Strategies for Microsphere-Mediated Cellular Delivery

Ideas in Chemistry and Molecular Sciences: Where Chemistry Meets Life

Volumn , Issue , 2010, Pages 117-140

  Sanchez Martin, Rosario M ^a   Alexander, Lois M ^a   Manuel Cardenas Maestre, Juan ^a   Bradley, Mark ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

Bioconjugation; Cleavable linker; Delivery device; Intracellular sensing; Microspheres; Sirna delivery; Solid phase chemistry

Indexed keywords

EID: 84885511494     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527630516.ch5     Document Type: Chapter

References (92)

1. Adrian, C. and Hogben, M. (1960) Movement of material across cell membranes. Physiologist, 3, 56-62.
2. Gregoriadis, G. (1995) Engineering liposomes for drug delivery: progress and problems. Trends Biotechnol., 13 (12), 527-537.
3. Gregoriadis, G. (1976) Carrier potential of liposomes in biology and medicine.New England. J. Med., 295 (13), 704-710.
4. Poste, G. and Papahadjopoulos, D. (1976) Drug-containing lipid vesicles render drug-resistant tumor-cells sensitive to Actinomycin-D. Nature, 261 (5562), 699-701.
5. Torchilin, V.P.Z.F. and Huang, L.J. (1993) pH-sensitive liposomes. J. Liposome Res., 3, 201-255.
6. Simoes, S., Moreira, J.N., Fonseca, C., Duzgunes, N., and de Lima, M.C.P. (2004) On the formulation of pH-sensitive long circulation times. Adv. Drug Deliv. Rev., 56 (7), 947-965.
7. Sakurai, F., Nishioka, T., Yamashita, F., Takakura, Y., and Hashida, M. (2001) Effects of erythrocytes and serum proteins on lung accumulation of lipoplexes containing cholesterol or DOPE as a helper lipid in the single-pass rat lung perfusion system. Eur. J. Pharm. Biopharm., 52 (2), 165-172.
8. Yessine, M.A. and Leroux, J.C. (2004) Membrane-destabilizing polyanions: interaction with lipid bilayers and endosomal escape of biomacromolecules. Adv. Drug Deliv. Rev., 56 (7), 999-1021.
9. Chang, J.S., Choi, M.J., Cheong, H.S., and Kim, K. (2001) Development of Th1-mediated CD8+effector T cells by vaccination with epitope peptides encapsulated in pH-sensitive liposomes. Vaccine, 19 (27), 3608-3614.
10. Meyer, O., Kirpotin, D., Hong, K.L., Sternberg, B., Park, J.W., Woodle, M.C., and Papahadjopoulos, D. (1998) Cationic liposomes coated with polyethylene glycol as carriers for oligonucleotides. J. Biol. Chem., 273 (25), 15621-15627.
11. Zelphati, O. and Szoka, F.C. (1996) Liposomes as a carrier for intracellular delivery of antisense oligonucleotides: a real or magic bullet? J. Control. Release, 41 (1-2), 99-119.
12. Clark, H.A., Hoyer, M., Philbert, M.A., and Kopelman, R. (1999) Optical nanosensors for chemical analysis inside single living cells. 1. Fabrication, characterization, and methods for intracellular delivery of PEBBLE sensors. Anal. Chem., 71 (21), 4831-4836.
13. Zhao, M. and Weissleder, R. (2004) Intracellular cargo delivery using tat peptide and derivatives. Med. Res. Rev., 24 (1), 1-12.
14. Ruben, S., Perkins, A., Purcell, R., Joung, K., Sia, R., Burghoff, R., Haseltine, W.A., and Rosen, C.A. (1989) Structural and functional-characterization of human immunodeficiency virus tat protein. J. Virol., 63 (1), 1-8.
15. Jarver, P. and Langel, U. (2004) The use of cell-penetrating peptides as a tool for gene regulation. Drug Discov. Today, 9 (9). doi: PII S1359-6446(04)03042-9.
16. Temsamani, J. and Vidal, P. (2004) The use of cell-penetrating peptides for drug delivery. Drug Discov. Today, 9 (23). doi: PII S1359-6446(04)03279-9.
17. Wender, P.A., Mitchell, D.J., Pattabiraman, K., Pelkey, E.T., Steinman, L., and Rothbard, J.B. (2000) The design, synthesis, and evaluation of molecules that enable or enhance cellular uptake: peptoid molecular transporters. Proc. Natl. Acad. Sci. U.S.A., 97 (24), 13003-13008.
