Drug delivery of oligonucleotides by peptides

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 58, Issue 2, 2004, Pages 237-251

  Lochmann, Dirk ^a   Jauk, Edith ^b   Zimmer, Andreas ^b  

^a GOETHE UNIVERSITY   (Germany)

^b UNIVERSITY OF GRAZ   (Austria)

Author keywords

Drug delivery; Fusogenic peptides; NLS; Oligonucleotides; Poly L lysine; Protamine

Indexed keywords

ANTIVIRUS AGENT; ASIALOFETUIN; ASIALOGLYCOPROTEIN; EXCIPIENT; GALACTOSE; GROWTH FACTOR; INSULIN; OLIGONUCLEOTIDE; PEPTIDE; TRANSFERRIN; VACCINE;

COMPLEX FORMATION; DEVICE; DNA SEQUENCE; DOWN REGULATION; DRUG DELIVERY SYSTEM; DRUG FORMULATION; IN VITRO STUDY; MEDICAL LITERATURE; PROTEIN LOCALIZATION; REVIEW; TUMOR;

ANIMALS; BIOLOGICAL TRANSPORT; CELL MEMBRANE; CHEMISTRY, PHARMACEUTICAL; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; EXCIPIENTS; HUMANS; OLIGONUCLEOTIDES; PEPTIDES;

EID: 3843081851     PISSN: 09396411     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejpb.2004.03.031     Document Type: Review

References (177)

1. Stephenson M.L., Zamecnik P.C. Inhibition of Rous sarcoma viral RNA translation by a specific oligodeoxyribonucleotide. Proc. Natl Acad. Sci. USA. 75:1978;285-288
2. Zamecnik P.C., Stephenson M.L. Inhibition of Rous sarcoma virus replication and cell transformation by a specific oligodeoxynucleotide. Proc. Natl Acad. Sci. USA. 75:1978;280-284
3. Crooke S.T. Therapeutic applications of oligonucleotides. Annu. Rev. Pharmacol. Toxicol. 32:1992;329-376
4. Askari F.K., McDonnell W.M. Antisense-oligonucleotide therapy. N. Engl J. Med. 334:1996;316-318
5. Tamm I., Dorken B., Hartmann G. Antisense therapy in oncology: new hope for an old idea? Lancet. 358:2001;489-497
6. Elbashir S.M., Harborth J., Lendeckel W., Yalcin A., Weber K., Tuschl T. Duplexes of 21-nucleotide RNAs mediate RNA interference in cultured mammalian cells. Nature. 411:2001;494-498
7. Gewirtz A.M., Sokol D.L., Ratajczak M.Z. Nucleic acid therapeutics: state of the art and future prospects. Blood. 92:1998;712-736
8. Couvreur P., Malvy C. Pharmaceutical Aspects of Oligonuceotides. vol. 1:2000;Taylor and Francis, London
9. Stryer L. Biochemistry. vol. 4:1988;Freeman and Company, New York
10. Merdan T., Kopecek J., Kissel T. Prospects for cationic polymers in gene and oligonucleotide therapy against cancer. Adv. Drug Delivery Rev. 54:2002;715-758
11. Lebedeva I., Benimetskaya L., Stein C.A., Vilenchik M. Cellular delivery of antisense oligonucleotides. Eur. J. Pharmaceut. Biopharmaceut. 50:2000;101-119
12. Lebedeva I., Stein C.A. Antisense oligonucleotides: promise and reality. Annu Rev. Pharmacol. Toxicol. 41:2001;403-419
13. Vlassov V.V., Balakireva L.A., Yakubov L.A. Transport of oligonucleotides across natural and model membranes. Biochim. Biophys. Acta (BBA). 1197:1994;95-108
14. Kabanov A.V., Kabanov V.A. DNA complexes with polycations for the delivery of genetic material into cells. Bioconj. Chem. 6:1995;7-20
15. Vivès E., Lebleu B. Couvreur P., Malvy C. Pharmaceutical Aspects of Oligonuceotides. 2000;111-127 Taylor and Francis, London
16. Garcia-Chaumont C., Seksek O., Grzybowska J., Borowski E., Bolard J. Delivery systems for antisense oligonucleotides. Pharmacol. Therapeut. 87:2000;255-277
17. Monsigny M., Midoux P., Mayer R., Roche A.C. Glycotargeting: influence of the sugar moiety on both the uptake and the intracellular trafficking of nucleic acid carried by glycosylated polymers. Biosci. Rep. 19:1999;125-132
