A cationic derivative of amphotericin B as a novel delivery system for antisense oligonucleotides

Antisense and Nucleic Acid Drug Development

Volumn 10, Issue 3, 2000, Pages 177-184

  Garcia Chaumont, Christine ^a   Seksek, Olivier ^a   Jolles, Béatrice ^a   Bolard, Jacques ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN B; ANTISENSE OLIGONUCLEOTIDE; CATION; FLUORESCEIN; GLYCOPROTEIN P; LIPOFECTIN; OLIGODEOXYNUCLEOTIDE; PHOSPHOROTHIOIC ACID; POLYENE ANTIBIOTIC AGENT;

ANIMAL CELL; ARTICLE; CELL MEMBRANE PERMEABILITY; COMPLEX FORMATION; CONTROLLED STUDY; GENE TARGETING; MOUSE; NONHUMAN; NUCLEIC ACID TRANSPORT; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANIMALIA;

EID: 0033931851     PISSN: 10872906     EISSN: None     Source Type: Journal    
DOI: 10.1089/oli.1.2000.10.177     Document Type: Article

References (51)

1. ALAHARI, S.K., DEAN, N.M., FISHER, M.H., DELONG, R., MANOHARAN, M., TIVEL, K.L., and JULIANO, R.L. (1996). Inhibition of expression of the multidrug resistance-associated P-glycoprotein by phosphorothioate and 5′cholesterol-conjugated phosphorothioate antisense oligonucleotides. Mol. Pharmacol. 50, 808-819.
2. BELTINGER, C., SARAGOVI, H.U., SMITH, R.M., LESAUTEUR, L., SHAH, N., DEDIONISIO, L., CHRISTENSEN, L., RAIBLE, A., JARRETT, L., and GEWIRTZ, A.M. (1995). Binding, uptake, and intracellular trafficking of phosphorothioate-modified oligodeoxyribonucleotides. J. Clin. Invest. 95, 1814-1823.
3. BINET, A., and BOLARD, J. (1988). Recovery of hepatocytes from attack by the pore former amphotericin B. Biochem. J. 253, 435-440.
4. BLANC, I., BUENO DA COSTA, M.-H., BOLARD, J., and SAINTPIERRE CHAZALET, M. (2000). Oligonucleotide delivery by a cationic derivative of the polyene antibiotic amphotericin B. I. Interaction oligonucleotide/vector as studied by optical spectroscopy and electron microscopy. Biochim. Biophys. Acta 1464, 299-308.
5. BLANC, I., and SAINT-PIERRE CHAZALET, M. (2000). Oligonucleotide delivery by a cationic derivative of the polyene antibiotic amphotericin B. II. Study of the interactions of the oligonucleotide/cationic vector complexes with lipid monolayers and lipid unilamellar vesicles. Biochim. Biophys. Acta 1464, 309-321.
6. BOUSSIF, O., LEZOUALC'H, P., ZANTA, M.A., MERGNY, M.J., SCHERMAN, D., DEMENEIX, B., and BEHR, J.-P. (1995). A versatile vector for gene and Oligonucleotide transfer into cells in culture and in vivo: Polyethylenimine. Proc. Natl. Acad. Sci. USA 92, 7297-7301.
7. BOUTORINE, A.S., and KOSTINA, E.V. (1993). Reversible covalent attachment of cholesterol to oligodeoxyribonucleotides for studies of the mechanisms of their penetration into eucaryotic cells. Biochimie 75, 35-41.
8. CAPACCIOLI, S., DIPASQUALE, G., MINI, B., MAZZEI, T., and QUATTRONE, A. (1993). Cationic lipids improve antisense Oligonucleotide uptake and prevent degradation in cultured cells and in human serum. Biochem. Biophys. Res. Commun. 197, 818-825.
9. CHALOIN, L., VIDAL, P., LORY, P., MERY, J., LAUTREDOU, N., DIVITA, G., and HEITZ, F. (1998). Design of carrier peptide- oligonucleotide conjugates with rapid membrane translocation and nuclear localization properties. Biochem. Biophys. Res. Commun. 243, 601-608.
10. CHÉRON, M., CYBULSKA, B., MAZERSKI, J., GRZYBOWSKA, J., CZERWINSKI, A., and BOROWSKI, E. (1988). Quantitative structure-activity relationships in amphotericin B derivatives. Biochem. Pharmacol. 37, 827-836.
11. COMPAGNON, B., MILHAUD, P., BIENVENUE, A., and PHILIPPOT, J.R. (1992). Targeting of poly(rI)-poly(rC) by fusogenic (F protein) immunoliposomes. Exp. Cell Res. 200, 333-338.
12. CORRIAS, M.V., and TONINI, G.P. (1992). An oligomer complementary to the 5′ end region of MDR1 gene decreases resistance to doxorubicin of human adenocarcinoma-resistant cells. Anticancer Res. 12, 1431-1438.