18. Wender, P.A., Rothbard, J.B., Jessop, T.C., Kreider, E.L., and Wylie, B.L. (2002) Oligocarbamate molecular transporters: design, synthesis, and biological evaluation of a new class of transporters for drug delivery. J. Am. Chem. Soc., 124 (45), 13382-13383.
19. Peretto, I., Sanchez-Martin, R.M., Wang, X.H., Ellard, J., Mittoo, S., and Bradley, M. (2003) Cell penetrable peptoid carrier vehicles: synthesis and evaluation. Chem. Commun., 18, 2312-2313.
20. Fara, M.A., Diaz-Mochon, J.J., and Bradley, M. (2006) Microwave-assisted coupling with DIC/HOBt for the synthesis of difficult peptoids and fluorescently labelled peptides - a gentle heat goes a long way. Tetrahedron Lett., 47 (6), 1011-1014.
21. Unciti-Broceta, A., Diezmann, F., Ou-Yang, C.Y., Fara, M.A., and Bradley, M. (2009) Synthesis, penetrability and intracellular targeting of fluorescein-tagged peptoids and peptide-peptoid hybrids. Bioorg. Med. Chem., 17 (3), 959-966.
22. Aulenta, F., Hayes, W., and Rannard, S. (2003) Dendrimers: a new class of nanoscopic containers and delivery devices. Eur. Polym. J., 39 (9), 1741-1771.
23. Capitosti, G.J., Guerrero, C.D., Binkley, D.E., Rajesh, C.S., and Modarelli, D.A. (2003) Efficient synthesis of porphyrin-containing, benzoquinone-terminated, rigid polyphenylene dendrimers. J. Org. Chem., 68 (2), 247-261.
24. Milhem, O.M., Myles, C., McKeown, N.B., Attwood, D., and D'Emanuele, A. (2000) Polyamidoamine Starburst (R) dendrimers as solubility enhancers. Int. J. Pharm., 197 (1-2), 239-241.
25. How, S.E., Yingyongnarongkul, B., Fara, M.A., Diaz-Mochon, J.J., Mittoo, S., and Bradley, M. (2004) Polyplexes and lipoplexes for mammalian gene delivery: from traditional to microarray screening. Comb. Chem. High Throughput Screen., 7 (5), 423-430.
26. How, S.E., Unciti-Broceta, A., Sanchez-Martin, R.M., and Bradley, M. (2008) Solid-phase synthesis of a lysine-capped bis-dendron with remarkable DNA delivery abilities. Org. Biomol. Chem., 6 (13), 2266-2269.
27. Diaz-Mochon, J.J., Fara, M.A., Sanchez-Martin, R.M., and Bradley, M. (2008) Peptoid dendrimers-microwave-assisted solid-phase synthesis and transfection agent evaluation. Tetrahedron Lett., 49 (5), 923-926.
28. Gillies, E.R. and Frechet, J.M.J. (2005) Dendrimers and dendritic polymers in drug delivery. Drug Discov. Today, 10 (1). doi: PII S1359-6446(04)03276-3.
29. Sahoo, S.K. and Labhasetwar, V. (2003) Nanotech approaches to delivery and imaging drug. Drug Discov. Today, 8 (24). doi: PII S1359-6446(03)02903-9.
30. Kam, N.W.S., Jessop, T.C., Wender, P.A., and Dai, H.J. (2004) Nanotube molecular transporters: internalization of carbon nanotube-protein conjugates into mammalian cells. J. Am. Chem. Soc., 126 (22), 6850-6851.
31. Kam, N.W.S. and Dai, H.J. (2005) Carbon nanotubes as intracellular protein transporters: generality and biological functionality. J. Am. Chem. Soc., 127 (16), 6021-6026.
32. Pantarotto, D., Briand, J.P., Prato, M., and Bianco, A. (2004) Translocation of bioactive peptides across cell membranes by carbon nanotubes. Chem. Commun., 1, 16-17.
33. Kam, N.W.S., Liu, Z., and Dai, H.J. (2005) Functionalization of carbon nanotubes via cleavable disulfide bonds for efficient intracellular delivery of siRNA and potent gene silencing. J. Am. Chem. Soc., 127 (36), 12492-12493.
34. Son, S.J., Reichel, J., He, B., Schuchman, M., and Lee, S.B. (2005) Magnetic nanotubes for magnetic-field-assisted bioseparation, biointeraction, and drug delivery. J. Am. Chem. Soc., 127 (20), 7316-7317.
