The use of solid supports to generate nucleic acid carriers

Accounts of Chemical Research

Volumn 45, Issue 7, 2012, Pages 1140-1152

  Unciti Broceta, Asier ^a,b   Díaz Mochón, Juan José ^c   Sánchez Martín, Rosario M ^c   Bradley, Mark ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b Deliverics Ltd   (United Kingdom)

^c UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE; DENDRIMER; DNA; LIPID; MICROSPHERE; NUCLEIC ACID; POLYAMINE; RNA;

ARTICLE; CHEMISTRY; GENETIC TRANSFECTION; HUMAN; METABOLISM; SOLID PHASE SYNTHESIS;

ARGININE; DENDRIMERS; DNA; HUMANS; LIPIDS; MICROSPHERES; NUCLEIC ACIDS; POLYAMINES; RNA; SOLID-PHASE SYNTHESIS TECHNIQUES; TRANSFECTION;

EID: 84863946644     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar200263c     Document Type: Article

References (65)

1. Pannier, A. K; Shea, L. D. Controlled Release Systems for DNA Delivery Mol. Ther. 2004, 10, 19-26
2. Akhtar Ibrahim, S.; Benter, F. Nonviral delivery of synthetic siRNAs in vivo J. Clin. Invest. 2007, 117, 3623-3632
3. Anderson, J. L.; Hope, T. J. Intracellular trafficking of retroviral vectors: obstacles and advances Gene Ther. 2005, 12, 1667-1678
4. Campos, S. K.; Barry, M. A. Current advances and future challenges in Adenoviral vector biology and targeting Curr. Gene Ther. 2007, 7, 189-204
5. Lu, Y. Transcriptionally regulated, prostate-targeted gene therapy for prostate cancer Adv. Drug Delivery Rev. 2009, 61, 572-88
6. Excoffon, K. J. D. A.; Koerber, J. T.; Dickey, D. D.; Murtha, M.; Keshavjee, S.; Kaspar, B. K.; Zabner, J.; Schaffer, D. V. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 3865-3870
7. Woods, N. B.; Bottero, V.; Schmidt, M.; von Kalle, C.; Verma, I. M. Gene therapy: therapeutic gene causing lymphoma Nature 2006, 440, 1123
8. Kustikova, O.; Brugman, M.; Baum, C. The genomic risk of somatic gene therapy Semin. Cancer Biol. 2010, 20, 269-278
9. Martin, B.; Sainlos, M.; Aissaoui, A.; Oudrhiri, N.; Hauchecorne, M.; Vigneron, J.-P.; Lehn, J.-M.; Lehn, P. The design of cationic lipids for gene delivery Curr. Pharm. Des. 2005, 11, 375-394
10. Bhattacharya, S.; Bajaj, A. Advances in gene delivery through molecular design of cationic lipids Chem. Commun. 2009, 4632-4656
11. Srinivas, R.; Samanta, S.; Chaudhuri, A. Cationic amphiphiles: promising carriers of genetic materials in gene therapy Chem. Soc. Rev. 2009, 38, 3326-3338
12. Unciti-Broceta, A.; Bacon, M.; Bradley, M. Chemical Strategies for the Preparation of Synthetic Transfection Vectors Top. Curr. Chem. 2010, 296, 15-49
13. Mintzer, M. A.; Simanek, E. E. Synthetic Vectors for Gene Delivery Chem. Rev. 2009, 109, 259-302
14. Putnam, D. Polymers for gene delivery across length scales Nat. Mater. 2006, 5, 439-451
15. Liu, F.; Qi, H.; Huang, L.; Liu, D. Factors controlling the efficiency of cationic lipid-mediated transfection in vivo via intravenous administration Gene Ther. 1997, 4, 517-523
16. Miller, A. D. The problem with cationic liposome/micelle-based non-viral vector systems for gene therapy Curr. Med. Chem. 2003, 10, 1195-1211
17. Frechet, J. M. J. Polymer-Supported Reactions in Organic Synthesis; Wiley: New York, 1980.
