Polycationic adamantane-based dendrons of different generations display high cellular uptake without triggering cytotoxicity

Journal of the American Chemical Society

Volumn 136, Issue 2, 2014, Pages 810-819

  Grillaud, Maxime ^a   Russier, Julie ^a   Bianco, Alberto ^a  

^a INSTITUT DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMEDICAL APPLICATIONS; CELLULAR INTERNALIZATION; CELLULAR TOXICITIES; CLINICAL DEVELOPMENT; CYTOTOXIC EFFECTS; CYTOTOXICITY EFFECTS; DENDRITIC STRUCTURES; FLUORESCENT PROBES;

CELL CULTURE; CYTOTOXICITY; DRUG DELIVERY; ETHYLENE GLYCOL; MEDICAL APPLICATIONS;

DENDRIMERS;

ADAMANTANE; CYANINE DYE 5; DENDRON; DRUG CARRIER; ETHYLENE GLYCOL; POLYAMMONIUM; POLYGUANIDINIUM; POLYMER; UNCLASSIFIED DRUG;

ANIMAL CELL; APOPTOSIS; ARTICLE; BIOCOMPATIBILITY; CELL TRANSPORT; CELL VIABILITY; CLICK CHEMISTRY; CONFOCAL LASER MICROSCOPY; CYTOTOXICITY; DEPROTECTION REACTION; FLOW CYTOMETRY; HELA CELL; HUMAN; HUMAN CELL; HYDROGENOLYSIS; INTERNALIZATION; MACROPHAGE; NONHUMAN; PHAGOCYTOSIS; SYNTHESIS;

ADAMANTANE; ANIMALS; CARBOCYANINES; CELL LINE; CELL SURVIVAL; CLICK CHEMISTRY; DENDRIMERS; FLUORESCENT DYES; HELA CELLS; HUMANS; MICE; MOLECULAR STRUCTURE; POLYAMINES;

EID: 84892725788     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja411987g     Document Type: Article

References (84)

