Bivalent ligands of CXCR4 with rigid linkers for elucidation of the dimerization state in cells

Journal of the American Chemical Society

Volumn 132, Issue 45, 2010, Pages 15899-15901

  Tanaka, Tomohiro ^a   Nomura, Wataru ^a   Narumi, Tetsuo ^a   Masuda, Akemi ^a   Tamamura, Hirokazu ^a  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIVALENT LIGANDS; CANCEROUS CELLS; G PROTEIN COUPLED RECEPTORS; IN-CELL; MOLECULAR PROBES; MOLECULAR RULER; RIGID LINKERS;

OLIGOMERIZATION;

LIGANDS;

CHEMOKINE RECEPTOR CXCR4; G PROTEIN COUPLED RECEPTOR;

ARTICLE; BINDING AFFINITY; CANCER CELL; DIMERIZATION; ENDOTHELIUM CELL; FLUORESCENCE ACTIVATED CELL SORTING; HUMAN; HUMAN CELL; MOLECULAR PROBE; OLIGOMERIZATION;

BINDING, COMPETITIVE; HELA CELLS; HUMANS; JURKAT CELLS; LIGANDS; PROTEIN MULTIMERIZATION; RECEPTORS, CXCR4;

EID: 78449262856     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja107447w     Document Type: Article

References (28)

1. Overington, J. P., Al-Lazikani, B., and Hopkins, A. L. Nat. Rev. Drug. Discovery 2006, 5, 993-996
2. Wang, J., He, L., Combs, C. A., Roderiquez, G., and Norcross, M. A. Mol. Cancer Ther. 2006, 5, 2474-2483
3. Percherancier, Y., Berchiche, Y. A., Slight, I., Volkmer-Engert, R., Tamamura, H., Fujii, N., Bouvier, M., and Heveker, N. J. Biol. Chem. 2005, 280, 9895-9903
4. Babcock, G. J., Farzan, M., and Sodroski, J. J. Biol. Chem. 2003, 278, 3378-3385
5. Luker, K. E., Gupta, M., and Luker, G. D. FASEB J. 2009, 23, 823-834
6. Handl, H. L., Sankaranarayanan, R., Josan, J. S., Vagner, J., Mash, E. A., Gillies, R. J., and Hruby, V. J. Bioconjugate Chem. 2007, 18, 1101-1109
7. Zheng, Y., Akgün, E., Harikumar, K. G., Hopson, J., Powers, M. D., Lunzer, M. M., Miller, L. J., and Portoghese, P. S. J. Med. Chem. 2009, 52, 247-258
8. Panetta, R. and Greenwood, M. T. Drug Discovery Today 2008, 13, 1059-1066
9. Tamamura, H., Xu, Y., Hattori, T., Zhang, X., Arakaki, R., Kanbara, K., Omagari, A., Otaka, A., Ibuka, T., Yamamoto, N., Nakashima, H., and Fujii, N. Biochem. Biophys. Res. Commun. 1998, 253, 877-882
10. Fujii, N., Oishi, S., Hiramatsu, K., Araki, T., Ueda, S., Tamamura, H., Otaka, A., Kusano, S., Terakubo, S., Nakashima, H., Broach, J. A., Trent, J. O., Wang, Z., and Peiper, S. C. Angew. Chem., Int. Ed. 2003, 42, 3251-3253
11. Tamamura, H., Araki, T., Ueda, S., Wang, Z., Oishi, S., Esaka, A., Trent, J. O., Nakashima, H., Yamamoto, N., Peiper, S. C., Otaka, A., and Fujii, N. J. Med. Chem. 2005, 48, 3280-3289
12. Tanaka, T., Tsutsumi, H., Nomura, W., Tanabe, Y., Ohashi, N., Esaka, A., Ochiai, C., Sato, J., Itotani, K., Murakami, T., Ohba, K., Yamamoto, N., Fujii, N., and Tamamura, H. Org. Biomol. Chem. 2008, 6, 4374-4377
13. Arora, P. S., Ansari, A. Z., Best, T. P., Ptashne, M., and Dervan, P. B. J. Am. Chem. Soc. 2002, 124, 13067-13071
14. Sato, S., Kwon, Y., Kamisuki, S., Srivastava, N., Mao, Q., Kawazoe, Y., and Uesugi, M. J. Am. Chem. Soc. 2007, 129, 873-880
15. Kuemin, M., Schweizer, S., Ochsenfeld, C., and Wennemers, H. J. Am. Chem. Soc. 2009, 131, 15474-15482
16. Schuler, B., Lipman, E. A., Steinbach, P. J., Kumke, M., and Eaton, W. A. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 2754-2759
17. For synthesis details, see the Supporting Information.
18. Våbenø, J., Nikiforovich, G. V., and Marshall, G. R. Chem. Biol. Drug Des. 2006, 67, 346-354
19. Balkwill, F. Semin. Cancer Biol. 2004, 14, 171-178
20. Carnec, X., Quan, L., Olson, W. C., Hazan, U., and Dragic, T. J. Virol. 2005, 79, 1930-1933
21. Majka, M., Rozmyslowicz, T., Honczarenko, M., Ratajczak, J., Wasik, M. A., Gaulton, G. N., and Ratajczak, M. Z. Leukemia 2000, 14, 1821-1832
22. Schwartz, V., Lue, H., Kraemer, S., Korbiel, J., Krohn, R., Ohl, K., Bucala, R., Weber, C., and Bernhagen, J. FEBS Lett. 2009, 583, 2749-2757
23. Nomura, W., Tanabe, Y., Tsutsumi, H., Tanaka, T., Ohba, K., Yamamoto, N., and Tamamura, H. Bioconjugate Chem. 2008, 19, 1917-1920
24. Murdoch, C., Monk, P. N., and Finn, A. Immunology 1999, 98, 36-41
25. Salcedo, R., Wasserman, K., Young, H. A., Grimm, M. C., Howard, O. M. Z., Anver, M. R., Kleinman, H. K., Murphy, W. J., and Oppenheim, J. J. Am. J. Pathol. 1999, 154, 1125-1135
26. Sohy, D., Parmentier, M., and Springael, J. J. Biol. Chem. 2007, 282, 30062-30069
27. Contento, R. L., Molon, B., Boularan, C., Pozzan, T., Manes, S., Marullo, S., and Viola, A. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 10101-10106
28. Pello, O. M., Martínez-Muñoz, L., Parrillas, V., Serrano, A., Rodríguez-Frade, J. M., Toro, M. J., Lucas, P., Monterrubiol, M., Martínez-A, C., and Mellado, M. Eur. J. Immunol. 2008, 38, 537-549