Conjugation chemistry through acetals toward a dextran-based delivery system for controlled release of siRNA

Journal of the American Chemical Society

Volumn 134, Issue 38, 2012, Pages 15840-15848

  Cui, Lina ^a,c   Cohen, Jessica L ^a   Chu, Crystal K ^a   Wich, Peter R ^a   Kierstead, Paul H ^a   Fréchet, Jean M J ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Saudi Arabia)

^c STANFORD UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL GROUPS; ACIDIC CONDITIONS; AMINE MOIETIES; AMINE STRUCTURES; CHEMICAL BEHAVIOR; CONJUGATION CHEMISTRY; CONTROLLED RELEASE; DELIVERY SYSTEMS; FUNCTIONAL MOIETIES; IN-VITRO; RELEASE RATE; STERIC PROPERTIES; STRUCTURAL COMPOSITION;

CYTOTOXICITY; DEXTRAN; ORGANIC COMPOUNDS;

DEGRADATION;

ACETAL DERIVATIVE; AMINE; DEXTRAN; SMALL INTERFERING RNA; WATER;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED RELEASE FORMULATION; CONTROLLED STUDY; CYTOTOXICITY; DEGRADATION; GENE DELIVERY SYSTEM; HUMAN; HUMAN CELL; IN VITRO GENE TRANSFER; SOLUBILITY;

ACETALS; DEXTRANS; DRUG DELIVERY SYSTEMS; RNA, SMALL INTERFERING;

EID: 84866679606     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja305552u     Document Type: Article

References (42)

