Chemical synthesis of cell-permeable apoptotic peptides from in vivo produced proteins

Bioconjugate Chemistry

Volumn 22, Issue 9, 2011, Pages 1763-1767

  Fricke, Thomas ^a   Mart, Robert J ^a   Watkins, Catherine L ^b,c   Wiltshire, Marie ^b   Errington, Rachel J ^b   Smith, Paul J ^b   Jones, Arwyn T ^c   Allemann, Rudolf K ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b CARDIFF UNIVERSITY SCHOOL OF MEDICINE   (United Kingdom)

^c CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOSYNTHESIS; CELL DEATH;

APOPTOTIC; CELL-PERMEABLE; CYANOGEN BROMIDE; FACILE MODIFICATIONS; GENE PRODUCTS; HOMOSERINE LACTONES; IN-VIVO; METHIONINE; SOLID PHASE PEPTIDE SYNTHESIS; VIVO METHODS;

PEPTIDES;

ANTILEUKEMIC AGENT; CYTOCHROME C; FLUORESCENT DYE; HOMOSERINE; LACTONE; METHIONINE; OCTA ARGININE; PEPTIDE; PROPARGYLAMINE; PROTEIN BAK; PROTEIN BAX; PROTEIN BCL XL; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CELL TRANSPORT; HUMAN; HUMAN CELL; IN VIVO STUDY; MITOCHONDRION; MYELOID LEUKEMIA; PEPTIDE SYNTHESIS; PROTEIN PROTEIN INTERACTION;

BACTERIA (MICROORGANISMS);

EID: 80053071355     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc200338u     Document Type: Article

References (43)