18. Godbey W.T., Mikos A.G. Recent progress in gene delivery using non-viral transfer complexes. J. Control Release. 72:2001;115-125
19. Rodriguez-Hernandez J., Gatti M., Klok H.A. Highly branched poly(L-lysine). Biomacromolecules. 4:2003;249-258
20. Inaki Y., Ishikawa T., Takemoto K. Synthesis and interactions of poly-L-lysines containing nucleic acid bases. Nucl. Acids Symp. Ser. 1980;s137-s140
21. Choksakulnimitr S., Masuda S., Tokuda H., Takakura Y., Hashida M. In vitro cytotoxicity of macromolecules in different cell culture systems. J. Control Release. 34:1995;233-241
22. Lemaitre M., Bayard B., Lebleu B. Specific antiviral activity of a poly(L-lysine)-conjugated oligodeoxyribonucleotide sequence complementary to vesicular stomatitis virus N protein mRNA initiation site. Proc. Natl Acad. Sci. USA. 84:1987;648-652
23. Degols G., Leonetti J.P., Gagnor C., Lemaitre M., Lebleu B. Antiviral activity and possible mechanisms of action of oligonucleotides-poly(L-lysine) conjugates targeted to vesicular stomatitis virus mRNA and genomic RNA. Nucl. Acids Res. 17:1989;9341-9350
24. Leonetti J.P., Degols G., Lebleu B. Biological activity of oligonucleotide-poly(L-lysine) conjugates: mechanism of cell uptake. Bioconj. Chem. 1:1990;149-153
25. Stevenson M., Iversen P.L. Inhibition of human immunodeficiency virus type 1-mediated cytopathic effects by poly(L-lysine)-conjugated synthetic antisense oligodeoxyribonucleotides. J Gen Virol. 70:(Pt 10):1989;2673-2682
26. Degols G., Leonetti J.P., Lebleu B. Sequence-specific activity of antisense oligonucleotides conjugated to poly (L-lysine) carriers. Ann NY Acad Sci. 660:1992;331-333
27. Degols G., Leonetti J.P., Benkirane M., Devaux C., Lebleu B. Poly(L-lysine)-conjugated oligonucleotides promote sequence-specific inhibition of acute HIV-1 infection. Antisense Res Dev. 2:1992;293-301
28. Degols G., Devaux C., Lebleu B. Oligonucleotide-poly(L-lysine)-heparin complexes: potent sequence-specific inhibitors of HIV-1 infection. Bioconj. Chem. 5:1994;8-13
29. Degols G., Leonetti J.-P., Mechti N., Lebleu B. Antiproliferative effects of antisense oligonucleotides directed to the RNA of c-myc oncogene. Nucl. Acids Res. 19:1991;945-948
30. Gonzalez Ferreiro M., Tillman L., Hardee G., Bodmeier R. Characterization of alginate/poly-L-lysine particles as antisense oligonucleotide carriers. Int. J. Pharm. 239:2002;47-59
31. Gonzalez Ferreiro M., Tillman L.G., Hardee G., Bodmeier R. Alginate/poly-L-lysine microparticles for the intestinal delivery of antisense oligonucleotides. Pharm. Res. 19:2002;755-764
32. Kataoka K., Togawa H., Harada A., Yasugi K., Matsumoto T., Katayose S. Spontaneous formation of polyion complex micelles with narrow distribution from anti-sense oligonucleotide and cationic block copolymer in physiological saline. Macromolecules. 29:1996;8556-8557
33. Jones M., Leroux J. Polymeric micelles-a new generation of colloidal drug carriers. Eur. J. Pharm. Biopharm. 48:1999;101-111
34. Harada A., Togawa H., Kataoka K. Physicochemical properties and nuclease resistance of antisense-oligodeoxynucleotides entrapped in the core of polyion complex micelles composed of poly(ethylene glycol)-poly(L-lysine) block copolymers. Eur. J. Pharm. Sci. 13:2001;35-42
