메뉴 건너뛰기




Volumn 2, Issue 8, 2010, Pages 1295-1304

The nitroimidazooxazines (PA-824 and analogs): Structure-activity relationship and mechanistic studies

Author keywords

[No Author keywords available]

Indexed keywords

6,7 DIHYDRO 2 NITRO 6 (4 TRIFLUOROMETHOXYBENZYLOXY) 5H IMIDAZO[2,1 B][1,3]OXAZINE; BIPHENYL DERIVATIVE; NITRIC OXIDE; NITROIMIDAZOOXAZINE; NITROREDUCTASE; OXAZINE DERIVATIVE; REACTIVE NITROGEN SPECIES; UNCLASSIFIED DRUG;

EID: 77956040170     PISSN: 17568919     EISSN: None     Source Type: Journal    
DOI: 10.4155/fmc.10.207     Document Type: Review
Times cited : (19)

References (35)
  • 1
    • 4644371358 scopus 로고    scopus 로고
    • Prospects for clinical introduction of nitroimidazole antibiotics for the treatment of tuberculosis
    • Barry CE, Boshoff HIM, Dowd CS. Prospects for clinical introduction of nitroimidazole antibiotics for the treatment of tuberculosis. Curr. Pharm. Des. 10, 3239-3262 (2004).
    • (2004) Curr. Pharm. Des. , vol.10 , pp. 3239-3262
    • Barry, C.E.1    Boshoff, H.I.M.2    Dowd, C.S.3
  • 2
  • 4
    • 33845947982 scopus 로고    scopus 로고
    • Synthesis and anti-tuberculosis activity of a novel series of optically active 6-nitro-2, 3- dihydroimidazo[2,1-b]oxazoles
    • Sasaki H, Haraguchi Y, Itotani M et al. Synthesis and anti-tuberculosis activity of a novel series of optically active 6-nitro-2,3- dihydroimidazo[2,1- b]oxazoles. J. Med. Chem. 49, 7854-7860 (2006).
    • (2006) J. Med. Chem. , vol.49 , pp. 7854-7860
    • Sasaki, H.1    Haraguchi, Y.2    Itotani, M.3
  • 5
    • 0034702247 scopus 로고    scopus 로고
    • A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis
    • Stover CK, Warrener P, Van Devanter DR et al. A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis. Nature 405, 962-966 (2000).
    • (2000) Nature , vol.405 , pp. 962-966
    • Stover, C.K.1    Warrener, P.2    Van Devanter, D.R.3
  • 6
    • 38349010517 scopus 로고    scopus 로고
    • Comparison of the sterilizing activities of the nitroimidazopyran PA-824 and moxifloxacin against persisting Mycobacterium tuberculosis
    • Hu Y, Coates ARM, Mitchison DA. Comparison of the sterilizing activities of the nitroimidazopyran PA-824 and moxifloxacin against persisting Mycobacterium tuberculosis. Int. J. Tuberc. Lung Dis. 12, 69-73 (2007).
    • (2007) Int. J. Tuberc. Lung Dis. , vol.12 , pp. 69-73
    • Hu, Y.1    Coates, A.R.M.2    Mitchison, D.A.3
  • 8
    • 47749152561 scopus 로고    scopus 로고
    • 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
    • Bashiri G, Squire CJ, Moreland NJ, Baker EN. 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 (2008).
    • (2008) J. Biol. Chem. , vol.283 , pp. 17531-17541
    • Bashiri, G.1    Squire, C.J.2    Moreland, N.J.3    Baker, E.N.4
  • 9
    • 34247515586 scopus 로고    scopus 로고
    • Expression, purification and crystallization of native and selenomethionine labeled Mycobacterium tuberculosis FGD1 (Rv0407) using a Mycobacterium smegmatis expression system
    • Bashiri G, Squire CJ, Baker EN, Moreland NJ. 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. 2007.
    • (2007) Protein Expr. Purif. , vol.54 , pp. 38-44
    • Bashiri, G.1    Squire, C.J.2    Baker, E.N.3    Moreland, N.J.4
  • 10
    • 31044452898 scopus 로고    scopus 로고
    • Identification of a nitroimidazo-oxazine-specific protein involved in PA-824 resistance in Mycobacterium tuberculosis
    • Manjunatha UH, Boshoff H, Dowd CS et al. Identification of a nitroimidazo-oxazine-specific protein involved in PA-824 resistance in Mycobacterium tuberculosis. Proc. Natl Acad. Sci. USA 103, 431-436 (2006).