18. Diaz-Mochon, J. J.; Tourniaire, G.; Bradley, M. Microarray Platforms for Enzymatic and Cell-based Assays Chem. Soc. Rev. 2007, 36, 449-457
19. Felgner, P. L.; Gadek, T. R.; Holm, M.; Roman, R.; Chan, H. W.; Wenz, M.; Northrop, J. P.; Ringold, G. M.; Danielsen, M. Lipofection: a highly efficient, lipid-mediated DNA-transfection procedure Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 7413-7417
20. Behr, J. P.; Demeneix, B.; Loeffler, J. P.; Perez-Mutul, J. Efficient gene transfer into mammalian primary endocrine cells with lipopolyamine-coated DNA Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 6982-6986
21. Yingyongnarongkul, B.-E.; Howarth, M.; Elliott, T.; Bradley, M. Solid-Phase Synthesis of 89 Polyamine-Based Cationic Lipids for DNA Delivery to Mammalian Cells Chem.-Eur. J. 2004, 10, 463-473
22. Lv, H.; Zhang, S.; Wang, B.; Cui, S.; Yan, J. Toxicity of cationic lipids and cationic polymers in gene delivery J. Controlled Release 2006, 114, 100-109
23. Unciti-Broceta, A.; Holder, E.; Jones, L. J.; Stevenson, B.; Turner, A. R.; Porteous, D. J.; Boyd, A. C.; Bradley, M. Tripod-like cationic lipids as novel gene carriers J. Med. Chem. 2008, 51, 4076-4084
24. Lebreton, S.; How, S. E.; Buchholz, M.; Yingyongnarongkul, B.; Bradley, M. Solid-phase construction: high efficiency dendrimer synthesis using AB(3) isocyanate-type monomers Tetrahedron 2003, 59, 3945-3953
25. Unciti-Broceta, A.; Moggio, L.; Dhaliwal, K.; Pidgeon, L.; Finlayson, K.; Haslett, C.; Bradley, M. Safe and efficient in vitro and in vivo gene delivery: tripodal cationic lipids with programmed biodegradability J. Mater. Chem. 2011, 21, 2154-2158
26. Yingyongnarongkul, B. E.; Howarth, M.; Elliott, T.; Bradley, M. DNA transfection screening from single beads J. Comb. Chem. 2004, 6, 753-760
27. Lebreton, S.; Newcombe, N.; Bradley, M. A novel 1 > 3 C-branched isocyanate monomer for resin amplification-a pseudo PS-PEG high-loading resin Tetrahedron Lett. 2002, 43, 2479-2482
28. Liberska, A.; Unciti-Broceta, A.; Bradley, M. Very Long-Chain Fatty Tails for Enhanced Transfection Org. Biomol. Chem. 2009, 7, 61-68
29. Kirby, A. J.; Camilleri, P.; Engberts, J. B.; Feiters, M. C.; Nolte, R. J.; Söderman, O.; Bergsma, M.; Fielden, M. L.; Garcia Rodriguez, C. L.; Guedat, P.; Kremer, A.; McGregor, C.; Perrin, C.; Ronsin, G.; Van Eijk, M. C. Gemini surfactants: new synthetic vectors for gene transfection Angew. Chem., Int. Ed. 2003, 42, 1448-1457
30. Liberska, A.; Liliemkapf, A.; Unciti-Broceta, A.; Bradley, M. Solid-Phase Synthesis of Arginine-Based Double-Tailed Cationic Lipopeptides: Potent Nucleic Acid Carriers Chem. Commun. 2011, 47, 12774-12776
31. Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Starburst cascade polymers: Molecular-level control of size, shape, surface chemistry, topology, and flexibility from atoms to macroscopic matter Angew. Chem., Int. Ed. Engl. 1990, 29, 138-175
32. Lee, C. C.; MacKay, J. A.; Fréchet, J. M. J.; Szoka, F. C. Designing dendrimers for biological applications Nat. Biotechnol. 2005, 23, 1517-526
