메뉴 건너뛰기




Volumn 57, Issue 20, 2009, Pages 9593-9598

Rational prediction of the herbicidal activities of novel protoporphyrinogen oxidase inhibitors by quantitative structure-activity relationship model based on docking-guided active conformation

Author keywords

Genetic algorithm multiple linear regression (GA MLR); Molecular clocking; Protoporphyrinogen oxidase (PPO); Quantitative structure activity relationship (QSAR)

Indexed keywords

ENZYME INHIBITOR; HERBICIDE; PROTOPORPHYRINOGEN OXIDASE; VEGETABLE PROTEIN;

EID: 70350316493     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf902010g     Document Type: Article
Times cited : (18)

References (41)
  • 1
    • 45449121911 scopus 로고
    • Effects of acifluorfen-methyl on cucumber cotyledons: Porphyrin accumulation
    • Matringe, M.; Scalla, R. Effects of acifluorfen-methyl on cucumber cotyledons: Porphyrin accumulation. Pestic. Bioehem. Physiol. 1988, 32, 164-172.
    • (1988) Pestic. Biochem. Physiol. , vol.32 , pp. 164-172
    • Matringe, M.1    Scalla, R.2
  • 2
    • 84969822750 scopus 로고
    • Protoporphyrin IX content correlates with activity of photobleaching herbicides
    • Becerril, J. M.; Duke, S. O. Protoporphyrin IX content correlates with activity of photobleaching herbicides. Plant Physiol. 1989, 90, 1175-1181.
    • (1989) Plant Physiol. , vol.90 , pp. 1175-1181
    • Becerril, J.M.1    Duke, S.O.2
  • 4
    • 0030798711 scopus 로고    scopus 로고
    • Selectivity and mode of action of carfentrazone-ethyl, anovel phenyl triazolinone herbicide
    • Dayan, F. E.; Duke, S. O.; Weete, J. D.; Hancock, H. G. Selectivity and mode of action of carfentrazone-ethyl, anovel phenyl triazolinone herbicide. Pestic. Sci. 1997, 51, 65-73.
    • (1997) Pestic. Sci. , vol.51 , pp. 65-73
    • Dayan, F.E.1    Duke, S.O.2    Weete, J.D.3    Hancock, H.G.4
  • 5
    • 0038632867 scopus 로고    scopus 로고
    • Inhibitory activity of sulfentrazone and its metabolic derivatives on soybean (Glycine max.) protoporphyrinogen oxidase
    • Dayan, F. E.; Armstrong, B. M.; Weete, J. D. Inhibitory activity of sulfentrazone and its metabolic derivatives on soybean (Glycine max.) protoporphyrinogen oxidase. J. Agric. Food Chem. 1998, 46, 2024-2029.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 2024-2029
    • Dayan, F.E.1    Armstrong, B.M.2    Weete, J.D.3
  • 6
    • 0001162836 scopus 로고    scopus 로고
    • Effects of isoxazole herbicides on protoporphyrinogen oxidase and porphyrin physiology
    • Dayan, F. E.; Duke, S. O.; Reddy, K. N.; Hamper, B. C.; Leschinsky, K. L. Effects of isoxazole herbicides on protoporphyrinogen oxidase and porphyrin physiology. J. Agric. Food. Chem. 1997, 45, 961-1915
    • (1997) J. Agric. Food. Chem. , vol.45 , pp. 961-1915
    • Dayan, F.E.1    Duke, S.O.2    Reddy, K.N.3    Hamper, B.C.4    Leschinsky, K.L.5
  • 7
    • 0026613985 scopus 로고
    • Characterization of [3H]acifluorfen binding to purified pea etioplasts, and evidence that protoporphyrinogen oxidase specifically binds acifluorfen
    • Matringe, M.; Scalla, R. Characterization of [3H]acifluorfen binding to purified pea etioplasts, and evidence that protoporphyrinogen oxidase specifically binds acifluorfen. Eur. J. Bioehem. 1992, 209, 861-868.
    • (1992) Eur. J. Biochem. , vol.209 , pp. 861-868
    • Matringe, M.1    Scalla, R.2
  • 8
    • 27144537134 scopus 로고    scopus 로고
    • Synthesis and herbicidal activity of 2-(7-fluoro-3-oxo-3,4-dihydro-2H- benzo[b][l,4]oxazin-6-yl)isoindoline-l,3-diones
    • Huang, M. Z.; Huang, K. L.; Ren, Y. G.; Lei, M. X.; Huang, L.; Hou, Z. K.; Liu, A. P.; Ou, X. M. Synthesis and herbicidal activity of 2-(7-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][l,4]oxazin-6-yl)isoindoline-l, 3-diones. J. Agic. Food Chem. 2005, 53, 7908-7914.