35. Cherukuri, P., Bachilo, S.M., Litovsky, S.H., and Weisman, R.B. (2004) Near-infrared fluorescence microscopy of single-walled carbon nanotubes in phagocytic cells. J. Am. Chem. Soc., 126 (48), 15638-15639.
36. Bianco, A., Hoebeke, J., Godefroy, S., Chaloin, O., Pantarotto, D., Briand, J.P., Muller, S., Prato, M., and Partidos, C.D. (2005) Cationic carbon nanotubes bind to CpG oligodeoxynucleotides and enhance their immunostimulatory properties. J. Am. Chem. Soc., 127 (1), 58-59.
37. Kawaguchi, H. (2000) Functional polymer microspheres. Prog. Polym. Sci., 25 (8), 1171-1210.
38. Zhang, Y., Eniola, A.O., Graves, D.J., and Hammer, D.A. (2003) Specific adhesion of micron-sized colloids to surfaces mediated by hybridizing DNA chains. Langmuir, 19 (17), 6905-6911.
39. Rogers, P.H., Michel, E., Bauer, C.A., Vanderet, S., Hansen, D., Roberts, B.K., Calvez, A., Crews, J.B., Lau, K.O., Wood, A., Pine, D.J., and Schwartz, P.V. (2005) Selective, controllable, and reversible aggregation of polystyrene latex microspheres via DNA hybridization. Langmuir, 21 (12), 5562-5569.
40. Steinkamp, J.A., Wilson, J.S., Saunders, G.C., and Stewart, C.C. (1982) Phagocytosis - flow cytometric quantitation with fluorescent microspheres. Science, 215 (4528), 64-66.
41. Freiberg, S. and Zhu, X. (2004) Polymer microspheres for controlled drug release. Int. J. Pharm., 282 (1-2), 1-18.
42. Christie, R.J. and Grainger, D.W. (2003) Design strategies to improve soluble macromolecular delivery constructs. Adv. Drug Deliv. Rev., 55 (3), 421-437.
43. Piirma, I. (1985) Colloids, in Encyclopedia of Polymer Science and Engineering, 2nd edn (eds H.F. Mark, N.M. Bikales, C.G. Overberger, G. Menges, and J.I. Kroschwitz), John Wiley & Sons, Inc., New York, pp. 125-130.
44. Barrett, K.E.J. (1975) Dispersion Polymerisation in Organic Media, John Wiley & Sons, Ltd, London.
45. Strover, H.D.H. and Li, K. (1996) 1900-1905: dispersion polymerisation, Polymer Materials Encyclopedia, CRC Press, Boca Raton.
46. Weissman, J.M., Sunkara, H.B., Tse, A.S., and Asher, S.A. (1996) Thermally switchable periodicities and diffraction from mesoscopically ordered materials. Science, 274 (5289), 959-960.
47. Ogawa, Y., Yamamoto, M., Okada, H., Yashiki, T., and Shimamoto, T. (1988) A new technique to efficiently entrap leuprolide acetate into microcapsules of polylactic acid or copoly(Lactic Glycolic) acid. Chem. Pharm. Bull., 36 (3), 1095-1103.
48. Vasir, J.K., Tambwekar, K., and Garg, S. (2003) Bioadhesive microspheres as a controlled drug delivery system. Int. J. Pharm., 255 (1-2), 13-32.
49. Edlund, U. and Albertsson, A.C. (2002) Degradable polymer microspheres for controlled drug delivery. Degradable Aliphatic Polyesters, 157, 67-112.
50. Bodmeier, R. and Chen, H.G. (1988) Preparation of biodegradable poly (+/-) lactide microparticles using a spray-drying technique. J. Pharm. Pharmacol., 40 (11), 754-757.
51. Pratten, M.K. and Lloyd, J.B. (1986) Pinocytosis and phagocytosis - the effect of size of a particulate substrate on its mode of capture by rat peritoneal-macrophages cultured in vitro. Biochim. Biophys. Acta, 881 (3), 307-313.
52. Ng, K., Stringer, K.A., Cohen, Z., Serravo, R., Tian, B., Meyer, J.D., Falk, R., Randolph, T., Manning, M.C., and Thompson, D.C. (1998) Alveolar macrophage cell line is not activated by exposure to polymeric microspheres. Int. J. Pharm., 170 (1), 41-49.
