Design and Synthesis of Selenazole-Containing Peptides for Cocrystallization with P-Glycoprotein

ChemBioChem

Volumn 12, Issue 6, 2011, Pages 868-873

  Tao, Houchao ^a   Weng, Yue ^a,b   Zhuo, Rupeng ^c   Chang, Geoffrey ^a   Urbatsch, Ina L ^c   Zhang, Qinghai ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b WUHAN UNIVERSITY   (China)

^c TEXAS TECH UNIVERSITY HEALTH SCIENCES CENTER SCHOOL OF MEDICINE   (United States)

Author keywords

Cyclic peptides; Glycoproteins; Ligand design; Selenium; X ray diffraction

Indexed keywords

GLYCOPROTEIN P; SELENAZOLE DERIVATIVE;

ARTICLE; BINDING SITE; CRYSTALLIZATION; ENANTIOSELECTIVITY; LIGAND BINDING; PRIORITY JOURNAL; PROTEIN STRUCTURE; RACEMIZATION; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

AZOLES; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; P-GLYCOPROTEIN; PEPTIDES, CYCLIC; SELENIUM; STEREOISOMERISM;

EID: 79953725116     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201100048     Document Type: Article

References (28)

1. G. Szakacs, J. K. Paterson, J. A. Ludwig, C. Booth-Genthe, M. M. Gottesman, Nat. Rev. Drug Discovery 2006, 5, 219.
2. P. D. Eckford, F. J. Sharom, Chem. Rev. 2009, 109, 2989.
3. A. B. Shapiro, V. Ling, Eur. J. Biochem. 1997, 250, 130.
4. T. W. Loo, M. C. Bartlett, D. M. Clarke, J. Biol. Chem. 2003, 278, 39706.
5. T. W. Loo, D. M. Clarke, Biochem. Biophys. Res. Commun. 2005, 329, 419.
6. C. Martin, G. Berridge, C. F. Higgins, P. Mistry, P. Charlton, R. Callaghan, Mol. Pharmacol. 2000, 58, 624.
7. S. G. Aller, J. Yu, A. Ward, Y. Weng, S. Chittaboina, R. Zhuo, P. M. Harrell, Y. T. Trinh, Q. Zhang, I. L. Urbatsch, G. Chang, Science 2009, 323, 1718.
8. P. R. Twentyman, N. E. Fox, D. J. G. White, Br. J. Cancer 1987, 56, 55.
9. L. M. Slater, P. Sweet, M. Stupecky, S. Gupta, J. Clin. Invest. 1986, 77, 1405.
10. F. Loor, Expert Opin. Invest. Drugs 1999, 8, 807.
11. S. Y. Ko, C. Dalvit, Int. J. Pept. Protein Res. 1992, 40, 380.
12. M. F. O'Donohue, A. W. Burgess, M. D. Walkinshaw, H. R. Treutlein, Protein Sci. 1995, 4, 2191.
13. J. Ogino, R. E. Moore, G. M. L. Patterson, C. D. Smith, J. Nat. Prod. 1996, 59, 581.
14. X. Fu, T. Do, F. J. Schmitz, V. Andrusevich, M. H. Engel, J. Nat. Prod. 1998, 61, 1547.
15. V. S. C. Yeh, Tetrahedron 2004, 60, 11995.
16. P. Wipf, Chem. Rev. 1995, 95, 2115.
17. S. L. You, H. Razavi, J. W. Kelly, Angew. Chem. 2003, 115, 87; Angew. Chem. Int. Ed. 2003, 42, 83.
18. M. Riedrich, S. Harkal, H. D. Arndt, Angew. Chem. 2007, 119, 2755; Angew. Chem. Int. Ed. 2007, 46, 2701.
19. C. D. J. Boden, G. Pattenden, T. Ye, Synlett 1995, 417.
20. K. Geisler, W. D. Pfeiffer, A. Kunzler, H. Below, E. Bulka, P. Langer, Synthesis 2004, 875.
21. W. J. Hennen, B. C. Hinshaw, T. A. Riley, S. G. Wood, R. K. Robins, J. Org. Chem. 1985, 50, 1741.
22. E. A. Merritt, M. C. Bagley, Synthesis 2007, 3535.
23. E. Aguilar, A. I. Meyers, Tetrahedron Lett. 1994, 35, 2473.
24. A. Ogawa, J. Miyake, Y. Karasaki, S. Murai, N. Sonoda, J. Org. Chem. 1985, 50, 384.
25. A. Bertram, J. S. Hannam, K. A. Jolliffe, F. G.-L. de Turiso, G. Pattenden, Synlett 1999, 11, 1723.
26. A. Bertram, N. Maulucci, O. M. New, S. M. M. Nor, G. Pattenden, Org. Biomol. Chem. 2007, 5, 1541.
27. M. K. al-Shawi, A. E. Senior, J. Biol. Chem. 1993, 268, 4197.
28. M. C. Bagley, J. W. Dale, E. A. Merritt, X. Xiong, Chem. Rev. 2005, 105, 685.