    • (2005) J. Agic. Food Chem. , vol.53 , pp. 7908-7914
    • Huang, M.Z.1    Huang, K.L.2    Ren, Y.G.3    Lei, M.X.4    Huang, L.5    Hou, Z.K.6    Liu, A.P.7    Ou, X.M.8
  • 10
    • 10044249049 scopus 로고    scopus 로고
    • Quantitative structureactivity relationship for cyclic imide derivatives of protoporphyrinogen oxidase inhibitors: A Study of quantum chemical descriptors from density functional theory
    • Wan, J.; Zhang, L.; Yang, G. F.; Zhan, C. G. Quantitative structureactivity relationship for cyclic imide derivatives of protoporphyrinogen oxidase inhibitors: a Study of quantum chemical descriptors from density functional theory. J. Chem. Inf. Comput. Sci. 2004, 44, 2099-2105.
    • (2004) J. Chem. Inf. Comput. Sci. , vol.44 , pp. 2099-2105
    • Wan, J.1    Zhang, L.2    Yang, G.F.3    Zhan, C.G.4
  • 11
    • 7444257868 scopus 로고    scopus 로고
    • A DFT-based QSARs study of protoporphyrinogen oxidase inhibitors: Phenyl triazolinones
    • Zhang, L.; Wan, L.; Yang, G. F. A DFT-based QSARs study of protoporphyrinogen oxidase inhibitors: phenyl triazolinones. Bioorg. Med. Chem. Lett. 2004, 12, 6183-6191.
    • (2004) Bioorg. Med. Chem. Lett. , vol.12 , pp. 6183-6191
    • Zhang, L.1    Wan, L.2    Yang, G.F.3
  • 12
    • 8344289100 scopus 로고    scopus 로고
    • Quantitative structure-activity relationships for phenyl triazolinones of protoporphyrinogen oxidase inhibitors: A density functional theory study
    • Wan, J.; Zhang, L.; Yang, G. F. Quantitative structure-activity relationships for phenyl triazolinones of protoporphyrinogen oxidase inhibitors: a density functional theory study. J. Comnut. Chem. 2004, 25, 1827-1832.
    • (2004) J. Comnut. Chem. , vol.25 , pp. 1827-1832
    • Wan, J.1    Zhang, L.2    Yang, G.F.3
  • 13
    • 33750440543 scopus 로고    scopus 로고
    • Of molecules and humans
    • Gasteiger, J. Of molecules and humans. J. Med. Chem. 2006, 49, 6429-6434.
    • (2006) J. Med. Chem. , vol.49 , pp. 6429-6434
    • Gasteiger, J.1
  • 15
    • 11644261806 scopus 로고    scopus 로고
    • Automated docking using alamarckian genetic algorithm and and empirical binding free energy function
    • Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using alamarckian genetic algorithm and and empirical binding free energy function. J. Comnut, Chem. 1998, 19, 1639-1662.
    • (1998) J. Comnut, Chem. , vol.19 , pp. 1639-1662
    • Morris, G.M.1    Goodsell, D.S.2    Halliday, R.S.3    Huey, R.4    Hart, W.E.5    Belew, R.K.6    Olson, A.J.7
  • 16
    • 84885183258 scopus 로고    scopus 로고
    • Tripos Associates: St. Louis, MO
    • Sybyl version6.9; Tripos Associates: St. Louis, MO, 1999.
    • (1999) Sybyl Version6.9
  • 17
    • 11944251068 scopus 로고
    • Maximally diagonal force constants in dependent angle-bending coordinates. II. Implications for the design of empirical force fields
    • Halgren, T. A. Maximally diagonal force constants in dependent angle-bending coordinates. II. Implications for the design of empirical force fields. J. Am. Chem. Soc. 1990, 112, 4710-4723.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 4710-4723
    • Halgren, T.A.1
  • 18
    • 70350306226 scopus 로고    scopus 로고
    • http://www.rcsb.org/pdb/.
  • 19
    • 2442563409 scopus 로고    scopus 로고
    • Crystal structure of protoporphyrinogen IX oxidase: A key enzyme in haem and chlorophyll biosynthesis
    • DOI 10.1038/sj.emboj.7600189
    • (19) Koch, M.; Breithaupt, C.; Kiefersauer, R.; Freigang, J.; Huber, R.; Messerschmidt, A. Crystal structure of protoporphyrinogen IX oxidase: a key enzyme in haem and chlorophyll biosynthesis. EMBO J. 2004, 23, 1720-1728. (Pubitemid 38649635)