53. Tseng, C.M., Lu, Y.Y., Elaasser, M.S., and Vanderhoff, J.W. (1986) Uniform polymer particles by dispersion polymerization in alcohol. J. Polym. Sci. A, Polym. Chem., 24 (11), 2995-3007.
54. Paine, A.J. and McNulty, J. (1990) Uniform polymer particles by dispersion polymerization in alcohol [Comment]. J. Polym. Sci. A, Polym. Chem., 28 (9), 2569-2574.
55. Delair, T., Marguet, V., Pichot, C., and Mandrand, B. (1994) Synthesis and characterization of cationic amino functionalized polystyrene latexes. Colloid Polym. Sci., 272 (8), 962-970.
56. Ober, C.K. and Lok, K.P. (1987) Formation of large monodisperse copolymer particles by dispersion polymerization. Macromolecules, 20 (2), 268-273.
57. Ye, Q., Zhang, Z.C., Jia, H.T., He, W.D., and Ge, X.W. (2002) Formation of monodisperse polyacrylamide particles by radiation-induced dispersion polymerization: particle size and size distribution. J. Colloid Interface Sci., 253 (2), 279-284.
58. Paine, A.J. (1990) Dispersion polymerization of styrene in polar-solvents .1. Grafting mechanism of stabilization by hydroxypropyl cellulose. J. Colloid Interface Sci., 138 (1), 157-169.
59. Whitby, G.S. and Katz, M. (1933) Synthetic rubber (concluded). Ind. Eng. Chem., 25, 1338-1348.
60. Farbenfabrik, A.G. (1909) First Process for Manufacturing artificial rubber Germany.
61. Luther, M. and Heuck C. (1927) Polymerizing Butadiene Hydrocarbons, Germany.
62. Smith, W.V. and Ewart, R.H. (1948) Kinetics of emulsion polymerization. J. Chem. Phys., 16 (6), 592-599.
63. Harkins, W.D. (1947) A general theory of the mechanism of emulsion polymerization. J. Am. Chem. Soc., 69 (6), 1428-1444.
64. Gilbert, R.G. (1996) Emulsion Polymerisation: A Mechanistic Approach, Academic Press, London.
65. Zhang, H.T., Huang, J.X., and Jiang, B.B. (2002) Kinetics of polymerization and particle stabilization mechanism on dispersion copolymerization of styrene and divinylbenzene. J. Appl. Polymer Sci., 85 (10), 2230-2238.
66. Sanchez-Martin, R.M., Muzerelle, M., Chitkul, N., How, S.E., Mittoo, S., and Bradley, M. (2005) Bead-based cellular analysis, sorting and multiplexing. Chembiochem, 6 (8), 1341-1345.
67. Page, P., Bradley, M., Walters, I., and Teague, S. (1999) Solid-phase synthesis of tyrosine peptide aldehydes. Analogues of (S)-MAPI. J. Org. Chem., 64 (3), 794-799.
68. Harris, J.M. (1992) Poly(ethylene glycol) chemistry: biotechnical and biomedical applications, in Topics in Applied Chemistry (ed. J.M. Harris), Plenum Press, New York.
69. Bycroft, B.W., Chan, W.C., Chhabra, S.R., and Hone, N.D. (1993) A novel lysine-protecting procedure for continuous-flow solid-phase synthesis of branched peptides. J. Chem. Soc. Chem. Commun., (9), 778-779.
70. Diaz-Mochon, J.J., Bialy, L., and Bradley, M. (2004) Full orthogonality between Dde and Fmoc: the direct synthesis of PNA-peptide conjugates. Org. Lett., 6 (7), 1127-1129.
71. Sanchez-Martin, R.M., Cuttle, M., Mittoo, S., and Bradley, M. (2006) Microsphere-based real-time calcium sensing. Angew. Chem. Int. Ed., 45 (33), 5472-5474.
72. Grynkiewicz, G., Poenie, M., and Tsien, R.Y. (1985) A new generation of Ca-2+ indicators with greatly improved fluorescence properties. J. Biol. Chem., 260 (6), 3440-3450.
73. Bradley, M., Alexander, L., Duncan, K., Chennaoui, M., Jones, A.C., and Sanchez-Martin, R.M. (2008) pH sensing in living cells using fluorescent microspheres. Bioorg. Med. Chem. Lett., 18 (1), 313-317.
74. Fire, A., Xu, S.Q., Montgomery, M.K., Kostas, S.A., Driver, S.E., and Mello, C.C. (1988) Potent and specific genetic interference by double-stranded RNA in Caenorhabditis elegans. Nature, 391 (6669), 806-811.
