DprE1 Is a Vulnerable Tuberculosis Drug Target Due to Its Cell Wall Localization

ACS Chemical Biology

Volumn 10, Issue 7, 2015, Pages 1631-1636

  Brecik, Miroslav ^a   Centárová, Ivana ^a   Mukherjee, Raju ^b,c   Kolly, Gaëlle S ^b   Huszár, Stanislav ^a   Bobovská, Adela ^a   Kilacsková, Emöke ^a   Mokošová, Veronika ^a   Svetlíková, Zuzana ^a   Šarkan, Michal ^a   Neres, João ^b   Korduláková, Jana ^a   Cole, Stewart T ^b   Mikušová, Katarína ^a  

^a Faculty of Natural Sciences   (Slovakia)

^b EPFL   (Switzerland)

^c UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ARABINOSE; DPRE1 ENZYME; FLAVOPROTEIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; ALCOHOL DEHYDROGENASE; BACTERIAL PROTEIN; DPRE1 PROTEIN, MYCOBACTERIUM TUBERCULOSIS;

ARTICLE; CELL WALL; CELLULAR DISTRIBUTION; CONTROLLED STUDY; CYTOPLASM; DRUG TARGETING; FLUORESCENCE MICROSCOPY; ISOTOPE LABELING; MYCOBACTERIUM SMEGMATIS; NONHUMAN; PRECURSOR; PRIORITY JOURNAL; CYTOLOGY; DRUG EFFECTS; ENZYMOLOGY; HUMAN; METABOLISM; MICROBIOLOGY; MYCOBACTERIUM TUBERCULOSIS; TUBERCULOSIS;

ALCOHOL OXIDOREDUCTASES; ANTITUBERCULAR AGENTS; BACTERIAL PROTEINS; CELL WALL; HUMANS; MYCOBACTERIUM TUBERCULOSIS; TUBERCULOSIS;

EID: 84937148144     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/acschembio.5b00237     Document Type: Article

References (29)

