Amphiphilic oligoethyleneimine-β-cyclodextrin "click" clusters for enhanced DNA delivery

Journal of Organic Chemistry

Volumn 78, Issue 16, 2013, Pages 8143-8148

  Martínez, Álvaro ^a   Bienvenu, Céline ^b   Jiménez Blanco, José L ^a   Vierling, Pierre ^b   Mellet, Carmen Ortiz ^a   García Fernández, José M ^c   Di Giorgio, Christophe ^b  

^a UNIVERSITY OF SEVILLE   (Spain)

^b UNIVERSITÉ DE NICE SOPHIA ANTIPOLIS   (France)

^c INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILICITY; AMPHIPHILICS; BENEFICIAL EFFECTS; GENE DELIVERY SYSTEMS; MONO-DISPERSE; NANOCOMPLEXES; NON-AMPHIPHILIC; TRANSFECTION EFFICIENCY;

DRUG THERAPY; GENE TRANSFER;

CYCLODEXTRINS;

AMPHOPHILE; BETA CYCLODEXTRIN; DRUG CARRIER; NANOPARTICLE; OLIGOETHYLENEIMINE BETA CYCLODEXTRIN; UNCLASSIFIED DRUG;

ARTICLE; CELL VIABILITY; COMBUSTION; COMPLEX FORMATION; CONJUGATE; CONTROLLED STUDY; FEMALE; GENE DELIVERY SYSTEM; GENE TARGETING; GENETIC TRANSFECTION; HELA CELL; HUMAN; HUMAN CELL; HYDRODYNAMICS; IN VITRO GENE TRANSFER; IN VITRO STUDY; LIVER CELL; NONVIRAL GENE DELIVERY SYSTEM; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; ZETA POTENTIAL;

ANIMALS; AZIRIDINES; BETA-CYCLODEXTRINS; CELL LINE; CLICK CHEMISTRY; DNA; HEPATOCYTES; MICE; MOLECULAR STRUCTURE; NANOSTRUCTURES; PLASMIDS; SURFACE-ACTIVE AGENTS;

EID: 84882329202     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400993y     Document Type: Article

References (45)

