Substrate-initiated synthesis of cell-penetrating poly(disulfide)s

Journal of the American Chemical Society

Volumn 135, Issue 6, 2013, Pages 2088-2091

  Bang, Eun Kyoung ^a   Gasparini, Giulio ^a   Molinard, Guillaume ^a   Roux, Aurélien ^a   Sakai, Naomi ^a   Matile, Stefan ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CELLULAR UPTAKE; DITHIOTHREITOL; FLUORESCENCE RESONANCE ENERGY TRANSFER; FLUOROGENICS; GUANIDINIUM CATIONS; LIPOIC ACIDS; REDUCTIVE DEPOLYMERIZATION; ROOM TEMPERATURE; SURFACE INITIATED POLYMERIZATION; TRANSPORT ACTIVITY;

CATIONIC POLYMERIZATION; ENERGY TRANSFER; SULFUR COMPOUNDS;

SUBSTRATES;

CATION; DISULFIDE; DITHIOTHREITOL; GUANIDINE; POLY(DISULFIDE) DERIVATIVE; THIOCTIC ACID; UNCLASSIFIED DRUG;

ARTICLE; FLUORESCENCE RESONANCE ENERGY TRANSFER; GEL PERMEATION CHROMATOGRAPHY; PH; POLYMERIZATION; REACTION TIME; ROOM TEMPERATURE;

DISULFIDES; FLUORESCENCE RESONANCE ENERGY TRANSFER; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE; POLYMERIZATION; POLYMERS; TEMPERATURE;

EID: 84873650354     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja311961k     Document Type: Article

References (45)