    • (2006) Proc. Natl Acad. Sci. USA , vol.103 , pp. 431-436
    • Manjunatha, U.H.1    Boshoff, H.2    Dowd, C.S.3
  • 11
    • 1642304529 scopus 로고    scopus 로고
    • Cyclic voltammetric determination of free radical species from nitroimidazopyran: A new antutuberculosis agent
    • Bollo S, Nunez-Vergara LJ, Squella JA. Cyclic voltammetric determination of free radical species from nitroimidazopyran: a new antutuberculosis agent. J. Electroanalytical Chem. 562, 9-14 (2004).
    • (2004) J. Electroanalytical Chem. , vol.562 , pp. 9-14
    • Bollo, S.1    Nunez-Vergara, L.J.2    Squella, J.A.3
  • 12
    • 0034759760 scopus 로고    scopus 로고
    • Voltammetric determination of nitroimidazopyran drug candidate for the treatment of tuberculosis
    • Yanez C, Bollo S, Nunez-Vergara LJ, Squella JA. Voltammetric determination of nitroimidazopyran drug candidate for the treatment of tuberculosis. Anal. Lett. 34, 2335-2348(2001).
    • (2001) Anal. Lett. , vol.34 , pp. 2335-2348
    • Yanez, C.1    Bollo, S.2    Nunez-Vergara, L.J.3    Squella, J.A.4
  • 13
    • 43749100470 scopus 로고    scopus 로고
    • Intermediates in the reduction of the anti-tuberculosis 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
    • Anderson RF, Shinde SS, Maroz A, Boyd M, Palmer BD, Denny WA. Intermediates in the reduction of the anti-tuberculosis 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 (2008).
    • (2008) Org. Biomol. Chem. , vol.6 , pp. 1973-1980
    • Anderson, R.F.1    Shinde, S.S.2    Maroz, A.3    Boyd, M.4    Palmer, B.D.5    Denny, W.A.6
  • 14
    • 57149099588 scopus 로고    scopus 로고
    • PA-824 kills nonreplicating Mycobacterium tuberculosis by intracellular NO release
    • Singh R, Manjunatha U, Boshoff HIM et al. PA-824 kills nonreplicating Mycobacterium tuberculosis by intracellular NO release. Science 322, 1392-1395 (2008).
    • (2008) Science , vol.322 , pp. 1392-1395
    • Singh, R.1    Manjunatha, U.2    Him, B.3
  • 15
    • 33845323336 scopus 로고    scopus 로고
    • OPC-67683, a nitro-dihydro-imidazooxazole derivative with promising action against tuberculosis in vitro and in mice
    • Matsumoto M, Hashizume H, Tomishige T et al. OPC-67683, a nitro-dihydro-imidazooxazole derivative with promising action against tuberculosis in vitro and in mice. PLoS Med. 3, 2131-2134 (2006).
    • (2006) PLoS Med , vol.3 , pp. 2131-2134
    • Matsumoto, M.1    Hashizume, H.2    Tomishige, T.3
  • 16
    • 77951298792 scopus 로고    scopus 로고
    • The mechanism of action of PA-824: Novel insights from transcriptional profiling
    • Manjuanatha U, Boshoff HI, Barry CE. The mechanism of action of PA-824: novel insights from transcriptional profiling. Commun. Integr. Biol. 2, 215-218(2009).
    • (2009) Commun. Integr. Biol. , vol.2 , pp. 215-218
    • Manjuanatha, U.1    Boshoff, H.I.2    Barry, C.E.3
  • 17
    • 77956041158 scopus 로고    scopus 로고
    • Release of nitrite from the anti-tubercular nitroimidazole drug PA-824 and analogs upon one-electron reduction in protic, non-aqueous solvent
    • Maroz A, Shinde SS, Franzblau SG et al. Release of nitrite from the anti-tubercular nitroimidazole drug PA-824 and analogs upon one-electron reduction in protic, non-aqueous solvent. Org. Biol. Chem. 6, 1973-1980 (2008).
    • (2008) Org. Biol. Chem. , vol.6 , pp. 1973-1980
    • Maroz, A.1    Shinde, S.S.2    Franzblau, S.G.3
  • 18
    • 61449105900 scopus 로고    scopus 로고
    • Synthesis reduction potentials and anti-tubercular activity of ring A/B analogs of the bioreductive drug (6S)-2-nitro-6-{[4- (trifluoromethoxy)benzyl] oxy}-67-dihydro- 5H-imidazo[2,1-b][1,3]oxazine (PA-824)