1. Cartier, N.; Hacein-Bey-Abina, S.; Bartholomae, C. C.; Veres, G.; Schmidt, M.; Kutschera, I.; Vidaud, M.; Abel, U.; Dal-Cortivo, L.; Caccavelli, L.; Mahlaoui, N.; Kiermer, V.; Mittelstaedt, D.; Bellesme, C.; Lahlou, N.; Lefrère, F.; Blanche, S.; Audit, M.; Payen, E.; Leboulch, P.; l'Homme, B.; Bougnères, P.; Von Kalle, C.; Fischer, A.; Cavazzana-Calvo, M.; Aubourg, P. Science 2009, 326, 818-823
2. Nayak, S.; Herzog, R. W. Gene Ther. 2010, 17, 295-304
3. Mintzer, M. A.; Simanek, E. E. Chem. Rev. 2009, 109, 259-302
4. Jafari, M.; Soltani, M.; Naahidi, S.; Karunaratne, D. N.; Chen, P. Curr. Med. Chem. 2012, 19, 197-208
5. Davis, M. E. Mol. Pharmaceutics 2009, 6, 659-668
6. Ortiz Mellet, C.; García Fernández, J. M.; Benito, J. M. Chem. Soc. Rev. 2011, 40, 1586-1680
7. Pun, S. H.; Bellocq, N. C.; Liu, A.; Jensen, G.; Machemer, T.; Quijano, E.; Shluep, T.; Wen, S.; Engler, H.; Heidel, J.; Davis, M. E. Bioconjugate Chem. 2004, 15, 831-840
8. In the particular case of βCD, permeation of the cell membrane by extraction of cholesterol through inclusion complex formation has been proposed to contribute to transfection enhancement. See: Bienvenu, C.; Martínez, A.; Jiménez Blanco, J. L.; Di Giorgio, C.; Vierling, P.; Ortiz Mellet, C.; Defaye, J.; García Fernández, J. M. Org. Biomol. Chem. 2012, 10, 5570-5581
9. Li, J.; Loh, X. J. Adv. Drug Delivery Rev. 2008, 60, 1000-1017
10. Li, Z.; Yin, H.; Zhang, Z.; Liu, K. L.; Li, J. Biomacromolecules 2012, 13, 3162-3172
11. Ping, Y.; Liu, C.; Zhang, Z.; Liu, K. L.; Chen, J.; Li, J. Biomaterials 2011, 32, 8328-8341
12. Ke, C.-F; Hou, S.; Zhang, H.-Y.; Liu, Y.; Yang, K.; Feng, X.-Z. Chem. Commun. 2007, 3374-3376
13. Wang, H.; Chen, Y.; Li, X.-Y.; Liu, Y. Mol. Pharmaceutics 2007, 4, 189-198
14. Davis, M. E.; Zuckerman, J. E.; Choi, C. H. J.; Seligson, D.; Tolcher, A.; Alabi, C. A; Yen, Y.; Heidel, J. D.; Ribas, A. Nature 2010, 464, 1067-1070
15. Heidel, J. D.; Yu, Z.; Liu, J. Y.-C.; Rele, S. M.; Liang, Y.; Zeidan, R. K.; Kornbrust, D. J.; Davis, M. E. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 5715-5721
16. Deng, J.; Li, N.; Mai, K.; Yang, C.; Yan, L.; Zhang, L.-M. J. Mater. Chem. 2011, 21, 5273-5281
17. Cryan, S.-A.; Holohan, A.; Donohue, R.; Darcy, R.; O'Driscoll, C. M. Eur. J. Pharm. Sci. 2004, 21, 625-628
18. Mourtzis, N.; Paravatou, M.; Mavridis, I. M.; Roberts, M. L.; Yannakopoulou, K. Chem.-Eur. J. 2008, 14, 4188-4200
19. Bennevault-Celton, V.; Urbach, A.; Martin, O.; Pichon, C.; Guégan, P.; Midoux, P. Bioconjugate Chem. 2011, 22, 2404-2414
20. Srinivasachari, S.; Fichter, K. M.; Reineke, T. M. J. Am. Chem. Soc. 2008, 130, 4618-4627
21. McMahon, A.; O'Neill, M. J.; Gomez, E.; Donohue, R.; Forde, D.; Darcy, R.; O'Driscoll, C. M. J. Pharm. Pharmacol. 2012, 64, 1063-1073
22. O'Mahony, A. M.; Ogier, J.; Desgranges, S.; Cryan, J. F.; Darcy, R.; O'Driscoll, C. M. Org. Biomol. Chem. 2012, 10, 4954-4960
23. O'Mahony, A. M.; Godinho, B. M. D. C.; Ogier, J.; Devocelle, M.; Darcy, R.; Cryan, J. F.; O'Driscoll, C. M. ACS Chem. Neurosci. 2012, 3, 744-752
24. Villari, V.; Mazzaglia, A.; Darcy, R.; O'Driscoll, C. M; Micalli, N. Biomacromolecules 2013, 14, 811-817
