Abstract
The inhibition of the oxygen evolution rate (OER) in Chlorella vulgaris by 2-alkylsulphanyl-4-pyridinecarbothioamides (APCTs; alkyl = methyl up to hexadecyl) was studied. APCTs were found to inhibit photosynthetic electron transport (PET) which resulted in the inhibition of OER in algae. The inhibitory activity of APCTs was highly dependent on the alkyl chain length of the 2-alkylsulphanyl substituent and the corresponding dependence showed a bilinear course with the decyl derivative as being the most active inhibitor. Using EPR spectroscopy, the site of APCT action in the algal photosynthetic apparatus was determined. It was confirmed that APCT interacted mainly with the D. intermediate, i.e. with tyrosine radical (TyrD) occurring at the 161st position in D2 protein which is situated on the donor side of photosystem 2.
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References
Balgavy, P., & Devínsky, F. (1996). Cut-off effects in biological activities of surfactants. Advances in Colloid and Interface Science, 66, 23–63. DOI: 10.1016/0001-8686(96)00295-3.
Bartoš, J., Berková, E., & Šetlík, I. (1975). A versatile chamber for gas exchange measurements in suspension of algae and chloroplasts. Photosynthetica, 9, 395–406.
Chioua, M., Samadi, A., Soriano, E., Lozach, O., Meijer, L., & Marco-Contelles, J. (2009). Synthesis and biological evaluation of 3,6-diamino-1H-pyrazolo[3,4-b]pyridine derivatives as protein kinase inhibitors. Bioorganic & Medicinal Chemistry Letters, 19, 4566–4569. DOI: 10.1016/j.bmcl.2009.06.099.
Debus, R. J., Barry, B. A., Babcock, G. T., & McIntosh, L. (1988a). Site-directed mutagenesis identifies a tyrosine radical involved in the photosynthetic oxygen-evolving system. Proceedings of the National Academy of Sciences of the United States of America, 85, 427–430.
Debus, R. J., Barry, B. A., Sithole, I., Babcock, G. T., & McIntosh, L. (1988b). Directed mutagenesis indicates that donor to P +680 in photosystem II is tyrosine-161 of the D1 polypeptide. Biochemistry, 27, 9071–9074. DOI: 10.1021/bi00426a001.
Hoff, A. J. (1979). Applications of ESR in photosynthesis. Physics Reports, 54, 75–200. DOI: 10.1016/0370-1573(79)90016-4.
Klimešová, V., Otčenášek, M., & Waisser, K. (1996a). Potential antifungal agents. Synthesis and activity of 2-alkylthiopyridine-4-carbothioamides. European Journal of Medicinal Chemistry, 31, 389–395. DOI: 10.1016/0223-5234(96)89165-3.
Klimešová, V., Svoboda, M., Waisser, K., Macháček, M., Buchta, V., & Odlerová, Ž. (1996b). Research on antifungal and antimycobacterial agents. Synthesis and activity of 4-alkylthiopyridine-2-carbothioamides. Archiv der Pharmazie, 329, 438–442. DOI: 10.1002/ardp.19963291003.
Kráľová, K., Loos, D., Šeršeň F., & Sidóová, E. (1994). QSAR study concerning photosynthesis inhibition in algae and plant chloroplasts by 2-alkylthio-6-R-benzothiazoles. I. 2-Alkylthio-6-aminobenzothiazoles, 3-(2-alkyltio-6-benzothiazolylaminomethyl)-2-benzothiazolinethiones, 3-(2-alkylthio-6-benzothiazolyl-aminomethyl)-6-bromo-2-benzothiazolinones. Chemical Papers, 48, 198–202.
Kráľová, K., Miletín, M., & Doležal, M. (2001). Inhibition of oxygen evolution rate in freshwater algae Chlorella vulgaris by some anilides of substituted pyridine-4-carboxylic acids. Chemical Papers, 55, 251–253.
Kráľová, K., Šeršeň, F., Gašparová, R., & Lácová, M. (1998c). Effect of chromone-substituted benzothiazolium halides on photosynthetic processes. Chemical Papers, 52, 776–779.
Kráľová, K., Šeršeň, F., Klimešová, V., & Waisser, K. (1997). Effect of 2-alkylthio-4-pyridinecarbothiamides on photosynthetic electron transport in spinach chloroplasts. Collection of Czechoslovak Chemical Communications, 62, 516–520. DOI: 10.1135/cccc19970516.
Kráľová, K., Šeršeň, F., & Melník, M. (1998b). Inhibition of photosynthesis in Chlorella vulgaris by Cu(II) complexes with biologically active ligands. Journal of Trace and Microprobe Techniques, 16, 491–500.
Kráľová, K., Šeršeň, F., Miletín, M., & Hartl, J. (1998a). Inhibition of photosynthetic electron transport by some anilides of 2-alkylpyridine-4-carboxylic acids in spinach chloroplasts. Chemical Papers, 52, 52–55.
Kráľová, K., Šeršeň, F., & Sidóová, E. (1992). Photosynthesis inhibition produced by 2-alkylthio-6-R-benzothiazoles. Chemical Papers, 46, 348–350.
Krauze, A., Gērmane, S., Eberliņš, O., Šturms, I., Klusā, V., & Duburs, G. (1999). Dervivatives of 3-cyano-6-phenyl-4-(3′-pyridyl)-pyridine-2(1H)-thione and their neurotropic activity. European Journal of Medicinal Chemistry, 34, 301–310. DOI: 10.1016/S0223-5234(99)80081-6.
Okazaki, K., Maeda, T., Nagamune, H., & Kourai, H. (1997). Antibacterial characteristics of N-alkyl-2-alkylthiopyridinium and N-alkyl-4-alkylthiopyridinium salts. Japanese Journal of Toxicology and Environmental Health, 43, 251–260.
Ren, Q., Mo, W., Gao, L., He, H., & Gu, Y. (2010). Facile synthesis and herbicidal activity of novel multisubstituted pyridine derivatives. Journal of Heterocyclic Chemistry, 47, 171–178. DOI: 10.1002/jhet.296.
Svensson, B., Vass, I., & Styring, S. (1991). Sequence analysis of the D1 and D2 reaction center proteins of photosystem II. Zeitschrift für Naturforschung C, 46c, 765–776.
Waisser, K., Klimešová, V., & Buchta, V. (1996a). New groups of potential antifungal agents: 2-Alkylthio-4-pyridinecarbothioamides. Folia Pharmaceutica Universitatis Carolinae, 20, 53–57.
Waisser, K., Klimešová, V., & Odlerová, Ž. (1996b). Relationships between the chemical structure of substances and their antimycobacterial activity to atypical strains. VII. 2-Alkylthio-4-pyridinecarbothioamides. Folia Pharmaceutica Universitatis Carolinae, 20, 59–62.
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Kráľová, K., Šeršeň, F., Klimešová, V. et al. 2-Alkylsulphanyl-4-pyridinecarbothioamides — inhibitors of oxygen evolution in freshwater alga Chlorella vulgaris . Chem. Pap. 65, 909–912 (2011). https://doi.org/10.2478/s11696-011-0082-6
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DOI: https://doi.org/10.2478/s11696-011-0082-6