Comparative bioactivation of the novel anti-tuberculosis agent PA-824 in Mycobacteria and a subcellular fraction of human liver

British Journal of Pharmacology

Volumn 162, Issue 1, 2011, Pages 226-236

  Dogra, M ^a   Palmer, B D ^b,c   Bashiri, G ^c   Tingle, M D ^a   Shinde, S S ^b   Anderson, R F ^b   O'Toole, R ^d   Baker, E N ^c   Denny, W A ^b,c   Helsby, N A ^a,b  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

^c UNIVERSITY OF AUCKLAND   (New Zealand)

^d VICTORIA UNIVERSITY OF WELLINGTON   (New Zealand)

Author keywords

metabolism of PA 824; Mycobacterium tuberculosis; nitroimidazoles

Indexed keywords

6,7 DIHYDRO 2 NITRO 6 (4 TRIFLUOROMETHOXYBENZYLOXY) 5H IMIDAZO[2,1 B][1,3]OXAZINE; DRUG METABOLITE; NITROREDUCTASE;

ADULT; AGED; ARTICLE; CATALYSIS; CELL FRACTIONATION; CONTROLLED STUDY; DRUG METABOLISM; FEMALE; HUMAN; HUMAN TISSUE; HYDRATION; IN VITRO STUDY; LIVER; MALE; MOLECULAR CLONING; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NITRIFICATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; REDUCTION;

ANTITUBERCULAR AGENTS; BASE SEQUENCE; BIOTRANSFORMATION; DNA PRIMERS; HUMANS; LIVER; MASS SPECTROMETRY; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NITROIMIDAZOLES; SUBCELLULAR FRACTIONS;

EID: 78650080351     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2010.01040.x     Document Type: Article

References (20)

1. Anderson RF, Shinde SS, Maroz A, Boyd M, Palmer BD, Denny WA, (2008). Intermediates in the reduction of the antituberculosis drug PA-824, (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2, 1-b][1,3]oxazine, in aqueous solution. Org Biomol Chem 6: 1973-1980.
2. Baker WR, Shaopei C, Keeler EL, (2000). Nitro-[2,1-b]imidazopyran compounds and antibacterial uses thereof. U.S. 6 087 358.
3. Bashiri G, Squire CJ, Baker EN, Moreland NJ, (2007). Expression, purification and crystallization of native and selenomethionine labeled Mycobacterium tuberculosis FGD1 (Rv0407) using a Mycobacterium smegmatis expression system. Protein Expr Purif 54: 38-44.
4. Bashiri G, Squire CJ, Moreland NJ, Baker EN, (2008). Crystal structures of F420-dependent glucose-6-phosphate dehydrogenase FGD1 involved in the activation of the anti-tuberculosis drug candidate PA-824 reveal the basis of coenzyme and substrate binding. J Biol Chem 283: 17531-17541.
5. Bollo S, Nunez-Vergara LJ, Squella JA, (2004). Cyclic voltammetric determination of free radical species from nitroimidazopyran: a new antituberculosis agent. J Electroanal Chem 562: 9-14.
6. Carr JL, Tingle MD, McKeage MJ, (2006). Satraplatin activation by haemoglobin, cytochrome C and liver microsomes in vitro. Cancer Chemother Pharmacol 57: 483-490.
7. Church DL, Rabin HR, Laishley EJ, (1990). Reduction of 2-, 4- and 5-nitroimidazole drugs by hydrogenase 1 in Clostridium pasteurianum. J Antimicrob Chemother 25: 15-23.
8. Diacon AH, Dawson R, Hanekom M, Narunsky K, Maritz SJ, Venter A, et al. (2010). Early bactericidal activity and pharmacokinetics of PA-824 in smear-positive tuberculosis patients. Antimicrob Agents Chemother 54: 3402-3407.
9. Ginsberg AM, Laurenzi MW, Rouse DJ, Whitney KD, Spigelman MK, (2009a). Assessment of the effects of the nitroimidazo-oxazine PA-824 on renal function in healthy subjects. Antimicrob Agents Chemother 53: 3726-3733.
10. Ginsberg AM, Laurenzi MW, Rouse DJ, Whitney KD, Spigelman MK, (2009b). Safety, tolerability, and pharmacokinetics of PA-824 in healthy subjects. Antimicrob Agents Chemother 53: 3720-3725.
11. Goldstone RM, Moreland NJ, Bashiri G, Baker EN, Shaun Lott J, (2008). A new Gateway vector and expression protocol for fast and efficient recombinant protein expression in Mycobacterium smegmatis. Protein Expr Purif 57: 81-87.
12. Manjunatha UH, Boshoff H, Dowd CS, Zhang L, Albert TJ, Norton JE, et al. (2006). Identification of a nitroimidazo-oxazine-specific protein involved in PA-824 resistance in Mycobacterium tuberculosis. Proc Natl Acad Sci USA 103: 431-436.
13. Singh R, Manjunatha U, Boshoff HI, Ha YH, Niyomrattanakit P, Ledwidge R, et al. (2008). PA-824 kills nonreplicating Mycobacterium tuberculosis by intracellular NO release. Science 322: 1392-1395.
14. Spigelman MK, (2007). New tuberculosis therapeutics: a growing pipeline. J Infect Dis 196 (Suppl. 1): S28-S34.
15. Stover CK, Warrener P, VanDevanter DR, Sherman DR, Arain TM, Langhorne MH, et al. (2000). A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis. Nature 405: 962-966.
16. Studier FW, (2005). Protein production by auto-induction in high density shaking cultures. Protein Expr Purif 41: 207-234.
17. Thompson AM, Blaser A, Anderson RF, Shinde SS, Franzblau SG, Ma Z, et al. (2009). Synthesis, reduction potentials, and antitubercular activity of ring A/B analogues of the bioreductive drug (6S)-2-nitro-6-{[4-(trifluoromethoxy) benzyl]oxy}-6,7-dihydro-5H-imidazo[2, 1-b][1,3]oxazine (PA-824). J Med Chem 52: 637-645.
18. WHO (2009). World Health Organization Report 2009: Global Tuberculosis Control Epidemiology, Strategy, Financing. WHO: Geneva, Switzerland.
19. Yanez C, Bollo S, Nunez-Vergara LJ, Squella JA, (2001). Voltammetric determination of nitroimdazopyran candidate for the treatment of tuberculosis. Anal Lett 34: 2335-2348.
20. Zhou S, Paxton JW, Tingle MD, Kestell P, (2000). Identification of the human liver cytochrome P450 isoenzyme responsible for the 6-methylhydroxylation of the novel anticancer drug 5,6-dimethylxanthenone-4-acetic acid. Drug Metab Dispos 28: 1449-1456.