Effects of charge and intramolecular structure on the lipophilicity of nitrophenols

Journal of the American Chemical Society

Volumn 121, Issue 8, 1999, Pages 1743-1747

  Chopineaux Courtois, Véronique ^a   Reymond, Frédéric ^a   Bouchard, Géraldine ^b   Carrupt, Pierre Alain ^b   Testa, Bernard ^b   Girault, Hubert H ^a  

^a EPFL   (Switzerland)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROPHENOL; PHENOL DERIVATIVE; WATER;

ARTICLE; DIFFUSION; ELECTROCHEMICAL ANALYSIS; ENZYME ACTIVITY; HYDROGEN BOND; ION TRANSPORT; IONIZATION; LIPOPHILICITY; MAMMAL; PH; POTENTIOMETRY; PROTEIN CONFORMATION; PROTEIN STRUCTURE; SKELETAL MUSCLE; SOLVATION;

EID: 0033518897     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9836139     Document Type: Article

References (29)

1. Salerno, V. P.; Ribeiro, A. S.; Dinucci, A. N.; Mignaco, J. A.; Sorenson, M. M. Biochem. J. 1997, 324, 877-884.
2. Ohkouchi, T.; Kakutani, T.; Senda, M. Bioelectrochem. Bioenerg. 1991, 25, 71-80.
3. Jetzer, W. E.; Huq, A. S.; Ho, N. F. H.; Flynn, G.; Duraiswamy, N.; Condie, L. J. Pharm. Sci. 1986, 75, 1098-1103.
4. Roberts, M. S.; Anderson, R. A.; Swarbrick, J.; Moore, D. E. J. Pharm. Pharmacol. 1978, 30, 486-490.
5. Huq, A. S.; Ho, N. F. H.; Husari, N.; Flynn, G. L.; Jetzer, W. E.; Condie, L. J. Arch. Environ. Contam. Toxicol. 1986, 15, 557-566.
6. Petty, H. R. Molecular Biology of Membranes. Structure and Function; Plenum Press, New York, 1993.
7. Reymond, F.; Steyaert, G.; Carrupt, P.-A.; Testa, B.; Girault, H. H. Helv. Chim. Acta 1996, 79, 101-117.
8. Ohkouchi, T.; Kakutani, T.; Senda, M. Bioelectrochem. Bioenerg. 1991, 25, 81-89.
9. Girault, H. H. Charge Transfer across Liquid/Liquid Interfaces; Plenum Press: New York, 1993; Vol. 25, pp 1-62.
10. Abraham, M. H. Chem. Soc. Rev. 1993, 73-83.
11. Steyaert, G.; Guiseppe, L.; Gaillard, P.; Boss, G.; Reymond, F.; Girault, H. H.; Carrupt, P. A.; Testa, B. J. Chem. Soc. Faraday Trans. 1997, 93, 401-406.
12. Seiler, P. Eur. J. Med. Chem. 1974, 9, 473-479.
13. Abraham, M. H.; Chadha, H. S.; Whiting, G. S.; Mitchell, R. C. J. Pharm. Sci. 1994, 83, 1085.
14. Reymond, F.; Steyaert, G.; Carrupt, P.-A.; Testa, B.; Girault, H. H. J. Am. Chem. Soc. 1996, 118, 11951-11957.
15. Reymond, F.; Carrupt, P. A.; Testa, B.; Girault, H. H. Chem. Eur. J. 1999, 5, 39-47.
16. International program on chemistal safety, 1,2-Dichloroethane; 2nd ed.; World Health Organization: Geneva, 1995; Vol. 176, p 148.
17. Grunwald, E.; Baughman, G.; Kohnstam, G. J. Am. Chem. Soc. 1960, 82, 5801-5811.
18. Shao, Y. Ion Transfer across Liquid/Liquid Interfaces: Shao, University of Edinburgh: Edinburgh, 1991; p 187.
19. van de Waterbeemd, H. Hydrophobicity of Organic Compounds; Compudrug: Vienna, 1986; Vol. 1.
20. Borisenko, K. B.; Bock, C. W.; Hargittai, I. J. Phys. Chem. 1994, 98, 1442-1448.
21. Bock, C. W.; Hargittai, I. Struct. Chem. 1994, 5, 307-312.
22. Hanstein, W. G. Biochim. Biophys. Acta 1976, 456, 129-148.
23. Mitchell, P. Biol. Rev. 1966, 41, 445-502.
24. Alberts, B.; Bray, D.; Lewis, J.; Raff, M.; Roberts, K.; Watson, J. D. Molecular Biology of the Cell, 3rd ed.; Garland Publishing: New York, 1994.
25. Terada, H. Biochim. Biophys. Acta 1981, 639, 225-242.
26. Parker, V. H. Biochem. J. 1965, 97, 658-662.
27. Hansch, C.; Kiehs, K.; Lawrence, G. L. J. Am. Chem. Soc. 1965, 87, 5770-5773.
28. Fujita, T. J. Med Chem. 1966, 9, 797-803.
29. Tollenaere, J. P. J. Med. Chem. 1973, 16, 791-796.