33. Haensler, J.; Szoka, F. C., Jr. Polyamidoamine cascade polymers mediate efficient transfection of cells in culture Bioconjugate Chem. 1993, 4, 372-379
34. Boussif, O.; Lezoualch, F.; Zanta, M. A.; Mergny, M. D.; Scherman, D.; Demeneix, B.; Behr, J. P. A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo: polyethylenimine Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7297-7301
35. Sonawane, N. D.; Szoka, F. C., Jr.; Verkman, A. S. Chloride Accumulation and Swelling in Endosomes Enhances DNA Transfer by Polyamine-DNA Polyplexes J. Biol. Chem. 2003, 278, 44826-44831
36. Akinc, A.; Thomas, M.; Klibanov, A. M.; Langer, R. Exploring polyethylenimine-mediated DNA transfection and the proton sponge hypothesis J. Gene Med. 2005, 7, 657-63
37. Swali, V.; Wells, N. J.; Langley, G. J.; Bradley, M. Solid-Phase Dendrimer Synthesis and the Generation of Super-High-Loading Resin Beads for Combinatorial Chemistry J. Org. Chem. 1997, 62, 4902-4903
38. How, S. E.; Yingyongnarongkul, B.; Fara, M. A.; Diaz-Mochon, J. J.; Mittoo, S.; Bradley, M. Polyplexes and lipoplexes for mammalian gene delivery: from traditional to microarray screening Comb. Chem. High Throughput Screening 2004, 7, 423-430
39. How, S. E.; Unciti-Broceta, A.; Sanchez-Martin, R. M.; Bradley, M. Solid-phase synthesis of a lysine-capped bis-dendron with remarkable DNA delivery abilities Org. Biomol. Chem. 2008, 6, 2266-2269
40. Diaz-Mochon, J. J.; Fara, M. A.; Sanchez-Martin, R. M.; Bradley, M. Peptoid dendrimers-microwave-assisted solid-phase synthesis and transfection agent evaluation Tetrahedron Lett. 2008, 49, 923-926
41. Culf, A. S.; Ouellette, R. J. Solid-Phase Synthesis of N-Substituted Glycine Oligomers (α-Peptoids) and Derivatives Molecules 2010, 15, 5282-5335
42. Unciti-Broceta, A.; Diezmann, F.; Ou-Yang, C. Y.; Fara, M. A.; Bradley, M. Synthesis, Penetrability and Intracellular Targeting of Fluorescein-Tagged Peptoids and Peptide-Peptoid Hybrids Bioorg. Med. Chem. 2009, 17, 959-966
43. Dhaliwal, K.; Escher, G.; Unciti-Broceta, A.; Mcdonald, N.; Simpson, J.; Haslett, C.; Bradley Far red and NIR dye-peptoid conjugates for efficient immune cell labelling and tracking in preclinical models MedChemComm 2011, 2, 1050-1053
44. Diaz-Mochon, J. J.; Bialy, L.; Watson, J.; Sanchez-Martin, R. M.; Bradley, M. Synthesis and cellular uptake of cell delivering PNA-peptide conjugates Chem. Commun. 2005, 3316-3318
45. Fara, M.; A. Diaz-Mochon, J. J.; Bradley, M. Microwave-assisted coupling with DIC/HOBt for the synthesis of difficult peptoids and fluorescently labeled peptides-a gentle heat goes a long way Tetrahedron Lett. 2006, 47, 1011-1014
46. Dhaliwal, K.; Alexander, L.; Escher, G.; Unciti-Broceta, A.; Jansen, M.; Mcdonald, N.; Cardenas-Maestre, J. M.; Sanchez-Martin, R.; Simpson, J.; Haslett, C.; Bradley, M. Multi-modal molecular imaging approaches to detect primary cells in preclinical models Faraday Discuss. 2011, 149, 107-114
47. Sanchez-Martin, R. M.; Mittoo, S.; Bradley, M. The impact of combinatorial methodologies on medicinal chemistry Curr. Top. Med. Chem. 2004, 4, 653-669
48. Zhao, F.; Zhao, Y.; Liu, Y.; Chang, X.; Chen, C.; Zhao, Y. Cellular Uptake, Intracellular Trafficking, and Cytotoxicity of Nanomaterials Small 2011, 7, 1322-1337