1. Tian, W.-D.; Ma, Y.-Q. Chem. Soc. Rev. 2013, 42, 705-727
2. Khandare, J.; Calderon, M.; Dagia, N. M.; Haag, R. Chem. Soc. Rev. 2012, 41, 2824-2848
3. Mintzer, M. A.; Grinstaff, M. W. Chem. Soc. Rev. 2011, 40, 173-190
4. Medina, S. H.; El-Sayed, M. E. H. Chem. Rev. 2009, 109, 3141-3157
5. Svenson, S.; Tomalia, D. A. Adv. Drug Delivery Rev. 2005, 57, 2106-2129
6. Gillies, E. R.; Fréchet, J. M. J. Drug Discovery Today 2005, 10, 35-43
7. Cloninger, M. J. Curr. Opin. Chem. Biol. 2002, 6, 742-748
8. Van der Poll, D. G.; Kieler-Ferguson, H. M.; Floyd, W. C.; Guillaudeu, S. J.; Jerger, K.; Szoka, F. C.; Fréchet, J. M. J. Bioconjugate Chem. 2010, 21, 764-773
9. Newkome, G. R.; Schreiner, C. Chem. Rev. 2010, 110, 6338-6442
10. Newkome, G. R.; Schreiner, C. D. Polymer 2008, 49, 1-173
11. Newkome, G. R.; Yao, Z.; Baker, G. R.; Gupta, V. K. J. Org. Chem. 1985, 50, 2003-2004
12. Buhleier, E.; Wehner, W.; Vögtle, F. Synthesis 1978, 155
13. Welsh, D. J.; Smith, D. K. Org. Biomol. Chem. 2011, 9, 4795-4801
14. Rolland, O.; Turrin, C.-O.; Caminade, A.-M.; Marjoral, J.-P. New J. Chem. 2009, 33, 1809-1824
15. Huskens, J. Curr. Opin. Chem. Biol. 2006, 10, 537-543
16. Badjic, J. D.; Nelson, A.; Cantrill, S. J.; Turnbull, W. B.; Stoddart, J. F. Acc. Chem. Res. 2005, 38, 723-732
17. Mulder, A.; Huskens, J.; Reinhoudt, D. N. Org. Biomol. Chem. 2004, 2, 3409-3424
18. Woller, E. K.; Cloninger, M. J. Org. Lett. 2002, 4, 7-10
19. Mammen, M.; Choi, S. K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754-2794
20. Newkome, G. R.; Kotta, K. K.; Moorefield, C. N. Chem.-Eur. J. 2006, 12, 3726-3734
21. Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638-7647
22. Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138-175
23. Lee, C. C.; MacKay, J. A.; Fréchet, J. M. J.; Szoka, F. C. Nat. Biotechnol. 2005, 23, 1517-1526
24. Boas, U.; Heegaard, P. M. Chem. Soc. Rev. 2004, 33, 43-63
25. Nishikawa, M.; Takakura, Y.; Hashida, M. Adv. Drug Delivery Rev. 1996, 21, 135-155
26. Cui, L.; Cohen, J. L.; Chu, C. K.; Wich, P. R.; Kierstead, P. H.; Fréchet, J. M. J. J. Am. Chem. Soc. 2012, 134, 15840-15848
27. Ornelas-Megiatto, C.; Wich, P. R.; Fréchet, J. M. J. J. Am. Chem. Soc. 2012, 134, 1902-1905
28. Barnard, A.; Posocco, P.; Pricl, S.; Calderon, M.; Haag, R.; Hwang, M. E.; Shum, V. W. T.; Pack, D. W.; Smith, D. K. J. Am. Chem. Soc. 2011, 133, 20288-20300
29. Smith, D. K. Curr. Top. Med. Chem. 2008, 8, 1187-1203
30. Guillot-Nieckowski, M.; Eisler, S.; Diederich, F. New J. Chem. 2007, 31, 1111-1127
31. Dufès, C.; Uchegbu, I. F.; Schätzlein, A. G. Adv. Drug Delivery Rev. 2005, 57, 2177-2202
32. Turunen, M. P.; Hiltunen, M. O.; Ruponen, M.; Virkamaki, L.; Szoka, F. C.; Urtti, A.; Yla-Herttuala, S. Gene Ther. 1999, 6, 6-11
33. Kukowska-Latallo, J.-F.; Bielinska, A. U.; Johnson, J.; Spindler, R.; Tomalia, D. A.; Baker, J. R. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 4897-4902
34. Haensler, J.; Szoka, F. C. Bioconjugate Chem. 1993, 4, 372-379
35. Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polym. J. (Tokyo) 1985, 17, 117-132
36. Lv, H.; Zhang, S.; Wang, B.; Cui, S.; Yan, J. J. Controlled Release 2006, 114, 100-109
37. Duncan, R.; Izzo, L. Adv. Drug Delivery Rev. 2005, 57, 2215-2237
38. Kuo, J. H. S.; Jan, M. S.; Chiu, H. W. J. Pharm. Pharmacol. 2005, 57, 489-495
39. Jevprasesphant, R.; Penny, J.; Jalal, R.; Attwood, D.; McKeown, N. B.; D'Emanuele, A. Int. J. Pharm. 2003, 252, 263-266
40. Malik, N.; Wiwattanapatapee, R.; Klopsch, R.; Lorenz, K.; Frey, H.; Weener, J. W.; Meijer, E. W.; Paulus, W.; Duncan, R. J. Controlled Release 2000, 65, 133-148
41. Roberts, J. C.; Bhalgat, M. K.; Zera, R. T. J. Biomed. Mater. Res. 1996, 30, 53-65
42. Chen, D. P.; Yu, C.; Chang, C.-Y.; Wan, Y.; Fréchet, J. M. J.; Goddard, W. A., III; Diallo, M. S. Environ. Sci. Technol. 2012, 46, 10718-10726
43. Boussif, O.; Lezoualc'h, F.; Zanta, M. A.; Mergny, M. D.; Scherman, D.; Demeneix, B.; Behr, J.-P. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7297-7301
44. Berna, M.; Dalzoppo, D.; Pasut, G.; Manunta, M.; Izzo, L.; Jones, A. T.; Duncan, R.; Veronese, F. M. Biomacromolecules 2006, 7, 146-153
45. Fernandez-Megia, E.; Correa, J.; Riguera, R. Biomacromolecules 2006, 7, 3104-3111
