Abstract
Inhibition of photosynthetic electron transport (PET) in spinach chloroplasts by nineteen 2-benzylsulphanylbenzimidazoles (BZA) was studied. BZA were found to inhibit photosynthetic electron transport (PET) and for their inhibitory efficiency, electronic properties of the R substituent on the benzyl moiety are decisive. The PET inhibiting activity of the studied BZA expressed as IC50 varied in the range from 28.5 μM (R = 3,5-(CF3)2) to 394.5 μM (R = 2,4-(NO2)2). For compounds with R = H, 4-CH3, 3-CH3, 3-OCH3, 4-F, 3-F, 4-Cl, 3-Cl, 2-Cl, 4-Br, 3-Br, 3,4-F2, 3,4-Cl2, 3-CF3, 3,5-(CF3)2 linear increase of the inhibitory activity with the increasing value of the substituent’s σ constant up to 0.86 was observed. Further increase of the σ constant resulted in a sharp activity decrease of the corresponding compounds (R = 2-F-6-Cl, 2-NO2, 3,5-(NO2)2, 2,4-(NO2)2). Using EPR spectroscopy and an artificial electron donor diphenyl carbazide it was found that the site of BZA action in the photosynthetic apparatus is situated on the donor side of PS 2, prior to the Z·/D· intermediate.
[1] Bocion, P. F., Cattanach, C. J., Eggenberg, P., Gressel, J., Hagmann, M. L., Malkin, S., & Wenger, J. (1987). Synthesis and characterization of a group of dihydropyrimidobenzimidazole photosystem II herbicides. Pesticide Biochemistry and Physiology, 28, 75–84. DOI: 10.1016/0048-3575(87)90115-5. http://dx.doi.org/10.1016/0048-3575(87)90115-510.1016/0048-3575(87)90115-5Search in Google Scholar
[2] Burton, D. E., Lambie, A. J., Ludgate, J. C. L., Newbold, G. T., Percival, A., & Saggers, D. T. (1965). 2-Trifluoromethylbenzimidazoles: a new class of herbicidal compounds. Nature, 208, 1166–1170. DOI: 10.1038/2081166a0. http://dx.doi.org/10.1038/2081166a010.1038/2081166a0Search in Google Scholar
[3] Dane, F., & Dalgiç, Ö. (2005). The effects of fungicide benomyl (benlate) on growth and mitosis in onion (Allium cepa L.) root apical meristem. Acta Biologica Hungarica, 56, 119–128. DOI: 10.1556/ABiol.56.2005.1-2.12. http://dx.doi.org/10.1556/ABiol.56.2005.1-2.1210.1556/ABiol.56.2005.1-2.12Search in Google Scholar
[4] Garcia, P. C., Rivero, R. M., López-Lefebre, L. R., Sánchez, E., Ruiz, J. M., & Romero, L. (2001). Direct action of the biocide carbendazim on phenolic metabolism in tobacco plants. Journal of Agricultural and Food Chemistry, 49, 131–137. DOI: 10.1021/jf000850y. http://dx.doi.org/10.1021/jf000850y10.1021/jf000850ySearch in Google Scholar
[5] Hoff, A. J. (1979). Application of ESR in photosynthesis. Physics Reports, 54, 75–200. DOI: 10.1016/0370-1573(79) 90016-4. http://dx.doi.org/10.1016/0370-1573(79)90016-410.1016/0370-1573(79)90016-4Search in Google Scholar
[6] Jampilek, J., Musiol, R., Finster, J., Pesko, M., Carroll, J., Kralova, K., Vejsova, M., O’Mahony, J., Coffey, A., Dohnal, J., & Polanski, J. (2009). Investigating biological activity spectrum for novel styrylquinazoline analogues. Molecules, 14, 4246–4265. DOI: 10.3390/molecules14104246. http://dx.doi.org/10.3390/molecules1410424610.3390/molecules14104246Search in Google Scholar
[7] Klimešová, V., Kočí, J., Pour, M., Stachel, J., Waisser, K., & Kaustová, J. (2002). Synthesis and preliminary evaluation of benzimidazole derivatives as antimicrobial agents. European Journal of Medicinal Chemistry, 37, 409–418. DOI: 10.1016/s0223-5234(02)01342-9. http://dx.doi.org/10.1016/S0223-5234(02)01342-910.1016/S0223-5234(02)01342-9Search in Google Scholar
[8] Kráľová, K., Miletín, M., & Doležal, M. (2001). IInhibition of oxygen evolution rate in freshwater algae Chlorella vulgaris by some anilides of substituted pyridine-4-carboxylic acids. Chemical Papers, 55, 251–253. Search in Google Scholar
[9] Kráľová, K., Šeršeň, F., Klimešová, V., & Waisser, K. (2011). 2-Alkylsulphanyl-4-pyridine-carbothioamides-inhibitors of oxygen evolution in freshwater alga Chlorella vulgaris. Chemical Papers, 65, 909–912 DOI: 10.2478/s11696-011-0082-6. http://dx.doi.org/10.2478/s11696-011-0082-610.2478/s11696-011-0082-6Search in Google Scholar
[10] Kráľová, K., Šeršeň, F., Miletín, M., & Doležal, M. (2002). Inhibition of photosynthetic electron transport in spinach chloroplasts by 2,6-disubstituted pyridine-4-thiocarboxamides. Chemical Papers, 56, 214–217. Search in Google Scholar
[11] Kráľová, K., Šeršeň, F., Miletín, M., & Hartl, J. (1998). Inhibition of photosynthetic electron transport by some anilides of 2-alkylpyridine-4-carboxylic acids in spinach chloroplasts. Chemical Papers, 52, 52–55. Search in Google Scholar
