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Photosynthesis-inhibiting Effects of Cationic Biodegradable Gemini Surfactants

  • K. Král'ová , F. Šeršeň , F. Devínsky and I. Lacko
Published/Copyright: April 5, 2013
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Tenside Surfactants Detergents
From the journal Tenside Surfactants Detergents Volume 47 Issue 5

Abstract

Cationic biodegradable gemini surfactants 3,8-diaza-4,7-dioxodecane-1,10-diylbis(alkyldimethylammonium bromide) (I) with R = C9H19–C18H37 inhibited photosynthetic electron transport (PET) in spinach chloroplasts and reduced chlorophyll (Chl) content in Chlorella vulgaris. The inhibitory effects of I intensively depended on the length of alkyl chain showing quasi-parabolic (Chlorella vulgaris) or bilinear (PET) course. IC50 value related to reduction of Chl content in C. vulgaris for dodecyl derivative was 0.6 × 10−6 mol dm−3 indicating its strong anti-algal effect. Using EPR spectroscopy as the site of inhibitory action of I in the photosynthetic apparatus the intermediates Z∗ and D∗ or their close surroundings were determined. As a further target of I inhibitory action the manganese cluster occurring on the donor side of photosystem II was estimated.

Kurzfassung

Die kationischen biologisch abbaubaren Geminitenside 3,8-Diaza-4,7-dioxodekan-1,10-diylbis(alkyldimethylammoniumbromid) (I) mit R = C9H19–C18H37 hemmen den photosynthetischen Elektronentransport (PET) in Spinatchloroplasten und reduzierten den Chlorophyllgehalt (Chl) in Chlorella vulgaris. Der hemmende Effekt von (I) hing stark von der Alkylkettenlänge ab, wobei die Abhängigkeiten entweder einen quasi-parabolische (Chlorella vulgaris) oder einen bilinearen Verlauf zeigten. Der IC50-Wert bezogen auf den Chl-Gehalt in C. vulgaris betrug für das Dodecylderivat 0.6 × 10−6 mol dm−3, was auf eine starke Hemmung des Grünalgenwachstums hindeutet. Als Stellen der Inhibierung von I in dem photosynthetischen Apparat wurden die Zwischenprodukte Z∗ und D∗ oder ihrer näheren Umgebung mittels Elektronenspinresonanzspektroskopie bestimmt. Als ein weiteres Ziel des hemmenden Einflusses von I wurde der Mangankluster, der auf der Donorseite des Photosystems II erscheint, angesehen.

Key words:: Chlorella vulgaris; derivatives of diamides of succinic acid; EPR; inhibition of photosynthetic electron transport; spinach chloroplasts
Stichwörter:: Chlorella vulgaris; Bernsteinsäurediamidderivate; EPR; Hemmung des photosynthetischen Elektronentransports; Spinatchloroplasten
∗ Dr. Katarína Král'ová, Comenius University in Bratislava, Faculty of Natural Sciences, Institute of Chemistry, Mlynská dolina, SK-842 15 Bratislava, Slovak Republic, Tel.: +421-2-60296412, Fax: +421-2-654-29-064. E-Mail:

Dr. Katarína Král'ová, born 1944, graduated in 1967 at the Faculty of Natural Sciences, Eötvos Loránd University, Budapest (Hungary) where she also obtained her Doctor's degree in 1971. From 1971 she has been working at the Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava (Slovakia) as scientific researcher. Her main research interests are effects of environmental pollutants on photosynthesizing organisms and phytoremediation.

Dr. František Šeršeň, born 1944, has obtained its engineering degree in 1966 at Electrotechnical Faculty of Slovak Technical University (Bratislava, Slovakia). In 1984 he obtained his Doctor's degree. From 1970 he has been working working at the Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava as scientific researcher. His main research interests are EPR spectroscopy, photosynthesis and antioxidants.

Professor Ferdinand Devinsky, DSc. (1947), professor of pharmaceutical chemistry, graduated at Faculty of Chemical Technology, Slovak Technical University, Bratislava, Slovakia – technology of drugs (Dipl. Ing.). From 1972 he is lecturing (organic chemistry) at the School of Pharmacy, Comenius University, Bratislava, Slovakia. From 1990 till now he is the Head of Department of Inorganic and Organic Chemistry (now Department of Chemical Theory of Drugs). His main research interests are organic synthesis of membrane active amphiphiles, organic physical chemistry and relationships between structure – properties and activities of bioactive amine oxides and cationic gemini surfactants.

