Browse > Article

3D-QSAR Analysis on the Photosystem II Inhibition Activity of 6-Bromobenzo[4,5]imidazo[$1,2{\alpha}$]pyridin-8,9-dione Analogues  

Kim, Se-Gon (Division of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University)
Cho, Yun-Gi (Division of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University)
Hwang, Tae-Yeon (Division of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University)
Sung, Nack-Do (Division of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University)
Publication Information
The Korean Journal of Pesticide Science / v.12, no.1, 2008 , pp. 18-23 More about this Journal
Abstract
3D-QSAR on the inhibitory activities of 6-bromobenzo-[4,5]imidazo[$1,2{\alpha}$]-pyridin-8,9-diones analogues as substrate molecule were studied quantitatively using CoMFA and CoMSIA methods. The statistical values of CoMFA model was better predictability and fitness than CoMSIA model. The inhibitory activities according to the optimized CoMFA 2 model were dependent on the steric field (90.4%). From the CoMFA contour maps, it is found that the branched side chain as R-group will be directly attached to the carbon atom (ipso carbon) of substituent, the inhibitory activities had expected to increase. The positive charge favor groups were placed in the position between imidazol ring and pyridine ring, the inhibitory activities would increase. And if the groups of liner type will be substituted, hydrophilic favor group would raise inhibitory activities.
Keywords
6-Bromobenzo[4,5]imidazo[$1,2{\alpha}$; ]pyridin-8,9-diones; CoMFA; CoMSIA; 3D-QSAR; photosystem II inhibitory activity;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 Man, X., A. Zhang, S. Han and L. Wang (2002) Studies of 3D-Quantitative Structure-Activity Relationships on a set of nitroaromatic compounds: CoMFA, advanced CoMFA and CoMSIA, Chemosphere. 48:707-715   DOI   ScienceOn
2 McConnell, I. L., M. R. Badger, T. Wydrzynski and W. Hillier (2007) A quantitative assessment of the carbonic anhydrase activity in photosystem II, Biochimica Biophysica Acta. 1767:639-647   DOI   ScienceOn
3 Oettmeier, W. (1999) Herbicide resistance and supersensitivity in photosystem II, CMLS Cellular and Molecular Life Sciences, 1256-1277
4 Wold, S., E. Johansson and M. Cocchi (1993) In 3D-QSAR in Drug Design. PLS: Parti al Least-Squares Projections to Latent Structures. (Kubinyi, H. ed.), ESCOM, Leiden. pp. 523-554
5 Folkers, G., A. Merz and D. Rognan (1993) In 3D-QSAR in Drug Design. CoMFA: Scope and Limitations. (Kubinyi, H. ed.), ESCOM, Leiden. pp. 583-618
6 Okubo, T., T. Noguchi (2007) Selective detection of the structual change upon photoreactions of several redox cofactors in Photosystem II by means of light-induces ATR-FTIR difference spectroscopy, Spectrochimica Acta Part A. 66:863-868   DOI   ScienceOn
7 Krivanek, R., J. Kern, A. Zouni, H. Dau and M. Haumann (2007) Spare quinones in the QB cavity of crystallized photosystem II from Thermosynechococcus elongatus, Biochimica et Biophysica Acta. 1767:520-527   DOI   ScienceOn
8 Reddy, M. R. and A. L. Parrill (1999) Overview of rational drug design. In Rational Drug, (ed. Eddy, M. R. and Parrill). Ch. 1., ACS Symposium Series. 719:1-11
9 Hiraki, M., W. J. Vredenberg, van J. J. Rensen and Ko. Wakabayashi (2004) A modified fluorometric method to quantify the concentration effect ($pI_{50}$) of photosystem, Pestic. Biochemi. Physiol. 80:183-191   DOI   ScienceOn
10 Apostolova, E., T. Markova, T. Filipova and M. T. Molina (2003) Influence of substituted 1,4-anthraquinones on the chlorophyll fluorescence and photochemical activity of pea thylakoid membranes, J. Photochem. Photobiol. B Biology. 70:75-80   DOI   ScienceOn
11 Zhu, X. G., Govindjee, N. R. Baker, E. Desturler, D. R. Ort and S. P. Long (2005) Chlorophyll $\alpha$ fluorescence induction kinetics in leaves predicted from a model describing each discrete step of excitation energy and electron transfer associated with photosystem II. Planta. 223:114-133   DOI
12 Oettmeier, W., K. Masson and H. J. Hecht (2001) Heterocyclic ortho-quinones, a novel type of Photosystem II inhibitors, Biochimica et Biophysica Acta. 1504:346-351   DOI   ScienceOn
13 Vasil'ev S., G. W. Brudvig and D. Bruce (2003) The X-ray structure of photosystem II reveals a novel electron transport pathway between P680, cytochrome b559 and the energy-quenching cation. $Chl_Z^+$, FEBS Letters. 543:159-163   DOI   ScienceOn
14 Oettmeier, W., J. Jager and K. Masson (2006) Inhibition of photosystem II electron transport by acyl derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid), Biochimica et Biophysica Acta. 1757:727-729   DOI   ScienceOn
15 Dudekula, S., M. Fragata (2006) Investigation of the electron transfer site of p-benzoquinone in isolated Photosystem II particles and thylakoid membranes using $\alpha$ and $\beta$-cyclodextrins, J. Photochem. Photobiol. B; Biology. 85:177-183   DOI   ScienceOn
16 Loll, B., J. Kern, W. Saenger, A. Zouni and J. Biesiadka (2005) Towards complete cofactor arrangement in the 3.0 A resolution structure of photosystem II Nature. 438:1040-1044   DOI   ScienceOn
17 Roberts, A. G., W. Gregor, R. D. Britt and D. M. Kramer (2003) Acceptor and donor-side interactions of phenolic inhibitors in Photosystem II. Biochimica et Biophysica Acta. 1604:23-32   DOI   ScienceOn
18 Rochaix, J. D. (2007) Role of thylakoid protein kinases in Photosynthetic acclimation, FEBS Letters. 581:2768-2775   DOI   ScienceOn
19 Sung, N. D., M. K. Soung, J. W. You and S. C. Jang (2006) Comparative molecular field analysis on the fungicidal activity of N-phenylthionocarbamate derivatives based on different approaches. Korean J. Pestic. Sci. 10:157-164   과학기술학회마을
20 Reil, E., G. Hofle, W. Draber and W. Oettmeier (2001) Quinones and their N-oxides as inhibitors of photosystem II and the cytochrome $b_6/f$-complex. Biochimica et Biophysica Acta. 1506:127-132   DOI   ScienceOn