35. Kakizawa Y., Harada A., Kataoka K. Glutathione-sensitive stabilization of block copolymer micelles composed of antisense DNA and thiolated poly(ethylene glycol)-block-poly(L-lysine): a potential carrier for systemic delivery of antisense DNA. Biomacromolecules. 2:2001;491-497
36. Dautzenberg H., Konak C., Reschel T., Zintchenko A., Ulbrich K. Cationic graft copolymers as carriers for delivery of antisense-oligonucleotides. Macromol. Biosci. 3:2003;425-435
37. Citro G., Szczylik C., Ginobbi P., Zupi G., Calabretta B. Inhibition of leukaemia cell proliferation by folic acid-polylysine-mediated introduction of c-myb antisense oligodeoxynucleotides into HL-60 cells. Br. J. Cancer. 69:1994;463-467
38. Spiess M. The asialoglycoprotein receptor: a model for endocytic transport receptors. Biochemistry. 29:1990;10009-10018
39. Bunnell B.A., Askari F.K., Wilson J.M. Targeted delivery of antisense oligonucleotides by molecular conjugates. Somat. Cell Mol. Genet. 18:1992;559-569
40. Wu G.Y., Wu C.H. Specific inhibition of hepatitis B viral gene expression in vitro by targeted antisense oligonucleotides. J. Biol. Chem. 267:1992;12436-12439
41. Chiou H.C., Tangco M.V., Levine S.M., Robertson D., Kormis K., Wu C.H., Wu G.Y. Enhanced resistance to nuclease degradation of nucleic acids complexed to asialoglycoprotein-polylysine carriers. Nucl. Acids Res. 22:1994;5439-5446
42. Reinis M., Damkova M., Korec E. Receptor-mediated transport of oligodeoxynucleotides into hepatic cells. J. Virol Methods. 42:1993;99-105
43. Monsigny M., Kieda C., Roche A.C. Membrane glycoproteins, glycolipids and membrane lectins as recognition signals in normal and malignant cells. Biol. Cell. 47:1983;95-110
44. Monsigny M., Roche A.C., Midoux P. Endogenous lectins and drug targeting. Ann. NY Acad. Sci. 551:1988;399-413 discussion 413-4
45. Stewart A.J., Pichon C., Meunier L., Midoux P., Monsigny M., Roche A.C. Enhanced biological activity of antisense oligonucleotides complexed with glycosylated poly-L-lysine. Mol. Pharmacol. 50:1996;1487-1494
46. Stahl P.D., Rodman J.S., Miller M.J., Schlesinger P.H. Evidence for receptor-mediated binding of glycoproteins, glycoconjugates, and lysosomal glycosidases by alveolar macrophages. Proc. Natl Acad. Sci. USA. 75:1978;1399-1403
47. Stahl P., Schlesinger P.H., Sigardson E., Rodman J.S., Lee Y.C. Receptor-mediated pinocytosis of mannose glycoconjugates by macrophages: characterization and evidence for receptor recycling. Cell. 19:1980;207-215
48. Liang W.W., Shi X., Deshpande D., Malanga C.J., Rojanasakul Y. Oligonucleotide targeting to alveolar macrophages by mannose receptor-mediated endocytosis. Biochim Biophys. Acta. 1279:1996;227-234
49. Rojanasakul Y., Weissman D.N., Shi X., Castranova V., Ma J.K., Liang W. Antisense inhibition of silica-induced tumor necrosis factor in alveolar macrophages. J. Biol. Chem. 272:1997;3910-3914
50. Mahato R.I., Takemura S., Akamatsu K., Nishikawa M., Takakura Y., Hashida M. Physicochemical and disposition characteristics of antisense oligonucleotides complexed with glycosylated poly(L-lysine). Biochem. Pharmacol. 53:1997;887-895
51. Libermann T.A., Nusbaum H.R., Razon N., Kris R., Lax I., Soreq H., Whittle N., Waterfield M.D., Ullrich A., Schlessinger J. Amplification, enhanced expression and possible rearrangement of EGF receptor gene in primary human brain tumours of glial origin. Nature. 313:1985;144-147
52. Slamon D.J., Godolphin W., Jones L.A., Holt J.A., Wong S.G., Keith D.E., Levin W.J., Stuart S.G., Udove J., Ullrich A., et al. Studies of the HER-2/neu proto-oncogene in human breast and ovarian cancer. Science. 244:1989;707-712
