Stabilization of peptides for intracellular applications by phosphoramidate-linked polyethylene glycol chains

Angewandte Chemie - International Edition

Volumn 52, Issue 45, 2013, Pages 11920-11924

  Nischan, Nicole ^a,b,c   Chakrabarti, Alokta ^d   Serwa, Remigiusz A ^a,b,c   Bovee Geurts, Petra H M ^d   Brock, Roland ^d   Hackenberger, Christian P R ^a,b,c  

^a LEIBNIZ INSTITUT FÜR MOLEKULARE PHARMAKOLOGIE   (Germany)

^b HUMBOLDT UNIVERSITY   (Germany)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

^d RADBOUD UNIVERSITY MEDICAL CENTER   (Netherlands)

Author keywords

apoptosis; PEGylation; peptides; proteolysis; Staudinger phosphite reaction

Indexed keywords

APOPTOTIC ACTIVITY; BIOLOGICAL PROBES; INTRACELLULAR DISTRIBUTION; JURKAT CELL; LIMITED ATTENTIONS; PEGYLATED; PEGYLATION; STAUDINGER-PHOSPHITE REACTION;

CELL DEATH; ENZYME ACTIVITY; PROTEOLYSIS;

PEPTIDES;

AMIDE; MACROGOL DERIVATIVE; PEPTIDE; PHOSPHORAMIDIC ACID; PHOSPHORIC ACID;

APOPTOSIS; ARTICLE; CHEMISTRY; HUMAN; JURKAT CELL LINE; PEGYLATION; PROTEIN DEGRADATION; STAUDINGER-PHOSPHITE REACTION;

APOPTOSIS; PEGYLATION; PEPTIDES; PROTEOLYSIS; STAUDINGER-PHOSPHITE REACTION;

AMIDES; APOPTOSIS; HUMANS; JURKAT CELLS; PEPTIDES; PHOSPHORIC ACIDS; POLYETHYLENE GLYCOLS; PROTEOLYSIS;

EID: 84882973531     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201303467     Document Type: Article

References (39)

