Functional consequences of retro-inverso isomerization of a miniature protein inhibitor of the p53-MDM2 interaction

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 14, 2013, Pages 4045-4050

  Li, Chong ^a   Zhan, Changyou ^b   Zhao, Le ^b   Chen, Xishan ^c   Lu, Wei Yue ^c   Lu, Wuyuan ^b,c  

^a SOUTHWEST UNIVERSITY   (China)

^b UNIVERSITY OF MARYLAND SCHOOL OF MEDICINE   (United States)

^c FUDAN UNIVERSITY   (China)

Author keywords

Apamin; d Peptide; MDM2; MDMX; p53; Retro inverso peptide; Stingin

Indexed keywords

PROTEIN INHIBITOR; PROTEIN MDM2; PROTEIN P53; STINGIN; UNCLASSIFIED DRUG;

ALPHA HELIX; AMINO TERMINAL SEQUENCE; ARTICLE; BINDING AFFINITY; CARBOXY TERMINAL SEQUENCE; COMPLEX FORMATION; CONTROLLED STUDY; DISULFIDE BOND; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENANTIOMER; FLUORESCENCE POLARIZATION; ISOMERIZATION; PROTEIN BINDING; PROTEIN FOLDING; PROTEIN FUNCTION; PROTEIN PROTEIN INTERACTION; SURFACE PLASMON RESONANCE;

CIRCULAR DICHROISM; HUMANS; ISOMERISM; PEPTIDES; PROTEIN BINDING; PROTO-ONCOGENE PROTEINS C-MDM2; TUMOR SUPPRESSOR PROTEIN P53;

EID: 84879023357     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.04.039     Document Type: Article

References (54)

