Hydrophobicity and sorption of chlorophenolates to lipid membranes

Chemosphere

Volumn 33, Issue 1, 1996, Pages 177-201

  Smejtek, Pavel ^a   Blochel, Andreas ^a   Wang, Shanru ^a  

^a PORTLAND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROPHENOL; PHOSPHATIDYLCHOLINE;

ADSORPTION; ARTICLE; DIELECTRIC CONSTANT; EGG; ELECTRICITY; HYDROPHOBICITY; LIPID MEMBRANE; MODEL; PARTITION COEFFICIENT;

HYDROPHOBICITY; MEMBRANES; SORPTION;

EID: 0029663585     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/0045-6535(96)00158-0     Document Type: Article

References (51)

1. Geyer, H. J., I. Scheunert, and F. Korte, Distribution and bioconcentration potential of the environmentai chemical pentachlorophenol (PCP) in different tissues of humans. Chemosphere, 16, 887-899, 1987.
2. Haque, A., and W. Ebing, Uptake and accumulation of pentachlorophenol and sodium pentachlorophenate by earthworms from water and soil. Science Total. Env., 68, 113-125, 1988.
3. Hattemer-Frey, H. A., and C. C. Travis, Pentachlorophenol: Environmental partitioning and human exposure. Arch. Environ. Contam. Toxicol., 18, 482-489, 1989.
4. Izushi, F., T. Mori, and M. Ogata, Effect of phenol and halogenated phenols on energy transfer reactions of rat liver mitochondria. Acta Med. Okayama, 42, 7-14, 1988.
5. Jansson, K., and V. Jansson, The toxicity of chlorophenols in V79 Chinese hamster cells. Toxicology Letters, 69, 289-294, 1993.
6. Paasivirta, J., H. Tenhola, H. Palm, and R. Lammi, Free and bound chlorophenols in Kraft pulp bleaching effluents. Chemosphere, 24, 1253-1258, 1992.
7. Shannon, R. D., G. D. Boardman, A. M. Dietrich, and D. R. Bevan, Mitochondrial response to chlorophenols as a short-term toxicity assay. Environ. Toxicol. Chem., 7, 57-66, 1991.
8. Weinbach, E. C., Biochemical basis for the toxicity of pentachlorophenol. Science, 124, 940, 1956.
9. _, and J. Garbus, The interaction of uncoupling phenols with mitochondria and mitochondrial protein. J. Biol. Chem., 240, 1811-1819, 1965.
10. Wild, S. R., S. J. Harrad, and K. C. Jones, Pentachlorophenol in the UK environment I: A budget and source inventory. Chemosphere, 24, 833-845, 1992.
11. _, and K. C. Jones, Pentachlorophenol in the UK environment II: Human exposure and an assessment of pathways. Chemosphere, 24, 847-855, 1992.
12. McLaughlin, S. G., A., and J. P. Dilger, Transport of protons across membranes by weak acids. Physiol. Rev., 60, 825-863, 1980.
13. Nichols, D. G., Bioenergetics. An introduction to the chemiosmotic theory, Academic Press, London, New York, 1982.
14. Terada, H., Uncouplers of oxidative phosphorylation. Env. Health Perspect., 87, 213-218, 1990.
15. Finkelstein, A., Weak acid uncouplers of oxidative phosphorylation. Mechanism of action on thin lipid membranes. Biochim. Biophys. Acta, 205, 1-6, 1970.
16. Smejtek, P., K. Hsu, and W. H. Perman, Electrical conductivity of lipid bliyer membranes induced by pentachlorophenol. Biophys. J., 16, 319-336, 1976.
17. Barstad, A. W., D. H. Peyton, and P. Smejtek, AHA-heterodimer of a class-2 uncoupler: Pentachlorophenol. Biochim. Biophys. Acta, 1140, 262-270, 1993.
18. Westall, J. C., Influence of pH and ionic strength on the aqueous-nonaqueous distribution of chlorinated phenols. Environ. Sci. Technol., 19, 193-198, 1985.
19. Jafvert, C. T., J. C. Westall, E. Grieder, and R. P. Schwarzenbach, Distribution of hydrophobic ionogenic organic compounds between octanol and water: Organic acids. Environ. Sci. Technol., 24, 1795-1803, 1990.
20. Westall, J. C., C. A. Johnson, and W. Zhang, Distribution of LiCl, NaCl, KCl, HCl, MgCl2, and CaCl2 between octanol and water. Environ. Sci. Technol., 24, 1803-1810, 1990.
21. Smejtek, P., Permeability of lipophilic ions across lipid bilayers, in Permeability and Stability of Lipid Bilayers, edited by E. A. Disalvo, and S. A. Simon, pp. 197-240, CRC Press, Boca Raton, 1995.
22. Escher, B. I., and R. P. Schwarzenbach, Partitioning of substituted phenols in liposome-water, biomembrane-water, and octanol-water systems. Environ. Sci. Technol., 30, 260-270, 1996.
23. Gobas, A. P., C., J. M. Lahittete, G. Garofalo, and W. Y. Shiu, A novel method for measuring membrane-water partition coefficients of hydrophobic organic chemicals: Comparison with 1-octanol-water partitioning. J. Pharm. Sci., 77, 265-272, 1988.
24. Smejtek, P., and S. Wang, Distribution of hydrophobic ionizable xenobiotics between water and lipid membranes: Pentachlorophenol and pentachlorophenate. A comparison with octanol-water partition. Arch. Environ. Contam. Toxicol., 25, 394-404, 1993.
