High-affinity small molecule-phospholipid complex formation: Binding of siramesine to phosphatidic acid

Journal of the American Chemical Society

Volumn 130, Issue 39, 2008, Pages 12953-12960

  Parry, Mikko J ^a   Alakoskela, Juha Matti I ^a   Khandelia, Himanshu ^b   Kumar, Subramanian Arun ^b,c   Jäättelä, Marja ^d   Mahalka, Ajay K ^a   Kinnunen, Paavo K J ^a,b  

^a UNIVERSITY OF HELSINKI   (Finland)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^c UNIVERSITY OF READING   (United Kingdom)

^d DANISH CANCER SOCIETY RESEARCH CENTER   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC PHOSPHOLIPIDS; AFFINITY INTERACTIONS; ANIONIC PHOSPHOLIPIDS; ANTICANCER DRUG; BILAYER SURFACE; CANCER CELLS; CELL BEHAVIORS; COMPLEX FORMATIONS; HYDROCARBON CORES; LANGMUIR FILMS; MD SIMULATION; MOLE FRACTION; PARTITION COEFFICIENT; PHOSPHATIDIC ACIDS; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID MEMBRANE; SIGNALING CASCADES; SIGNALING MOLECULES; SMALL MOLECULES;

ACIDS; BINDING ENERGY; BINDING SITES; DRUG INTERACTIONS; FLUORESCENCE SPECTROSCOPY; GROWTH KINETICS; HYDROCARBONS; MOLECULES; PHOSPHOLIPIDS; SIGNALING; STOICHIOMETRY;

CELL MEMBRANES;

INDOLE DERIVATIVE; LIPOSOME; LU 28 179; LU 28-179; PHOSPHATIDIC ACID; PHOSPHOLIPID; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; COMPUTER SIMULATION; DIFFERENTIAL SCANNING CALORIMETRY; KINETICS; LIPID BILAYER; METABOLISM; SECOND MESSENGER; SPECTROFLUOROMETRY;

CALORIMETRY, DIFFERENTIAL SCANNING; COMPUTER SIMULATION; INDOLES; KINETICS; LIPID BILAYERS; LIPOSOMES; PHOSPHATIDIC ACIDS; PHOSPHOLIPIDS; SECOND MESSENGER SYSTEMS; SPECTROMETRY, FLUORESCENCE; SPIRO COMPOUNDS;

EID: 58149165243     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800516w     Document Type: Article

References (38)

