Cellular uptake of substrate-initiated cell-penetrating poly(disulfide)s

Journal of the American Chemical Society

Volumn 136, Issue 16, 2014, Pages 6069-6074

  Gasparini, Giulio ^a   Bang, Eun Kyoung ^a,c   Molinard, Guillaume ^a   Tulumello, David V ^a,b   Ward, Sandra ^a   Kelley, Shana O ^b   Roux, Aurelien ^a   Sakai, Naomi ^a   Matile, Stefan ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b UNIVERSITY OF TORONTO   (Canada)

^c Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ION EXCHANGE; MOLECULAR BIOLOGY; RING OPENING POLYMERIZATION; SULFUR COMPOUNDS;

AROMATICITIES; CELL-PENETRATING PEPTIDE; CELLULAR UPTAKE; EXPERIMENTAL EVIDENCE; INTRACELLULAR LOCALIZATION; POLYMER COMPOSITION; RING OPENING; STRUCTURAL VARIATIONS;

SUBSTRATES;

BORONIC ACID DERIVATIVE; CELL PENETRATING PEPTIDE; CELL PENETRATING POLYDISULFIDE; COUNTERION; DISULFIDE; FLUORESCENT DYE; GUANIDINE; POLYMER; THIOL; UNCLASSIFIED DRUG; THIOL DERIVATIVE;

ARTICLE; CELL MEMBRANE PERMEABILITY; CELL VIABILITY; CELLULAR DISTRIBUTION; CHEMICAL COMPOSITION; COVALENT BOND; CYTOSOL; CYTOTOXICITY; DEPOLYMERIZATION; ENDOCYTOSIS; ENDOSOME; FLOW CYTOMETRY; HELA CELL LINE; HYDROPHOBICITY; NUCLEOLUS; RING OPENING METATHESIS POLYMERIZATION; SYNTHESIS; CELL MEMBRANE; CHEMISTRY; DRUG EFFECTS; HUMAN; METABOLISM; POLYMERIZATION;

CELL MEMBRANE; CELL-PENETRATING PEPTIDES; DISULFIDES; ENDOCYTOSIS; HELA CELLS; HUMANS; POLYMERIZATION; SULFHYDRYL COMPOUNDS;

EID: 84899540695     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja501581b     Document Type: Article

References (71)