46. Fernandez-Megia, E.; Correa, J.; Rodriguez-Meizoso, I.; Riguera, R. Macromolecules 2006, 39, 2113-2120
47. Newkome, G. R.; Kotta, K. K.; Mishra, A.; Moorefield, C. N. Macromolecules 2004, 37, 8262-8268
48. Iyer, A. K.; Khaled, G.; Fang, J.; Maeda, H. Drug Discovery Today 2006, 11, 812-818
49. Duncan, R. Pharm. Sci. Technol. Today 1999, 2, 441-449
50. Matsumura, Y.; Maeda, H. Cancer Res. 1986, 46, 6387-6392
51. Bonduelle, C. V.; Gillies, E. R. Pharmaceuticals 2010, 3, 636-666
52. Wender, P. A.; Galliher, W. C.; Goun, E. A.; Jones, L. R.; Pillow, T. H. Adv. Drug Delivery Rev. 2008, 60, 452-472
53. Theodossiou, T. A.; Pantos, A.; Tsogas, I.; Paleos, C. M. ChemMedChem 2008, 3, 1635-1643
54. Zhi, D.; Zhang, S.; Cui, S.; Zhao, Y.; Wang, Y.; Zhao, D. Bioconjugate Chem. 2013, 24, 487-519
55. Wender, P. A.; Kreider, E.; Pelkey, E. T.; Rothbard, J.; VanDeusen, C. L. Org. Lett. 2005, 7, 4815-4818
56. Pantos, A.; Tsiourvas, D.; Nounesis, G.; Paleos, C. M. Langmuir 2005, 21, 7483-7490
57. Rothbard, J. B.; Jessop, T. C.; Wender, P. A. Adv. Drug Delivery Rev. 2005, 57, 495-504
58. Wender, P. A.; Mitchell, D. J.; Pattabiraman, K.; Pelkey, E. T.; Steinman, L.; Rothbard, J. B. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 13003-13008
59. Tsogas, I.; Sideratou, Z.; Tsiourvas, D.; Theodossiou, T. A.; Paleos, C. M. ChemBioChem 2007, 8, 1865-1876
60. Chung, H.-H.; Harms, G.; Seong, C. M.; Choi, B. H.; Min, C.; Taulane, J. P.; Goodman, M. Biopolymers 2004, 76, 83-96
61. Albertazzi, L.; Serresi, M.; Albanese, A.; Beltram, F. Mol. Pharmaceutics 2010, 7, 680-688
62. Albertazzi, L.; Fernandez-Villamarin, M.; Riguera, R.; Fernandez-Megia, E. Bioconjugate Chem. 2012, 23, 1059-1068
63. Albertazzi, L.; Mickler, F. M.; Pavan, G. M.; Salomone, F.; Bardi, G.; Panniello, M.; Amir, E.; Kang, T.; Killops, K. L.; Bräuchle, C.; Amir, R. J.; Hawker, C. J. Biomacromolecules 2012, 13, 4089-4097
64. Battigelli, A.; Tzu-Wen Wang, J.; Russier, J.; Da Ros, T.; Kostarelos, K.; Al-Jamal, K. T.; Prato, M.; Bianco, A. Small 2013, 9, 3610-3619
65. Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. J. Org. Chem. 1992, 57, 2497-2500
66. Lamanna, G.; Smulski, C. R.; Chekkat, N.; Estieu-Gionnet, K.; Guichard, G.; Fournel, S.; Bianco, A. Chem.-Eur. J. 2013, 19, 1762-1768
67. Lamanna, G.; Russier, J.; Dumortier, H.; Bianco, A. Biomaterials 2012, 33, 5610-5617
68. Lamanna, G.; Russier, J.; Ménard-Moyon, C.; Bianco, A. Chem. Commun. 2011, 47, 8955-8957
69. Nasr, K.; Pannier, N.; Frangioni, J. V.; Maison, W. J. Org. Chem. 2008, 73, 1056-1060
70. Pannier, N.; Maison, W. Eur. J. Org. Chem. 2008, 1278-1284
71. Maison, W.; Frangioni, J. V.; Pannier, N. Org. Lett. 2004, 6, 4567-4569
72. Reichert, V. R.; Mathias, L. J. Macromolecules 1994, 27, 7015-7023
73. Hong, S.; Bielinska, A. U.; Mecke, A.; Keszler, B.; Beals, J. L.; Shi, X.; Balogh, L.; Orr, B. G.; Baker, J. R.; Banaszak Holl, M. M. Bioconjugate Chem. 2004, 15, 774-782
74. Godbey, W. T.; Wu, K. K.; Mikos, A. G. Biomaterials 2001, 22, 471-480
75. Kordatos, K.; Da Ros, T.; Bosi, S.; Vazquez, E.; Bergamin, M.; Cusan, C.; Pellarini, F.; Tomberli, V.; Baiti, B.; Pantarotto, D.; Georgakilas, V.; Spalluto, G.; Prato, M. J. Org. Chem. 2001, 66, 4915-4920
76. Mujumdar, R. B.; Ernst, L. A.; Mujumdar, S. R.; Lewis, C. J.; Waggoner, A. S. Bioconjugate Chem. 1993, 4, 105-111
77. Thomas, T. P.; Majoros, I.; Kotlyar, A.; Mullen, D.; Holl, M. M.; Baker, J. R., Jr. Biomacromolecules 2009, 10, 3207-3214
78. Naha, P. C.; Davoren, M.; Lyng, F. M.; Byrne, H. J. Toxicol. Appl. Pharmacol. 2010, 246, 91-99
79. Maiolo, J. R.; Ferrer, M.; Ottinger, E. A. Biochim. Biophys. Acta 2005, 1712, 161-172
80. Mitchell, D. J.; Kim, D. T.; Steinman, L.; Fathman, C. G.; Rothbard, J. B. J. Pept. Res. 2000, 56, 318-325
81. Rothbard, J. B.; Jessop, T. C.; Lewis, R. S.; Murray, B. A.; Wender, P. A. J. Am. Chem. Soc. 2004, 126, 9506-9507
82. Aidley, D.; Stanfield, P. Ion Channels; Cambridge University Press: Cambridge, U.K., 1996.
83. Huang, K.; Voss, B.; Kumar, D.; Hamm, H. E.; Harth, E. Bioconjugate Chem. 2007, 18, 403-409
84. Wender, P. A.; Jessop, T. C.; Pattabiraman, K.; Pelkey, E. T.; VanDeusen, C. L. Org. Lett. 2001, 3, 3229-3232