A new method for simultaneous quantification of uncoupling and inhibitory activity of organic pollutants in energy-transducing membranes

Environmental Toxicology and Chemistry

Volumn 16, Issue 3, 1997, Pages 405-414

  Escher, Beate I ^a   Snozzi, Mario ^a   Häberli, Katharina ^a   Schwarzenbach, René P ^a  

^a SWISS FEDERAL INSTITUTE OF AQUATIC SCIENCE AND TECHNOLOGY   (Switzerland)

Author keywords

Chloro nitrophenols; Energy transduction; In vitro toxicity test; Inhibition; Uncoupling

Indexed keywords

ANISOLE DERIVATIVE; ENVIRONMENTAL CHEMICAL; PHENOL DERIVATIVE;

ARTICLE; CALCULATION; ENERGY TRANSFER; MEMBRANE POTENTIAL; NONHUMAN; PHOTOSYNTHESIS; POLLUTANT; PRIORITY JOURNAL; RHODOBACTER SPHAEROIDES; TOXICITY TESTING;

BACTERIA (MICROORGANISMS); PHOTOBACTERIA; RHODOBACTER SPHAEROIDES; RHODOPSEUDOMONAS;

EID: 0030891604     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/1551-5028(1997)016<0405:ANMFSQ>2.3.CO;2     Document Type: Article

References (50)