1. Pecot, C. V.; Calin, G. A.; Coleman, R. L.; Lopez-Berestein, G.; Sood, A. K. Nat. Rev. Cancer 2011, 11, 59
2. Whitehead, K. A.; Langer, R.; Anderson, D. G. Nat. Rev. Drug Discovery 2009, 8, 129
3. Huang, C.; Li, M.; Chen, C. Y.; Yao, Q. Z. Expert Opin. Ther. Targets 2008, 12, 637
4. Lares, M. R.; Rossi, J. J.; Ouellet, D. L. Trends Biotechnol. 2010, 28, 570
5. Zhu, L.; Mahato, R. I. Expert Opin. Drug Delivery 2010, 7, 1209
6. Akinc, A.; Zumbuehl, A.; Goldberg, M.; Leshchiner, E. S.; Busini, V.; Hossain, N.; Bacallado, S. A.; Nguyen, D. N.; Fuller, J.; Alvarez, R.; Borodovsky, A.; Borland, T.; Constien, R.; de Fougerolles, A.; Dorkin, J. R. Nat. Biotechnol. 2008, 26, 561
7. Zhang, S. B.; Zhao, B.; Jiang, H. M.; Wang, B.; Ma, B. C. J. Controlled Release 2007, 123, 1
8. Thomas, C. E.; Ehrhardt, A.; Kay, M. A. Nat. Rev. Genet. 2003, 4, 346
9. Zimmermann, T. S.; Lee, A. C. H.; Akinc, A.; Bramlage, B.; Bumcrot, D.; Fedoruk, M. N.; Harborth, J.; Heyes, J. A.; Jeffs, L. B.; John, M.; Judge, A. D.; Lam, K.; McClintock, K.; Nechev, L. V.; Palmer, L. R. Nature 2006, 441, 111
10. Devroe, E.; Silver, P. A. Expert Opin. Biol. Ther. 2004, 4, 319
11. Minakuchi, Y.; Takeshita, F.; Kosaka, N.; Sasaki, H.; Yamamoto, Y.; Kouno, M.; Honma, K.; Nagahara, S.; Hanai, K.; Sano, A.; Kato, T.; Terada, M.; Ochiya, T. Nucleic Acids Res. 2004, 32
12. Janes, K. A.; Calvo, P.; Alonso, M. J. Adv. Drug Delivery Rev. 2001, 47, 83
13. Liu, W. G.; De Yao, K. J. Controlled Release 2002, 83, 1
14. Jiang, X.; Dai, H.; Leong, K. W.; Goh, S. H.; Mao, H. Q.; Yang, Y. Y. J. Gene Med. 2006, 8, 477
15. Kumar, M.; Behera, A. K.; Lockey, R. F.; Zhang, J.; Bhullar, G.; De La Cruz, C. P.; Chen, L. C.; Leong, K. W.; Huang, S. K.; Mohapatra, S. S. Hum. Gene Ther. 2002, 13, 1415
16. Pille, J. Y.; Li, H.; Blot, E.; Bertrand, J. R.; Pritchard, L. L.; Opolon, P.; Maksimenko, A.; Lu, H.; Vannier, J. P.; Soria, J.; Malvy, C.; Soria, C. Hum. Gene Ther. 2006, 17, 1019
17. Katas, H.; Alpar, H. O. J. Controlled Release 2006, 115, 216
18. Liu, X. D.; Howard, K. A.; Dong, M. D.; Andersen, M. O.; Rahbek, U. L.; Johnsen, M. G.; Hansen, O. C.; Besenbacher, F.; Kjems, J. Biomaterials 2007, 28, 1280
19. Heinze, T.; Liebert, T.; Heublein, B.; Hornig, S. Adv. Polym. Sci. 2006, 205, 199
20. Baldwin, A. D.; Kiick, K. L. Biopolymers 2010, 94, 128
21. Hosseinkhani, H.; Azzam, T.; Tabata, Y.; Domb, A. J. Gene Ther. 2004, 11, 194
22. Ghosn, B.; Kasturi, S. P.; Roy, K. Curr. Top. Med. Chem. 2008, 8, 331
23. In Polysaccharides for Drug Delivery and Pharmaceutical Application s; American Chemical Society: 2006; Vol. 934.
24. Wuts, P. G. M.; Greene, T. W. Greenes Protective Groups in Organic Synthesis; 2007; Vol. 4 th Edition.
25. Mellman, I.; Fuchs, R.; Helenius, A. Annu. Rev. Biochem. 1986, 55, 663
26. Standley, S. M.; Kwon, Y. J.; Murthy, N.; Kunisawa, J.; Shastri, N.; Guillaudeu, S. J.; Lau, L.; Fréchet, J. M. J. Bioconjugate Chem. 2004, 15, 1281
27. Bachelder, E. M.; Beaudette, T. T.; Broaders, K. E.; Paramonov, S. E.; Dashe, J.; Fréchet, J. M. J. Mol. Pharmaceutics 2008, 5, 876
28. Murthy, N.; Xu, M. C.; Schuck, S.; Kunisawa, J.; Shastri, N.; Fréchet, J. M. J. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 4995
29. Broaders, K. E.; Cohen, J. A.; Beaudette, T. T.; Bachelder, E. M.; Fréchet, J. M. J. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 5497
30. Bachelder, E. M.; Beaudette, T. T.; Broaders, K. E.; Dashe, J.; Fréchet, J. M. J. J. Am. Chem. Soc. 2008, 130, 10494
31. Cohen, J. A.; Beaudette, T. T.; Cohen, J. L.; Broaders, K. E.; Bachelder, E. M.; Fréchet, J. M. J. Adv. Mater. 2010, 22, 3593
32. Cohen, J. L.; Schubert, S.; Wich, P. R.; Cui, L.; Cohen, J. A.; Mynar, J. L.; Fréchet, J. M. J. Bioconjugate Chem. 2011, 22, 1056
33. Cui, L.; Cohen, J. A.; Broaders, K. E.; Beaudette, T. T.; Fréchet, J. M. J. Bioconjugate Chem. 2011, 22, 949
34. Chau, Y.; Dang, N. M.; Tan, F. E.; Langer, R. J. Pharm. Sci. 2006, 95, 542
35. Demeneix, B.; Behr, J. In Adv. Genet.; Leaf Huang, M.-C. H.; Ernst, W., Eds.; Academic Press: 2005; Vol. Vol. 53, p 215.
36. Reineke, T. M.; Davis, M. E. Bioconjugate Chem. 2003, 14, 255
37. Bhise, N. S.; Gray, R. S.; Sunshine, J. C.; Htet, S.; Ewald, A. J.; Green, J. J. Biomaterials 2010, 31, 8088
38. Tamura, A.; Oishi, M.; Nagasaki, Y. J. Controlled Release 2010, 146, 378
39. Wang, J.; Gao, S.-J.; Zhang, P.-C.; Wang, S.; Mao, H.-Q.; Leong, K. W. Gene Ther. 2004, 11, 1001
40. Wong, S. Y.; Sood, N.; Putnam, D. Mol. Ther. 2009, 17, 480
41. Zhang, K.; Fang, H.; Wang, Z.; Li, Z.; Taylor, J.-S. A.; Wooley, K. L. Biomaterials 2010, 31, 1805
42. Ou, M.; Wang, X.-L.; Xu, R.; Chang, C.-W.; Bull, D. A.; Kim, S. W. Bioconjugate Chem. 2008, 19, 626