49. Sanchez-Martin, R. M.; Muzerelle, M.; Chitkul, N.; How, S. E.; Mittoo, S.; Bradley, M. Bead-based cellular analysis, sorting and multiplexing ChemBioChem 2005, 6, 1341-1345
50. Alexander, L. M.; Pernagallo, S.; Livigni, A.; Sanchez-Martin, R. M.; Brickman, J. M.; Bradley, M. Investigation of microsphere-mediated cellular delivery by chemical microscopic and gene expression analysis Mol. BioSyst. 2010, 6, 399-409
51. Sanchez-Martin, R. M.; Cuttle, M.; Mittoo, S.; Bradley, M. Microsphere-based real-time calcium sensing Angew. Chem., Int. Ed. 2006, 45, 5472-5474
52. Bradley, M.; Alexander, L.; Duncan, K.; Chennaoui, M.; Jones, A. C.; Sanchez-Martin, R. M. pH sensing in living cells using fluorescent microspheres Bioorg. Med. Chem. Lett. 2008, 18, 313-317
53. Sanchez-Martin, R. M.; Alexander, L.; Muzerelle, M.; Cardenas-Maestre, J. M.; Tsakiridis, A.; Brickman, J. M.; Bradley, M. Microsphere-Mediated Protein Delivery into Cells ChemBioChem 2009, 10, 1453-1456
54. Gennet, N.; Alexander, L. M.; Sanchez-Martin, R. M.; Behrendt, J. M.; Sutherland, A. J.; Brickman, J. M.; Bradley, M.; Li, M. Microspheres as a vehicle for biomolecule delivery to neural stem cells New Biotechnol. 2009, 25, 442-449
55. Yusop, R. M.; Unciti-Broceta, A.; Johansson, E. M.; Sánchez- Martín, R. M.; Bradley, M. Palladium-mediated intracellular chemistry Nat. Chem. 2011, 3, 239-243
56. Tsakiridis, A.; Alexander, L. M.; Gennet, N.; Sanchez-Martin, R. M.; Livigni, A.; Li, M.; Bradley, M.; Brickman, J. M. Microsphere-based tracing and molecular delivery in embryonic stem cells Biomaterials 2009, 30, 5853-5861
57. Green, N. M. Avidin and streptavidin Methods Enzymol. 1990, 184, 51-67
58. Bradley, M.; Alexander, L.; Sanchez-Martin, R. M. Cellular uptake of fluorescent labelled biotin-streptavidin microspheres J. Fluoresc. 2008, 18, 733-739
59. Borger, J. G.; Cardenas-Maestre, J. M.; Zamoyska, R.; Sanchez-Martin, R. M. Novel Strategy for Microsphere-Mediated DNA Transfection Bioconjugate Chem. 2011, 22, 1904-1908
60. Fire, A.; Xu, S. Q.; Montgomery, M. K.; Kostas, S. A.; Driver, S. E.; Mello, C. C. Potent and specific genetic interference by double-stranded RNA in Caenorhabditis elegans Nature 1998, 391, 806-811
61. Alexander, L. M.; Sanchez-Martin, R. M.; Bradley, M. Knocking (Anti)-Sense into Cells: The Microsphere Approach to Gene Silencing Bioconjugate Chem. 2009, 20, 422-426
62. Diaz-Mochon, J. J; Bialy, L.; Bradley, M. Full orthogonality between Dde and Fmoc: The direct synthesis of PNA-peptide conjugates Org. Lett. 2004, 6, 1127-1129
63. Cardenas-Maestre, J. M.; Panadero-Fajardo, S.; Perez-Lopez, A. M.; Sanchez-Martin, R. M. Sulfhydryl reactive microspheres for the efficient delivery of thiolated bioactive cargoes J. Mater. Chem. 2011, 21, 12735-12743
64. Shi Kam, N. W.; Liu, Z.; Dai, H. Functionalization of Carbon Nanotubes via Cleavable Disulfide Bonds for Efficient Intracellular Delivery of siRNA and Potent Gene Silencing J. Am. Chem. Soc. 2005, 127, 12492-12493
65. http://www.wiley.com/legacy/wileychi/genmed/clinical/.