1. Hermens, J.L.M. 1989. Quantitative structure-activity relationships of environmental pollutants. In J. Hutzinger, ed., The Handbook of Environmental Chemistry, Reaction and Processes. Springer, Berlin, Germany, pp. 111-162.
2. Smejtek, P. 1987. The physicochemical basis of the membrane toxicity of pentachlorophenol. J. Membrane Sci. 33:249-268.
3. Mitchell, P. 1961. Coupling of phosphorylation to electron and proton transfer by a chemi-osmotic type of mechanism. Nature 191:144-148.
4. Terada, H. 1990. Uncouplers of oxidative phosphorylation. Environ. Health Perspect. 87:213-218.
5. McLaughlin, S.G.A. and J.P. Dilger. 1980. Transport of protons across membranes by weak acids. Physiol. Rev. 60:825-863.
6. Finkelstein, A. 1970. Weak-acid uncouplers of oxidative phosphorylation: Mechanism of action on thin lipid membranes. Biochim. Biophys. Acta 205:1-6.
7. Draber, W., J. Kluth, K. Tietjen and A. Trebst. 1991. Herbizide in der Photosyntheseforschung. Angew. Chem. 103:1650-1663.
8. Frank, K. and A. Trebst. 1995. Quinone binding sites on cytochrome b/c complexes. Photochem. Photobiol. 61:2-9.
9. Stein, R.R., A.L. Castellvi, J.P. Bogacz and C.A. Wraight. 1984. Herbicide-quinone competition in the acceptor complex of photosynthetic reaction centers from Rhodopseudomonas sphaeroides: A bacterial model for PSII-herbicide activity in plants. J. Cell. Biochem. 24:243-259.
10. Moreland, D.E. 1980. Mechanism of action of herbicides. Ann. Rev. Plant Physiol. 31:597-638.
11. Nicholls, D.G. and S.J. Ferguson. 1991. Bioenergetics 2. Academic, New York, NY, USA.
12. 1 complex by nitrophenols. Biochim. Biophys. Acta 1143:23-28.
13. Crofts, A.R. and C.A. Wraight. 1983. The electrochemical domain of photosynthesis. Biochim. Biophys. Acta 726:149-185.
14. 1 complex of photosynthetic purple bacteria. Photosynth. Res. 35:177-133.
15. Cramer, W. and A.R. Crofts. 1982. Electron and proton transport. In Govindjee, ed., Photosynthesis: Energy Conversion by Plant and Bacteria. Academic, New York, NY, USA, pp. 387-467.
16. Melandri, B.A., R.J. Mehlhorn and L. Packer. 1984. Light-induced proton gradient and internal volumes in chromatophores of Rhodopseudomonas sphaeroides. Arch. Biochem. Biophys. 235:97-105.
17. Escher, B.I. 1995. The relationship between membrane-water partitioning, uncoupling, and inhibitory activity of substituted phenols in chromatophores of Rhodobacter sphaeroides. Ph.D. thesis. Swiss Federal Institute of Technology, Zürich. Switzerland.
18. Garcia, A.F., G. Venturoli, J.G. Fernández-Velasco, B.A. Melandri and G. Drews. 1987. The adaptation of the electron transfer chain of Rhodopseudomonas capsulata to different light intensities. Biochim. Biophys. Acta 890:335-345.
19. Siström, W.R. 1960. A requirement for sodium in the growth of Rhodopseudomonas sphaeroides. J. Gen. Microbiol. 22:778-785.
20. Bowyer, J.R., G.V. Tierney and A.R. Crofts. 1979. Secondary electron transfer in chromatophores of Rhodopseudomonas capsulata Ala pho. FEBS Lett. 101:201-206.
21. 2 and reaction center of Rhodopseudomonas sphaeroides Ga. membranes: Extinction coefficient, half reduction potentials, kinetics and electric field alterations. Biochim. Biophys. Acta 387:536-556.
22. 2 oxidoreductase complex in chromatophores from Rhodobacter sphaeroides. Biochim. Biophys. Acta 851:340-352.
23. Meinhardt, S.W. 1984. Electron transfer reactions of the ubiquinol: cyt c-2 oxidoreductase of Rhodopseudomonas sphaeroides. Ph.D. thesis. University of Illinois, Urbana, IL, USA.
24. Junge, W. and J.B. Jackson. 1982. The development of electrochemical potential gradients across photosynthetic membranes. In Govindjee, ed., Photosynthesis: Energy Conversion by Plants and Bacteria. Academic. New York, NY, USA, pp. 589-646.
25. Smejtek, P., K. Hsu and W.H. Perman. 1976. Electrical conductivity in lipid bilayer membranes induced by pentachlorophenol. Biophys. J. 16:319-336.
26. McLaughlin, S. 1972. The mechanism of action of DNP on phospholipid bilayer membrane. J. Membrane Biol. 9:361-372.
27. Miyoshi, H., T. Nishioka and T. Fujita. 1987. Quantitative relationship between protonophoric and uncoupling activities of substituted phenols. Biochim. Biophys. Acta 891:194-204.
28. Escher, B.I., M. Snozzi and R.P. Schwarzenbach. 1996. Uptake, speciation, and toxic effect of substituted phenols in energy transducing membranes. Environ. Sci. Technol. 30:160-170.
29. Escher, B.I. and R.P. Schwarzenbach. 1996. Partitioning of substituted phenols in liposome-water, biomembrane-water, and octanol-water systems. Environ. Sci. Technol. 30:260-270.
30. Miyoshi, H., H. Tsujishita, N. Tokutake and T. Fujita. 1990. Quantitative analysis of uncoupling activity of substituted phenols with a physicochemical substituent and molecular parameters. Biochim. Biophys. Acta 1016:99-106.
31. Miyoshi, H. and T. Fujita. 1988. Quantitative analysis of the uncoupling activity of substituted phenols with mitochondria from flight muscles of house flies. Biochim. Biophys. Acta 935:312-321.
32. Miyoshi, H. and T. Fujita. 1987. Quantitative analyses of uncoupling activities of SF 6847 (2,6-di-t-butyl-4-(2,2′-dicyanovinyl)phenol) and its analogs with spinach chloroplasts. Biochim. Biophys. Acta 894:339-345.
33. Ravanel, P., G. Taillandier and M. Tissut. 1989. Uncoupling properties of a chlorophenol series on Acer cell suspensions: A QSAR study. Ecotoxical. Environ. Saf. 18:337-345.
34. Argese, E., C. Bettiol, A. Ghelli, R. Todeschini and P. Miani. 1995. Submitochondrial particles as toxicity biosensors of chlorophenols. Environ. Toxicol. Chem. 14:363-368.
35. Shigeoka, T., Y. Sato, Y. Takeda, I. Yoshida and F. Yamauchi. 1988. Acute toxicity of chlorophenols to green algae Selenastrum capricornutum and Chlorella vulgaris and quantitative structure-activity relationships. Environ. Toxicol. Chem. 7:847-854.
36. Fent, K. and J. Hunn. 1996. Cytotoxicity of organic environmental chemicals to fish hepatoma cells (PLHC-1). Mar. Environ. Res. 42:377-382.
37. Saito, H., M. Sudo, T. Shigeoka and F. Yamauchi. 1991. In vitro cytotoxicity of chlorophenols to goldfishscale (GFS) cells and quantitative structure-activity relationship. Environ. Toxicol. Chem. 10:235-241.
38. Ribo, J.M. and K.L.E. Kaiser. 1983. Effects of selected chemicals to photoluminescent bacteria and their correlation with acute and sublethal effects on other organisms. Chemosphere 12:1421-1442.
39. Saarikoski, J. and M. Viluksela. 1982. Relation between physicochemical properties of phenols and their toxicity and accumulation in fish. Ecotoxicol. Environ. Saf. 6:501-512.
40. Crofts, A.R., S.W. Meinhardt, K.R. Jones and M. Snozzi. 1983. The role of the quinone pool in the cyclic electron-transfer chain of Rhodopseudomonas sphaeroides: A modified Q-cycle mechanism. Biochim. Biophys. Acta 723:202-218.
41. 1 complex of rat-liver mitochondria. Biosci. Biotechnol. Biochem. 56:919-923.
42. Lipnick, R.L. 1989. Narcosis, electrophile and proelectrophile toxicity mechanism: Application of SAR and QSAR. Environ. Toxicol. Chem. 8:1-12.
43. Crofts, A.R. 1985. The mechanism of the ubiquinol : cytochrome c oxidoreductase of mitochondria and of Rhodopseudomonas sphaeroides. In M. Martonosi, ed. The Enzymes of Biological Membranes. Plenum, New York, NY, USA, pp. 347-383.
44. 2 oxidoreductase of respiratory and photosynthetic systems. J. Biol. Chem. 259:1758-1763.
45. Rutherford, A.W. and M.C.W. Evans. 1980. Direct measurement of the redox potential of the primary and secondary quinone electron acceptors in Rhodobacter sphaeroides (wild type) by EPR spectrophotometry. FEBS Lett. 110:257-261.
46. 1 complexes of microorganisms. Microbiol. Rev. 54:101-129.
47. B-site). Eur. J. Biochem. 209:73-79.
48. Brandt, U., J. Schubert, P. Geck and G. von Jagow. 1992. Uncoupling activity and physicochemical properties of derivatives of fluazinam. Biochim. Biophys. Acta 1101:41-47.
49. Fent, K. 1996. Ecotoxicology of organotin compounds. Crit. Rev. Toxicol. 26:1-117.
50. Schultz, T.W. 1987. The use of ionization constant (pKa) in selecting models of toxicity in phenols. Ecotoxicol. Environ. Saf. 14:178-183.