53. Rohmann A., Lochmann D., Weyermann J., Bertling W., Dingermann T., Zimmer A. Rapid screening method for antisense oligonucleotides against human growth factor receptor p185erbB-2. Oligonucleotides Spring. 14:2004;1-9
54. Deshpande D., Toledo-Velasquez D., Thakkar D., Liang W., Rojanasakul Y. Enhanced cellular uptake of oligonucleotides by EGF receptor-mediated endocytosis in A549 cells. Pharm. Res. 13:1996;57-61
55. Scott J.M., Weir D.G. Folic acid, homocysteine and one-carbon metabolism: a review of the essential biochemistry. J. Cardiovasc. Risk. 5:1998;223-227
56. Citro G., Ginobbi P., Szczylik C. Receptor-mediated oligodeoxynucleotides delivery by estradiol and folic acid polylysine conjugates. Cytotechnology. 11:(Suppl. 1):1993;S30-S34
57. Citro G., Ginobbi P., Candiloro A., Meloni A., Sarti P., Milani A. Chemical modification of ligands for cell receptors to introduce foreign compounds into the cells. Dis. Colon Rectum. 37:1994;S127-S132
58. Ginobbi P., Geiser T.A., Ombres D., Citro G. Folic acid-polylysine carrier improves efficacy of c-myc antisense oligodeoxynucleotides on human melanoma (M14) cells. Anticancer Res. 17:1997;29-35
59. Sorokin L.M., Morgan E.H., Yeoh G.C. Transformation-induced changes in transferrin and iron metabolism in myogenic cells. Cancer Res. 49:1989;1941-1947
60. Huebers H.A., Finch C.A. The physiology of transferrin and transferrin receptors. Physiol. Rev. 67:1987;520-582
61. Chung J., Wessling-Resnick M. Molecular mechanisms and regulation of iron transport. Crit. Rev. Clin. Lab Sci. 40:2003;151-182
62. Wagner E., Zenke M., Cotten M., Beug H., Birnstiel M.L. Transferrin.polycation conjugates as carriers for DNA uptake into cells. Proc. Natl Acad. Sci. USA. 87:1990;3410-3414
63. Citro G., Perrotti D., Cucco C., D'Agnano I., Sacchi A., Zupi G., Calabretta B. Inhibition of leukemia cell proliferation by receptor-mediated uptake of c-myb antisense oligodeoxynucleotides. Proc. Natl Acad. Sci. USA. 89:1992;7031-7035
64. Ebbinghaus S.W., Vigneswaran N., Miller C.R., Chee-Awai R.A., Mayfield C.A., Curiel D.T., Miller D.M. Efficient delivery of triplex forming oligonucleotides to tumor cells by adenovirus-polylysine complexes. Gene Ther. 3:1996;287-297
65. Tengvall U., Auriola S., Antopolsky M., Azhayev A., Biegelman L. Characterization of antisense oligonucleotide-peptide conjugates with negative ionization electrospray mass spectrometry and liquid chromatography-mass spectrometry. J. Pharmaceut. Biomed. Anal. 32:2003;581-590
66. Rojanasakul Y. Antisense oligonucleotide therapeutics: drug delivery and targeting. Adv. Drug Delivery Rev. 18:1996;115-131
67. Hughes M.D., Hussain M., Nawaz Q., Sayyed P., Akhtar S. The cellular delivery of antisense oligonucleotides and ribozymes. Drug Discovery Today. 6:2001;303-315
68. Akhtar S., Hughes M.D., Khan A., Bibby M., Hussain M., Nawaz Q., Double J., Sayyed P. The delivery of antisense therapeutics. Adv. Drug Delivery Rev. 44:2000;3-21
69. Luo D., Saltzmann W.M. Synthetic DNA delivery systems. Nat. Biotechnol. 18:2000;33-37
70. Lundberg P., Langel Ü. A brief introduction to cell-penetrating peptides. J. Mol. Recogn. 16:2003;227-233
71. Schwartz J.J., Zhang S. Peptide-mediated cellular delivery. Curr. Opin. Mol. Therapeut. 2:2000;162-167