[12] Kráľová, K., Šeršeň, F., & Sidóová, E. (1992). Photosynthesis inhibition produced by 2-alkylthio-6-R-benzothiazoles. Chemical Papers, 46, 348–350. Search in Google Scholar
[13] Kráľová, K., Šeršeň, F., & Sidóová, E. (1993). Effect of 2-alkylthio-6-aminobenzothiazoles and their 6-N-substituted derivatives on photosynthesis inhibition in spinach chloroplasts. General Physiology and Biophysics, 12, 421–427 Search in Google Scholar
[14] Norrington, F. E., Hyde, R. M., Williams, S. G., & Wotton, R. (1975). Physiochemical-activity relations in practice. 1. Rational and self-consistent data bank. Journal of Medicinal Chemistry, 18, 604–607. DOI: 10.1021/jm00240a016. http://dx.doi.org/10.1021/jm00240a01610.1021/jm00240a016Search in Google Scholar PubMed
[15] Roh, K. S., Oh, M. J., Song, S. D., Chung, H. S., & Song, J. S. (2001). Influence of benomyl on photosynthetic capacity in soybean leaves. Biotechnolology and Bioprocess Engineering, 6, 100–106. http://dx.doi.org/10.1007/BF0293195410.1007/BF02931954Search in Google Scholar
[16] Stefańska, Z., Gralewska, R., Starościak, B. J., & Kazimierczuk, Z. (1999). Antimicrobial activity of substituted azoles and their nucleosides. Pharmazie, 54, 879–884 Search in Google Scholar
[17] Svensson, B., Vass, I., & Styring, S. (1991). Sequence analysis of the D1 and D2 reaction center proteins of photosystem II. Zeitschrift für Naturforschung, 46, 765–776. 10.1515/znc-1991-9-1008Search in Google Scholar PubMed
[18] van Iersel, M. W., & Bugbee, B. (1996). Phytotoxic effects of benzimidazole fungicides on bedding plants. Journal of the American Society for Horticultural Science, 121, 1095–1102. 10.21273/JASHS.121.6.1095Search in Google Scholar
[19] van Iersel, M. W., & Bugbee B. (1997). Dibutylurea reduces photosynthesis, growth and flowering of petunia and impatiens. Journal of the American Society for Horticultural Science, 122, 536–541. 10.21273/JASHS.122.4.536Search in Google Scholar
© 2012 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- Determination of total petroleum hydrocarbons in soil from different locations using infrared spectrophotometry and gas chromatography
- Effect of Ag-doping of nanosized FeMgO system on its structural, surface, spectral, and catalytic properties
- Synthesis of new dendritic antenna-like polypyridine ligands
- Solvothermal synthesis of hollow Eu2O3 microspheres using carbon template-assisted method
- Effect of substrate on phase formation and surface morphology of sol-gel lead-free KNbO3, NaNbO3, and K0.5Na0.5NbO3 thin films
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- Spectroscopic investigation of interaction of 6-methoxyflavanone and its β-cyclodextrin inclusion complex with calf thymus DNA
- Photosynthesis-inhibiting effects of 2-benzylsulphanylbenzimidazoles in spinach chloroplasts
- Investigation of structure of milled wood and dioxane lignins of Populus nigra and Cupressus sempervirens using the DFRC method
Articles in the same Issue
- Determination of total petroleum hydrocarbons in soil from different locations using infrared spectrophotometry and gas chromatography
- Effect of Ag-doping of nanosized FeMgO system on its structural, surface, spectral, and catalytic properties
- Synthesis of new dendritic antenna-like polypyridine ligands
- Solvothermal synthesis of hollow Eu2O3 microspheres using carbon template-assisted method
- Effect of substrate on phase formation and surface morphology of sol-gel lead-free KNbO3, NaNbO3, and K0.5Na0.5NbO3 thin films
- Surfactant-assisted synthesis of polyaniline nanofibres without shaking and stirring: effect of conditions on morphology and conductivity
- Novel ammonium phosphinates containing peptide moiety: Synthesis, structure, and in vitro antimicrobial activity
- Reduction of aromatic nitro compounds to amines using zinc and aqueous chelating ethers: Mild and efficient method for zinc activation
- Ethylcellulose, polycaprolactone, and eudragit matrices for controlled release of piroxicam from tablets and microspheres
- Spectroscopic investigation of interaction of 6-methoxyflavanone and its β-cyclodextrin inclusion complex with calf thymus DNA
- Photosynthesis-inhibiting effects of 2-benzylsulphanylbenzimidazoles in spinach chloroplasts
- Investigation of structure of milled wood and dioxane lignins of Populus nigra and Cupressus sempervirens using the DFRC method