75. Elbashir, S.M., Harborth, J., Lendeckel, W., Yalcin, A., Weber, K. and Tuschl, T. (2001) Duplexes of 21-nucleotide RNAs mediate RNA interference in cultured mammalian cells. Nature, 411 (6836), 494-498.
76. Hamilton, A.J. and Baulcombe, D.C. (1999) A species of small antisense RNA in posttranscriptional gene silencing in plants. Science, 286 (5441), 950-952.
77. Hong, J., Wei, N., Chalk, A., Wang, J., Song, Y.T., Yi, F., Qiao, R.P., Sonnharnmer, E.L.L., Wahlestedt, C., Liang, Z.C., and Du, Q. (2008) Focusing on RISC assembly in mammalian cells. Biochem. Biophys. Res. Commun., 368 (3), 703-708.
78. Schwarz, D.S., Hutvagner, G., Du, T., Xu, Z.S., Aronin, N., and Zamore, P.D. (2003) Asymmetry in the assembly of the RNAi enzyme complex. Cell, 115 (2), 199-208.
79. Schubert, S., Grunweller, A., Erdmann, V.A., and Kurreck, J. (2005) Local RNA target structure influences siRNA efficacy: systematic analysis of intentionally designed binding regions. J. Mol. Biol., 348 (4), 883-893.
80. Wang, K.P., Wang, C.H., Xiao, F., Wang, H.X., and Wu, Z.G. (2008) JAK2/STAT2/STAT3 are required for myogenic differentiation. J. Biol. Chem., 283 (49), 34029-34036.
81. Berg, K., Folini, M., Prasmickaite, L., Selbo, P.K., Bonsted, A., Engesaeter, B.O., Zaffaroni, N., Weyergang, A., Dietze, A., Maelandsmo, G.M., Wagner, E., Norum, O.J., and Hogset, A. (2007) Photochemical internalization: a new tool for drug delivery. Curr. Pharm. Biotechnol., 8 (6), 362-372.
82. Simpson, D.J., Unkefer, C.J., Whaley, T.W., and Marrone, B.L. (1991) A mechanism-based fluorogenic probe for the cytochrome-P-450 cholesterol side-chain cleavage enzyme. J. Org. Chem., 56 (18), 5391-5396.
83. Gao, W.Z., Xing, B.G., Tsien, R.Y., and Rao, J.H. (2003) Novel fluorogenic substrates for imaging 6-lactamase gene expression. J. Am. Chem. Soc., 125 (37), 11146-11147.
84. Ishiyama, M., Furusawa, H., Shiga, M., Ohseto, F., and Sasamoto, K. (1999) A resorufin derivative as a fluorogenic indicator for cell viability. Anal. Sci., 15 (10), 1025-1028.
85. Pardridge, W.M. (2007) shRNA and siRNA delivery to the brain. Adv. Drug Deliv. Rev., 59 (2-3), 141-152.
86. Susumu, K., Uyeda, H.T., Medintz, I.L., Pons, T., Delehanty, J.B., and Mattoussi, H. (2007) Enhancing the stability and biological functionalities of quantum dots via compact multifunctional ligands. J. Am. Chem. Soc., 129, 13987-13996.
87. Niemeyer, C.M., Adler, M., and Wacker, R. (2007) Detecting antigens by quantitative immuno-PCR. Nat. Protoc., 2 (8), 1918-1930.
88. Diamandis, E.P. and Christopoulos, T.K. (1991) The Biotin (Strept)Avidin System - principles and applications in biotechnology. Clin. Chem., 37 (5), 625-636.
89. Green, N.M. (1990) Avidin and Streptavidin. Methods. Enzymol., 184, 51-67.
90. Bradley, M., Alexander, L., and Sanchez-Martin, R.M. (2008) Cellular uptake of fluorescent labelled biotin-streptavidin microspheres. J. Fluoresc., 18 (3-4), 733-739.
91. Wu, C.W., Lee, J.G., and Lee, W.C. (1998) Protein and enzyme immobilization on non-porous microspheres of polystyrene. Biotechnol. Appl. Biochem., 27, 225-230.
92. Kada, G., Falk, H., and Gruber, H.J. (1999) Accurate measurement of avidin and streptavidin in crude biofluids with a new, optimized biotin-fluorescein conjugate. Biochimi. Biophys. Acta, 1427 (1), 33-43.