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Volume 66, Issue 8


Photosynthesis-inhibiting effects of 2-benzylsulphanylbenzimidazoles in spinach chloroplasts

Katarína Kráľová / František Šeršeň / Matúš Peško
  • Department of Ecosozology and Physiotactics, Faculty of Natural Sciences, Comenius University, SK-842 15, Bratislava, Slovakia
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/ Věra Klimešová
  • Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, CZ-501 65, Hradec Králové, Czech Republic
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/ Karel Waisser
  • Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, CZ-501 65, Hradec Králové, Czech Republic
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Published Online: 2012-06-19 | DOI: https://doi.org/10.2478/s11696-012-0192-9


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.

Keywords: alkylsulfanyl; benzimidazole; EPR spectroscopy; photosynthetic electron transport; site of action

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About the article

Published Online: 2012-06-19

Published in Print: 2012-08-01

Citation Information: Chemical Papers, Volume 66, Issue 8, Pages 795–799, ISSN (Online) 1336-9075, DOI: https://doi.org/10.2478/s11696-012-0192-9.

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