1. Fletcher, S. and Hamilton, A. D. (2006) Targeting protein-protein interactions by rational design: mimicry of protein surfaces J. R. Soc. Interface 3, 215
2. Vlieghe, P., Lisowski, V., Martinez, J., and Khrestchatisky, M. (2010) Synthetic therapeutic peptides: science and market Drug Discovery Today 15, 40
3. Che, Y., Brooks, B. R., and Marshall, G. R. (2007) Protein recognition motifs: design of peptidomimetics of helix surfaces Biopolymers 86, 288
4. Robinson, J. A. (2008) β-hairpin peptidomimetics: design, structures and biological activities Acc. Chem. Res. 41, 1278
5. Williamson, M. P. and Sutcliffe, M. J. (2010) Protein-protein interactions Biochem. Soc. Trans. 38, 875
6. Vassilev, L. T., Vu, B. T., Graves, B., Carvajal, D., Podlaski, F., Filipovic, Z., Kong, N., Kammlott, U., Lukacs, C., Klein, C., Fotouhi, N., and Liu, E. A. (2004) In vivo activation of the p53 pathway by small-molecule antagonists of MDM2 Science 303, 844
7. Shangary, S., Qin, D. G., McEachern, D., Liu, M. L., Miller, R. S., Qiu, S., Nikolovska-Coleska, Z., Ding, K., Wang, G. P., Chen, J. Y., Bernard, D., Zhang, J., Lu, Y. P., Gu, Q. Y., Shah, R. B., Pienta, K. J., Ling, X. L., Kang, S. M., Guo, M., Sun, Y., Yang, D. J., and Wang, S. M. (2008) Temporal activation of p53 by a specific MDM2 inhibitor is selectively toxic to tumors and leads to complete tumor growth inhibition Proc. Natl. Acad. Sci. U.S.A. 105, 3933
8. Tse, C., Shoemaker, A. R., Adickes, J., Anderson, M. G., Chen, J., Jin, S., Johnson, E. F., Marsh, K. C., Mitten, M. J., Nimmer, P., Roberts, L., Tahir, S. K., Mao, Y., Yang, X. F., Zhang, H. C., Fesik, S., Rosenberg, S. H., and Elmore, S. W. (2008) A potent and orally bioavailable Bcl-2 family inhibitor Cancer Res. 68, 3421
9. Stewart, M. L., Fire, E., Keating, A. E., and Walensky, L. D. (2010) The MCL-1 BH3 helix is an exclusive MCL-1 inhibitor and apoptosis sensitizer Nat. Chem. Biol. 6, 595
10. Bird, G. H., Madani, N., Perry, A. F., Princiotto, A. M., Supko, J. G., He, X., Gavathiotis, E., Sodroski, J. G., and Walensky, L. D. (2010) Hydrocarbon double-stapling remedies the proteolytic instability of a lengthy peptide therapeutic Proc. Natl. Acad. Sci. U.S.A. 107, 14093
11. He, Y., Cheng, J., Lu, H., Li, J., Hu, J., Qi, Z., Liu, Z., Jiang, S., and Dai, Q. (2008) Potent HIV fusion inhibitors against Enfuvirtide-resistant HIV-1 strains Proc. Natl. Acad. Sci. U.S.A. 105, 16332
12. Moellering, R. E., Cornejo, M., Davis, T. N., Del Bianco, C., Aster, J. C., Blacklow, S. C., Kung, A. L., Gilliland, D. G., Verdine, G. L., and Bradner, J. E. (2009) Direct inhibition of the NOTCH transcription factor complex Nature 462, 182
13. Therapeutic peptides in clinical study in 2000-07 nearly doubled 1990s rate (2009) Tufts CSDD Impact Report, Tufts Center for the Study of Drug Development, Tuft University, Vol 11.
14. Frankel, A. D. and Pabo, C. O. (1988) Cellular uptake of the tat protein from human immunodeficiency virus Cell 55, 1189
15. Green, M. and Loewenstein, P. M. (1988) Autonomous functional domains of chemically synthesized human immunodeficiency virus tat trans-activator protein Cell 55, 1179
16. Joliot, A., Pernelle, C., Deagostini-Bazin, H., and Prochiantz, A. (1991) Antennapedia homeobox peptide regulates neural morphogenesis Proc. Natl. Acad. Sci. U.S.A. 88, 1864
17. Wender, P. A., Mitchell, D. J., Pattabiraman, K., Pelkey, E. T., Steinman, L., and Rothbard, J. B. (2000) The design, synthesis, and evaluation of molecules that enable or enhance cellular uptake: peptoid molecular transporters Proc. Natl. Acad. Sci. U.S.A. 97, 13003
18. Stewart, K. M., Horton, K. L., and Kelley, S. O. (2008) Cell-penetrating peptides as delivery vehicles for biology and medicine Org. Biomol. Chem. 6, 2242
19. Nakase, I., Takeuchi, T., Tanaka, G., and Futaki, S. (2008) Methodological and cellular aspects that govern the internalization mechanisms of arginine-rich cell-penetrating peptides Adv. Drug Delivery Rev. 60, 598
20. Futaki, S., Nakase, I., Tadokoro, A., Takeuchi, T., and Jones, A. T. (2007) Arginine-rich peptides and their internalization mechanisms Biochem. Soc. Trans. 35, 784
21. Chugh, A., Eudes, F., and Shim, Y. S. (2010) Cell-penetrating peptides: nanocarrier for macromolecule delivery in living cells Iubmb. Life 62, 183
22. Sawant, R. and Torchilin, V. (2010) Intracellular transduction using cell-penetrating peptides Mol. Biosyst. 6, 628
