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Volumn 99, Issue 2, 2011, Pages 189-193

Chiral β-arylalkyl-1H-1,2,4-triazoles as demethylase inhibitors: Biological evaluation and its stereoselective interaction with sterol 14α-demethylase from Penicillium digitatum

Author keywords

Binding constant; Chiral triazole; Inhibitory activity; Molecular docking; P. digitatum

Indexed keywords

PENICILLIUM DIGITATUM;

EID: 78751704507     PISSN: 00483575     EISSN: 10959939     Source Type: Journal    
DOI: 10.1016/j.pestbp.2010.12.003     Document Type: Article
Times cited : (6)

References (28)
  • 2
    • 64549163712 scopus 로고    scopus 로고
    • Curative and preventive activity of hydroxypropyl methylcellulose-lipid edible composite coatings containing antifungal food additives to control citrus postharvest green and blue molds
    • Valencia-Chamorro S.A., Pérez-Gago M.B., Del Río M.A., Palou L. Curative and preventive activity of hydroxypropyl methylcellulose-lipid edible composite coatings containing antifungal food additives to control citrus postharvest green and blue molds. J. Agric. Food. Chem. 2009, 57:2770-2777.
    • (2009) J. Agric. Food. Chem. , vol.57 , pp. 2770-2777
    • Valencia-Chamorro, S.A.1    Pérez-Gago, M.B.2    Del Río, M.A.3    Palou, L.4
  • 3
    • 69249222540 scopus 로고    scopus 로고
    • Combined effect of curing followed by acetic acid vapour treatments improves postharvest control of Penicillium digitatum on mandarins
    • Venditti T., Dore A., Molinu M.G., Agabbio M., D'Hallewin G. Combined effect of curing followed by acetic acid vapour treatments improves postharvest control of Penicillium digitatum on mandarins. Postharvest Biol. Technol. 2009, 54:111-114.
    • (2009) Postharvest Biol. Technol. , vol.54 , pp. 111-114
    • Venditti, T.1    Dore, A.2    Molinu, M.G.3    Agabbio, M.4    D'Hallewin, G.5
  • 4
    • 67649908400 scopus 로고    scopus 로고
    • Essential oil amended coatings as alternatives to synthetic fungicides in citrus postharvest management
    • du Plooy W., Regnier T., Combrinck S. Essential oil amended coatings as alternatives to synthetic fungicides in citrus postharvest management. Postharvest Biol. Technol. 2009, 53:117-122.
    • (2009) Postharvest Biol. Technol. , vol.53 , pp. 117-122
    • du Plooy, W.1    Regnier, T.2    Combrinck, S.3
  • 7
    • 36849082564 scopus 로고    scopus 로고
    • Control of citrus postharvest green mold and sour rot by potassium sorbate combined with heat and fungicides
    • Smilanick J.L., Mansour M.F., Gabler F.M., Sorenson D. Control of citrus postharvest green mold and sour rot by potassium sorbate combined with heat and fungicides. Postharvest Biol. Technol. 2008, 47:226-238.
    • (2008) Postharvest Biol. Technol. , vol.47 , pp. 226-238
    • Smilanick, J.L.1    Mansour, M.F.2    Gabler, F.M.3    Sorenson, D.4
  • 8
    • 70349335640 scopus 로고    scopus 로고
    • Synthesis and antifungal activity of trifluoroalkyl aminovinyl ketone derivatives
    • Gellerman G., Pariente N., Paz Z., Shnaiderman A., Yarden O. Synthesis and antifungal activity of trifluoroalkyl aminovinyl ketone derivatives. J. Agric. Food. Chem. 2009, 57:8303-8307.
    • (2009) J. Agric. Food. Chem. , vol.57 , pp. 8303-8307
    • Gellerman, G.1    Pariente, N.2    Paz, Z.3    Shnaiderman, A.4    Yarden, O.5
  • 9
    • 0001057391 scopus 로고
    • Occurrence of Penicillium digitatum and P. italicum resistant to benomyl, thiabendazole, and imazalil on citrus fruit from different geographic origins
    • Bus V.G., Bongers A.J., Risse L.A. Occurrence of Penicillium digitatum and P. italicum resistant to benomyl, thiabendazole, and imazalil on citrus fruit from different geographic origins. Plant Dis. 1991, 75:1098-1100.
    • (1991) Plant Dis. , vol.75 , pp. 1098-1100
    • Bus, V.G.1    Bongers, A.J.2    Risse, L.A.3
  • 10
    • 33847618261 scopus 로고    scopus 로고
    • Imazalil resistance linked to a unique insertion sequence in the PdCYP51 promoter region of Penicillium digitatum
    • Ghosoph J.M., Schmidt L.S., Margosan D.A., Smilanick J.L. Imazalil resistance linked to a unique insertion sequence in the PdCYP51 promoter region of Penicillium digitatum. Postharvest Biol. Technol. 2007, 44:9-18.
