COSMOmic: A mechanistic approach to the calculation of membrane-water partition coefficients and internal distributions within membranes and micelles

Journal of Physical Chemistry B

Volumn 112, Issue 38, 2008, Pages 12148-12157

  Klamt, Andreas ^a,b   Huniar, Uwe ^a   Spycher, Simon ^a,c   Keldenich, Jörg ^d  

^a COSMOlogic GmbH and COKG ^*  (Germany)

^b UNIVERSITY OF REGENSBURG   (Germany)

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

^d BAYER PHARMA AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL PROPERTIES; COLLOIDS; CYTOLOGY; MOLECULES; QUANTUM CHEMISTRY; SURFACE ACTIVE AGENTS;

ADJUSTABLE PARAMETERS; BIOMEMBRANES; COSMO-RS; ELASTIC ENERGIES; FLUID-PHASE; MICELLAR SYSTEMS; NEW APPROACHES; QUANTUM CHEMICAL CALCULATIONS; SOLUTE MOLECULES; WATER PARTITION COEFFICIENTS;

BIOLOGICAL MEMBRANES;

EID: 53849136267     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp801736k     Document Type: Article

References (57)

1. Mouritsen, O. G.; Andersen, H. K.; Andersen, J. S.; Davidsen, J.; Nielsen, L. K.; Jorgensen, K. Pharmacokinetic Optimization in Drug Research: Biological, Physicochemical, and Computational Strategies, LogP2000, 2nd Lipophilicity Symposium, Lausanne, Switzerland, Mar 5-9, 2000; 2001; p 33.
2. Krämer, S. D. In Pharmacokinetic Optimization in Drug Research: Biological, Physicochemical, and Computational Strategies; Testa, B., van de Waterbeemd, H., Folkers, G., Guy, R., Eds.; Wiley-VCH: Weinheim, Germany,2001; p401.
3. Avdeef, A. Curr. Top. Med. Chem 2001, 1, 277.
4. Escher, B. I.; Sigg, L. In IUPAC Series on Analytical and Physical Chemistry of Environmental Systems; Buffle, J., van Leuwen, H. P., Eds.; John Wiley:Chichester, U.K.,2004; Vol. 9, p 205.
5. Liu, H.; Ong, S.; Glunz, L.; Pidgeon, C. Anal. Chem. 1995, 67, 3550.
6. Ong, S.; Liu, H.; Pidgeon, C. J. Chromatogr, A 1996, 728, 113.
7. Vergeres, G.; Manenti, S.; Weber, T.; Sturzinger, C. J. Biol. Chem. 1995, 270, 19879.
8. Loidl-Stahlhofen, A.; Ulrich, A. S.; Kaufmann, S.; Bayerl, T. M. Eur. Biophys. J. 1996, 25, 151.
9. Loidl-Stahlhofen, A.; Hartmann, T.; Schottner, M.; Rohring, C.; Brodowsky, H.; Schmitt, J.; Keldenich, J. Pharm. Res. 2001, 18, 1782.
10. Mannhold, R.; Van de Waterbeemd, H. J. Comput.-Aided Mol. Des. 2001, 15, 337.
11. Avdeef, A. Absorption and Drug Development: Solubility, Permeability and Charge State; John Wiley & Sons, Inc.: Hoboken, NJ, 2003.
12. Spycher, S.; Smejtek, P.; Netzeva, T. I.: Escher, B. I. Chem. Res. Toxicol. 2008, 21, 911.
13. Gobas, F. A. P. C.; Lahittete, J. M.; Garofalo, G.; Shiu, W. Y.; Mackay, D. J.. Pharm. Sci. 1988, 77, 265.
14. Jabusch, T. W.; Swackhamer, D. L. Chemosphere 2005, 60, 1270.
15. Jonker, M. T. O.; van der Heijden, S. A. Environ. Sci. Technol. 2007, 41, 7363.
16. Smejtek, P.; Wang, S. Arch. Environ. Contam. Toxicol. 1993, 25, 394.
17. Escher, B. I.; Schwarzenbach, R. P. Environ. Sci. Technol. 1996, 30, 260.
18. Avdeef, A.; Box, K. J.; Comer, J. E. A.; Hibbert, C.; Tam, K. Y. Pharm. Res. 1998, 15, 209.
19. Comer, J.; Tam, K. In Pharmacokinetic Optimization in Drug Research: Biological, Physicochemical, and Computational Strategies; Testa, B., van de Waterbeemd, H., Folkers, G., Guy, R. , Eds.; Wiley-VCH: Weinheim, Germany, 2001; p 275.
20. Vaes, W. H. J.; Ramos, E. U.; Verhaar, H. J. M.; Cramer. C. J.; Hermens, J. L. M. Chem. Res. Toxicol. 1998, 11, 847.
21. Patel, H.; Schultz, T. W.: Cronin, M. T. D. THEOCHEM 2002, 593, 9.
22. Mukhopadhyay, P.; Vogel, H. J.; Tieleman, P. D. Biophys. J. 2004, 86, 337.