72. Ando T., Yamasaki M., Suzuki K. Protamines: Isolation, characterisation, structure and function. vol. 1:1973;Springer Verlag, Berlin, Heidelberg, New York
73. Kossel A. Protamine und Histone. vol. 1:1929;Deuticker Verlag, Leipzig-Wien
74. Sorgi F.L., Bhattacharya S., Huang L. Protamine sulfate enhances lipid-mediated gene transfer. Gene Ther. 4:1997;961-968
75. Boulikas T., Martin F. Histones, protamine, and polylysine but not poly(E:K) enhance transfection efficiency. Int. J. Oncol. 10:1997;317-322
76. Li S., Huang L. Protamine sulfate provides enhanced and reproducible intravenous gene transfer by cationic liposome/DNA complex. J. Liposome Res. 7:1997;207-219
77. Sabelnikov A.G., Ditjatkin S.J., Iljashenko B.N. About the role of protamine in transfection. Biochimica et Biophysica Acta. 299:1973;492-495
78. Delie F., Gurny R., Zimmer A. Fluorescence correlation spectroscopy for the characterisation of drug delivery systems. Biol. Chem. 382:2001;487-490
79. Junghans M., Kreuter J., Zimmer A. Antisense delivery using protamine-oligonucleotide particles. Nucl. Acids Res. 28:2000;E45
80. Junghans M., Kreuter J., Zimmer A. Phosphodiester and phosphorothioate oligonucleotide condensation and preparation of antisense nanoparticles. Biochim. Biophys. Acta. 1544:2001;177-188
81. Gonzalez Ferreiro M., Crooke R.M., Tillman L., Hardee G., Bodmeier R. Stability of polycationic complexes of an antisense oligonucleotide in rat small intestine homogenates. Eur. J. Pharm. Biopharm. 55:2003;19-26
82. Ferreiro Gonzalez M., Tillman L., Hardee G., Bodmeier R. Characterization of complexes of an antisense oligonucleotide with protamine and poly-L-lysine salts. J. Control Release. 73:2001;381-390
83. Lochmann D., Weyermann J., Georgens C., Prassl R., Zimmer A. Albumin-protamine-oligonucleotide nanoparticles as a new antisense delivery system: Part 1, physicocemical characterisation. Eur. J. Pharm. Biopharm. 2004;. in press
84. Dinauer N., Lochmann D., Demirhan I., Zimmer A., Chandra A., Kreuter J., von Briesen H. Intracellular tracking of protamine/antisense oligonucleotide nanoparticles and their inhibitory effect on HIV-1 transactivation. J. Controlled Release. 96:2004;497-507
85. Weyermann J., Lochmann D., Georgens C., Kreuter J., Zimmer A. Albumin-protamine-oligonucleotide-nanoparticles as a new antisense delivery system: Part 2, Cellular uptake, release and effect. Eur. J. Pharm. Biopharm. 2004;. submitted for publication
86. Yoon K., Cole-Strauss A., Kmiec E.B. Targeted gene correction of episomal DNA in mammalian cells mediated by a chimeric RNA.DNA oligonucleotide. Proc. Natl Acad. Sci. USA. 93:1996;2071-2076
87. Welz C., Neuhuber W., Schreier H., Metzler M., Repp R., Rascher W., Fahr A. Nuclear transport of oligonucleotides in HepG2-cells mediated by protamine sulfate and negatively charged liposomes. Pharm. Res. 17:2000;1206-1211
88. Welz C., Neuhuber W., Schreier H., Repp R., Rascher W., Fahr A. Nuclear gene targeting using negatively charged liposomes. Int. J. Pharm. 196:2000;251-252
89. Moulton H.M., Moulton J.D. Peptide-assisted delivery of steric-blocking antisense oligomers. Curr. Opin. Mol. Ther. 5:2003;123-132
90. Wei Z., Tung C.H., Zhu T., Stein S. Synthesis of oligoarginine- oligonucleotide conjugates and oligoarginine-bridged oligonucleotide pairs. Bioconj. Chem. 5:1994;468-474
91. Chen C.P., Zhang L.R., Peng Y.F., Wang X.B., Wang S.Q., Zhang L.H. A concise method for the preparation of peptide and arginine-rich peptide-conjugated antisense oligonucleotide. Bioconj. Chem. 14:2003;532-538