25. O'Mahony, A. M.; Desgranges, S.; Ogier, J.; Quinlan, A.; Devocelle, M.; Darcy, R.; Cryan, J. F.; O'Driscoll, C. M. Pharm. Res. 2013, 30, 1086-1098
26. Díaz-Moscoso, A.; Le Gourriérec, L.; Gómez- García, M.; Benito, J. M.; Balbuena, P.; Ortega-Caballero, F.; Guilloteau, N.; Di Giorgio, C.; Vierling, P.; Defaye, J.; Ortiz Mellet, C.; García Fernández, J. M. Chem.-Eur. J. 2009, 15, 12871-12888
27. Méndez-Ardoy, A.; Guilloteau, N.; Di Giorgio, C.; Vierling, P.; Santoyo-González, F.; Ortiz Mellet, C.; García Fernández, J. M. J. Org. Chem. 2011, 76, 5882-5894
28. Díaz-Moscoso, A.; Vercauteren, D.; Rejman, J.; Benito, J. M.; Ortiz Mellet, C.; De Smedt, S. C.; García Fernández, J. M. J. Controlled Release 2010, 146, 318-325
29. Díaz-Moscoso, A.; Guilloteau, N.; Bienvenu, C.; Méndez-Ardoy, A.; Jiménez Blanco, J. L.; Benito, J. M.; Le Gourriérec, L.; Di Giorgio, C.; Vierling, P.; Defaye, J.; Ortiz Mellet, C.; García Fernández, J. M. Biomaterials 2011, 32, 7263-7273
30. Symens, N.; Méndez-Ardoy, A.; Díaz-Moscoso, A.; Sánchez-Fernández, E.; Remaut, K.; Demeester, J.; García Fernández, J. M.; De Smedt, S. C.; Rejman, J. Bioconjugate Chem. 2012, 23, 1276-1289
31. Ortiz Mellet, C.; Benito, J. M.; García Fernández, J. M. Chem.-Eur. J. 2010, 16, 6728-6742
32. Bagnacani, V.; Franceschi, V.; Fantuzzi, L.; Casnati, A.; Donofrio, G.; Sansone, F.; Ungaro, R. Bioconjugate Chem. 2012, 23, 993-1002
33. Méndez-Ardoy, A.; Urbiola, K.; Aranda, C.; Ortiz-Mellet, C.; García Fernández, J. M.; Tros de Ilarduya, C. Nanomedicine 2011, 6, 1697-1707
34. Aranda, C.; Urbida, K.; Méndez-Ardoy, A.; García Fernández, J. M.; Ortiz Mellet, C.; Tros de Ilarduya, C. Eur. J. Pharm. Biopharm. 2013, 10.1016/j.ejpb.2013.06.011
35. Louis, M.-H.; Dutoit, S.; Denoux, Y.; Erbacher, P.; Deslandes, E.; Behr, J.-P.; Gauduchon, P.; Poulain, L. Cancer Gene Ther. 2006, 13, 367-374
36. 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
37. Méndez-Ardoy, A.; Gómez- García, M.; Ortiz Mellet, C.; Sevillano, N.; Girón, M. D.; Salto, R.; Santoyo-González, F.; García Fernández, J. M. Org. Biomol. Chem. 2009, 7, 2681-2684
38. For an update on "click" multiconjugation in the carbohydrate field, see: Click Chemistry in Glycoscience: New Developments and Strategies; Witczak, Z. J.; Bielski, R., Eds.; John Wiley & Sons: Hoboken, NJ, 2013.
39. For a recent review discussing cyclodextrin multiconjugation, see: Martínez, A.; Ortiz Mellet, C.; García Fernández, J. M. Chem. Soc. Rev. 2013, 42, 4746-4773
40. For a recent report illustrating the potential of the thiourea-forming reaction in cyclodextrin multiconjugation, see: Gómez-García, M.; Benito, J. M.; Butera, A. P.; Ortiz Mellet, C.; García Fernández, J. M.; Jiménez Blanco, J. L. J. Org. Chem. 2012, 77, 1273-1288
41. Geall, A. J.; Taylor, R. J.; Earll, M. E.; Eaton, M. A. W.; Blagbrough, I. S. Bioconjugate Chem. 2000, 11, 314-326
42. Dash, P. R.; Read, M. L.; Barrett, L. B.; Wolfert, M. A.; Seymour, L. W. Gene Ther. 1999, 6, 643-650
43. Khalil, I. A.; Kogure, K.; Akita, H.; Harashima, H. Pharmacol. Rev. 2006, 58, 32-45
44. Boyd, A. P.; Sory, M.-P.; Iriarte, M.; Cornelis, G. R. Mol. Microbiol. 1998, 27, 425-436
45. Breton, M.; Leblond, J.; Tranchant, I.; Scherman, D.; Bessodes, M.; Herscovici, J.; Mignet, N. Pharmaceuticals 2011, 4, 1381-1399