25. Bangham, A. D., M. W. Hill, and N. G. Miller, A., Preparation and use of liposomes as models of biological membranes. Methods Membr. Biol., 1, 1-68, 1974.
26. Aveyard, R., and D. A. Haydon, An introduction to the principles of surface chemistry, Cambridge University Press, London, 1973.
27. McLaughlin, S., and H. Harary, The hydrophobic adsorption of charged molecules to bilayer membranes A test of applicability of the Stern Equation. Biochemistry, 15, 1941-1948, 1976.
28. _, N. Mulrine, T. Gresalfi, G. Vaio, and A. McLaughlin, Adsorption of divalent cations to bilayer membranes containing phosphatidylserine. J. Gen. Physiol., 77, 445-473, 1981.
29. Smejtek, P., W. K. Riker, A. Oxyzoglou, C. Wright, and M. Bennett, Adsorption of aminopyridines to phosphatidylserine membranes. Biochim. Biophys. Acta, 1029, 259-266, 1990.
30. _, and S. Wang, Adsorption to DPPC membranes in gel and fluid state: Pentachlorophenolate, dipicrylamine and tetraphenylborate. Biophys. J., 58, 1285-1294, 1990.
31. Tatulian, S., Ionization and ion binding, in Phospholipids Handbook, edited by G. Cevc, pp. 511-552, Marcell Dekker, New York, 1993.
32. Dilger, J. P., L. R. Fisher, and D. A. Haydon, A critical comparison of electrical and optical methods for bilayer thickness determination. Chem. Phys. Lipids, 30, 159-176, 1982.
33. _, and R. Benz, Optical and electrical properties of thin monoolein lipid bilayers. J. Membrane Biol., 181-189, 1985.
34. Bevington, P. R., Data reduction and error analysis for the physical sciences, McGraw-Hill, New York, 1969.
35. McIntosh, T. J., and S. A. Simon, Hydration force and bilayer deformation: A reevaluation. Biochemistry, 25, 4058-4066, 1986.
36. Xie, T., B. Hulthe, and S. Folestad, Determination of partition coefficients of chlorinated phenols, guiacols and catechols by shake-flask GC and HPLC. Chemosphere, 13, 445-459, 1984.
37. Bowman, B. T., and W. W. Sans, Determination of octanol-water partitioning coefficients (Kow) of 61 organophosphorus and carbamate insecticides and their relationship to respective water solubility (S) values. J. Environ. Sci. Health, B 18, 667-683, 1983.
38. Chiou, C., D. W. Schmedding, and M. Manes, Partitioning of organic compounds in octanol-water systems Environ. Sci. Technol., 16, 4-10, 1982.
39. Small, D., Handbook of lipid research. The physical chemistry of lipids, Plenum Press, New York, 1986.
40. Cafiso, D. S., Influence of charges and dipoles on macromolecular adsorption and permeability, in Permeability and Stability of Lipid Bilayers, edited by E. A. Disalvo, and S. A. Simon, pp. 179-195, CRC Press, Boca Raton, 1995.
41. Flewelling, R. F., and W. L. Hubbell, The membrane dipole potential in a total membrane potential model. Biophys. J., 49, 541-552, 1986.
42. Smejtek, P., A. W. Barstad, and K. Hsu, Dielectric properties of adsorption/ionization site of pentachlorophenol in lipid membranes. Biochim. Biophys. Acta, 902, 109-127, 1987.
43. Marcus, Y., Ion solvation, John Wiley, New York, 1985.
44. Jacobs, R. E., and S. H. White, Mixtures of a series of homologous hydrophobic peptides with lipid bilayers: A simple model system for examining the proteinlipid interface. Biochemistry, 1986, 2605-2612, 1986.
45. Jacobs, E. R., and S. H. White, The nature of the hydrophobic binding of small peptides at the bilayer interface: Implications for the insertion of transbilayer helices. Biochemistry, 28, 3421-3437, 1989.
46. Uhlig, H. H., The solubilities of gases and surface tension. J. Phys. Chem., 41, 1215-1224, 1937.
47. Pearlman, R. S., Molecular surface areas and volumes and their use in structure/activity relationships, in Physical chemical properties of drugs, edited by S. H. Yalkowsky, A. A. Sinkula, and S. C. Valvani, pp. 321-347, Marcel Dekker, New York, 1980.
48. Kamlet, M. J., R. M. Doherty, M. H. Abraham, P. W. Carr, R. F. Doherty, and R. W. Taft, Linear solvation energy relationships. 41. Important differences between aqueous solubility relationships for aliphatic and aromatic solutes. J. Phys. Chem., 91, 1996-2004, 1987.
49. DeBruijn, J., and J. Hermens, Relationship between octanol/water partition coefficients and total molecular surface area and total molecular volume of hydrophobic organic chemicals. Quant. Struct.-Act. Relat., 9, 11-21, 1990.
50. _, F. Busser, W. Seinen, and J. Hermens, Determination of octanol/water partition coefficients for hydrophobic organic chemicals with the "low-stirring" method. Environment. Tox. Chem., 8, 499-512, 1989.
51. Griffith, O. H., P. J. Dehlinger, and S. P. Van, Shape of the hydrophobic barrier of phospholipid bilayers Evidence for water penetration in biological membranes. J. Membrane Biol., 15, 159-192, 1974.