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Photosynthesis-inhibiting Effects of Cationic Biodegradable Gemini Surfactants

  • K. Král'ová , F. Šeršeň , F. Devínsky und I. Lacko
Veröffentlicht/Copyright: 5. April 2013
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Tenside Surfactants Detergents
Aus der Zeitschrift Tenside Surfactants Detergents Band 47 Heft 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.

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

© 2010, Carl Hanser Publisher, Munich

Artikel in diesem Heft

  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?
https://doi.org/10.3139/113.110079
Schlagwörter für diesen Artikel
Chlorella vulgaris; derivatives of diamides of succinic acid; EPR; inhibition of photosynthetic electron transport; spinach chloroplasts

Artikel in diesem Heft

  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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