1. Torres, A. G.; Gait, M. J. Trends Biotechnol. 2012, 30, 185-190
2. Green, M.; Lowenstein, P. M. Cell 1988, 55, 1179-1188
3. Frankel, A. O.; Pabo, C. O. Cell 1988, 55, 1189-1193
4. Stanzl, E. G.; Trantow, B. M.; Vargas, J. R.; Wender, P. A. Acc. Chem. Res. 2013, 135, 2944-2954
5. Sgolastra, F.; Deronde, B. M.; Sarapas, J. M.; Som, A.; Tew, G. N. Acc. Chem. Res. 2013, 135, 2977-2987
6. Futaki, S.; Hirose, H.; Nakase, I. Curr. Pharm. Des. 2013, 19, 2863-2868
7. Bautista, A. D.; Craig, C. J.; Harker, E. A.; Shepartz, A. Curr. Opin. Chem. Biol. 2007, 11, 685-692
8. Bechara, C.; Sagan, S. FEBS Lett. 2013, 587, 1693-1702
9. Torchilin, V. P. Adv. Drug Delivery Rev. 2008, 60, 548-558
10. Stewart, K. M.; Horton, K. L.; Kelley, S. O. Org. Biomol. Chem. 2008, 6, 2242-2255
11. Sgolastra, F.; Minter, L. M.; Osborne, B. A.; Tew, G. N. Biomacromolecules 2014, 10, 812-820
12. Weinstain, R.; Savariar, E. N.; Felsen, C. N.; Tsien, R. Y. J. Am. Chem. Soc. 2014, 136, 874-877
13. Lei, E. K.; Pereira, M. P.; Kelley, S. O. Angew. Chem., Int. Ed. 2013, 52, 9660-9663
14. Lnoue, M.; Tong, W.; Esko, J. D.; Tor, Y. ACS Chem. Biol. 2013, 8, 1383-1388
15. Tang, H.; Yin, L.; Kim, K. H.; Cheng, J. Chem. Sci. 2013, 4, 3839-3844
16. Ornelas-Megiatto, C.; Wich, P. R.; Fréchet, J. M. J. Am. Chem. Soc. 2012, 134, 1902-1905
17. Suzuki, Y.; Okuro, K.; Takeuchi, T.; Aida, T. J. Am. Chem. Soc. 2012, 134, 15273-15276
18. Som, A.; Reuter, A.; Tew, G. N. Angew. Chem., Int. Ed. 2012, 51, 980-983
19. Appelbaum, J. S.; LaRochelle, J. R.; Smith, B. A.; Balkin, D. M.; Holub, J. M.; Schepartz, A. Chem. Biol. 2012, 19, 819-830
20. He, J.; Hristova, K.; Wimley, W. C. Angew. Chem., Int. Ed. 2012, 51, 7150-7153
21. 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
22. Kolonko, E. M.; Pontrello, J. K.; Mangold, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 2009, 131, 7327-7333
23. McNaughton, B. R.; Cronican, J. J.; Thompson, D. B.; Liu, D. R. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 6111-6116
24. 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
25. Herce, H. D.; Garcia, A. E.; Litt, J.; Kane, R. S.; Martin, P.; Enrique, N.; Rebolledo, A.; Milesi, V. Biophys. J. 2009, 97, 1917-1925
26. Shimanouchi, T.; Walde, P.; Gardiner, J.; Mahajan, Y. R.; Seebach, D.; Thomae, A.; Kraemer, S. D.; Voser, M.; R. Kuboi, R. Biochim. Biophys. Acta, Biomembr. 2007, 1768, 2726-2736
27. Fernandez-Carneado, J.; Van Gool, M.; Martos, V.; Castel, S.; Prados, P.; De Mendoza, J.; Giralt, E. J. Am. Chem. Soc. 2005, 127, 869-874
28. Fillon, Y.; Anderson, J.; Chmielewski, J. J. Am. Chem. Soc. 2005, 127, 11798-11803
29. Pantarotto, D.; Briand, J.-P.; Prato, M.; Bianco, A. Chem. Commun. 2004, 16-17
30. 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
31. Zhou, P.; Wang, M.; Du, L.; Fisher, G. W.; Waggoner, A.; Ly, D. H. J. Am. Chem. Soc. 2003, 125, 6878-6879
32. Luedtke, N. W.; Carmichael, P.; Tor, Y. J. Am. Chem. Soc. 2003, 125, 12374-12375
33. Umezawa, N.; Gelman, M. A.; Haigis, M. C.; Raines, R. T.; Gellman, S. H. J. Am. Chem. Soc. 2002, 124, 368-369
34. Sakai, N.; Baumeister, B.; Matile, S. ChemBioChem 2000, 1, 123-125
35. Schwarze, S. R.; Ho, A.; Vocero-Akbani, A.; Dowdy, S. F. Science 1999, 285, 1569-1572