    • (2007) Postharvest Biol. Technol. , vol.44 , pp. 9-18
    • Ghosoph, J.M.1    Schmidt, L.S.2    Margosan, D.A.3    Smilanick, J.L.4
  • 11
    • 33846347872 scopus 로고    scopus 로고
    • Characterization of fungicide-resistant isolates of Penicillium digitatum collected in California
    • Kinay P., Mansour M.F., Gabler F.M., Margosan D.A., Smilanick J.L. Characterization of fungicide-resistant isolates of Penicillium digitatum collected in California. Crop Prot. 2007, 26:647-656.
    • (2007) Crop Prot. , vol.26 , pp. 647-656
    • Kinay, P.1    Mansour, M.F.2    Gabler, F.M.3    Margosan, D.A.4    Smilanick, J.L.5
  • 12
    • 33846363482 scopus 로고    scopus 로고
    • Comparison of the declining triazole sensitivity of Gibberella zeae and increased sensitivity achieved by advances in triazole fungicide development
    • Klix M.B., Verreet J.-A., Beyer M. Comparison of the declining triazole sensitivity of Gibberella zeae and increased sensitivity achieved by advances in triazole fungicide development. Crop Prot. 2007, 26:683-690.
    • (2007) Crop Prot. , vol.26 , pp. 683-690
    • Klix, M.B.1    Verreet, J.-A.2    Beyer, M.3
  • 13
    • 33847318713 scopus 로고    scopus 로고
    • Differential effect of triazole on mycelial growth and disease measurements of Monilinia fructicola isolates with reduced sensitivity to DMI fungicides
    • Holb I.J., Schnabel G. Differential effect of triazole on mycelial growth and disease measurements of Monilinia fructicola isolates with reduced sensitivity to DMI fungicides. Crop Prot. 2007, 26:753-759.
    • (2007) Crop Prot. , vol.26 , pp. 753-759
    • Holb, I.J.1    Schnabel, G.2
  • 14
    • 58949087547 scopus 로고    scopus 로고
    • Chiral γ-aryl-1H-1,2,4-triazole derivatives as highly potential antifungal agents: Design, synthesis, structure and in vitro fungicidal activities
    • Cao X., Li F., Hu M., Lu W., Yu G.-A., Liu S. Chiral γ-aryl-1H-1,2,4-triazole derivatives as highly potential antifungal agents: Design, synthesis, structure and in vitro fungicidal activities. J. Agric. Food. Chem. 2008, 56:11367-11375.
    • (2008) J. Agric. Food. Chem. , vol.56 , pp. 11367-11375
    • Cao, X.1    Li, F.2    Hu, M.3    Lu, W.4    Yu, G.-A.5    Liu, S.6
  • 15
    • 68249130485 scopus 로고    scopus 로고
    • Determination of stereoselective interaction between enantiomers of chiral γ-aryl-1H-1,2,4-triazole derivatives and Penicillium digitatum
    • Cao X., Hu M., Zhang J., Li F., Yang Y., Liu D., Liu S. Determination of stereoselective interaction between enantiomers of chiral γ-aryl-1H-1,2,4-triazole derivatives and Penicillium digitatum. J. Agric. Food. Chem. 2009, 57:6914-6919.
    • (2009) J. Agric. Food. Chem. , vol.57 , pp. 6914-6919
    • Cao, X.1    Hu, M.2    Zhang, J.3    Li, F.4    Yang, Y.5    Liu, D.6    Liu, S.7
  • 16
    • 80051890631 scopus 로고    scopus 로고
    • A highly enantioselective strategy providing convenient access to chiral β-aryl-1H-1,2,4-triazole derivatives as agricultural bactericides
    • Lu W., Cao X., Hu M., Li F., Yu G.-A., Liu S. A highly enantioselective strategy providing convenient access to chiral β-aryl-1H-1,2,4-triazole derivatives as agricultural bactericides. Chem. Biodivers. 2010, 10.1002/cbdv.201000180.
    • (2010) Chem. Biodivers.
    • Lu, W.1    Cao, X.2    Hu, M.3    Li, F.4    Yu, G.-A.5    Liu, S.6
  • 17
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford M.M. A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72:248-254.
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 18
    • 0035876976 scopus 로고    scopus 로고
    • Azole-antifungal binding to a novel cytochrome P450 from Myobacterium wtuberculosis: implications for treatment of tuberculosis
    • Guardiola-Diaz H.M., Foster L.A., Mushrush D., Vaz A.D. Azole-antifungal binding to a novel cytochrome P450 from Myobacterium wtuberculosis: implications for treatment of tuberculosis. Biochem. Pharmacol. 2001, 61:1463-1470.
    • (2001) Biochem. Pharmacol. , vol.61 , pp. 1463-1470
    • Guardiola-Diaz, H.M.1    Foster, L.A.2    Mushrush, D.3    Vaz, A.D.4
  • 19
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes. 1. Evidence for its hemoprotein nature
    • Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes. 1. Evidence for its hemoprotein nature. J. Biol. Chem. 1964, 239:2370-2378.
    • (1964) J. Biol. Chem. , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 20
    • 33846446220 scopus 로고
    • Restart procedures for the conjugate gradient method
    • Powell M.J.D. Restart procedures for the conjugate gradient method. Math. Program. 1977, 12:241-254.
    • (1977) Math. Program. , vol.12 , pp. 241-254
    • Powell, M.J.D.1
  • 21
    • 0032738842 scopus 로고    scopus 로고
    • Evaluation of the FLEXX incremental construction algorithm for protein-ligand docking
    • Kramer B., Rarey M., Lengauer T. Evaluation of the FLEXX incremental construction algorithm for protein-ligand docking. Proteins 1999, 37:228-241.
    • (1999) Proteins , vol.37 , pp. 228-241
    • Kramer, B.1    Rarey, M.2    Lengauer, T.3
  • 22
    • 0014059179 scopus 로고
    • Spectral studies of drug interaction with hepatic microsomal cytochrome
    • Schenkman J.B., Remmer H., Estabrook R.W. Spectral studies of drug interaction with hepatic microsomal cytochrome. Mol. Pharmacol. 1967, 3:113-123.
    • (1967) Mol. Pharmacol. , vol.3 , pp. 113-123
    • Schenkman, J.B.1    Remmer, H.2    Estabrook, R.W.3
  • 23
    • 0035853108 scopus 로고    scopus 로고
    • Crystal structure of cytochrome P450 14α-sterol demethylase (CYP51) from Mycobacterium tuberculosis in complex with azole inhibitors
    • Podust L.M., Poulos T.L., Waterman M.R. Crystal structure of cytochrome P450 14α-sterol demethylase (CYP51) from Mycobacterium tuberculosis in complex with azole inhibitors. Proc. Natl. Acad. Sci. 2001, 98:3068-3073.
    • (2001) Proc. Natl. Acad. Sci. , vol.98 , pp. 3068-3073
    • Podust, L.M.1    Poulos, T.L.2    Waterman, M.R.3
  • 24
    • 33745216665 scopus 로고    scopus 로고
    • Designing better drugs: predicting cytochrome P450 metabolism
    • de Groot M.J. Designing better drugs: predicting cytochrome P450 metabolism. Drug Discovery Today 2006, 11:601-606.
    • (2006) Drug Discovery Today , vol.11 , pp. 601-606
    • de Groot, M.J.1
  • 25
    • 62549145789 scopus 로고    scopus 로고
    • Expression and homology modelling of sterol 14α-demethylase of Magnaporthe grisea and its interaction with azoles
    • Yang J., Zhang Q., Liao M., Xiao M., Xiao W., Yang S., Wan J. Expression and homology modelling of sterol 14α-demethylase of Magnaporthe grisea and its interaction with azoles. Pest Manag. Sci. 2009, 65:260-265.
    • (2009) Pest Manag. Sci. , vol.65 , pp. 260-265
    • Yang, J.1    Zhang, Q.2    Liao, M.3    Xiao, M.4    Xiao, W.5    Yang, S.6    Wan, J.7
  • 26
    • 0035967880 scopus 로고    scopus 로고
    • FUGUE: sequence-structure homology recognition using environment-specific substitution tables and structure-dependent gap penalties
    • Shi J., Blundell T.L., Mizuguchi K. FUGUE: sequence-structure homology recognition using environment-specific substitution tables and structure-dependent gap penalties. J. Mol. Biol. 2001, 310:243-257.
    • (2001) J. Mol. Biol. , vol.310 , pp. 243-257
    • Shi, J.1    Blundell, T.L.2    Mizuguchi, K.3
  • 27
    • 0035893831 scopus 로고    scopus 로고
    • Substrate recognition sites in 14α-sterol demethylase from comparative analysis of amino acid sequences and X-ray structure of Mycobacterium tuberculosis CYP51
    • Podust L.M., Stojan J., Poulos T.L., Waterman M.R. Substrate recognition sites in 14α-sterol demethylase from comparative analysis of amino acid sequences and X-ray structure of Mycobacterium tuberculosis CYP51. J. Inorg. Biochem. 2001, 87:227-235.
    • (2001) J. Inorg. Biochem. , vol.87 , pp. 227-235
    • Podust, L.M.1    Stojan, J.2    Poulos, T.L.3    Waterman, M.R.4
  • 28
    • 35748979110 scopus 로고    scopus 로고
    • Expression and homology modeling of sterol 14α-demethylase from Penicillium digitatum
    • Zhao L., Liu D., Zhang Q., Zhang S., Wan J., Xiao W. Expression and homology modeling of sterol 14α-demethylase from Penicillium digitatum. FEMS Microbiol. Lett. 2007, 277:37-43.
    • (2007) FEMS Microbiol. Lett. , vol.277 , pp. 37-43
    • Zhao, L.1    Liu, D.2    Zhang, Q.3    Zhang, S.4    Wan, J.5    Xiao, W.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.