    • Thompson AM, Blaser A, Anderson RF et al. Synthesis, reduction potentials and anti-tubercular activity of ring A/B analogs 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 (2009).
    • (2009) J. Med. Chem. , vol.52 , pp. 637-645
    • Thompson, A.M.1    Blaser, A.2    Anderson, R.F.3
  • 19
    • 34948909563 scopus 로고    scopus 로고
    • Integration of solventless reaction in a multistep process: Application to an efficient synthesis of PA-824
    • Orita A, Miwa K, Uehara G, Otera J. Integration of solventless reaction in a multistep process: application to an efficient synthesis of PA-824. Adv. Synth. Catal. 349, 2136-2144 (2007).
    • (2007) Adv. Synth. Catal. , vol.349 , pp. 2136-2144
    • Orita, A.1    Miwa, K.2    Uehara, G.3    Otera, J.4
  • 20
    • 0017069834 scopus 로고
    • Oxygen inhibition of nitroreductase: Electron transfer from nitro radical-anions to oxygen
    • Wardman P, Clarke DE. Oxygen inhibition of nitroreductase: electron transfer from nitro radical-anions to oxygen. Biochem. Biophys. Res. Commun. 69, 942-949 (1976).
    • (1976) Biochem. Biophys. Res. Commun. , vol.69 , pp. 942-949
    • Wardman, P.1    De, C.2
  • 21
    • 41149173349 scopus 로고    scopus 로고
    • Synthesis and anti-tubercular activity of 7-(R)- and 7-(S)-methyl-2- nitro-6-(S)-(4- (trifluoromethoxy)benzyloxy)-6, 7-dihydro- 5H-imidazo[2,1-b][1, 3]oxazines, analogs of PA-824
    • Li X, Manjunatha UH, Goodwin MB et al. Synthesis and anti-tubercular activity of 7-(R)- and 7-(S)-methyl-2-nitro-6-(S)-(4- (trifluoromethoxy) benzyloxy)-6,7-dihydro- 5H-imidazo[2,1-b][1,3]oxazines, analogs of PA-824. Bioorg. Med. Chem. Lett. 18, 2256-2262 (2008).
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 2256-2262
    • Li, X.1    Manjunatha, U.H.2    Goodwin, M.B.3
  • 22
    • 77249095085 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of anti-tubercular 2-nitroimidazooxazines bearing heterocyclic side chains
    • Sutherland HS, Blaser B, Kmentova I et al. Synthesis and structure-activity relationships of anti-tubercular 2-nitroimidazooxazines bearing heterocyclic side chains. J. Med. Chem. 53, 855-866, 2010.
    • (2010) J. Med. Chem. , vol.53 , pp. 855-866
    • Sutherland, H.S.1    Blaser, B.2    Kmentova, I.3
  • 23
    • 33746888286 scopus 로고    scopus 로고
    • Combination chemotherapy with the nitroimidazopyran PA-824 and first-line drugs in a murine model of tuberculosis
    • Nuermberger E, Rosenthal I, Tyagi S et al. Combination chemotherapy with the nitroimidazopyran PA-824 and first-line drugs in a murine model of tuberculosis. Antimicrob. Agents Chemother. 50, 2621-2625 (2006).
    • (2006) Antimicrob. Agents Chemother. , vol.50 , pp. 2621-2625
    • Nuermberger, E.1    Rosenthal, I.2    Tyagi, S.3
  • 24
    • 77954221104 scopus 로고    scopus 로고
    • The differential gene expression pattern of Mycobacterium tuberculosis in response to capreomycin and PA-824 versus first-line TB drugs reveals stress- and PE/PPE-related drug targets
    • DOI: 10.1155/2009/879621, Epub ahead of print
    • Fu LM, Tai SC. The differential gene expression pattern of Mycobacterium tuberculosis in response to capreomycin and PA-824 versus first-line TB drugs reveals stress- and PE/PPE-related drug targets. Int. J. Microbiol. DOI: 10.1155/2009/879621 (2009) (Epub ahead of print).
    • (2009) Int. J. Microbiol.
    • Fu, L.M.1    Tai, S.C.2
  • 25
    • 54449084104 scopus 로고    scopus 로고
    • Diarylquinolines are bactericidal for dormant Mycobacteria as a result of disturbed ATP homeostasis
    • Koul A, Vranckx L, Dendouga N et al. Diarylquinolines are bactericidal for dormant Mycobacteria as a result of disturbed ATP homeostasis. J. Biol. Chem. 283, 25273-25280 (2008).
    • (2008) J. Biol. Chem. , vol.283 , pp. 25273-25280
    • Koul, A.1    Vranckx, L.2    Dendouga, N.3
  • 26
    • 0026087709 scopus 로고
    • Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity
    • Debnath AK, Lopez de Compadre RL, Debnath G, Shusterman AJ, Hansch C. Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity. J. Med. Chem. 34, 786-797 (1991).
    • (1991) J. Med. Chem. , vol.34 , pp. 786-797
    • Debnath, A.K.1    Lopez De Compadre, R.L.2    Debnath, G.3    Shusterman, A.J.4    Hansch, C.5
  • 28
    • 64349096833 scopus 로고    scopus 로고
    • Structure-activity relationships of anti-tubercular nitroimidazoles. 2. Determinants of aerobic activity and quantitative structure-activity relationships
    • Kim P, Kang S, Boshoff HI et al. Structure-activity relationships of anti-tubercular nitroimidazoles. 2. Determinants of aerobic activity and quantitative structure-activity relationships. J. Med. Chem. 52, 1329-1344 (2009).
    • (2009) J. Med. Chem. , vol.52 , pp. 1329-1344
    • Kim, P.1    Kang, S.2    Boshoff, H.I.3
  • 29
    • 64349089269 scopus 로고    scopus 로고
    • Structure-activity relationships of anti-tubercular nitroimidazoles.1. Structural features associated with aerobic and anaerobic activities of 4- and 5-nitroimidazoles
    • Kim P, Zhang L, Manjunatha UH et al. Structure-activity relationships of anti-tubercular nitroimidazoles. 1. Structural features associated with aerobic and anaerobic activities of 4- and 5-nitroimidazoles. J. Med. Chem. 52, 1317-1328(2009).
    • (2009) J. Med. Chem. , vol.52 , pp. 1317-1328
    • Kim, P.1    Zhang, L.2    Manjunatha, U.H.3
  • 30
    • 74849116658 scopus 로고    scopus 로고
    • Synthesis and structure-activity studies of biphenyl analogs of the nitroimidazooxazine tuberculosis drug PA-824
    • Palmer BD, Thompson AM, Sutherland HS et al. Synthesis and structure-activity studies of biphenyl analogs of the nitroimidazooxazine tuberculosis drug PA-824. J. Med. Chem. 53, 282-294 (2010).
    • (2010) J. Med. Chem. , vol.53 , pp. 282-294
    • Palmer, B.D.1    Thompson, A.M.2    Sutherland, H.S.3
  • 32
    • 45749089015 scopus 로고    scopus 로고
    • Crystal structure of the oxazolidinone antibiotic linezolid bound to the 50S ribosomal subunit
    • Ippolito JA, Kanyo ZF, Wang D et al. Crystal structure of the oxazolidinone antibiotic linezolid bound to the 50S ribosomal subunit. J. Med. Chem. 51, 3353-3356 (2008).
    • (2008) J. Med. Chem. , vol.51 , pp. 3353-3356
    • Ippolito, J.A.1    Kanyo, Z.F.2    Wang, D.3
  • 34
    • 77955055120 scopus 로고    scopus 로고
    • Extended early bactericidal activity (EBA) of PA-824, a novel drug for tuberculosis treatment
    • Presented at: Washington DC, USA. 25-28October
    • Ginsberg AM, Diacon A, Dawson R et al. Extended early bactericidal activity (EBA) of PA-824, a novel drug for tuberculosis treatment. Presented at: 48th Annual ICAAC/ IDSA 46th Annual Meeting, Washington DC, USA. 25-28October 2008.
    • (2008) 48th Annual ICAAC/ IDSA 46th Annual Meeting
    • Ginsberg, A.M.1    Diacon, A.2    Dawson, R.3
  • 35
    • 70349647606 scopus 로고    scopus 로고
    • Nitazoxanide kills replicating and nonreplicating Mycobacterium tuberculosis and evades resistance
    • de Carvalho LPS, Lin G, Jiang X, Nathan C. Nitazoxanide kills replicating and nonreplicating Mycobacterium tuberculosis and evades resistance. J. Med. Chem. 52, 5789-5792 (2009).
    • (2009) J. Med. Chem. , vol.52 , pp. 5789-5792
    • De Carvalho, L.P.S.1    Lin, G.2    Jiang, X.3    Nathan, C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.