92. Uster P.S., Deamer D.W. pH-dependent fusion of liposomes using titratable polycations. Biochemistry. 24:1985;1-8
93. Pichon C., Roufai M.B., Monsigny M., Midoux P. Histidylated oligolysines increase the transmembrane passage and the biological activity of antisense oligonucleotides. Nucl. Acids Res. 28:2000;504-512
94. Pichon C., Goncalves C., Midoux P. Histidine-rich peptides and polymers for nucleic acids delivery. Adv. Drug Delivery Rev. 53:2001;75-94
95. Morris M.C., Depollier J., Mery J., Heitz F., Divita G. A peptide carrier for the delivery of biologically active proteins into mammalian cells. Nat. Biotechnol. 19:2001;1173-1176
96. Zubin E.M., Romanova E.A., Volkov E.M., Tashlitsky V.N., Korshunova G.A., Shabarova Z.A., Oretskaya T.S. Oligonucleotide-peptide conjugates as potential antisense agents. FEBS Lett. 456:1999;59-62
97. Chaloin L., Vidal P., Lory P., Mery J., Lautredou N., Divita G., Heitz F. Design of carrier peptide-oligonucleotide conjugates with rapid membrane translocation and nuclear localization properties. Biochem. Biophys. Res. Commun. 243:1998;601-608
98. Tung C.-H., Stein S. Preparation and applications of peptide- oligonucleotide conjugates. Bioconj. Chem. 11:2000;605-618
99. Sugiyama T., Kittaka A., Takayama H., Tomioka M., Ida Y., Kuroda R. Aggregation of RecA-derived peptides on single-stranded oligonucleotides triggered by schiff base-mediated crosslinking. Bioorgan. Med. Chem. Lett. 13:2003;2847-2851
100. Brandén L., Christensson B., Edvard Smith C. In vivo nuclear delivery of oligonucleotides via hybridizing bifunctional peptides. Gene Ther. 8:2001;84-87
101. Gait M.J. Peptide-mediated cellular delivery of antisense oligonucleotides and their analogues. Cell. Mol. Life Sci. 60:2003;844-853
102. Kubo T., Yokoyama K., Ueki R., Yano M., Anno Y., Sasaki K., Ohba H., Fujii M. DNA conjugates as novel functional olionucleotides. Nucleosides, Nucleotides Nucl. Acids. 22:2003;1359-1361
103. Dokka S., Rojanasakul Y. Novel non-endocytic delivery of antisense oligonucleotides. Adv. Drug Delivery Rev. 44:2000;35-49
104. Kabouridis P.S. Biological applications of protein transduction technology. Trends Biotechnol. 21:2003;498-503
105. Mukherjee S., Gosh R., Maxfield F. Endocytosis. Physiol. Rev. 77:1997;759-803
106. Cho Y.W., Kim J.D., Park K. Polycation gene delivery systems: escape from endosomes to cytosol. J Pharm Pharmacol. 55:2003;721-734
107. Miller K.J., Das S.K. Antisense oligonucleotides: strategies for delivery. Pharmaceut. Sci. Technol. Today. 1:1998;377-386
108. Mahato R.I., Monera O.D., Smith L.C., Rolland A. Peptide-based gene delivery. Curr. Opin. Mol. Therapeut. 1:1999;226-243
109. Milligan J.F., Matteucci M.D., Martin J.C. Current concepts in antisense drug design. J. Med. Chem. 36:1993;1923-1937
110. Shadidi M., Sioud M. Identification of novel carrier peptides for the specific delivery of therapeutics into cancer cells. Fed. Am. Soc. Exp. Biol. J. 17:2003;256-258
111. Dokka S., Toledo-Velasquez D., Shi X., Wang L., Rojanasakul Y. Cellular delivery of oligonucleotides by synthetic import peptide carrier. Pharmaceut. Res. 14:1997;1759-1764
112. Midoux P., Mayer R., Monsigny M. Membrane permeabilization by [alpha]-helical peptides: a flow cytometry study. Biochim. Biophys. Acta (BBA)-Biomembr. 1239:1995;249-256