1. Tezgel, A. O.; Gonzalez-Perez, G.; Telfer, J. C.; Osborne, B. A.; Minter, L. M.; Tew, G. N. Mol. Ther. 2013, 21, 201-209
2. Som, A.; Reuter, A.; Tew, G. N. Angew. Chem., Int. Ed. 2012, 51, 980-983
3. Appelbaum, J. S.; LaRochelle, J. R.; Smith, B. A.; Balkin, D. M.; Holub, J. M.; Schepartz, A. Chem. Biol. 2012, 19, 819-830
4. Ornelas-Megiatto, C.; Wich, P. R.; Fréchet, J. M. J. Am. Chem. Soc. 2012, 134, 1902-1905
5. Treat, N. J.; Smith, D.; Teng, C.; Flores, J. D.; Abel, B. A.; York, A. W.; Huang, F.; McCormick, C. L. ACS Macro Lett. 2012, 1, 100-104
6. Budhathoki-Uprety, J.; Peng, L.; Melander, C.; Novak, B. M. ACS Macro Lett. 2012, 1, 370-374
7. Song, A.; Walker, S. G.; Parker, K. A.; Sampson, N. S. ACS Chem. Biol. 2011, 6, 590-599
8. Tezgel, A. O.; Telfer, J. C.; Tew, G. N. Biomacromolecules 2011, 12, 3078-3083
9. Gorska, K.; Manicardi, A.; Barluenga, S.; Winssinger, N. Chem. Commun. 2011, 47, 4364-4366
10. Dix, A. V.; Fischer, L.; Sarrazin, S.; Redgate, C. P. H.; Esko, J. D.; Tor, Y. ChemBioChem 2010, 11, 2302-2310
11. Inomata, K.; Ohno, A.; Tochio, H.; Isogai, S.; Tenno, T.; Nakase, I.; Takeuchi, T.; Futaki, S.; Ito, Y.; Hiroaki, H.; Shirakawa, M. Nature 2009, 458, 106-109
12. McNaughton, B. R.; Cronican, J. J.; Thompson, D. B.; Liu, D. R. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 6111-6116
13. Trantow, B. M.; Cooley, C. B.; Nederberg, F.; Kiesewetter, M. K.; Hedrick, J. L.; Waymouth, R. M.; Wender, P. A. J. Am. Chem. Soc. 2009, 131, 16401-16403
14. Kolonko, E. M.; Pontrello, J. K.; Mangold, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 2009, 131, 7327-7333
15. Wender, P. A.; Galliher, W. C.; Goun, E. A.; Jones, L. R.; Pillow, T. H. Adv. Drug Delivery Rev. 2008, 60, 452-472
16. Esbjorner, E. K.; Lincoln, P.; Norden, B. Biochem. Biophys. Acta 2007, 1768, 1550-1558
17. Shimanouchi, T.; Walde, P.; Gardiner, J.; Mahajan, Y. R.; Seebach, D.; Thomae, A.; Kraemer, S. D.; Voser, M.; R. Kuboi, R. Biochem. Biophys. Acta 2007, 1768, 2726-2736
18. Kale, A. A.; Torchilin, V. P. Bioconjugate Chem. 2007, 18, 363-370
19. Martinell, M.; Salvatella, X.; Fernández-Carneado, J.; Gordo, S.; Feliz, M.; Menéndez, M.; Giralt, E. ChemBioChem 2006, 7, 1105-1113
20. Schmidt, D.; Jiang, Q. X.; MacKinnon, R. Nature 2006, 444, 775-779
21. Fischer, R.; Fotin-Mleczek, M.; Hufnagel, H.; Brock, R. ChemBioChem 2005, 6, 2126-2142
22. Pantarotto, D.; Briand, J.-P.; Prato, M.; Bianco, A. Chem. Commun. 2004, 16-17
23. Jiang, T.; Olson, E. S.; Nguyen, Q. T.; Roy, M.; Jennings, P. A.; Tsien, R. Y. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 17867-17872
24. Umezawa, N.; Gelman, M. A.; Haigis, M. C.; Raines, R. T.; Gellman, S. H. J. Am. Chem. Soc. 2002, 124, 368-369
25. Sakai, N.; Matile, S. J. Am. Chem. Soc. 2003, 125, 14348-14356
26. Takeuchi, T.; Kosuge, M.; Tadokoro, A.; Sugiura, Y.; Nishi, M.; Kawata, M.; Sakai, N.; Matile, S.; Futaki, S. ACS Chem. Biol. 2006, 1, 299-303
27. Bang, E.-K.; Lista, M.; Sforazzini, G.; Sakai, N.; Matile, S. Chem. Sci. 2012, 3, 1752-1763
28. Kim, T. I.; Rothmund, T.; Kissel, T.; Kim, S. W. J. Controlled Release 2011, 152, 110-119
29. Kim, T.; Kim, S. W. React. Funct. Polym. 2011, 71, 344-349
30. Lin, C.; Engbersen, J. F. J. Expert Opin. Drug Delivery 2009, 6, 421-439
31. Son, S.; Namgung, R.; Kim, J.; Singha, K.; Kim, W. J. Acc. Chem. Res. 2011, 152, 110-119
32. Meng, F.; Hennink, W. E.; Zhong, Z. Biomaterials 2009, 30, 2180-2198
33. Thiols at the cell surface have been proposed to further contribute to the uptake of disulfide-containing systems. Torres, A. G.; Gait, M. J. Trends Biotechnol. 2012, 30, 185-190
34. Sakai, N.; Lista, M.; Kel, O.; Sakurai, S.; Emery, D.; Mareda, J.; Vauthey, E.; Matile, S. J. Am. Chem. Soc. 2011, 133, 15224-15227
35. Lista, M.; Areephong, J.; Sakai, N.; Matile, S. J. Am. Chem. Soc. 2011, 133, 15228-15230
36. Sakai, N.; Matile, S. J. Am. Chem. Soc. 2011, 133, 18542-18545
37. Charbonnaz, P.; Sakai, N.; Matile, S. Chem. Sci. 2012, 3, 1492-1496
38. Areephong, J.; Orentas, E.; Sakai, N.; Matile, S. Chem. Commun. 2012, 48, 10618-10620
39. Orentas, E.; Lista, M.; Lin, N.-T.; Sakai, N.; Matile, S. Nat. Chem. 2012, 4, 746-750
40. Takeuchi, T.; Matile, S. Chem. Commun. 2013, 49, 19-29
41. Litvinchuk, S.; Tanaka, H.; Miyatake, T.; Pasini, D.; Tanaka, T.; Bollot, G.; Mareda, J.; Matile, S. Nat. Mater. 2007, 6, 576-580
42. Sakai, N.; Sordé, N.; Matile, S. J. Am. Chem. Soc. 2003, 125, 7776-7777
43. Sordé, N.; Das, G.; Matile, S. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 11964-11969
44. Das, G.; Talukdar, P.; Matile, S. Science 2002, 298, 1600-1602
45. Burns, J. A.; Whitesides, G. M. J. Am. Chem. Soc. 1990, 112, 6296-6303