    • (2004) EMBO Journal , vol.23 , Issue.8 , pp. 1720-1728
    • Koch, M.1    Breithaupt, C.2    Kiefersauer, R.3    Freigang, J.4    Huber, R.5    Messerschmidt, A.6
  • 20
    • 0033397980 scopus 로고    scopus 로고
    • Python: A programming language for software integration and development
    • (20) Sanner, M. F. Python: A programming language for software integration and development. J. Mol. Graphics Modell. 1999, 17, 57-61. (Pubitemid 30029318)
    • (1999) Journal of Molecular Graphics and Modelling , vol.17 , Issue.1 , pp. 57-61
    • Sanner, M.F.1
  • 22
    • 34249905181 scopus 로고    scopus 로고
    • Three-dimensional topographic index applied to the prediction of acyclic C5-C8 alkenes Kovás retention indices on polydimethylsiloxane and squalane columns
    • Ren, Y. Y.; Liu, H. X.; Yao, X. J.; Liu, M. C. Three-dimensional topographic index applied to the prediction of acyclic C5-C8 alkenes Kovás retention indices on polydimethylsiloxane and squalane columns. J. Chromatogr. A 2007, 1155, 105-111.
    • (2007) J. Chromatogr. A , vol.1155 , pp. 105-111
    • Ren, Y.Y.1    Liu, H.X.2    Yao, X.J.3    Liu, M.C.4
  • 24
    • 56949090293 scopus 로고    scopus 로고
    • QSAR study of malonyl-CoA decarboxylase inhibitors using GA-MLR and a new strategy of consensus modeling
    • Li, J. Z.; Lei, B. L.; Liu, H. X.; Li, S. Y.; Yao, X. J.; Liu, M. C.; Gramatica, P. QSAR study of malonyl-CoA decarboxylase inhibitors using GA-MLR and a new strategy of consensus modeling. J. Comput. Chem. Chem. 2008, 29, 2636-2647.
    • (2008) J. Comput. Chem. Chem. , vol.29 , pp. 2636-2647
    • Li, J.Z.1    Lei, B.L.2    Liu, H.X.3    Li, S.Y.4    Yao, X.J.5    Liu, M.C.6    Gramatica, P.7
  • 25
    • 34249949155 scopus 로고    scopus 로고
    • QSAR study of selective ligands for the thyroid hormone receptor β
    • DOI 10.1016/j.bmc.2007.05.016, PII S0968089607004154
    • (25) Liu, H. X.; Gramatica, P. QSAR study of selective ligands for the thyroid hormone receptor β Bioorg. Med. Chem. 2007, 15, 5251-5261. (Pubitemid 46880369)
    • (2007) Bioorganic and Medicinal Chemistry , vol.15 , Issue.15 , pp. 5251-5261
    • Liu, H.1    Gramatica, P.2
  • 26
    • 64649095052 scopus 로고    scopus 로고
    • Novel approaches for retention time prediction of oligonucleotides in ionpair reversed-phase high-performance liquid chromatography
    • Lei, B. L.; Li, S. Y.; Xi, L. L.; Li, J. Z.; Liu, H. X.; Yao, X. J. Novel approaches for retention time prediction of oligonucleotides in ionpair reversed-phase high-performance liquid chromatography. J. Chromatogr. A 2009, 1216, 4434-4439.
    • (2009) J. Chromatogr. A , vol.1216 , pp. 4434-4439
    • Lei, B.L.1    Li, S.Y.2    Xi, L.L.3    Li, J.Z.4    Liu, H.X.5    Yao, X.J.6
  • 28
    • 34248655910 scopus 로고    scopus 로고
    • Utility-based double auction mechanism using genetic algorithms
    • DOI 10.1016/j.eswa.2006.08.024, PII S0957417406002648
    • (28) Choi, J. H.; Ahn, H.; Han, I. Utility-based double auction mechanism using genetic algorithms. Expert Svst. Appl. 2008, 34, 150-158. (Pubitemid 46773014)
    • (2008) Expert Systems with Applications , vol.34 , Issue.1 , pp. 150-158
    • Choi, J.H.1    Ahn, H.2    Han, I.3
  • 30
    • 0033557262 scopus 로고    scopus 로고
    • The K correlation index: Theory development and its applications in chemometrics
    • Todeschini, R.; Consonni, V.; Majocchi, A. The K correlation index: theory development and its applications in chemometrics. Chemom. Intell. Lab. Svst. 1999, 46, 13-29.
    • (1999) Chemom. Intell. Lab. Svst. , vol.46 , pp. 13-29