113. Epand R.M., Epand R.F. Modulation of membrane curvature by peptides. vol. 55:2000
114. Antopolsky M., Azhayeva E., Tengvall U., Auriola S., Jää skelainen I., Rönkkö S., Honkakoski P., Urtti A., Lönnberg H., Azhayev A. Peptide-oligonucleotide phosphorothioate conjugates with membrane translocation and nuclear localization propertiies. Bioconj. Chem. 10:1999;598-606
115. Plank C., Zauner W., Wagner E. Application of membrane-active peptides for drug and gene delivery across cellular membranes. Adv. Drug Delivery Rev. 34:1998;21-35
116. Tung C.-H., Weissleder R. Arginine containing peptides as delivery vectors. Adv. Drug Delivery Rev. 55:2003;281-294
117. Lindgren M., Hallbrink M., Prochiantz A., Langel U. Cell-penetrating peptides. Trends Pharmacol. Sci. 21:2000;99-103
118. Richard J.P., Melikov K., Vives E., Ramos C., Verbeure B., Gait M.J., Chernomordik L.V., Lebleu B. Cell-penetrating Peptides A Reevaluation of the mechanism of cellular uptake. J. Biol. Chem. 278:2003;585-590
119. Niidome T., Wakamatsu M., Wada A., Hirayama T., Aoyagi H. Required structure of cationic peptide for oligonucleotide-binding and -delivering into cells. J. Peptide Sci. 6:2000;271-279
120. Dathe M., Schumann M., Wieprecht T., Winkler A., Beyermann M., Krause E., Matsuzaki K., Murase O., Bienert M. Peptide helicity and membrane surface charge modulate the balance of electrostatic and hydrophobic interactions with lipid bilayers and biological membranes. Biochemistry. 35:1996;12612-12622
121. Krause E., Beyermann M., Fabian H., Dathe M., Rothemund S., Bienert M. Conformation of a water-soluble beta-sheet model peptide. A circular dichroism and Fourier-transform infrared spectroscopic study of double D-amino acid replacements. Int. J. Pept. Protein Res. 48:1996;559-568
122. Oehlke J., Krause E., Wiesner B., Beyermann M., Bienert M. Extensive cellular uptake into endothelial cells of an amphipathic beta-sheet forming peptide. FEBS Lett. 415:1997;196-199
123. Chaloin L., Vidal P., Heitz A., Van Mau N., Méry J., Divita G., Heitz F. Conformations of primary amphipathic carrier peptides in membrane mimicking enviroments. Biochemistry. 36:1997;11179-11187
124. Bellet-Amalric E., Blaudez D., Desbat B., Graner F., Gauthier F., Renault A. Biochim. Biophys. Acta (BBA)-Biomembr. 1467:2000;131-143
125. Parente R.A., Nadasdi L., Subbarao N.K., Szoka F.C.J. Association of a pH-sensitive peptide with membrane vesicles: role of amino acid sequence. Biochemistry. 29:1990;8713-8719
126. Parente R.A., Nir S., Szoka F.C.J. Mechanism of leakage of phospholipid vesicle contents induced by the peptide GALA. Biochemistry. 29:1990;8720-8728
127. Subbarao N.K., Parente R.A., Szoka F.C.J., Nadasdi L., Pongracz K. pH-dependent bilayer destabilization by an amphiphatic peptide. Biochemistry. 26:1987;2964-2972
128. Nir S., Nicol F., Szoka F. Surface aggregation and membrane penetration by peptides: relation to pore formation and fusion. Mol. Membr. Biol. 16:1999;95-101
129. Parente R., Nir S., Szoka F. Jr. pH-dependent fusion of phosphatidylcholine small vesicles. Induction by a synthetic amphipathic peptide. J. Biol. Chem. 263:1988;4724-4730
130. Hughes J.A., Aronsohn A.I., Avrutskaya A.V., Juliano R.L. Evaluation of adjuvants that enhance the effectiveness of antisense oligodeoxynucleotides. Pharmaceut. Res. 13:1996;404-410
