메뉴 건너뛰기




Volumn 57, Issue 15, 2009, Pages 6914-6919

Determination of stereoselective interaction between enantiomers of chiral γ-aryl-1 H-1,2,4-triazole derivatives and Penicillium digitatum

Author keywords

Binding constant; Chirality; CYP51; Fungicide; P. digitatum; Triazole

Indexed keywords

1,2,4 TRIAZOLE; 1,2,4-TRIAZOLE; ANTIFUNGAL AGENT; CYTOCHROME P450; FUNGAL PROTEIN; TRIAZOLE DERIVATIVE;

EID: 68249130485     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf901554x     Document Type: Article
Times cited : (21)

References (45)
  • 1
    • 0000907114 scopus 로고
    • Postharvest disorders and diseases of citrus fruit
    • Reuther, W, Calavan, E. C. Carman, G. E, Eds, University of California Press: Berkeley, CA
    • Eckert, J. W.; Eaks. I. L. Postharvest disorders and diseases of citrus fruit. In The Citrus Industry; Reuther, W., Calavan, E. C. Carman, G. E., Eds.; University of California Press: Berkeley, CA, 1989; Vol. 5, pp 179-260.
    • (1989) The Citrus Industry , vol.5 , pp. 179-260
    • Eckert, J.W.1    Eaks, I.L.2
  • 2
    • 0035088743 scopus 로고    scopus 로고
    • Control of postharvest blue and green molds of oranges by hot water, sodium carbonate and sodium bicarbonate
    • Palou, L.; Smilanick, J. L.; Usall, J.; Vigríäs, I. Control of postharvest blue and green molds of oranges by hot water, sodium carbonate and sodium bicarbonate. Plant Dis. 2001, 85, 371-376.
    • (2001) Plant Dis , vol.85 , pp. 371-376
    • Palou, L.1    Smilanick, J.L.2    Usall, J.3    Vigríäs, I.4
  • 4
    • 0001294501 scopus 로고
    • Recent developments in the chemical control of postharvest diseases
    • Eckert. J. W. Recent developments in the chemical control of postharvest diseases. Acta Hortic. 1990, 269, 477-494.
    • (1990) Acta Hortic , vol.269 , pp. 477-494
    • Eckert, J.W.1
  • 8
    • 0032872995 scopus 로고    scopus 로고
    • Sensitivity of Penicillium digitatum and P. italicum to postharvest citrus fungicides in California
    • Holmes, G. J.; Eckert, J. W. Sensitivity of Penicillium digitatum and P. italicum to postharvest citrus fungicides in California. Phytopathology 1999, 89, 716-721.
    • (1999) Phytopathology , vol.89 , pp. 716-721
    • Holmes, G.J.1    Eckert, J.W.2
  • 9
    • 33846347872 scopus 로고    scopus 로고
    • Characterization of fungicide-resistant isolates of Penicillium digitatum collected in California
    • Kinaya, P.; Mansourc, M. F.; Gablerb, F. M.; Margosanc, D. A.; Smilanick, J. L. Characterization of fungicide-resistant isolates of Penicillium digitatum collected in California. Croa Prot. 2001, 26, 647-656.
    • (2001) Croa Prot , vol.26 , pp. 647-656
    • Kinaya, P.1    Mansourc, M.F.2    Gablerb, F.M.3    Margosanc, D.A.4    Smilanick, J.L.5
  • 10
    • 19944362858 scopus 로고    scopus 로고
    • Sodium carbonate treatment induces scoparone accumulation, structural changes, and alkalinization in the albedo of wounded citrus fruits
    • Venditti, T.; Molinu, M. G.; Dore, A.; Agabbio, M.; D'hallewin, G. Sodium carbonate treatment induces scoparone accumulation, structural changes, and alkalinization in the albedo of wounded citrus fruits. J. Agric. Food Chem. 2005, 53, 3510-3518.
    • (2005) J. Agric. Food Chem , vol.53 , pp. 3510-3518
    • Venditti, T.1    Molinu, M.G.2    Dore, A.3    Agabbio, M.4    D'hallewin, G.5
  • 12
    • 29644437415 scopus 로고    scopus 로고
    • Pre- and postharvest treatments to control green mold of citrus fruit during ethylene degreening
    • Smilanick, J. L.; Mansour, M. F.; Sorenson, D. Pre- and postharvest treatments to control green mold of citrus fruit during ethylene degreening. Plant Dis. 2006, 90, 89-96.