13. DASSOW, H., LASSNER, D., REMKE, H., and PREISS, R. (1998). Modulation of P-glycoprotein-mediated multidrug resistance in a doxorubicin-resistant subline of the human lymphoblastoid cell line CCRF-CEM by phosphorothioate antisense oligonucleotides. Int. J. Clin. Pharmacol. Ther. 36, 93-96.
14. DEROSSI, D., CHASSAING, G., and PROCHIANTZ, A. (1998). Trojan peptides: The penetrating system for intracellular delivery. Trends Cell Biol. 8, 84-87.
15. EDER, P.S., DEVINE, R.J., DAGLE, J.M., and WALDER, J.A. (1991). Substrate specificity and kinetics of degradation of antisense oligonucleotides by a 3′ exonuclease in plasma. Antisense Res. Dev. 1, 141-151.
16. EFFERTH, T., and VOLM, M. 91993). Modulation of P-glycoprotein- mediated multidrug resistance by monoclonal antibodies, immunotoxins or antisense oligodeoxynucleotides in kidney carcinoma and normal kidney cells. Oncology 50, 303-308.
17. FALKOWSKI, L., JARZEBSKI, A., STEFANSKA, B., BYLEC, E., and BOROWSKI, E. (1980). The synthesis of amides of polyene macrolide antibiotics. J. Antibiot. 33, 103-107.
18. FELGNER, P.L., GADEK, T.R., HOMN, M., ROMAN, R., CHAN, H.W., WENZ, J.P., RINGOLD, G.M., and DANILESIN, M. (1987). Lipofection: A Highly efficient, lipid-mediated DNA-transfection procedure. Proc. Natl. Acad. Sci. USA 84, 7413-7417.
19. FELION, M.C., and PHILLIPS, N.C. (1997). Toxicity and immunomodulatory activity of liposomal vectors formulated with cationic lipids toward immune effector cells. Biochim. Biophys. Acta 1329, 345-356.
20. FILION, M.C., and PHILLIPS, N.C. (1998). Major limitations in the use of cationic liposomes for DNA delivery. Int. J. Pharmacol. 162, 159-170.
21. FISHER, P.B., BRYSON, V., and SCHAFFNER, C.P. (1978). Polyene macrolide antibiotic cytotoxicity and membrane permeability alterations. I. Comparative effects of four classes of polyene macrolides on mammalian cells. J. Cell. Physiol. 97, 345-351.
22. GARCIA-CHAUMONT, C., SEKSEK, O., GRZYBOWSKA, J., BOROWSKI, E., and BOLARD, J. (2000). Delivery systems for antisense oligonucleotides. Pharmacol. Ther. In press.
23. GOODCHILD, J., KIM, B., and ZAMECNIK, P.C. (1991). The clearance and degradation of oligonucleotides following intravenous injection into rabbits. Antisense Res. Dev. 1, 153-160.
24. HAENSLER, J., and SZOKA, F.C. (1993). Polyamidoamine cascade polymers mediate efficient transfection of cells in culture. Bioconjugate Chem. 4, 372-379.
25. HARTSEL, S., and BOLARD, J. (1996). Amphotericin B: New life for an old drug. Trends Pharmacol. Sci. 17, 445-449.
26. HIDAKA, K., AN, G., IP, P, KUWANA, M., and SIMINOVITCH, L. (1985). Amphotericin B enhances efficiency of DNA-mediated gene transfer in mammalian cells. Somatic Cell Mol. Genet. 11, 109-115.
27. KANE, S.E., REINHARD, D.H., MICHAEL FORDIS, C., PASTAN, I., and GOTTESMAN, M.M. (1989). A new vector using the multidrug resistance gene as a selectable marker enables overexpression of foreign genes in eukaryotic cells. Gene 84, 439-446.
28. KUMAR, B.V., MEDOFF, G., KOBAYASHI, G., and SCHLESSINGER, D. (1974). Uptake of Escherichia coli DNA into HeLa cells enhanced by amphotericin B. Nature 250, 323-325.
29. LASIC, D.D. (1997). Liposomes. In: Liposomes in Gene Delivery. D.D. Lasic, ed. (CRC Press Boca Raton, FL), pp. 67-75.
30. MALEWICZ, B., JENKIN, H.M., and BOROWSKI, E. (1980). Dissociation between the induction of potassium efflux and cystostatic activity of polyene macrolides in mammalian cells. Antimicrob. Agents Chemother. 17, 699-706.
31. MIDOUX, P., KICHLER, A., BOUTIN, V., MAURIZOT, J.C., and MONSIGNY, M. (1998). Membrane permeabilization and efficient gene transfer by a peptide containing several histidines. Bioconjugate Chem. 9, 260-267.
32. MILLER, K.J., and DAS, S.K. (1998). Antisense oligonucleotides: Strategies for delivery. Pharmacol. Sci. Technol. Today 1, 377-386.
33. MÖNKKÖNEN, J., and URTTI, A. (1998). Lipid fusion in oligonucleotide and gene delivery with cationic lipids. Adv. Drug Deliv. Rev. 34, 37-49.
34. MORISHITA, R., GIBBONS, G., ELLISON, K.E., NAKAJIMA, M., ZHANG, L., KANEDA, Y., OGIHARA, T., and DZAU, V.J. (1993). Single intraluminal delivery of antisense cdc2 kinase and proliferating-cell nuclear antigen oligonucleotides results in chronic inhibition of neointimal hyperplasia. Proc. Natl. Acad. Sci. USA 90, 8474-8478.
35. MORRIS, M.C., VIDAL, P., HEITZ, F., and DIVITA, G. (1997). A new peptide vector for efficient delivery of oligonucleotides into mammalian cells. Nucleic Acids Res. 25, 2730-2736.
36. MOSMANN, T. (1983). Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 55-63.
37. 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 Nucleic Acid Drug Dev. 7, 335-343.
38. QUATTRONE, A., PAPUCCI, L., MORGANTI, M., CORONELLO, M., MINI, E., MAZZEI, T., COLONNA, F.P., GARBESI, A., and CAPACCIOLI, S. (1994). Inhibition of MDR1 gene expression by antimessenger oligonucleotides lowers multiple drug resistance. Oncol. Res. 6, 311-320.
39. RIVOLTINI, L., COLOMBO, M.P., SUPINO, R., BALLINARI, D., TSURUO, T., and PARMIANI, G. (1990). Modulation of multidrug resistance by verapamil or mdrl anti-sense oligodeoxynucleotide does not change the high susceptibility to lymphokine-activated killers in mdr-resistant human carcinoma (LoVo) line. Int. J. Cancer 46, 727-732.
40. SAISON-BEHMOARAS, T., TOCQUÉ, B., REY, I., CHASSIGNOL M., THUONG, N.T., HÉLÈNE, C. (1991). Short modified antisense oligonucleotides directed against Ha-ras point mutation induce selective cleavage of the mRNA and inhibit T24 cells proliferation. EMBO J. 10, 1111-1118.
41. SHOJI, Y., SHIMADA, J., MIZUSHIMA, Y., IWASAWA, A., NAKAMURA, Y., INOUYE, K., AZUMA, T., SAKURAI, M., and NISHIMURA, T. (1996). Cellular uptake and biological effects of antisense oligodeoxynucleotide analogs targeted to herpes simplex virus. Antimicrob. Agents Chemother. 40, 1670-1675.
42. STEIN, C.A., and CHENG, Y.-C. (1993). Antisense oligonucleotide as therapeutic agents - Is the bullet really magical? Science 261, 1004-1012.
43. SUREAU, F., CHINSKY, L., DUQUESNE, M., LAIGLE, A., TURPIN, P.-Y., AMIRAND, C., BALLINI, J.-P., and VIGNY, P. (1990). Microspectrofluorimetric study of the kinetics of cellular uptake and metabolization of benzo(a)pyrene in human T 47D mammary tumor cells, evidence for cytochrome P450 induction. Eur. Biophys. J. 18, 301-307.
44. SZOKA, F.C., XU, Y., and ZELPHATI, O. (1996). How are nucleic acids released in cells from cationic lipid-nucleic acid complexes? J. Liposome Res. 6, 567-587.
45. TEICHMAN-WEIBERG, A., LITTAUER, U.Z., and GINZBURG, I. (1988). The inhibition of neurite outgrowth in PC12 cells by tubulin antisense oligodeoxyribonucleotides. Gene 72, 297-307.
46. THIERRY, A.R., RAHMAN, A., and DRITSCHILO, A. (1993). Overcoming multidrug resistance in human tumor cells using free and liposomally encapsulated antisense oligodeoxynucleotides. Biochem. Biophys. Res. Commun. 190, 952-960.
47. TONKINSON, J.L., and STEIN, C.A. (1994). Patterns of intracellular compartmentalization, trafficking and acidification of 5′-fluorescein-labeled phosphodiester and phosphorothioate oligodeoxynucleotides in HL60 cells. Nucleic Acids Res. 22, 4268-4275.
48. YAKUBOV, L.A., DEEVA, E.A., ZARYTOVA, V.F., IVANOVA, E.M., RYTE, A.S., YURCHENKO, L.V., and VLASSOV, V.V. (1989). Mechanism of oligonucleotide uptake by cells: Involvement of specific receptors: Proc. Natl. Acad. Sci. USA 86, 6454-6458.
49. ZAMECNIK, P., AGHAJANIAN, J., ZAMECNIK, M., GOODCHILD, J., and WITMAN, G. (1994). Electron micrographic studies of transport of oligodeoxynucleotides across eukaryotic cell membranes. Proc. Natl. Acad. Sci. USA 91, 3156-3160.
50. ZELPHATI, O., and SZOKA, J.F.C. (1996). Intracellular distribution and mechanism of delivery of oligonucleotides mediated by cationic lipids. Pharmacol. Res. 13, 1367-1372.
51. ZHOU, X.H., and HUANG, L. (1994). DNA transfection mediated by cationic liposomes containing lipopolylysine - Characterization and mechanism of action. Biochim. Biophys. Acta 1189, 195-203.