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Volumn 56, Issue 3, 2013, Pages 1064-1073

Discovery of 5-benzyl-3-phenyl-4,5-dihydroisoxazoles and 5-benzyl-3-phenyl-1,4,2-dioxazoles as potent firefly luciferase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; FIREFLY LUCIFERASE; PYRROLE DERIVATIVE; RESVERATROL;

EID: 84873897789     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301516q     Document Type: Article
Times cited : (33)

References (39)
  • 1
    • 77953689492 scopus 로고    scopus 로고
    • Illuminating insights into firefly luciferase and other bioluminescent reporters used in chemical biology
    • Thorne, N.; Inglese, J.; Auld, D. S. Illuminating insights into firefly luciferase and other bioluminescent reporters used in chemical biology Chem. Biol. 2010, 17, 646-657
    • (2010) Chem. Biol. , vol.17 , pp. 646-657
    • Thorne, N.1    Inglese, J.2    Auld, D.S.3
  • 2
    • 77952545106 scopus 로고    scopus 로고
    • Apparent activity in high-throughput screening: Origins of compound-dependent assay interference
    • Thorne, N.; Auld, D. S.; Inglese, J. Apparent activity in high-throughput screening: origins of compound-dependent assay interference Curr. Opin. Chem. Biol. 2010, 14, 315-324
    • (2010) Curr. Opin. Chem. Biol. , vol.14 , pp. 315-324
    • Thorne, N.1    Auld, D.S.2    Inglese, J.3
  • 3
    • 0014575021 scopus 로고
    • Mechanism of bioluminescence, chemiluminescence and enzyme function in the oxidation of firefly luciferin
    • McElroy, W. D.; Seliger, H. H.; White, E. H. Mechanism of bioluminescence, chemiluminescence and enzyme function in the oxidation of firefly luciferin Photochem. Photobiol. 1969, 10, 153-170
    • (1969) Photochem. Photobiol. , vol.10 , pp. 153-170
    • McElroy, W.D.1    Seliger, H.H.2    White, E.H.3
  • 4
    • 49449106910 scopus 로고    scopus 로고
    • False positives in a reporter gene assay: Identification and synthesis of substituted N -pyridin-2-ylbenzamides as competitive inhibitors of firefly luciferase
    • Heitman, L. H.; van Veldhoven, J. P.; Zweemer, A. M.; Ye, K.; Brussee, J.; IJzerman, A. P. False positives in a reporter gene assay: identification and synthesis of substituted N -pyridin-2-ylbenzamides as competitive inhibitors of firefly luciferase J. Med. Chem. 2008, 51, 4724-4729
    • (2008) J. Med. Chem. , vol.51 , pp. 4724-4729
    • Heitman, L.H.1    Van Veldhoven, J.P.2    Zweemer, A.M.3    Ye, K.4    Brussee, J.5    Ijzerman, A.P.6
  • 6
    • 84872384855 scopus 로고    scopus 로고
    • The nuclear factor κ B inhibitor (E)-2-Fluoro-4′- methoxystilbene inhibits firefly luciferase
    • Braeuning, A.; Vetter, S. The nuclear factor κ B inhibitor (E)-2-Fluoro-4′-methoxystilbene inhibits firefly luciferase Biosci. Rep. 2012, 32, 531-537
    • (2012) Biosci. Rep. , vol.32 , pp. 531-537
    • Braeuning, A.1    Vetter, S.2
  • 7
    • 84866234206 scopus 로고    scopus 로고
    • Identification and synthesis of substituted pyrrolo[2,3- d ]pyrimidines as novel firefly luciferase inhibitors
    • Liu, Y.; Fang, J.; Cai, H.; Xiao, F.; Ding, K.; Hu, Y. Identification and synthesis of substituted pyrrolo[2,3- d ]pyrimidines as novel firefly luciferase inhibitors Bioorg. Med. Chem. 2012, 20, 5473-5482
    • (2012) Bioorg. Med. Chem. , vol.20 , pp. 5473-5482
    • Liu, Y.1    Fang, J.2    Cai, H.3    Xiao, F.4    Ding, K.5    Hu, Y.6
  • 8
    • 84866733195 scopus 로고    scopus 로고
    • Pyrrolo[2,3- b ]quinoxalines as inhibitors of firefly luciferase: Their Cu-mediated synthesis and evaluation as false positives in a reporter gene assay