    • (2006) Plant Dis , vol.90 , pp. 89-96
    • Smilanick, J.L.1    Mansour, M.F.2    Sorenson, D.3
  • 13
    • 18944370113 scopus 로고    scopus 로고
    • 3 on effectiveness of imazalil to inhibit germination of Penicillium digitatum and to control postharvest green mold of citrus fruit
    • 3 on effectiveness of imazalil to inhibit germination of Penicillium digitatum and to control postharvest green mold of citrus fruit. Plant Dis. 2005, 89, 640-648.
    • (2005) Plant Dis , vol.89 , pp. 640-648
    • Smilanick, J.L.1    Mansour, M.F.2    Margosan, D.A.3    Mlikota Gabler, F.4
  • 14
    • 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
  • 15
    • 33746492938 scopus 로고    scopus 로고
    • Residue levels and effectiveness of pyrimethanil vs imazalil when using heated postharvest dip treatments for control of penicillium decay on citrus fruit
    • D'Aquino, S.; Schirra, M.; Palma, A.; Angioni, A.; Cabras, P.; Migheli, Q. Residue levels and effectiveness of pyrimethanil vs imazalil when using heated postharvest dip treatments for control of penicillium decay on citrus fruit. J. Agric. Food Chem. 2006, 54. 4721-4726.
    • (2006) J. Agric. Food Chem , vol.54 , pp. 4721-4726
    • D'Aquino, S.1    Schirra, M.2    Palma, A.3    Angioni, A.4    Cabras, P.5    Migheli, Q.6
  • 16
    • 0034122747 scopus 로고    scopus 로고
    • Use and challenges of novel compounds for plant disease control
    • Gullino, M. L.; Leroux, P.; Smith, C. M. Use and challenges of novel compounds for plant disease control. Crop Prot. 2000, 19, 1-11.
    • (2000) Crop Prot , vol.19 , pp. 1-11
    • Gullino, M.L.1    Leroux, P.2    Smith, C.M.3
  • 17
    • 0033737260 scopus 로고    scopus 로고
    • Botrytis cinereas-history of chemical control and novel fungicides for its management
    • Rosslenbroich. H. J.; Stuebler, D. Botrytis cinereas-history of chemical control and novel fungicides for its management. Crop Prot. 2000, 19, 557-561.
    • (2000) Crop Prot , vol.19 , pp. 557-561
    • Rosslenbroich, H.J.1    Stuebler, D.2
  • 21
    • 0001780349 scopus 로고    scopus 로고
    • Manufacture of optically active materials: An agrochemicals perspective
    • Crosby, J. Manufacture of optically active materials: An agrochemicals perspective, Pestic. Sci. 1996, 46, 11-31.
    • (1996) Pestic. Sci , vol.46 , pp. 11-31
    • Crosby, J.1
  • 24
    • 58949087547 scopus 로고    scopus 로고
    • Chiral γ-aryl-1 H-1,2,4-triazole derivatives as highly potential antifungal agents: Design, synthesis, structure and in vitro fungicidal activities
    • Cao, X. F.; Li, F.; Hu, M.; Lu, W. C.; Yu, G.-A.; Liu, S. H. Chiral γ-aryl-1 H-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.F.1    Li, F.2    Hu, M.3    Lu, W.C.4    Yu, G.-A.5    Liu, S.H.6
  • 25
    • 0342656026 scopus 로고
    • Biochemical mode of action of fungicides. Ergosterol biosynthesis inhibitors
    • Fungicide Chemistry: Advances and Practical Applications; Green, M. B, Spilker, D. A, Eds, American Chemical Society: Washington, DC
    • Berg, D. Biochemical mode of action of fungicides. Ergosterol biosynthesis inhibitors. In Fungicide Chemistry: Advances and Practical Applications; Green, M. B., Spilker, D. A., Eds.; ACS Symposium Series 304; American Chemical Society: Washington, DC, 1986; pp 25-51.
    • (1986) ACS Symposium Series , vol.304 , pp. 25-51
    • Berg, D.1
  • 26
    • 33947682816 scopus 로고    scopus 로고
    • Sterol biosynthesis inhibitors: Potential for transition state analogs and mechanism-based inactivators targeted at sterol methyltransferase