1. Global tuberculosis report 2014, World Health Organization, Geneva.
2. Zumla, A., Nahid, P., and Cole, S. T. (2013) Advances in the development of new tuberculosis drugs and treatment regimens Nat. Rev. Drug Discovery 12, 388-404
3. Makarov, V., Lechartier, B., Zhang, M., Neres, J., van der Sar, A. M., Raadsen, S. A., Hartkoorn, R. C., Ryabova, O. B., Vocat, A., Decosterd, L. A., Widmer, N., Buclin, T., Bitter, W., Andries, K., Pojer, F., Dyson, P. J., and Cole, S. T. (2014) Towards a new combination therapy for tuberculosis with next generation benzothiazinones EMBO Mol. Med. 6, 372-383
4. Makarov, V., Manina, G., Mikusova, K., Mollmann, U., Ryabova, O., Saint-Joanis, B., Dhar, N., Pasca, M. R., Buroni, S., Lucarelli, A. P., Milano, A., De Rossi, E., Belanova, M., Bobovska, A., Dianiskova, P., Kordulakova, J., Sala, C., Fullam, E., Schneider, P., McKinney, J. D., Brodin, P., Christophe, T., Waddell, S., Butcher, P., Albrethsen, J., Rosenkrands, I., Brosch, R., Nandi, V., Bharath, S., Gaonkar, S., Shandil, R. K., Balasubramanian, V., Balganesh, T., Tyagi, S., Grosset, J., Riccardi, G., and Cole, S. T. (2009) Benzothiazinones kill Mycobacterium tuberculosis by blocking arabinan synthesis Science 324, 801-804
5. Neres, J., Pojer, F., Molteni, E., Chiarelli, L. R., Dhar, N., Boy-Rottger, S., Buroni, S., Fullam, E., Degiacomi, G., Lucarelli, A. P., Read, R. J., Zanoni, G., Edmondson, D. E., De Rossi, E., Pasca, M. R., McKinney, J. D., Dyson, P. J., Riccardi, G., Mattevi, A., Cole, S. T., and Binda, C. (2012) Structural basis for benzothiazinone-mediated killing of Mycobacterium tuberculosis Sci. Transl. Med. 4, 150ra121
6. Trefzer, C., Rengifo-Gonzalez, M., Hinner, M. J., Schneider, P., Makarov, V., Cole, S. T., and Johnsson, K. (2010) Benzothiazinones: prodrugs that covalently modify the decaprenylphosphoryl-beta-D-ribose 2′-epimerase DprE1 of Mycobacterium tuberculosis J. Am. Chem. Soc. 132, 13663-13665
7. Huang, H., Scherman, M. S., D'Haeze, W., Vereecke, D., Holsters, M., Crick, D. C., and McNeil, M. R. (2005) Identification and active expression of the Mycobacterium tuberculosis gene encoding 5-phospho-α-d-ribose-1-diphosphate: decaprenyl-phosphate 5-phosphoribosyltransferase, the first enzyme committed to decaprenylphosphoryl-d-arabinose synthesis J. Biol. Chem. 280, 24539-24543
8. Jiang, T., He, L., Zhan, Y., Zang, S., Ma, Y., Zhao, X., Zhang, C., and Xin, Y. (2011) The effect of MSMEG-6402 gene disruption on the cell wall structure of Mycobacterium smegmatis Microb. Pathog. 51, 156-160
9. Kolly, G. S., Boldrin, F., Sala, C., Dhar, N., Hartkoorn, R. C., Ventura, M., Serafini, A., McKinney, J. D., Manganelli, R., and Cole, S. T. (2014) Assessing the essentiality of the decaprenyl-phospho-d-arabinofuranose pathway in Mycobacterium tuberculosis using conditional mutants Mol. Microbiol. 92, 194-211
10. Trefzer, C., Skovierova, H., Buroni, S., Bobovska, A., Nenci, S., Molteni, E., Pojer, F., Pasca, M. R., Makarov, V., Cole, S. T., Riccardi, G., Mikusova, K., and Johnsson, K. (2012) Benzothiazinones are suicide inhibitors of mycobacterial decaprenylphosphoryl-β-d-ribofuranose 2′-oxidase DprE1 J. Am. Chem. Soc. 134, 912-915
11. Mikusova, K., Makarov, V., and Neres, J. (2014) DprE1-from the discovery to the promising tuberculosis drug target Curr. Pharm. Des. 20, 4379-4403
12. Lechartier, B., Rybniker, J., Zumla, A., and Cole, S. T. (2014) Tuberculosis drug discovery in the post-post-genomic era EMBO Mol. Med. 6, 158-168
13. Scherman, M. S., Kalbe-Bournonville, L., Bush, D., Xin, Y., Deng, L., and McNeil, M. (1996) Polyprenylphosphate-pentoses in mycobacteria are synthesized from 5-phosphoribose pyrophosphate J. Biol. Chem. 271, 29652-29658