36. Sakai, N.; Matile, S. J. Am. Chem. Soc. 2003, 125, 14348-14356
37. 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
38. Schmidt, D.; Jiang, Q. X.; MacKinnon, R. Nature 2006, 444, 775-779
39. 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
40. Katayama, S.; Nakase, I.; Yano, Y.; Murayama, T.; Nakata, Y.; Matsuzaki, K.; Futaki, S. Biochim. Biophys. Acta, Biomembr. 2013, 1828, 2134-2142
41. Lin, C.; Engbersen, J. F. J. Expert Opin. Drug Delivery 2009, 6, 421-439
42. Meng, F. H.; Hennink, W. E.; Zhong, Z. Y. Biomaterials 2009, 30, 2180-2198
43. Kim, T.-I.; Kim, S. W. React. Funct. Polym. 2011, 71, 344-349
44. Bang, E.-K.; Lista, M.; Sforazzini, G.; Sakai, N.; Matile, S. Chem. Sci. 2012, 3, 1752-1763
45. Son, S.; Namgung, R.; Kim, J.; Singha, K.; Kim, W. J. Acc. Chem. Res. 2012, 45, 1100-1112
46. Piest, M.; Engbersen, J. F. J. J. Controlled Release 2011, 155, 331-340
47. Kim, T.; Rothmund, T.; Kissel, T.; Kim, S. W. J. Controlled Release 2011, 152, 110-119
48. Wua, C.; Li, J.; Zhua, Y.; Chena, J.; Oupický, D. Biomaterials 2013, 34, 8843-8850
49. Zeng, H.; Little, H. C.; Tiambeng, T. N.; Williams, G. A.; Guan, Z. J. Am. Chem. Soc. 2013, 135, 4962-4965
50. Drake, C. A.; Aissaoui, A.; Argyros, O.; Thanou, M.; Steinke, J. H. G.; Miller, A. D. J. Controlled Release 2013, 171, 81-90
51. Kang, H. C.; Kang, H.-J.; Bae, Y. H. Biomaterials 2011, 32, 1193-1203
52. Li, J.; Manickam, D. S.; Chen, J.; Oupicky, D. Eur. J. Pharm. Sci. 2012, 46, 173-180
53. Brülisauer, L.; Kathriner, N.; Prenrecaj, M.; Gauthier, M. A.; Leroux, J.-C. Angew. Chem., Int. Ed. 2012, 51, 12454-12458
54. Sakai, N.; Lista, M.; Kel, O.; Sakurai, S.; Emery, D.; Mareda, J.; Vauthey, E.; Matile, S. J. Am. Chem. Soc. 2011, 133, 15224-15227
55. Lista, M.; Areephong, J.; Sakai, N.; Matile, S. J. Am. Chem. Soc. 2011, 133, 15228-15231
56. Sakai, N.; Matile, S. J. Am. Chem. Soc. 2011, 133, 18542-18545
57. Orentas, E.; Lista, M.; Lin, N.-T.; Sakai, N.; Matile, S. Nat. Chem. 2012, 4, 746-750
58. Sforazzini, G.; Orentas, E.; Bolag, A.; Sakai, N.; Matile, S. J. Am. Chem. Soc. 2013, 135, 12082-12090
59. Bang, E.-K.; Gasparini, G.; Molinard, G.; Roux, A.; Sakai, N.; Matile, S. J. Am. Chem. Soc. 2013, 135, 2088-2091
60. Li, J.; Nowak, P.; Otto, S. J. Am. Chem. Soc. 2013, 135, 9222-9239
61. Lehn, J. M. Top. Curr. Chem. 2012, 322, 1-32
62. Black, S. P.; Sanders, J. K. M.; Stefankiewicz, A. R. Chem. Soc. Rev. 2014, 43, 1861-1872
63. Wilson, A.; Gasparini, G.; Matile, S. Chem. Soc. Rev. 2014, 43, 1948-1962
64. Bang, E.-K.; Ward, S.; Gasparini, G.; Sakai, N.; Matile, S. Polym. Chem. 2014, 5, 2433-2441
65. van Meer, G.; Voelker, D. R.; Feigenson, G. W. Nat. Rev. Mol. Cell Biol. 2008, 9, 112-124
66. Sakai, N.; Takeuchi, T.; Futaki, S.; Matile, S. ChemBioChem 2005, 6, 114-122
67. Khalil, I. A.; Kogure, K.; Akita, H.; Harashima, H. Pharmacol. Rev. 2006, 58, 32-45
68. Nishihara, M.; Perret, F.; Takeuchi, T.; Futaki, S.; Lazar, A. N.; Coleman, A. W.; Sakai, N.; Matile, S. Org. Biomol. Chem. 2005, 3, 1659-1669
69. Hennig, A.; Gabriel, G. J.; Tew, G. N.; Matile, S. J. Am. Chem. Soc. 2008, 130, 10338-10344
70. Ellis, G. A.; Palte, M. J.; Raines, R. T. J. Am. Chem. Soc. 2012, 134, 3631-3634
71. Mosmann, T. J. Immunol. Methods 1983, 65, 55-63