23. Bemporad, D.; Essex, J. W.; Luttmann, C. J. Phys. Chem. B 2004, 108, 4875.
24. Gullingsrud, J.; Schulten, K. Biophys. J. 2004, 86, 3496.
25. Spycher, S.; Escher, B. I.; Gasteiger, J. Chem. Res. Toxicol. 2005, 18, 1858.
26. Herbette, L. G.; Trumbore, M.; Chester, D. W.; Katz, A. M. J. Mol. Cell. Cardiol. 1988, 20, 373.
27. Rhodes, D. G.; Sarmiento, J. G.; Herbette, L. G. Mol. Pharmacol. 1985, 27, 612.
28. Herbette, L. G.; Chester, D. W.; Rhodes, D. G. Biophys. J. 1986, 49, 91.
29. Klamt, A. J. Phys. Chem. 1995, 99, 2224.
30. Klamt, A.; Jonas, V.; Buerger, T.; Lohrenz, J. C. W. J. Phys. Chem. A 1998, 102, 5074.
31. Klamt, A. COSMO-RS from Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design; Elsevier: Amsterdam, 2005.
32. Busalla, T. Berechnung von Membranverteilungskoeffizienten. Diploma Thesis, University of Cologne, Cologne, Germany, 1996.
33. Smejtek, P.; Barstad, A. W.; Wang, S. Chem.-Biol. Interact. 1989, 71, 37.
34. Miyoshi, H.; Nishioka, T.; Fujita, T. Biochim. Biophys. Acta-Bioenergetics 1987, 891, 194.
35. Word, R. C.; Smejtek, P. J. Membr. Biol. 2005, 203, 127.
36. Willmann, S.; Schmitt, W.; Keldenich, J.; Lippert, J.; Dressman, J. B. J. Med. Chem. 2004, 47, 4022.
37. CORINA, version 3.21; MolNet GmbH: Erlangen, Germany; http://www.mol-net.de.
38. Ahlrichs, R.; Baer, M.; Haeser, M.; Horn, H.; Koelmel, C. Chem. Phys. Lett. 1989, 162, 165.
39. Ahlrichs, R.; Bär, M.; Baron, H. P.; Bauernschmitt, R.; Böcker, S.; Crawford, N.; Deglmann, P.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Furche, F.; Haase, F.; Häser, M.; Horn, H.; Ḧattig, C.; Huber, C.; Huniar, U.; Kattannek, M.; Köhn, A.; Kölmel, C.; Kollwitz, M.; May, K.; Nava, P.; Ochsenfeld, C.; Öhm, H.; Patzelt, H.; Rappoport, D.; Rubner, O.; Schäfer, A.; Schneider, U.; Sierka, M.; Treutler, O.; Unterreiner, B.; von Arnim, M.; Weigend, F.; Weis, P.; Weiss, H. Turbomole, 5.8 ed.; Karlsruhe, Germany, 2005; distribution by COSMOlogic, http://www.cosmologic.de/ QuantumChemistry/main_turbomole.html.
40. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
41. Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
42. Eichkorn, K.; Treutler, O.; Oehm, H.; Haeser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 242, 652.
43. Xiang, T. X.; Anderson, B. D. Biophys. J. 1994, 66, 561.
44. Marsh, D. Biochim. Biophys. Acta-Rev. Biomembr. 1996, 1286, 183
45. Lindahl, E.; Edholm, O. J.. Chem. Phys. 2000, 113, 3882.
46. Eckert, F.; Klamt, A. COSMOtherm, version C2.1, revision 01.07 ed.; COSMOlogic GmbH&CoKG: Leverkusen, Germany, 2007.
47. Gurtovenko, A. A.; Patra, M.; Karttunen, M.; Vattulainen, I. Biophys. J. 2004, 86, 3461.
48. Eckert, F.; Klamt, A. AIChE J. 2002, 48, 369.
49. Klamt, A.; Eckert, F. Fluid Phase Equilib. 2000, 172, 43.
50. Mokrushina, L.; Buggert, M.; Smirnova, I.; Arlt, W.; Schomaecker, R. Ind. Eng. Chem. Res. 2007, 46, 6501.
51. Fruttero, R.; Caron, G.; Fornatto, E.; Boschi, D.; Ermondi, G.; Gaseo, A.; Carrupt, P. A.; Testa, B. Pharm. Res. 1998, 15, 1407.
52. Heller, H.; Schaefer, M.; Schulten, K. J. Phys. Chem. 1993, 97, 8343.
53. Sachs, J. N.; Crozier, P. S.; Woolf, T. B. J. Chem. Phys. 2004, 121, 10847.
54. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
55. Syracuse Research Corp. PhysProp-Database (KowWin Demo). http://www.syrres.com/esc/kowdemo.htm (accessed Jan 31, 2008).
56. Ottiger, C.; Wunderli-Allenspach, H. Eur. J. Pharm. Sei 1997, 5, 223.
57. Tieleman, P. D. Private communication.