Efficient solid-phase synthesis of a series of cyclic and linear peptoid-dexamethasone conjugates for the cell permeability studies

Journal of Combinatorial Chemistry

Volumn 12, Issue 3, 2010, Pages 321-326

  Cho, Suekyung ^a   Choi, Jiyoung ^a   Kim, Arim ^a   Lee, Yunyoung ^a   Kwon, Yong Uk ^a  

^a Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; DEXAMETHASONE; DRUG DERIVATIVE; PEPTOID;

AMINO ACID SEQUENCE; ARTICLE; CELL MEMBRANE PERMEABILITY; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG EFFECT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROGEN BOND; MASS SPECTROMETRY; METHODOLOGY; MICROWAVE RADIATION; MOLECULAR GENETICS; PHYSIOLOGY; SYNTHESIS; ANALOGS AND DERIVATIVES; DRUG EFFECTS; PROCEDURES;

AMINO ACID SEQUENCE; CELL MEMBRANE PERMEABILITY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMBINATORIAL CHEMISTRY TECHNIQUES; DEXAMETHASONE; HUMANS; HYDROGEN BONDING; MICROWAVES; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC; PEPTOIDS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 77952171246     PISSN: 15204766     EISSN: 15204774     Source Type: Journal    
DOI: 10.1021/cc9001857     Document Type: Article

References (37)

1. Hamada, Y. and Shioiri, T. Chem. Rev. 2005, 105, 4441-4482
2. Millward, S. W., Fiacco, S., Austin, R. J., and Roberts, R. W. ACS Chem. Biol. 2007, 2, 625-634
3. Zhang, Y., Zhou, S., Wavreille, A. S., DeWille, J., and Pei, D. J. Comb. Chem. 2008, 10, 247-255
4. George, E. A., Novick, R. P., and Muir, T. W. J. Am. Chem. Soc. 2008, 130, 4914-4924
5. Kohli, R. M., Walsh, C. T., and Burkart, M. D. Nature 2002, 418, 658-661
6. Tavassoli, A. and Benkovic, S. J. Angew. Chem., Int. Ed. 2005, 44, 2760-2763
7. Hruby, V. J., Al-Obeidi, F., and Kazmierski, W. Biochem. J. 1990, 268, 249-262
8. Rizo, J. and Gierasch, L. M. Annu. Rev. Biochem. 1992, 61, 387-418
9. March, D. R., Abbenante, G., Bergman, D. A., Brinkworth, R. I., Wickramasinghe, W., Begun, J., Martin, J. L., and Fairlie, D. P. J. Am. Chem. Soc. 1996, 118, 3375-3379
10. Gudmundsson, O. S., Pauletti, G. M., Wang, W., Shan, D., Zhang, H., Wang, B., and Borchardt, R. T. Pharm. Res. 1999, 16, 7-15
11. Di, L., Kerns, E. H., and Carter, G. T. Curr. Pharm. Design 2009, 15, 2184-2194
12. Mälkiä, Y. A., Murtomäki, L., Urtti, A., and Kontturi, K. Eur. J. Pharm. Sci. 2004, 23, 13-47
13. Veber, D. F., Johnson, S. R., Cheng, H. Y., Smith, B. R., Ward, K. W., and Kopple, K. D. J. Med. Chem. 2002, 45, 2615-2623
14. Goodwin, J. T., Conradi, R. A., Ho, N. F. H., and Burton, P. S. J. Med. Chem. 2001, 44, 3721-3729
15. Kansy, M., Senner, F., and Gubernator, K. J. Med. Chem. 1998, 41, 1007-1010
16. Lipinski, C. A., Lombardo, F., Dominy, B. W., and Feeney, P. J. Adv. Drug Delivery Rev. 1997, 23, 3-25
17. Burton, P. S., Conradi, R. A., Ho, N. F. H., Hilgers, A. R., and Borchardt, R. T. J. Pharm. Sci. 1996, 85, 1336-1340
18. Rezai, T., Bock, J. E., Zhou, M. V., Kalyanaraman, C., Lokey, R. S., and Jacobson, M. P. J. Am. Chem. Soc. 2006, 128, 14073-14080
19. Rezai, T., Yu, B., Millhauser, G. L., Jacobson, M. P., and Lokey, R. S. J. Am. Chem. Soc. 2006, 128, 2510-2511
20. Gudmundsson, O. S., Jois, S. D. S., Vander Velde, D. G., Siahaan, T. J., Wang, B., and Borchardt, R. T. J. Peptide Res. 1999, 53, 383-392
21. Kwon, Y. U. and Kodadek, T. Chem. Biol. 2007, 14, 671-677
22. Yu, P., Liu, B., and Kodadek, T. Nat. Biotechnol. 2005, 23, 746-751
23. Kwon, Y. U. and Kodadek, T. J. Am. Chem. Soc. 2007, 129, 1508-1509
24. Tan, N. C., Yu, P., Kwon, Y. U., and Kodadek, T. Bioorg. Med. Chem. Lett. 2008, 16, 5853-5861
25. Zuckermann, R. N., Kerr, J. M., Kent, S. B. H., and Moos, W. H. J. Am. Chem. Soc. 1992, 114, 10646-10647
26. Olivos, H. J., Alluri, P. G., Reddy, M. M., Salony, D., and Kodadek, T. Org. Lett. 2002, 4, 4057-4059
27. Miller, S. M., Simmon, R. J., Ng, S., Zuckermann, R. N., Kerr, J. M., and Moos, W. H. Drug Dev. Res. 1995, 35, 20-32
28. Masip, I., Pérez-Payá, E., and Messeguer, A. Comb. Chem. High Throughput Screening 2005, 8, 235-239
29. Udugamasooriya, D. G., Dineen, S. P., Brekken, R. A., and Kodadek, T. J. Am. Chem. Soc. 2008, 130, 5744-5752
30. Lim, H. S., Arther, C. T., and Kodadek, T. J. Am. Chem. Soc. 2007, 129, 7750-7751
31. Alluri, P. G., Reddy, M. M., Bachhawat-Sikder, K., Olivos, H. J., and Kodadek, T. J. Am. Chem. Soc. 2003, 125, 13995-14004
32. Kwon, Y. U. and Kodadek, T. Chem. Commun. 2008, 5704-5706
33. Shin, S. B., Yoo, B., Todaro, L. J., and Kirshenbaum, K. J. Am. Chem. Soc. 2007, 129, 3218-3225
34. Yoo, B. and Kirshenbaum, K. Curr. Opin. Chem. Biol. 2008, 12, 714-721
35. Fowler, S. A. and Blackwell, H. E. Org. Biomol. Chem. 2009, 7, 1508-1524
36. Liu, B. and Kodadek, T. J. Med. Chem. 2009, 52, 4604-4612
37. Abbreviation: Fmoc, 9-fluorenylmethyloxycarbonyl; Dpr, diaminopropionic acid; ivDde, 1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl; PyBOP, benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluoro-phosphonate; 2-PhiPr, 2-phenylisopropyl; DIC, N, N′ -diisopropylcarbodiimide; SDex-COOH, dexamethasone-21-thiopropionic acid; TFA, trifluoroacetic acid; HOBt, 1-hydroxybenzotriazole; Trt, trityl; Mtt, 4-methyltrityl; HATU, 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate