40
Views
8
CrossRef citations to date
0
Altmetric
Research Article

Cyclodextrins and Oligonucleotide Delivery to Solid Tumours

Pages 1-9 | Received 05 Jan 2004, Accepted 17 Feb 2004, Published online: 03 Oct 2008

References

  • Abdou, S., Collomb, J., Sallas, F., Marsura, A. and Finance, C. (1997) “Beta-cyclodextrin derivatives as carriers to enhance the antiviral activity of an antisense oligonucleotide directed toward a coronavirus intergenic consensus sequence”, Arch. Virol. 142, 1585–1602.
  • Agarwal, S. (1999) “Factors affecting the specificity and mechanism of action of antisense oligonucleotide”, Antisense Nucl. Acid Drug Dev. 9, 371–375.
  • Agu, U.R., Jorissen, M., Willems, T., van den Mooter, G., Kinget, R., Verbeke, N. and Augustijns, P. (2000) “Safety assessment of selected cyclodextrins—effect on ciliary activity using a human cell suspension culture model exhibiting in vitro ciliogenesis”, Int. J. Pharm. 193, 219–226.
  • Alvarez-Salas, L.M., Arpawong, T.E. and DiPaolo, J.A. (1999) “Growth inhibition of cervical tumor cells by antisense oligodeoxynucleotides directed to the Human Papillomavirus Type 16 E6 gene”, Antisense Nucl. Acid Drug Dev. 9, 441–450.
  • Beltinger, C., Saragovi, H.U., Smith, R.M., Lesauteur, L., Shah, N., Dedionisio, L., Christensen, L., Raible, A., Jarett, L. and Gerwirtz, A.M. (1995) “Binding, uptake, and intracellular trafficking of phosphorothioate-modified oligodeoxynucleotides”, J. Clin. Investig. 95, 1814–1823.
  • Benimetskaya, L., Loike, J.D., Kahangir, K., Loike, G., Silverstein, S., Cao, L., Khoury, J.E., Cai, T. and Stein, C.A. (1997) “Mac-1 (CD11b/CD18) is an oligodeoxynucleotide binding protein”, Nat. Med. 3, 414–420.
  • Benimetskaya, L., Tonkinson, J. and Stein, C.A. (1999) “Determination of cellular internalization of fluoresceinated oligonucleotides”, Meth. Enzymol. 212, 287–297.
  • Bergan, R., Hakim, F., Schwartz, G.N., Kyle, E., Cepada, R., Szabo, J.M., Fowler, D., Gress, R. and Neckers, L. (1996) “Electroporation of synthetic oligodeoxyribonucleotides: A novel technique for ex vivo bone marrow purging”, Blood 88, 731–741.
  • Bolyan, D. and Ganzler, K. (1998) “Chiral separation of antisense oligonucleotides: A feasibility study”, Biomed. Chromatogr. 12, 179–180.
  • Budker, V., Zhang, G., Knechtle, S. and Wolff, J.A. (1996) “Naked DNA delivered intraportally expresses in hepatocytes”, Gene Ther. 3, 593–598.
  • Budker, V., Budker, T., Zhang, G., Subbotin, V., Loomis, A. and Wolff, J.A. (2000) “Hypothesis: A naked plasmid DNA is taken up by cells in vivo by a receptor-mediated process”, J. Gene Med. 2, 76–88.
  • Cao, A., Briane, D., Coudert, R., Vassy, J., Lievre, J., Olsman, E., Tamboise, E., Salzmann, J.L., Rigaut, J.P. and Taillandier, E. (2000) “Delivery and pathway in MCF7 cells of DNA vectorized by cationic liposomes derived from cholesterol”, Antisense Nucl. Acid Drug Dev. 10, 369–380.
  • Carpenter, T.O., Gerloczy, A. and Pitha, J. (1995) “Safety of parenteral hydroxylpropyl b-cyclodextrin”, J. Pharm. Sci. 84, 222–225.
  • Childs, G.V. (1999). Biology of the cell. Accessed on 23/03/00 from the internet at http://cellbio.utmb.edu/cellbio/nuclear_envelope.htm Croyle, M.A., Roessler, B.J., Hsu, C.-P., Sun, R. and Amidon, G.L. (1998) “Beta cyclodextrins enhance adenoviral-mediated gene delivery to the intestine”, Pharm. Res. 15, 1348–1355.
  • Cserhati, T., Forgacs, E. and Szejtli, J. (1996) “Inclusion complex formation of antisense nucleotides with hydroxypropyl-b-cyclo- dextrin”, Int. J. Pharm. 141, 1–7.
  • Dass, C.R. (2000) “Apolipoprotein A-I, phospholipid vesicles and cyclodextrins as potential anti-atherosclerotic drugs: Delivery, pharmacokinetics and efficacy”, Drug Delivery 7, 161–182.
  • Dass, C.R. (2002) “Biochemical and biophysical characteristics of lipoplexes pertinent to solid tumour gene therapy”, Int. J. Pharm. 241(1),1–25.
  • Dass, C.R. and Burton, M.A. (1999) “Lipoplexes and tumours”, J. Pharmacy Pharmacol. 51, 755–770.
  • Dass, C.R. and Burton, M.A. (2002) “A model for evaluating selective delivery of plasmid DNA to tumours via the vasculature”, Cancer Biother. Radiopharm. 17(5),501–505.
  • Dass, C.R. and Burton, M.A. (2003) “Modified microplex vector enhances transfection of cells in culture while maintaining tumour-selective gene delivery in-vivo”, J. Pharm. Pharmacol. 55(1),19–25. Dass, C.R. and Su, T. (2000) “Delivery of lipoplexes for genotherapy of solid tumours: Role of vascular endothelial cells”, J. Pharm. Pharmacol. 52, 1301–1317.
  • Dass, C.R., Saravolac, E.G., Li, Y. and Sun, L.Q. (2002) “Cellular uptake, distribution, and stability of 10-23 deoxyribozymes”, Antisense Nucl. Acid Drug Dev. 12(5),289–299.
  • Davidson, W.S., Rodrigueza, W.V., Lund-Katz, S., Johnson, W.J., Rothblat, G.H. and Phillips, M.C. (1995) “Effects of particle size on the efflux of cellular free cholesterol”, J. Biol. Chem. 270, 17106–17113.
  • Dowty, M.E., Williams, P., Zhang, G., Hagstrom, J.E. and Wolff, J.A. (1995) “Plasmid DNA entry into postmitotic muclei of primary rat myotubes”, Proc. Natl Acad. Sci. USA 92, 4572–4576.
  • Dworetzky, S.I. and Feldherr, C.M. (1988) “Translocation of RNA- coated gold particles through the nuclear pores of oocytes”, J. Cell Biol. 106, 575–584.
  • Epa, W.R., Greferath, U., Shafton, A., Rong, P., Delbridge, L.M., Bennie, A. and Barrett, G.L. (2000) “Downregulation of the p75 neurotrophin receptor in tissue culture and in vivo, using b-cyclodextrin-adamantane- oligonucleotide conjugates”, Antisense Nucl. Acid Drug Dev. 10, 469– 478.
  • Ferezou, J., Riottot, M., Serougne, C., Cohen-Solal, C., Catala, I., Alquier, C., Parquet, M., Juste, C., Lafont, H., Mathe, D., Corring, T. and Lutton, C. (1997) “Hypocholesterolemic action of b-cyclodextrin and its effects on cholesterol metabolism in pigs fed a cholesterol- enriched diet”, J. Lipid Res. 38, 86–100.
  • Flourie, B., Molis, C. and Achour, L. (1993) “Fate of b-cyclodextrin in the human intestine”, J. Nutr. 123, 676–680.
  • Flynn, S.M., George, S.T., White, L., Devonish, W. and Takle, G.B. (1999) “Water-soluble, meso-substituted cationic porphyrins— a family of compounds for cellular delivery of oligonucleotides”, Biotechniques 26, 736–746.
  • Frijlink, H.W., Eissens, A.C., Hefting, N.R., Poelstra, K., Lerk, C.F. and Meijer, D.K.F. (1991) “The effect of parenterally administered cyclodextrins on cholesterol levels in the rat”, Pharm. Res. 8, 9-16. Geselowitz, D. and Neckers, L. (1992) “Analysis of oligonucleotide binding, internalization, and intracellular trafficking utilizing a novel radiolabeled crosslinker”, Antisense Res. Dev. 2, 17–25.
  • Gonzalez, H., Hwang, S.J. and Davis, M.E. (1999) “New class of polymers for the delivery of macromolecular therapeutics”, Bioconjug. Chem. 10, 1068–1074.
  • Go¨rlich, D. and Mattaj, I.W. (1996) “Nucleocytoplasmic transport”, Science 271, 1513–1518.
  • Habus, I., Zhao, Q. and Agarwal, S. (1995) “Hybridization properties, nuclease stability, and cellular uptake of the oligonucleotide-amino- b-cyclodextrins and adamantane conjugates”, Bioconjug. Chem. 6, 327–331.
  • Irie, T. and Uekama, K. (1997) “Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation”, J. Pharm. Sci. 86, 147–162.
  • Irie, T., Fukunaga, K., Garwood, M.K., Carpenter, T.O., Pitha, J. and Pitha, J. (1992) “Hydroxypropylcyclodextrins in parenteral use. II. Effects on transport and disposition of lipids in rabbit and humans”, J. Pharm. Sci. 81, 524–528.
  • Iversen, P.L., Zhu, S., Meyer, A. and Zon, G. (1992) “Cellular uptake and subcellular distribution of phosphorothioate oligonucleotides into cultured cells”, Antisense Res. Dev. 2(3),211–222.
  • Izaurralde, E. and Mattaj, I.W. (1995) “RNA export”, Cell 81, 153-159. Jain, R.K. (1996) “1995 Whitaker Lecture: Delivery of molecules, particles, and cells to solid tumors”, Ann. of Biomed. Eng. 24, 457–473.
  • Jansen, B., Wadl, H., Inoue, S.A., Trulzsch, B., Selzer, E., Duchene, M., Eichler, H.G., Wolff, K. and Pehamberger, H. (1995) “Phosphorothioate oligonucleotides reduce melanoma growth in a SCID-hu mouse model by a nonantisense mechanism”, Antisense Res. Dev. 5, 271–277.
  • Kohn, S., Nagy, J.A., Dvorak, H.F. and Dvorak, A.M. (1992) “Pathways of macromolecular tracer transport across venules and small veins. Structural basis for the hyperpermeability of tumor blood vessels”, Lab Investig. 67, 596–607.
  • Kong, G., Braun, R.D. and Dewhirst, M.W. (2000) “Hyperthermia enables tumor-specific nanoparticle delivery: Effect of particle size”, Cancer Res. 60, 4440–4445.
  • Laktionov, P.P., Dazard, J-E., Vives, E., Rykove, E.Y., Piette, J., Vlassov, V.V. and Lebleu, B. (1999) “Characterisation of membrane oligonucleotide-binding proteins and oligonucleotide uptake in keratinocytes”, Nucl. Acids Res. 27, 2315–2324.
  • Lappalainen, K., Urtti, A., Ja¨a¨skela¨inen, I., Syrja¨anen, K. and Syrja¨nen, S. (1994) “Cationic liposomes mediated delivery of antisense oligonucleotides targeted to HPV E7 mRNA in CaSki cells”, Antiviral Res. 23, 119–130.
  • Leonetti, J.P., Mechti, N., Degols, G., Gagnor, C. and Lebleu, B. (1991) “Intracellular distribution of microinjected antisense oligo- nucleotides”, Proc. Natl Acad. Sci. USA 88, 2701–2706.
  • Liu, S.M., Cogny, A., Kockx, M., Dean, R.T., Gaus, K., Jessup, W. and Kritharides, L. (2003 Jun) “Cyclodextrins differentially mobilize free and esterified cholesterol from primary human foam cell macro- phages”, J. Lipid Res. 44(6),1156–1166.
  • Matsukura, M., Shinozuka, K., Zon, G., Mitsuya, H., Reitz, M., Cohen, J.S. and Broder, S. (1987) “Phosphorothioate analogs of oligodeoxy- nucleotides: inhibitors of replication and cytopathic effects of human immunodeficiency virus”, Proc. Natl Acad. Sci. USA 84, 7706–7710.
  • Melchior, F. and Gerace, L. (1995) “Mechanisms of nuclear protein import”, Curr. Opin. Cell Biol. 7, 310–318.
  • Mellman, I. (1996) “Endocytosis and molecular sorting”, Annu. Rev. Cell Dev. Biol. 12, 575–625.
  • Noonberg, S.B., Garavoy, M.R. and Hunt, C.A. (1993) “Characteristics of oligonucleotide uptake in human keratinocyte cultures”, J. Investig. Dermatol. 101, 727–731.
  • Pichon, C., Freulon, I., Midoux, P., Mayer, R., Monsigny, M. and Roche, A.C. (1997) “Cytosolic and nuclear delivery of oligonucleotides mediated by an amphiphilic anionic peptide”, Antisense Res. Dev. 7, 335–343.
  • Pin˜ol-Roma, S. and Dreyfuss, G. (1992) “Shuttling of pre-mRNA binding proteins between nucleus and cytoplasm”, Nature 355, 730–732.
  • Pouton, C.W. (1998) “Nuclear import of polypeptides, polynucleotides and supramolecular complexes”, Adv. Drug Deliv. Rev. 34, 51–64.
  • Regnier, V., Tahiri, A., Andre, N., Lemaitre, M., Le Doan, T. and Preat, V. (2000) “Electroporation-mediated delivery of 30 -protected phospho- diester oligodeoxynucleotides to the skin”, J. Contr. Rel. 67, 337–346.
  • Riottot, M., Olivier, P., Huet, A., Caboche, J.-J., Parquet, M., Khallou, J. and Lutton, C. (1993) “Hypolipidemic effects of b-cyclodextrin in the hamster and in the genetically hypercholesterolemic Rico rat”, Lipids 28, 181–188.
  • Saison-Behmoaras, T., Tocque, B., Rey, I., Chassignol, M., Thuong, N.T. and Helene, C. (1991) “Short modified antisense oligonucleotides directed against Ha-ras point mutation induce selective cleavage of the mRNA and inhibit T24 cell proliferation”, EMBO J. 10, 1111–1118.
  • Santiago, F.S., Lowe, H.C., Kavurma, M.M., Chesterman, C.N., Baker, A., Atkins, D.G. and Khachigian, L.M. (1999) “New DNA enzyme targeting Egr-1 mRNA inhibits vascular smooth muscle proliferation and regrowth after injury”, Nat. Med. 5, 1264–1269.
  • Sharkey, E.M., O’Neill, H.B., Kavarana, M.J., Wang, H., Creighton, D.J., Sentz, D.L. and Eiseman, J.L. (2000) “Pharmacokinetics and antitumor properties in tumor-bearing mice of an enediol analogue inhibitor of glyoxalase I”, Cancer Chemother. Pharmacol. 46, 156–166.
  • Sinisterra, R.D., Shastri, V.P., Najjar, R. and Langer, R. (1999) “Encapsulation and release of rhodium (II) citrate and its association complex with hydroxypropyl-b-cyclodextrin from biodegradable polymer microspheres”, J. Pharm. Sci. 88, 574–576.
  • Spiller, D.G. and Tidd, D.M. (1995) “Nuclear delivery of antisense oligodeoxyribonucleotides through reversible permeabilization of human leukemia cells with streptolysin-O”, Antisense Res. Dev. 5, 13–21.
  • Stein, C.A., Tonkinson, J.L., Zhang, L.M., Yakubov, L., Gervasoni, J., Taub, R. and Rotenberg, S. (1993) “Dynamics of the internalization of phosphodiester oligodexoynucleotides in HL60 cells”, Biochem- istry 32, 4855–4862.
  • Stoffler, D., Fahrenkrog, B. and Aebi, U. (1999) “The nuclear pore complex: From molecular architecture to functional dynamics”, Curr. Opin. Cell Biol. 11, 391–401.
  • Sun, D. and Gilboe, D.D. (1994) “Effect of the platelet-activating factor antagonist BN50739 and its diluents on mitochondrial respiration and membrane lipids during and following cerebral ischemia”, J. Neurochem. 62, 1929–1938.
  • Sun, L-Q., Cairns, M.J., Saravolac, E.G., Baker, A. and Gerlach, W.L. (2000) “Catalytic nucleic acids: From lab to applications”, Pharmacol. Rev. 52, 325–347.
  • Toyoda, K., Shada, T., Uneyama, C., Takada, K. and Takahashi, M. (1997) “Carcinogenicity study of beta-cyclodextrin in F344 rats”, Food Chem. Toxicol. 35, 331–336.
  • Walker, T.L., Dass, C.R., DeCruz, E.E. and Burton, M.A. (1998) “A method for intratumoral continuous infusion of antisense oligodeoxynucleotides”, J. Pharm. Sci. 87, 387–389.
  • Walker, T.L., Dass, C.R. and Burton, M.A. (2002) “Enhanced in vivo tumour response from combination carboplatin and low dose c-myc antisense oligonucleotides”, Anticancer Res. 14, 2237–2245.
  • White, P.J., Fogarty, R.D., Liepe, I.J., Delany, P.M., Werther, G.A. and Wraight, C.J. (1999) “Live confocal microscopy of oligonucleotide uptake by keratinocytes in human skin grafts on nude mice”, J. Investig. Dermatol. 112, 887–892.
  • Wu, N.Z., Da, D., Rudoll, T.L., Needham, D., Whorton, A.R. and Dewhirst, M.W. (1993) “Increased microvascular permeability contributes to preferential accumulation of Stealth liposomes in tumor tissue”, Cancer Res. 53, 3756–3770.
  • Yakubov, L.A., Deeva, E.A., Zaryotova, V.F., Ivanova, E.M., Ryte, A.S., Yurchenko, L.V. and Vlassov, V.V. (1989) “Mechanisms of oligonucleotide uptake by cells: Involvement of specific receptors?”, Proc. Natl Acad. Sci. USA 86, 6454–6458.
  • Zamecnik, P., Aghajanian, J., Zamecnik, M., Goodchild, J. and Witman, G. (1994) “Electron micrographic studies of transport of oligodeoxy- nucleotides across eukaryotic cell membranes”, Proc. Natl Acad. Sci. USA 91, 3156–3160.
  • Zelphati, O. and Szoka, F.C., Jr. (1996) “Intracellular distribution and mechanism of delivery of oligonucleotides mediated by cationic lipids”, Pharmacol. Res. 13, 1367–1372.
  • Zhao, Q., Matson, S., Herrera, C.J., Fisher, E., Yu, H. and Krieg, A.M. (1993) “Comparison of cellular binding and uptake of antisense phosphodiester, phosphorothioate, and mixed phosphorothioate and methylphosphonate oligonucleotides”, Antisense Res. Dev. 3, 53-66. Zhao, Q., Temsamani, J. and Agarwal, S. (1995) “Use of cyclodextrin and its derivatives as carriers for oligonucleotide delivery”, Antisense Res. Dev. 5, 185–192.
  • Zhao, Q., Temsamani, J., Tadarola, P.L., Jiang, Z. and Agarwal, S. (1996) “Effect of different chemically modified oligodeoxynucleotides on immune stimulation”, Biochem. Pharmacol. 51, 173–182.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.