Assoc. Professor Ivan Lacko (1938), docent of pharmaceutical chemistry, graduated at Faculty of Chemical Technology, Slovak Technical University, Bratislava, Slovakia – technology of drugs (Dipl. Ing.). From 1972 he is lecturing (organic and bioorganic chemistry) at the School of Pharmacy, Comenius University, Bratislava, Slovakia. His main research interests are organic synthesis of membrane active amphiphiles, organic physical chemistry and relationships between structure – properties and activities of bioactive monoammonium, zwitterionic and cationic gemini surfactants.

References

1. Zana, R.: J. Colloid Interf. Sci.248 (2002) 203. 10.1006/jcis.2001.8104Search in Google Scholar

2. Zana, R.: Adv. Colloid Interface Sci.97 (2002) 205. 10.1016/S0001-8686(01)00069-0Search in Google Scholar

3. Wang, X. Y., Wang, J. B., Wang, Y. L., Yan, H. K., Li, P. X. and Thomas, R. K.: Langmuir20 (2004) 53. 10.1021/la0351008Search in Google Scholar

4. Menger, F. M. and Keiper, J. S.: Angew. Chem. Int. Ed.39 (2000) 1906. 10.1002/1521-3773(20000602)39:11<1906::AID-ANIE1906>3.0.CO;2-QSearch in Google Scholar

5. Karlsson, L., van Eijk, M. C. P. and Söderman, O.: J. Colloid Interf. Sci.252 (2002) 290. 10.1006/jcis.2002.8477Search in Google Scholar

6. Menger, F. M., Shi, L. and Rizvi, S. A. A.: J. Colloid Surf. Interf. Sci.344 (2010) 241. 10.1016/j.jcis.2010.01.031Search in Google Scholar

7. Kirby, A. J., Camilleri, P., Engberts, J. B. F. N., Feiters, M. C., Nolte, R. J. M., Soederman, O., Bergsma, M., Bell, P. C., Fielden, M. L., Garcia Rodriguez, C. L., Guedat, Ph., Kremer, A., McGregor, C., Perrin, Ch., Ronsin, G. and van Eijk, M. C. P.: Angew. Chem. Int. Ed.42 (2003) 1448. 10.1002/anie.200201597Search in Google Scholar

8. Zhang, Q. S., Guo, B. N. and Zhang, H. M.: Progress in Chemistry16 (2004) 343.Search in Google Scholar

9. Massi, L., Guittard, F., Levy, R., Duccini, Y. and Geribaldi, S.: Eur. J. Med. Chem.38 (2003) 519. 10.1016/S0223-5234(03)00059-XSearch in Google Scholar

10. Kurup, T. R. R., Wan, L. S. C. and Chan, L. W.: Pharm. Acta Helv.67 (1992) 204.Search in Google Scholar

11. Devínsky, F., Lacko, I., BittererováF. and Mlynarčík, D.: Chem. Pap.41 (1987) 803.Search in Google Scholar

12. Imam, T., Devinsky, F., Lacko, I., Mlynarčík, D. and Krasnec, L.: Pharmazie38 (1983) 308.Search in Google Scholar

13. Král9ová, K., Kallová, J., LoosD. and Devínsky, F.: Pharmazie49 (1994) 857.Search in Google Scholar

14. Král'ová, K. and Šeršeň, F.: Tenside Surfact. Det.31 (1994) 192.Search in Google Scholar

15. Král'ová, K., Loos, D., DevínskyF. and Lacko, I.: Chem. Pap.49 (1995) 39.Search in Google Scholar

16. Kourai, H., Yabuhara, T., Shirai, A., Maeda, T. and Nagamune, H.: Eur. J. Med. Chem.41 (2006) 437. 10.1016/j.ejmech.2005.10.021Search in Google Scholar

17. Tehrani-Bagha, A. and Holmberg, K.: Curr. Opin. Colloid In.12 (2007) 81–91. 10.1016/j.cocis.2007.05.006Search in Google Scholar

18. Slováková, A.: New Gemini Surfactants: Their Structural, Micellar, and Germicidal Properties, Thesis, Faculty of Pharmacy, Comenius University in Bratislava, 1998.Search in Google Scholar

19. Walker, D. A.: In S. P.Colowick and N. O.Kaplan (Eds.) Methods in Enzymology Part C, Academic Press, New York69 (1980) 94. 10.1016/S0076-6879(80)69011-9Search in Google Scholar