    • Song. Z.; Nes. W. D. Sterol biosynthesis inhibitors: potential for transition state analogs and mechanism-based inactivators targeted at sterol methyltransferase. Lipids 2007, 42, 15-33.
    • (2007) Lipids , vol.42 , pp. 15-33
    • Song, Z.1    Nes, W.D.2
  • 27
    • 68249091600 scopus 로고    scopus 로고
    • Zirngibl, L. Azoles-Antifungal Active Substances-Synthesis and Uses; Wiley-VCH: Weinheim. Gennany, 1998.
    • Zirngibl, L. Azoles-Antifungal Active Substances-Synthesis and Uses; Wiley-VCH: Weinheim. Gennany, 1998.
  • 29
    • 38349065310 scopus 로고    scopus 로고
    • Sterol biosynthesis inhibitors
    • Krämer, W, Schirmer, U, Eds, Wiley-VCH: Weinheim, Germany
    • Kuck, K. H.; Vors, J. P. Sterol biosynthesis inhibitors. In Modem Crop Protection; Krämer, W., Schirmer, U., Eds.; Wiley-VCH: Weinheim, Germany, 2007; Vol. 2, pp 605-650.
    • (2007) Modem Crop Protection , vol.2 , pp. 605-650
    • Kuck, K.H.1    Vors, J.P.2
  • 30
    • 37049010497 scopus 로고    scopus 로고
    • Application of binding spectrum in DMIs fungicide screening
    • Xiao, M.; Yang, J.-Y.; Xiao, W.- J.; Yang, S. Application of binding spectrum in DMIs fungicide screening. Chin. J. Biotechnol. 2007. 23. 1129-1134.
    • (2007) Chin. J. Biotechnol , vol.23 , pp. 1129-1134
    • Xiao, M.1    Yang, J.-Y.2    Xiao, W.J.3    Yang, S.4
  • 31
    • 42449108144 scopus 로고    scopus 로고
    • Jackson, C. J.; Lamb, D. C.; Kelly, S. L. P450s in microbial sterol biosynthesis and drug targets, Acta Chim. Slov. 2008, 55.58-62.
    • Jackson, C. J.; Lamb, D. C.; Kelly, S. L. P450s in microbial sterol biosynthesis and drug targets, Acta Chim. Slov. 2008, 55.58-62.
  • 32
    • 42449137848 scopus 로고    scopus 로고
    • Mechanisms of cytochrome P450 reactions
    • Guengerich, F. P.; Isin, E. M. Mechanisms of cytochrome P450 reactions, Acta Chim. Slov. 2008, 55, 7-19.
    • (2008) Acta Chim. Slov , vol.55 , pp. 7-19
    • Guengerich, F.P.1    Isin, E.M.2
  • 33
    • 21444433192 scopus 로고    scopus 로고
    • The effect of TTS12 on ergosterol bio-synthetic pathway in Candida albicans determined quantitatively with GC-MS method
    • Zhao, Q.; Zhang, J.; Cao, Y.; Chen, H.; Jiang, Y. The effect of TTS12 on ergosterol bio-synthetic pathway in Candida albicans determined quantitatively with GC-MS method. Pharm. Care Res. 2005. 5, 144-147.
    • (2005) Pharm. Care Res , vol.5 , pp. 144-147
    • Zhao, Q.1    Zhang, J.2    Cao, Y.3    Chen, H.4    Jiang, Y.5
  • 34
    • 37049009257 scopus 로고    scopus 로고
    • Effect of novel fungicide 5-(4chlorophenyl)-2.3-dimethyl-3-(pyridine-3)-oxazoline on ergosterol biosynthesis in botrytis cinerea by high performance liquid chroma tography
    • Han, P.; Liu, X.; Liu, P.; Si, N. Effect of novel fungicide 5-(4chlorophenyl)-2.3-dimethyl-3-(pyridine-3)-oxazoline on ergosterol biosynthesis in botrytis cinerea by high performance liquid chroma tography. Chin. J. Anal. Chem. 2006, 34, 1467-1470.
    • (2006) Chin. J. Anal. Chem , vol.34 , pp. 1467-1470
    • Han, P.1    Liu, X.2    Liu, P.3    Si, N.4
  • 35
    • 33744471798 scopus 로고    scopus 로고
    • Effect of fluconazole on ergosterol biosynthesis in fungi by TLC
    • Cao, Y.-B.; Sun, F.-H. Effect of fluconazole on ergosterol biosynthesis in fungi by TLC. Acad. J. Second Mil. Med. Univ. 1999, 20, 312-315.
    • (1999) Acad. J. Second Mil. Med. Univ , vol.20 , pp. 312-315
    • Cao, Y.-B.1    Sun, F.-H.2
  • 36
    • 0036775336 scopus 로고    scopus 로고
    • Azole antifungals are potent inhibitors of cytochrome P450 mono-oxygenases and bacterial growth in mycobateria and strepromycetes