1. Heading, C. Curr. Opin. Invest. Drugs 2001, 2, 266-270.
2. Soby, K. K.; Mikkelsen, J. D.; Meier, E.; Thomsen, C. Neuropharmacology 2002, 43, 95-100.
3. Guitart, X.; Codony, X.; Monroy, X. Psychopharmacology 2004, 174, 301-319.
4. Colabufo, N. A.; Berardi, F.; Abate, C.; Contino, M.; Niso, M.; Perrone, R. J. Med. Chem. 2006, 49, 4153-4158.
5. Gebreselassie, D.; Bowen, W. D. Eur. J. Pharmacol. 2004, 493, 19-28.
6. Vilner, B. J.; John, C. S.; Bowen, W. D. Cancer Res. 1995, 55, 408-413.
7. Ostenfeld, M. S.; Fehrenbacher, N.; Høyer-Hansen, M.; Thomsen, C.; Farkas, T.; Jäättelä, M. Cancer Res. 2005, 65, 8975-8983.
8. Jutila, A.; Söderlund, T.; Pakkanen, A. L.; Huttunen, M.; Kinnunen, P. K. J. Chem. Phys. Lipids 2001, 112, 151-163.
9. Söderlund, T.; Jutila, A.; Kinnunen, P. K. J. Biophys. J. 1999, 76, 896-907.
10. Coon, M.; Ball, A.; Pound, J.; Ap, S.; Hollenback, D.; White, T.; Tulinsky, J.; Bonham, L.; Morrison, D. K.; Finney, R.; Singer, J. W. Mol. Cancer Ther. 2003, 2, 1067-1078.
11. Kim, J.; Lee, Y. H.; Kwon, T. K.; Chang, J. S.; Chung, K. C.; Min, D. S. Cancer Res. 2006, 66, 784-793.
12. MacDonald, R. C.; MacDonald, R. I.; Menco, B. P.; Takeshita, K.; Subbarao, N. K.; Hu, L. R. Biochim. Biophys. Acta 1991, 1061, 297-303.
13. Parry, M. J.; Jutila, A.; Kinnunen, P. K. J.; Alakoskela, J. M. J. Fluoresc. 2007, 17, 97-103.
14. Brockman, H. Curr. Opin. Struct. Biol. 1999, 9, 438-443.
15. Lindahl, E.; Hess, B.; van der Spoel, D. J. Mol. Model. 2001, 7, 306-317.
16. Jutila, A.; Rytömaa, M.; Kinnunen, P. K. J. Mol. Pharmacol. 1998, 54, 722-732.
17. Hoff, B.; Strandberg, E.; Ulrich, A.; Tieleman, D.; Posten, C. Biophys. J. 2005, 88, 1818-1827.
18. Yau, W.; Wimley, W.; Gawrisch, K.; White, S. Biochemistry 1998, 37, 14713-14718.
19. Cantor, R. S. Toxicol. Lett. 1998, 100-101, 451-458.
20. Alakoskela, J. M.; Söderlund, T.; Holopainen, J. M.; Kinnunen, P. K. J. Mol. Pharmacol. 2004, 66, 161-168.
21. Mattila, J. P.; Sabatini, K.; Kinnunen, P. K. J. Biophys. J. 2007, 93, 3105-3112.
22. Reasor, M. J.; Kacew, S. Exp. Biol. Med. 2001, 226, 825-830.
23. Vitovic, P.; Alakoskela, J. M.; Kinnunen, P. K. J. J. Med. Chem. 2008, 51, 1842-1848.
24. Bible, K. C. Cancer Res. 2000, 60, 2419-2428.
25. Seeman, P. Mol. Psychiatr. 1998, 3, 123-134.
26. Kooijman, E. E.; Carter, K. M.; van Laar, E. G.; Chupin, V.; Burger, K. N.; de Kruijff, B. Biochemistry 2005, 44, 17007-17015.
27. Kooijman, E. E.; Tieleman, D. P.; Testerink, C.; Munnik, T.; Rijkers, D. T.; Burger, K. N.; de Kruijff, B. J. Biol. Chem. 2007, 282, 11356-11364.
28. Chowdary, T. Biochem. J. 2007, 401, 437-445.
29. Hornberger, T. A.; Chu, W. K.; Mak, Y. W.; Hsiung, J. W.; Huang, S. A.; Chien, S. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 4741-4746.
30. Ghosh, S.; Strum, J. C.; Sciorra, V. A.; Daniel, L.; Bell, R. M. J. Biol. Chem. 1996, 271, 8472-8480.
31. Andresen, B. FEBS Lett. 2002, 531, 65-68.
32. Zhao, C. Nat. Cell Biol. 2007, 9, 707-712.
33. Hancock, J. F. Nat. Cell Biol. 2007, 9, 615-617.
34. Williams, J. J. Am. Soc. Nephrol. 2007, 18, 1112-1120.
35. La Rosee, P.; Jia, T.; Demehri, S.; Hartel, N.; de Vries, P.; Bonham, L.; Hollenback, D.; Singer, J. W.; Melo, J. V.; Druker, B. J.; Deininger, M. W. Clin. Cancer Res. 2006, 12, 6540-6546.
36. Sakane, F.; Imai, S.; Kai, M.; Yasuda, S.; Kanoh, H. Biochim. Biophys. Acta 2007, 1771, 793-806.
37. Steed, P. M.; Chow, A. H. Curr. Pharm. Biotechnol. 2001, 2, 241-256.
38. Groth-Pedersen, L.; Ostenfeld, M. S.; Høyer-Hansen, M.; Nylandsted, J.; Jäättelä, M. Cancer Res. 2007, 67, 2217-2225.