20. Král'ová, K., ŠeršeňF. and Sidóová, E.: Chem. Pap.46 (1992) 348.Search in Google Scholar

21. Král'ová, K.; Šeršeň, F. and Melník, M.: J. Trace Microprobe Techn.16 (1998) 491.Search in Google Scholar

22. Wellburn, A. R.: J. Plant. Physiol.144 (1994) 307. 10.1016/S0176-1617(11)81192-2Search in Google Scholar

23. Hoff, A. J.: Phys. Rep.54 (1979) 75. 10.1016/0370-1573(79)90016-4Search in Google Scholar

24. Weaver, E. C.: Annu. Rev. Plant. Physiol.19 (1968) 283. 10.1146/annurev.pp.19.060168.001435Search in Google Scholar

25. Král'ová, K., Loos, D., Devínsky, F. and Lacko, I.: Chem. Pap.49 (1995) 39.Search in Google Scholar

26. Král'ová, K., Šeršeň, F., Mitterhauszerová, L., KrempaskáE. and Devínsky, F.: Photosynthetica26 (1992) 181.Search in Google Scholar

27. Král'ová, K., ŠeršeňF. and Čižmárik, J.: Gen. Physiol. Biophys.11 (1992) 261.Search in Google Scholar

28. Král'ová, K., ŠeršeňF. and Čižmárik, J.: Chem. Pap.46 (1992) 266.Search in Google Scholar

29. Král'ová, K., MitterhauszerováL. and Halgaš, J.: Biol. Plant.36 (1994) 477. 10.1007/BF02920951Search in Google Scholar

30. Yang, Z. L., Li, L. B. and Kuang, T. Y.: Acta Chim. Sinica60 (2002) 545.Search in Google Scholar

31. Yu, F., Tang, C. Q., Xin, Y. Y., Peng, D. C., Li, L. B., Kuang, T. Y., Li, J. Y. and Li, Z. S.: Acta Chim. Sinica43 (2001) 686.Search in Google Scholar

32. Corre, G., Templier, J., Largeau, C., Rousseau, B. and Berkaloff, C.: J. Phycol.32 (1996) 584. 10.1111/j.0022-3646.1996.00584.xSearch in Google Scholar

33. Devínsky, F., Kopecká-Leitmanová, A., ŠeršeňF. and Balgavý, P.: J. Pharm. Pharmacol.42 (1990) 790. 10.1111/j.2042-7158.1990.tb07022.xSearch in Google Scholar

34. Balgavý, P. and Devínsky, F.: Adv. Coll. Interface Sci.66 (1996) 23. 10.1016/0001-8686(96)00295-3Search in Google Scholar

35. Przestalski, S., Sarapuk, J., Kleszczyñska, H., Gabrielska, J., Hladyszowski, J., Trela, Z. and Kuczera, J.: Acta Biochem. Pol.47 (2000) 627.Search in Google Scholar

36. Sarapuk, J. and Kubica, K.: Cell. Mol. Biol. Lett.5 (1998) 261.Search in Google Scholar

37. Svensson, B., Vass, I. and StyringS: Z. Naturforsch.46c (1991) 765.10.1515/znc-1991-9-1008Search in Google Scholar PubMed

38. Good, N. E.: Plant. Physiol.36 (1961) 788. 10.1104/pp.36.6.788Search in Google Scholar PubMed PubMed Central

39. Moreland, D. E.: Z. Naturforsch. C – J. Biosci.48 (1993) 121.Search in Google Scholar

40. Sharma, P. C., Scharma, S. V., Singh, D. and Suresh, B.: Asian J. Chem.19 (2007) 5105.Search in Google Scholar

Received: 2010-06-07
Published Online: 2013-04-05
Published in Print: 2010-09-01

© 2010, Carl Hanser Publisher, Munich

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https://doi.org/10.3139/113.110079
Keywords for this article
Chlorella vulgaris; derivatives of diamides of succinic acid; EPR; inhibition of photosynthetic electron transport; spinach chloroplasts

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Environmental/Technical Chemistry
  6. Alkyl Polyglycoside-Sorbitan Ester Formulations for Improved Oil Recovery
  7. Novel Surfactants
  8. Photosynthesis-inhibiting Effects of Cationic Biodegradable Gemini Surfactants
  9. Synthesis and Characterization of a New Cationic Galactolipid with Carbamate for Gene Delivery
  10. Physical Chemistry
  11. Dynamics of Formation of Vesicles Studied by Highly Time-resolved Stopped-flow Experiments
  12. Ion Extractant as Cosurfactant at the Water-Oil Interface in Microemulsions
  13. Microemulsions with Mixed Nonionic Surfactants and Isopropylmyristate
  14. Micellization and Interfacial Behaviour of Amitriptyline-Nonionic Surfactant Systems in Aqueous Medium
  15. Synthesis
  16. Ordered Ferrocene-containing Mesoporous Materials with Tailor-made Pore Size
  17. Cleaning Technology
  18. Comparison of Standards for Testing Electrical Dishwashers or Dishwashing Detergents
  19. Manual Dishwashing – How can it be Optimized?
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