23. Kuliopulos, A. and Walsh, C. T. (1994) Production, purification, and cleavage of tandem repeats of recombinant peptides J. Am. Chem. Soc. 116, 4599
24. Fairlie, W. D., Uboldi, A. D., De Souza, D. P., Hemmings, G. J., Nicola, N. A., and Baca, M. (2002) A fusion protein system for the recombinant production of short disulfide-containing peptides Protein Expr. Purif. 26, 171
25. Yonemoto, I. T., Wood, M. R., Balch, W. E., and Kelly, J. W. (2009) A general strategy for the bacterial expression of amyloidogenic peptides using BCL-XL-1/2 fusions Protein Sci. 18, 1978
26. Gross, E. and Witkop, B. (1961) Selective cleavage of methionyl peptide bonds in ribonuclease with cyanogen bromide J. Am. Chem. Soc. 83, 1510
27. Shi, T., Weerasekera, R., Yan, C., Reginold, W., Ball, H., Kislinger, T., and Schmitt-Ulms, G. (2009) Method for the affinity purification of covalently linked peptides following cyanogen bromide cleavage of proteins Anal. Chem. 81, 9885
28. Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click chemistry: Diverse chemical function from a few good reactions Angew. Chem., Int. Ed. 40, 2004
29. Bock, V. D., Hiemstra, H., and van Maarseveen, J. H. (2005) Cu-I-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective Eur. J. Org. Chem. 51
30. Chittenden, T., Harrington, E. A., O'Connor, R., Flemington, C., Lutz, R. J., Evan, G. I., and Guild, B. C. (1995) Induction of apoptosis by the Bcl-2 homologue Bak Nature 374, 733
31. Rosen, K., Rak, J., Jin, J., Kerbel, R. S., Newman, M. J., and Filmus, J. (1998) Downregulation of the pro-apoptotic protein Bak is required for the ras-induced transformation of intestinal epithelial cells Curr. Biol. 8, 1331
32. Neise, D., Graupner, V., Gillissen, B. F., Daniel, P. T., Schulze-Osthoff, K., Janicke, R. U., and Essmann, F. (2008) Activation of the mitochondrial death pathway is commonly mediated by a preferential engagement of Bak Oncogene 27, 1387
33. Kneissl, S., Loveridge, E. J., Williams, C., Crump, M. P., and Allemann, R. K. (2008) Photocontrollable peptide-based switches target the anti-apoptotic protein Bcl-xL ChemBioChem 9, 3046
34. Sattler, M., Liang, H., Nettesheim, D., Meadows, R. P., Harlan, J. E., Eberstadt, M., Yoon, H. S., Shuker, S. B., Chang, B. S., Minn, A. J., Thompson, C. B., and Fesik, S. W. (1997) Structure of Bcl-xL-Bak peptide complex: recognition between regulators of apoptosis Science 275, 983
35. Adams, J. M. and Cory, S. (2007) The Bcl-2 apoptotic switch in cancer development and therapy. Structure of Bcl-xL-Bak peptide complex: recognition between regulators of apoptosis Oncogene 26, 1324
36. Li, R., Boehm, A. L., Miranda, M. B., Shangary, S., Grandis, J. R., and Johnson, D. E. (2007) Targeting antiapoptotic Bcl-2 family members with cell-permeable BH3 peptides induces apoptosis signaling and death in head and neck squamous cell carcinoma cells Neoplasia 9, 801
37. Holinger, E. P., Chittenden, T., and Lutz, R. J. (1999) Bak BH3 peptides antagonize Bcl-xL function and induce apoptosis through cytochrome c-independent activation of caspases J. Biol. Chem. 274, 13298
38. Albarran, B., Hoffman, A. S., and Stayton, P. S. (2011) Efficient intracellular delivery of a pro-apoptotic peptide with a pH-responsive carrier React. Funct. Polym. 71, 261
39. King, M. A., Eddaoudi, A., and Davies, D. C. (2007) A comparison of three flow cytometry methods for evaluating mitochondrial damage during staurosporine-induced apoptosis in Jurkat cells Cytom. Part A 71A, 668
40. Haag, P., Viktorsson, K., Lindberg, M. L., Kanter, L., Lewensohn, R., and Stenke, L. (2009) Deficient activation of Bak and Bax confers resistance to gemtuzumab ozogamicin-induced apoptotic cell death in AML Exp. Hematol. 37, 755
41. Campos, L., Sabido, O., Rouault, J. P., and Guyotat, D. (1994) Effects of BCL-2 antisense oligodeoxynucleotides on in vitro proliferation and survival of normal marrow progenitors and leukemic cells Blood 84, 595
42. King, M. A., Eddaoudi, A., and Davies, D. C. (2007) A comparison of three flow cytometry methods for evaluating mitochondrial damage during staurosporine-induced apoptosis in Jurkat cells Cytometry A 71, 668
43. Smith, P. J., Blunt, N., Wiltshire, M., Hoy, T., Teesdale-Spittle, P., Craven, M. R., Watson, J. V., Amos, W. B., Errington, R. J., and Patterson, L. H. (2000) Characteristics of a novel deep red/infrared fluorescent cell-permeant DNA probe, DRAQ5, in intact human cells analyzed by flow cytometry, confocal and multiphoton microscopy Cytometry 40, 280