14. Mikusova, K., Huang, H., Yagi, T., Holsters, M., Vereecke, D., D'Haeze, W., Scherman, M. S., Brennan, P. J., McNeil, M. R., and Crick, D. C. (2005) Decaprenylphosphoryl arabinofuranose, the donor of the D-arabinofuranosyl residues of mycobacterial arabinan, is formed via a two-step epimerization of decaprenylphosphoryl ribose J. Bact. 187, 8020-8025
15. Mikusova, K., Mikus, M., Besra, G. S., Hancock, I., and Brennan, P. J. (1996) Biosynthesis of the linkage region of the mycobacterial cell wall J. Biol. Chem. 271, 7820-7828
16. Morita, Y. S., Velasquez, R., Taig, E., Waller, R. F., Patterson, J. H., Tull, D., Williams, S. J., Billman-Jacobe, H., and McConville, M. J. (2005) Compartmentalization of lipid biosynthesis in mycobacteria J. Biol. Chem. 280, 21645-21652
17. Rezwan, M., Laneelle, M. A., Sander, P., and Daffe, M. (2007) Breaking down the wall: fractionation of mycobacteria J. Microbiol. Methods 68, 32-39
18. Jankute, M., Byng, C. V., Alderwick, L. J., and Besra, G. S. (2014) Elucidation of a protein-protein interaction network involved in Corynebacterium glutamicum cell wall biosynthesis as determined by bacterial two-hybrid analysis Glycoconjugate J. 6-7, 475-83
19. Meniche, X., Otten, R., Siegrist, M. S., Baer, C. E., Murphy, K. C., Bertozzi, C. R., and Sassetti, C. M. (2014) Subpolar addition of new cell wall is directed by DivIVA in mycobacteria Proc. Natl. Acad. Sci. U. S. A. 111, E3243-3251
20. Murty, M. V. and Venkitasubramanian, T. A. (1983) Growth and macromolecular synthesis of spheroplasts of Mycobacterium smegmatis ATCC 14468 Annal. Microbiol. 134B, 359-365
21. Dhiman, R. K., Dinadayala, P., Ryan, G. J., Lenaerts, A. J., Schenkel, A. R., and Crick, D. C. (2011) Lipoarabinomannan localization and abundance during growth of Mycobacterium smegmatis J. Bact. 193, 5802-5809
22. Huang, H., Berg, S., Spencer, J. S., Vereecke, D., D'Haeze, W., Holsters, M., and McNeil, M. R. (2008) Identification of amino acids and domains required for catalytic activity of DPPR synthase, a cell wall biosynthetic enzyme of Mycobacterium tuberculosis Microbiology 154, 736-743
23. Grover, S., Alderwick, L. J., Mishra, A. K., Krumbach, K., Marienhagen, J., Eggeling, L., Bhatt, A., and Besra, G. S. (2014) Benzothiazinones mediate killing of Corynebacterineae by blocking decaprenyl phosphate recycling involved in cell wall biosynthesis J. Biol. Chem. 289, 6177-6187
24. Villela, A. D., Ducati, R. G., Rosado, L. A., Bloch, C. J., Prates, M. V., Goncalves, D. C., Ramos, C. H., Basso, L. A., and Santos, D. S. (2013) Biochemical characterization of uracil phosphoribosyltransferase from Mycobacterium tuberculosis PloS one 8, e56445
25. Drew, D., Sjostrand, D., Nilsson, J., Urbig, T., Chin, C. N., de Gier, J. W., and von Heijne, G. (2002) Rapid topology mapping of Escherichia coli inner-membrane proteins by prediction and PhoA/GFP fusion analysis Proc. Natl. Acad. Sci. U. S. A. 99, 2690-2695
26. Bhamidi, S., Shi, L., Chatterjee, D., Belisle, J. T., Crick, D. C., and McNeil, M. R. (2012) A bioanalytical method to determine the cell wall composition of Mycobacterium tuberculosis grown in vivo Anal. Biochem. 421, 240-249
27. Phetsuksiri, B., Baulard, A. R., Cooper, A. M., Minnikin, D. E., Douglas, J. D., Besra, G. S., and Brennan, P. J. (1999) Antimycobacterial activities of isoxyl and new derivatives through the inhibition of mycolic acid synthesis Antimicrob. Ag. Chemother. 43, 1042-1051
28. Singh, V., Brecik, M., Mukherjee, R., Evans, J. C., Svetlikova, Z., Blasko, J., Surade, S., Blackburn, J., Warner, D. F., Mikusova, K., and Mizrahi, V. (2014) The complex mechanism of antimycobacterial action of 5-Fluorouracil Chem. Biol. 22, 63-75
29. Bochner, B. R. and Ames, B. N. (1982) Complete analysis of cellular nucleotides by two-dimensional thin layer chromatography J. Biol. Chem. 257, 9759-9769