1. M. Werle, A. Bernkop-Schnuerch, Amino Acids 2006, 30, 351-367.
2. F. M. Veronese, G. Pasut, Drug Discovery Today 2005, 10, 1451-1458
3. J. M. Harris, R. B. Chess, Nat. Rev. Drug Discovery 2003, 2, 214-221
4. K. Bellmann-Sickert, C. E. Elling, A. N. Madsen, P. B. Little, K. Lundgren, L.-O. Gerlach, R. Bergmann, B. Holst, T. W. Schwartz, A. G. Beck-Sickinger, J. Med. Chem. 2011, 54, 2658-2667.
5. C. Monfardini, O. Schiavon, P. Caliceti, M. Morpurgo, J. M. Harris, F. M. Veronese, Bioconjugate Chem. 1995, 6, 62-69
6. C. J. Fee, Biotechnol. Bioeng. 2007, 98, 725-731.
7. M. Hamidi, A. Azadi, P. Rafiei, Drug Delivery 2006, 13, 399-409.
8. R. Duncan, Adv. Drug Delivery Rev. 2009, 61, 1131-1148.
9. A. Skerra, I. Theobald, M. Schlapschy, Technische Universität München, WO2008155134(A1), 2008.
10. Y. Cheng, L. Zhao, Y. Li, T. Xu, Chem. Soc. Rev. 2011, 40, 2673-2703
11. H. Yu, Y. Nie, C. Dohmen, Y. Li, E. Wagner, Biomacromolecules 2011, 12, 2039-2047.
12. G. Pasut, F. M. Veronese, Adv. Polym. Sci. 2006, 192, 95-134.
13. F. M. Veronese, Biomaterials 2001, 22, 405-417.
14. B. Peschke, M. Zundel, S. Bak, T. R. Clausen, N. Blume, A. Pedersen, F. Zaragoza, K. Madsen, Bioorg. Med. Chem. 2007, 15, 4382-4395
15. R. E. Connor, K. Piatkov, A. Varshavsky, D. A. Tirrell, ChemBioChem 2008, 9, 366-369.
16. R. L. M. Teeuwen, S. S. van-Berkel, T. H. H. van-Dulmen, S. Schoffelen, S. A. Meeuwissen, H. Zuilhof, F. A. de-Wolf, J. C. M. van-Hest, Chem. Commun. 2009, 4022-4024.
17. C. S. Cazalis, C. A. Haller, L. Sease-Cargo, E. L. Chaikof, Bioconjugate Chem. 2004, 15, 1005-1009
18. A. Deiters, T. A. Cropp, D. Summerer, M. Mukherji, P. G. Schultz, Bioorg. Med. Chem. Lett. 2004, 14, 5743-5745
19. M. F. Debets, S. S. van-Berkel, S. Schoffelen, F. P. J. T. Rutjes, J. C. M. van-Hest, F. L. van-Delft, Chem. Commun. 2010, 46, 97-99.
20. R. Serwa, P. Majkut, B. Horstmann, J.-M. Swiecicki, M. Gerrits, E. Krause, C. P. R. Hackenberger, Chem. Sci. 2010, 1, 596-602
21. R. Serwa, I. Wilkening, S. G. Del, M. Muehlberg, I. Claussnitzer, C. Weise, M. Gerrits, C. P. R. Hackenberger, Angew. Chem. 2009, 121, 8382-8387
22. Angew. Chem. Int. Ed. 2009, 48, 8234-8239
23. V. Böhrsch, T. Mathew, M. Zieringer, M. R. J. Vallée, L. M. Artner, J. Dernedde, R. Haag, C. P. R. Hackenberger, Org. Biomol. Chem. 2012, 10, 6211-6216
24. M.-R.-J. Vallée, L.-M. Artner, J. Dernedde, C.-P.-R. Hackenberger, Angew. Chem. 2013, DOI:; Angew. Chem. Int. Ed. 2013, DOI:.
25. I. R. Ruttekolk, A. Chakrabarti, M. Richter, F. Duchardt, H. Glauner, W. P. R. Verdurmen, J. Rademann, R. Brock, Mol. Pharmacol. 2011, 79, 692-700.
26. J. Varghese, N. S. Khandre, A. Sarin, Apoptosis 2003, 8, 363-370.
27. A. Letai, M. C. Bassik, L. D. Walensky, M. D. Sorcinelli, S. Weiler, S. J. Korsmeyer, Cancer Cell 2002, 2, 183-192
28. R. Elkholi, K. V. Floros, J. E. Chipuk, Genes Cancer 2011, 2, 523-537.
29. M. Richter, A. Chakrabarti, I. R. Ruttekolk, B. Wiesner, M. Beyermann, R. Brock, J. Rademann, Chem. Eur. J. 2012, 18, 16708-16715.
30. L. D. Walensky, A. L. Kung, I. Escher, T. J. Malia, S. Barbuto, R. D. Wright, G. Wagner, G. L. Verdine, S. J. Korsmeyer, Science 2004, 305, 1466-1470.
31. J. L. Wang, Z. J. Zhang, S. Choksi, S. Shan, Z. Lu, C. M. Croce, E. S. Alnemri, R. Korngold, Z. Huang, Cancer Res. 2000, 60, 1498-1502.
32. P. Chandna, J. J. Khandare, E. Ber, L. Rodriguez-Rodriguez, T. Minko, Pharm. Res. 2010, 27, 2296-2306
33. P. Chandna, M. Saad, Y. Wang, E. Ber, J. Khandare, A. A. Vetcher, V. A. Soldatenkov, T. Minko, Mol. Pharm. 2007, 4, 668-678.
34. R. Fischer, O. Mader, G. Jung, R. Brock, Bioconjugate Chem. 2003, 14, 653-660.
35. R. A. Serwa, J.-M. Swiecicki, D. Homann, C. P. R. Hackenberger, J. Pept. Sci. 2010, 16, 563-567.
36. Y. Bae, K. Kataoka, Adv. Drug Delivery Rev. 2009, 61, 768-784.
37. I. R. Ruttekolk, J. J. Witsenburg, H. Glauner, P. H. Bovee-Geurts, E. S. Ferro, W. P. Verdurmen, R. Brock, Mol. Pharm. 2012, 9, 1077-1086.
38. J. Yang, M. H. Shen, Methods Mol. Biol. 2006, 325, 59-66.
39. P. Bailon, A. Palleroni, C. A. Schaffer, C. L. Spence, W. J. Fung, J. E. Porter, G. K. Ehrlich, W. Pan, Z. X. Xu, M. W. Modi, A. Farid, W. Berthold, M. Graves, Bioconjugate Chem. 2001, 12, 195-202.