    • Nakhi, A.; Rahman, M. S.; Kishore, R.; Meda, C. L.; Deora, G. S.; Parsa, K. V.; Pal, M. Pyrrolo[2,3- b ]quinoxalines as inhibitors of firefly luciferase: their Cu-mediated synthesis and evaluation as false positives in a reporter gene assay Bioorg. Med. Chem. Lett. 2012, 22, 6433-6441
    • (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 6433-6441
    • Nakhi, A.1    Rahman, M.S.2    Kishore, R.3    Meda, C.L.4    Deora, G.S.5    Parsa, K.V.6    Pal, M.7
  • 9
  • 10
    • 0014595824 scopus 로고
    • Substrate-binding properties of firefly luciferase. I. Luciferin-binding site
    • Denburg, J. L.; Lee, R. T.; McElroy, W. D. Substrate-binding properties of firefly luciferase. I. Luciferin-binding site Arch. Biochem. Biophys. 1969, 134, 381-394
    • (1969) Arch. Biochem. Biophys. , vol.134 , pp. 381-394
    • Denburg, J.L.1    Lee, R.T.2    McElroy, W.D.3
  • 11
    • 0014873578 scopus 로고
    • Substrate-binding properties of firefly luciferase. II. ATP-binding site
    • Lee, R. T.; Denburg, J. L.; McElroy, W. D. Substrate-binding properties of firefly luciferase. II. ATP-binding site Arch. Biochem. Biophys. 1970, 141, 38-52
    • (1970) Arch. Biochem. Biophys. , vol.141 , pp. 38-52
    • Lee, R.T.1    Denburg, J.L.2    McElroy, W.D.3
  • 13
    • 27144535390 scopus 로고    scopus 로고
    • Coenzyme A affects firefly luciferase luminescence because it acts as a substrate and not as an allosteric effector
    • Fraga, H.; Fernandes, D.; Fontes, R.; Esteves da Silva, J. C. Coenzyme A affects firefly luciferase luminescence because it acts as a substrate and not as an allosteric effector FEBS J. 2005, 272, 5206-5216
    • (2005) FEBS J. , vol.272 , pp. 5206-5216
    • Fraga, H.1    Fernandes, D.2    Fontes, R.3    Esteves Da Silva, J.C.4
  • 14
    • 0000693214 scopus 로고
    • The synthesis and function of luciferyl-adenylate and oxyluciferyl-adenylate
    • Rhodes, W. C.; McElroy, W. D. The synthesis and function of luciferyl-adenylate and oxyluciferyl-adenylate J. Biol. Chem. 1958, 233, 1528-1537
    • (1958) J. Biol. Chem. , vol.233 , pp. 1528-1537
    • Rhodes, W.C.1    McElroy, W.D.2
  • 17
    • 0032951370 scopus 로고    scopus 로고
    • Specific and non-specific binding of long-chain fatty acids to firefly luciferase: Cutoff at octanoate
    • Matsuki, H.; Suzuki, A.; Kamaya, H.; Ueda, I. Specific and non-specific binding of long-chain fatty acids to firefly luciferase: cutoff at octanoate Biochim. Biophys. Acta 1999, 1426, 143-150
    • (1999) Biochim. Biophys. Acta , vol.1426 , pp. 143-150
    • Matsuki, H.1    Suzuki, A.2    Kamaya, H.3    Ueda, I.4
  • 18
    • 4544325959 scopus 로고    scopus 로고
    • Inhibitory effect of lipoic acid on firefly luciferase bioluminescence
    • Niwa, K.; Ohmiya, Y. Inhibitory effect of lipoic acid on firefly luciferase bioluminescence Biochem. Biophys. Res. Commun. 2004, 323, 625-629
    • (2004) Biochem. Biophys. Res. Commun. , vol.323 , pp. 625-629
    • Niwa, K.1    Ohmiya, Y.2
  • 20
    • 79959753214 scopus 로고    scopus 로고
    • Identification of a naturally occurring quinazolin-4(3 H)-one firefly luciferase inhibitor
    • Somanadhan, B.; Leong, C.; Whitton, S. R.; Ng, S.; Buss, A. D.; Butler, M. S. Identification of a naturally occurring quinazolin-4(3 H)-one firefly luciferase inhibitor J. Nat. Prod. 2011, 74, 1500-1502
    • (2011) J. Nat. Prod. , vol.74 , pp. 1500-1502
    • Somanadhan, B.1    Leong, C.2    Whitton, S.R.3    Ng, S.4    Buss, A.D.5    Butler, M.S.6
  • 21
    • 0021211620 scopus 로고
    • Do general anaesthetics act by competitive binding to specific receptors?
