liver serine hydroxymethyltransferase. Acharya JK, Rao NA, J Biol Chem 1992 267 19066 19071 1527031
31. Kinetic mechanism of the interaction of D-cycloserine with serine hydroxymethyltransferase. Manohar R, Rao AG, Rao NA, Biochemistry 1984 23 4116 4122 10.1021/bi00313a016 6487593
32. Stable multisubstrate adducts as enzyme inhibitors. Potent inhibition of ornithine decarboxylase by N-(5'-phosphopyridoxyl)-ornithine. Heller JS, Canellakis ES, Bussolotti DL, Coward JK, Biochim Biophys Acta 1975 403 197 207 10.1016/0005-2744(75)90022-4 1174545
33. N-(5'-phosphopyridoxyl)glutamic acid and N-(5'-phosphopyridoxyl)-2- oxopyrrolidine-5-carboxylic acid and their action on the apoenzyme of aspartate aminotransferase. Khomutov RM, Dixon HB, Vdovina LV, Kirpichnikov MP, Morozov YV, Severin ES, Khurs EN, Biochem J 1971 124 99 106 5126478
34. Poisoning pyridoxal 5-phosphate-dependent enzymes: a new strategy to target the malaria parasitePlasmodium falciparum. Muller IB, Wu F, Bergmann B, Knockel J, Walter RD, Gehring H, Wrenger C, PLoS One 2009 4 4406 10.1371/journal.pone.0004406 19197387