    • Kristy, J. M.; Ker, R. M.; Alison, R.; Hunter, I. S.; Fowler, K.; Kieser, T.; Gurcha, S. S.; Besra, G. S.; Munro, A. W. Azole antifungals are potent inhibitors of cytochrome P450 mono-oxygenases and bacterial growth in mycobateria and strepromycetes. Microbiology 2002, 148, 2937-2949.
    • (2002) Microbiology , vol.148 , pp. 2937-2949
    • Kristy, J.M.1    Ker, R.M.2    Alison, R.3    Hunter, I.S.4    Fowler, K.5    Kieser, T.6    Gurcha, S.S.7    Besra, G.S.8    Munro, A.W.9
  • 37
    • 43149116071 scopus 로고    scopus 로고
    • Regioand diastereoselective conjugate addition of Grignard reagents to aryl substituted α.β-unsaturated carbonyl compounds derived from Oppolzer's sultam
    • Cao, X. F.; Liu, F.; Lu, W. C.; Chen, G.; Yu, G.-A.; Liu, S. H. Regioand diastereoselective conjugate addition of Grignard reagents to aryl substituted α.β-unsaturated carbonyl compounds derived from Oppolzer's sultam. Tetrahedron 2008, 64, 5629-5636.
    • (2008) Tetrahedron , vol.64 , pp. 5629-5636
    • Cao, X.F.1    Liu, F.2    Lu, W.C.3    Chen, G.4    Yu, G.-A.5    Liu, S.H.6
  • 38
    • 68249102818 scopus 로고    scopus 로고
    • Clough, J. M.; Godfrey, C. R. A. The strobilurin fungicides. In Fungicidal Activity, Chemical and Biological Approaches to Plant Protection; Hutson, D. H., Miyamoto, J., Eds.; Wiley Series in Agrochemicals and Plant Protection; John Wiley & Sons: Surrey, U.K., 1998; p 109.
    • Clough, J. M.; Godfrey, C. R. A. The strobilurin fungicides. In Fungicidal Activity, Chemical and Biological Approaches to Plant Protection; Hutson, D. H., Miyamoto, J., Eds.; Wiley Series in Agrochemicals and Plant Protection; John Wiley & Sons: Surrey, U.K., 1998; p 109.
  • 39
    • 35748979110 scopus 로고    scopus 로고
    • Expression and homologymodeling of sterol 14α-demethylase from Penicillium digitatum
    • Zhao, L.; Liu, D. L.; Zhang, Q. Y.; Zhang, S.; Wan, J.; Xiao, W. J. Expression and homologymodeling 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.L.2    Zhang, Q.Y.3    Zhang, S.4    Wan, J.5    Xiao, W.J.6
  • 40
    • 27144446823 scopus 로고    scopus 로고
    • The development of a medium throughput assay for lanosterol synthase from Leptosphaeria nodorum: Comparison of the enzyme from L. nodorum. Saccharomyces cerevisiae, and two species of Fusarium
    • Stephen, M. G.; Du, V.; Jennifer, D.-A.; Rebecca, T. The development of a medium throughput assay for lanosterol synthase from Leptosphaeria nodorum: Comparison of the enzyme from L. nodorum. Saccharomyces cerevisiae, and two species of Fusarium. Pestic. Biochem. Physiol 2005, 83, 97-106.
    • (2005) Pestic. Biochem. Physiol , vol.83 , pp. 97-106
    • Stephen, M.G.1    Du, V.2    Jennifer, D.-A.3    Rebecca, T.4
  • 41
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding
    • Braford, M. M.; Mcrorie, R. A.; Williams, W. L. 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
    • Braford, M.M.1    Mcrorie, R.A.2    Williams, W.L.3
  • 42
    • 0035876976 scopus 로고    scopus 로고
    • Azole-antifungal binding to a novel cytochrome P450 from Myobacterium tuberculosis: Implications for treatment of tuberculosis
    • Guardiola-Diaz, H. M.; Foster, L.-A.; Mushrush, D.; Vaz, A. D. N. Azole-antifungal binding to a novel cytochrome P450 from Myobacterium tuberculosis: 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.N.4
  • 43
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature
    • Omura, T.; Sato, R. The carbon monoxide-binding pigment of liver microsomes. I. 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
  • 45
    • 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


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.