    • Todeschini, R.1    Consonni, V.2    Majocchi, A.3
  • 31
    • 33846809281 scopus 로고    scopus 로고
    • oc prediction
    • DOI 10.1016/j.jmgm.2006.06.005, PII S1093326306001021
    • (31) Gramatica, P.; Giani, E.; Papa, E. Statistical external validation and consensus modeling: A QSPR case study for Koc prediction. J. Mol. Graphics Modell. 2007, 25, 755-766. (Pubitemid 46216110)
    • (2007) Journal of Molecular Graphics and Modelling , vol.25 , Issue.6 , pp. 755-766
    • Gramatica, P.1    Giani, E.2    Papa, E.3
  • 32
    • 34250628103 scopus 로고    scopus 로고
    • Principles of QSAR models validation: Internal and external
    • DOI 10.1002/qsar.200610151
    • (32) Gramatica, P. Principles of QSAR models validation: internal and external. OSAR Comb. Sci. 2007, 26, 694-701. (Pubitemid 46932857)
    • (2007) QSAR and Combinatorial Science , vol.26 , Issue.5 , pp. 694-701
    • Gramatica, P.1
  • 33
    • 0024716284 scopus 로고
    • Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics
    • Viswanadhan, V. N.; Ghose, A. K.; Revankar, G. R.; Robins, R. K. Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics. J. Chem. Inf. Comput. Sci. 1989, 29, 163-172.
    • (1989) J. Chem. Inf. Comput. Sci. , vol.29 , pp. 163-172
    • Viswanadhan, V.N.1    Ghose, A.K.2    Revankar, G.R.3    Robins, R.K.4
  • 37
    • 0036589086 scopus 로고    scopus 로고
    • Structure/response correlations and similarity/diversity analysis by GETAWAY descriptors. 1. Theory of the novel 3D molecular descriptors
    • DOI 10.1021/ci015504a
    • (37) Consonni, V.; Todeschini, R.; Pavan, M. Structure/Response correlations and similarity/diversity analysis by GETAWAY descriptors. 1. Theory of the novel 3D molecular descriptors. J. Chem. Inf. Comput. Sci. 2002, 42, 682-692. (Pubitemid 35355277)
    • (2002) Journal of Chemical Information and Computer Sciences , vol.42 , Issue.3 , pp. 682-692
    • Consonni, V.1    Todeschini, R.2    Pavan, M.3
  • 38
    • 0036589142 scopus 로고    scopus 로고
    • Structure/response correlations and similarity/diversity analysis by GETAWAY descriptors. 2. Application of the novel 3D molecular descriptors to QSAR/QSPR studies
    • DOI 10.1021/ci0155053
    • (38) Consonni, V.; Todeschini, R.; Pavan, M.; Gramatica, P. Structure/Response correlations and similarity/diversity analysis by GETAWAY descriptors. 2. application of the novel 3D molecular descriptors to QSAR/QSPR studies. J. Chem. Inf. Comput. Sci. 2002, 42, 693-705. (Pubitemid 35355278)
    • (2002) Journal of Chemical Information and Computer Sciences , vol.42 , Issue.3 , pp. 693-705
    • Consonni, V.1    Todeschini, R.2    Pavan, M.3    Gramatica, P.4
  • 39
    • 18144423852 scopus 로고    scopus 로고
    • 1 adenosine receptors agonists
    • DOI 10.1016/j.bmcl.2005.03.028
    • (39) González, M. P.; Terán, C.; Teijeirac, M.; Besadac, P. Geometry, topology, and atom-weights assembly descriptors to predicting Al adenosine receptors agonists. Bioorg. Med. Chem. Lett. 2005, 15, 2641-2645. (Pubitemid 40615005)
    • (2005) Bioorganic and Medicinal Chemistry Letters , vol.15 , Issue.10 , pp. 2641-2645
    • Gonzalez, M.P.1    Teran, C.2    Teijeira, M.3    Besada, P.4
  • 41
    • 0028922586 scopus 로고
    • LIGPLOT: A program to generate schematic diagrams of protein-ligand interactions
    • Wallace, A. C.; Laskowski, R. A.; Thornton, J. M. LIGPLOT: A program to generate schematic diagrams of protein-ligand interactions. Protein Eng. 1995, 8, 127-134.
    • (1995) Protein Eng. , vol.8 , pp. 127-134
    • Wallace, A.C.1    Laskowski, R.A.2    Thornton, J.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.