1. C. Li, M. Pazgier, J. Li, C. Li, M. Liu, G. Zou, Z. Li, J. Chen, S.G. Tarasov, W.-Y. Lu, and W. Lu J. Biol. Chem. 285 2010 19572
2. M.M. Shemyakin, Y.A. Ovchinnikov, and V.T. Ivanov Angew. Chem., Int. Ed. Engl. 8 1969 492
3. M. Goodman, and M. Chorev Acc. Chem. Res. 12 1979 1
4. M.H. Van Regenmortel, and S. Muller Curr. Opin. Biotechnol. 9 1998 377
5. D.T. Nair, K.J. Kaur, K. Singh, P. Mukherjee, D. Rajagopal, A. George, V. Bal, S. Rath, K.V.S. Rao, and D.M. Salunke J. Immunol. 170 2003 1362
6. P.M. Fischer Curr. Protein Pept. Sci. 4 2003 339
7. C. Li, M. Pazgier, M. Liu, W.-Y. Lu, and W. Lu Angew. Chem., Int. Ed. Engl. 48 2009 8712
8. E. Habermann Science 177 1972 314
9. M. Stocker Nat. Rev. Neurosci. 5 2004 758
10. D. Le-Nguyen, L. Chiche, F. Hoh, M.F. Martin-Eauclaire, C. Dumas, Y. Nishi, Y. Kobayashi, and A. Aumelas Biopolymers 86 2007 447
11. A.J. Levine, and M. Oren Nat. Rev. Cancer 9 2009 749
12. J.-C.W. Marine, M.A. Dyer, and A.G. Jochemsen J. Cell Sci. 120 2007 371
13. F. Toledo, and G.M. Wahl Nat. Rev. Cancer 6 2006 909
14. M. Wade, Y.V. Wang, and G.M. Wahl Trends Cell Biol. 20 2010 299
15. K.H. Vousden, and C. Prives J. Cell Sci. 137 2009 413
16. M. Wade, Y.-C. Li, and G.M. Wahl Nat. Rev. Cancer 13 2012 83
17. S. Shangary, and S. Wang Annu. Rev. Pharmacol. Toxicol. 49 2009 223
18. C.J. Brown, S. Lain, C.S. Verma, A.R. Fersht, and D.P. Lane Nat. Rev. Cancer 9 2009 862
19. L.T. Vassilev, B.T. Vu, B. Graves, D. Carvajal, F. Podlaski, Z. Filipovic, N. Kong, U. Kammlott, C. Lukacs, C. Klein, N. Fotouhi, and E.A. Liu Science 303 2004 844
20. S. Shangary, D. Qin, D. McEachern, M. Liu, R.S. Miller, S. Qiu, Z. Nikolovska-Coleska, K. Ding, G. Wang, J. Chen, D. Bernard, J. Zhang, Y. Lu, Q. Gu, R.B. Shah, K.J. Pienta, X. Ling, S. Kang, M. Guo, Y. Sun, D. Yang, and S. Wang Proc. Natl. Acad. Sci. U.S.A. 105 2008 3933
21. C. Zhan, and W. Lu Curr. Pharm. Des. 17 2011 603
22. J.A. Robinson Acc. Chem. Res. 41 2008 1278
23. T.N. Schumacher, L.M. Mayr, D.L. Minor, M.A. Milhollen, M.W. Burgess, and P.S. Kim Science 271 1996 1854
24. D.M. Eckert, V.N. Malashkevich, L.H. Hong, P.A. Carr, and P.S. Kim J. Cell Sci. 99 1999 103
25. P.E. Dawson, and S.B. Kent Annu. Rev. Biochem. 69 2000 923
26. P.E. Dawson, T.W. Muir, I. Clark-Lewis, and S.B. Kent Science 266 1994 776
27. M. Liu, C. Li, M. Pazgier, C. Li, Y. Mao, Y. Lv, B. Gu, G. Wei, W. Yuan, C. Zhan, W.-Y. Lu, and W. Lu Proc. Natl. Acad. Sci. U.S.A. 107 2010 14321
28. M. Liu, M. Pazgier, C. Li, W. Yuan, C. Li, and W. Lu Angew. Chem., Int. Ed. Engl. 49 2010 3649
29. C. Zhan, L. Zhao, X. Wei, X. Wu, X. Chen, W. Yuan, W.-Y. Lu, M. Pazgier, and W. Lu J. Med. Chem. 55 2012 6237
30. K. Sakurai, H.S. Chung, and D. Kahne J. Am. Chem. Soc. 126 2004 16288
31. M. Schnölzer, P. Alewood, A. Jones, D. Alewood, and S.B. Kent Int. J. Pept. Protein Res. 40 1992 180
32. Z. Wu, D.M. Hoover, D. Yang, C. Boulègue, F. Santamaria, J.J. Oppenheim, J. Lubkowski, and W. Lu Proc. Natl. Acad. Sci. U.S.A. 100 2003 8880
33. X. Li, G. Zou, W. Yuan, and W. Lu J. Biol. Chem. 282 2007 5318
34. C.N. Pace, F. Vajdos, L. Fee, G. Grimsley, and T. Gray Protein Sci. 4 1995 2411
35. E.A. Harker, D.S. Daniels, D.A. Guarracino, and A. Schepartz Bioorg. Med. Chem. 17 2009 2038
36. T. Wohland, K. Friedrich, R. Hovius, and H. Vogel Biochemistry 38 1999 8671
37. P.H. Kussie, S. Gorina, V. Marechal, B. Elenbaas, J. Moreau, A.J. Levine, and N.P. Pavletich Science 274 1996 948
38. M. Pazgier, M. Liu, G. Zou, W. Yuan, C. Li, C. Li, J. Li, J. Monbo, D. Zella, S.G. Tarasov, and W. Lu Proc. Natl. Acad. Sci. U.S.A. 106 2009 4665
39. C. Zhan, K. Varney, W. Yuan, L. Zhao, and W. Lu J. Am. Chem. Soc. 134 2012 6855
40. D.M. Jameson, and J.A. Ross Chem. Rev. 110 2010 2685
41. D.M. Jameson, and S.E. Seifried Methods 19 1999 222
42. C. Li, M. Pazgier, C. Li, W. Yuan, M. Liu, G. Wei, W.-Y. Lu, and W. Lu J. Mol. Biol. 398 2010 200
43. J. Rai Chem. Biol. Drug Des. 70 2007 552
44. I. Pal-Bhowmick, R.P. Pandey, G.K. Jarori, S. Kar, and D. Sahal Biochem. Biophys. Res. Commun. 364 2007 608
45. R.T. Raines Chem. Rev. 98 1998 1045
46. G. Guichard, N. Benkirane, G. Zeder-Lutz, M.H. Van Regenmortel, J.P. Briand, and S. Muller Proc. Natl. Acad. Sci. U.S.A. 91 1994 9765
47. R.M. Freidinger, and D.F. Veber J. Am. Chem. Soc. 101 1979 6129
48. J.M. McDonnell, A.J. Beavil, G.A. Mackay, B.A. Jameson, R. Korngold, H.J. Gould, and B.J. Sutton Nat. Struct. Biol. 3 1996 419
49. J.M. McDonnell, D. Fushman, S.M. Cahill, B.J. Sutton, and D. Cowburn J. Am. Chem. Soc. 119 1997 5321
50. R.C. Milton, S.C. Milton, and S.B. Kent Science 256 1992 1445
51. G. Wei, E. de Leeuw, M. Pazgier, W. Yuan, G. Zou, J. Wang, B. Ericksen, W.-Y. Lu, R.I. Lehrer, and W. Lu J. Biol. Chem. 284 2009 29180
52. D. Gerber, and Y. Shai J. Mol. Biol. 322 2002 491
53. K.A. Olszewski, A. Kolinski, and J. Skolnick Protein Eng. 9 1996 5
54. E. Lacroix, A.R. Viguera, and L. Serrano Fold Des. 3 1998 79