    • Franks, N. P.; Lieb, W. R. Do general anaesthetics act by competitive binding to specific receptors? Nature 1984, 310, 599-601
    • (1984) Nature , vol.310 , pp. 599-601
    • Franks, N.P.1    Lieb, W.R.2
  • 22
    • 84855573333 scopus 로고    scopus 로고
    • Inhibition of firefly luciferase by general anesthetics: Effect on in vitro and in vivo bioluminescence imaging
    • Keyaerts, M.; Remory, I.; Caveliers, V.; Breckpot, K.; Bos, T. J.; Poelaert, J.; Bossuyt, A.; Lahoutte, T. Inhibition of firefly luciferase by general anesthetics: effect on in vitro and in vivo bioluminescence imaging PLoS One 2012, 7, e30061
    • (2012) PLoS One , vol.7 , pp. 30061
    • Keyaerts, M.1    Remory, I.2    Caveliers, V.3    Breckpot, K.4    Bos, T.J.5    Poelaert, J.6    Bossuyt, A.7    Lahoutte, T.8
  • 23
    • 2142673078 scopus 로고    scopus 로고
    • The p53-inhibitor pifithrin-α inhibits firefly luciferase activity in vivo and in vitro
    • Rocha, S.; Campbell, K. J.; Roche, K. C.; Perkins, N. D. The p53-inhibitor pifithrin-α inhibits firefly luciferase activity in vivo and in vitro BMC Mol. Biol. 2003, 4, 9
    • (2003) BMC Mol. Biol. , vol.4 , pp. 9
    • Rocha, S.1    Campbell, K.J.2    Roche, K.C.3    Perkins, N.D.4
  • 24
    • 62549134976 scopus 로고    scopus 로고
    • Mechanism of PTC124 activity in cell-based luciferase assays of nonsense codon suppression
    • Auld, D. S.; Thorne, N.; Maguire, W. F.; Inglese, J. Mechanism of PTC124 activity in cell-based luciferase assays of nonsense codon suppression Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 3585-3590
    • (2009) Proc. Natl. Acad. Sci. U.S.A. , vol.106 , pp. 3585-3590
    • Auld, D.S.1    Thorne, N.2    Maguire, W.F.3    Inglese, J.4
  • 26
    • 84865455985 scopus 로고    scopus 로고
    • Firefly luciferase in chemical biology: A compendium of inhibitors, mechanistic evaluation of chemotypes, and suggested use as a reporter
    • Thorne, N.; Shen, M.; Lea, W. A.; Simeonov, A.; Lovell, S.; Auld, D. S.; Inglese, J. Firefly luciferase in chemical biology: a compendium of inhibitors, mechanistic evaluation of chemotypes, and suggested use as a reporter Chem. Biol. 2012, 19, 1060-1072
    • (2012) Chem. Biol. , vol.19 , pp. 1060-1072
    • Thorne, N.1    Shen, M.2    Lea, W.A.3    Simeonov, A.4    Lovell, S.5    Auld, D.S.6    Inglese, J.7
  • 28
    • 45749150002 scopus 로고    scopus 로고
    • Synthesis and evaluation of estrogen agonism of diaryl 4,5-dihydroisoxazoles, 3-hydroxyketones, 3-methoxyketones, and 1,3-diketones: A compound set forming a 4D molecular library
    • Pulkkinen, J. T.; Honkakoski, P.; Peräkylä, M.; Berczi, I.; Laatikainen, R. Synthesis and evaluation of estrogen agonism of diaryl 4,5-dihydroisoxazoles, 3-hydroxyketones, 3-methoxyketones, and 1,3-diketones: a compound set forming a 4D molecular library J. Med. Chem. 2008, 51, 3562-3571
    • (2008) J. Med. Chem. , vol.51 , pp. 3562-3571
    • Pulkkinen, J.T.1    Honkakoski, P.2    Peräkylä, M.3    Berczi, I.4    Laatikainen, R.5
  • 30
    • 0004288248 scopus 로고    scopus 로고
    • version 5.03 for Windows; GraphPad Software: San Diego, CA.
    • GraphPad Prism, version 5.03 for Windows; GraphPad Software: San Diego, CA, 2010.
    • (2010) GraphPad Prism
  • 32
    • 70350455344 scopus 로고    scopus 로고
    • Design and characterization of novel trypsin-resistant firefly luciferases by site-directed mutagenesis
    • Riahi-Madvar, A.; Hosseinkhani, S. Design and characterization of novel trypsin-resistant firefly luciferases by site-directed mutagenesis Protein Eng., Des. Sel. 2009, 22, 655-663
    • (2009) Protein Eng., Des. Sel. , vol.22 , pp. 655-663
    • Riahi-Madvar, A.1    Hosseinkhani, S.2
  • 36
    • 48349128547 scopus 로고    scopus 로고
    • version 1.171.35.19; Agilent Technologies: Oxford, U.K.
    • CrysalisPro, version 1.171.35.19; Agilent Technologies: Oxford, U.K., 2011.
    • (2011) CrysalisPro
  • 39
    • 33646767009 scopus 로고    scopus 로고
    • ORTEP-3 for Windows - A version of ORTEP-III with a graphical user interface (GUI)
    • Farrugia, L. J. ORTEP-3 for Windows-a version of ORTEP-III with a graphical user interface (GUI) J. Appl. Crystallogr. 1997, 30, 565
    • (1997) J. Appl. Crystallogr. , vol.30 , pp. 565
    • Farrugia, L.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.