131. Plank C., Oberhauser B., Mechtler K., Koch C., Wagner E. The influence of endosome-disruptive peptides on gene transfer using synthetic virus-like gene transfer systems. J. Biol. Chem. 269:1994;12918-12924
132. Wyman T.B., Nicol F., Zelphati O., Scaria P.V., Plank C., Szoka F.C.J. Design, synthesis, and characterization of a cationic peptide that binds to nucleic acids and permeabilizes bilayers. Biochemistry. 36:1997;3008-3017
133. Jeong J.H., Kim S.W., Park T.G. Novel intracellular delivery system of antisense oligonucleotide by self-assembled hybrid micelles composed of DNA/PEG conjugate and cationic fusogenic peptide. Bioconj. Chem. 14:2003;473-479
134. Gottschalk S., Sparrow J.T., Hauer J., Mims M.P., Leland F.E., Woo S.L., Smith L.C. A novel DNA-peptide complex for efficient gene transfer and expression in mammalian cells. Gene Ther. 3:1996;48-57
135. Jaaskelainen I., Peltola S., Honkakoski P., Monkkonen J., Urtti A. A lipid carrier with a membrane active component and a small complex size are required for efficient cellular delivery of anti-sense phosphorothioate oligonucleotides. Eur. J. Pharmaceut. Sci. 10:2000;187-193
136. Jaaskelainen I., Honkakoski P., Urtti A. In vitro delivery of antisense oligonucleotides. Cell. Mol. Biol. Lett. 7:2002;236-237
137. Kamata H., Yagisawa H., Takahashi S., Hirata H. Amphiphilic peptides enhance the efficiency of liposome-mediated DNA transfection. Nucl. Acids Res. 22:1994;536-537
138. Murata M., Takahashi S., Kagiwada S., Suzuki A. pH-dependent membran fusion and vesiculation of phospholipid large unilamellar vesicles induced by amphiphilic anionic and cationic peptides. Biochemistry. 31:1992;1986-1992
139. Pichon C., Freulon I., Midoux P., Mayer R., Monsigny M., Roche A.-C. Cytosolic and nuclear delivery of oligonucleotides mediated by an amphiphilic anionic peptide. Antisense Nucl. Acid Drug Dev. 7:1997;335-343
140. Freulon I., Roche A.-C., Monsigny M., Mayer R. Delivery of oligonucleotides into mammalian cells by anionic peptides: comparison between monomeric and dimeric peptides. Biochem. J. 354:2001;671-679
141. Freulon I., Monsigny M., Midoux P., Mayer R. Spacer length dependence on the efficiency of dimeric anionic peptides in gene transfer by glycosylated polylysine/plasmid complexes. Biosci. Reports. 20:2000;383-398
142. Midoux P., Kichler A., Boutin V., Maurizot J.-C., Monsigny M. Membrane permeabilization and efficient gene transfer by a peptide containing several histidines. Bioconj. Chem. 9:1998;260-267
143. Kichler A., Freulon I., Boutin V., Mayer R., Monsigny M., Midoux P. Glycofection™ in the presence of anionic fusogenic peptides: a study of the parameters affecting the peptide-mediated enhancement of the transfection efficiency. J. Gene Med. 1:1999;134-143
144. Midoux P., LeCam E., Coulaud D., Delain E., Pichon C. Histidine containing peptides and polypeptides as nucleic acid vectors. Somatic Cell Mol. Genet. 27:2002;27-47
145. Pichon C., Arar K., Stewart A.J., Duc Dodon M., Gazzolo L., Courtoy P.J., Mayer R., Monsigny M., Roche A.-C. Intracellular routing and inhibitory activity of oligonucleopeptides containing a KDEL motif. Mol. Pharmacol. 51:1997;431-438
146. Keller M., Tagawa T., Preuss M., Miller A.D. Biophysical characterization of the DNA binding and condensing properties of adenoviral core peptide μ (mu). Biochemistry. 41:2002;652-659
147. Normand N., van Leeuwen H., O'Hare P. Particle formation by the HSV protein VP22 enabling protein and nucleic acid delivery. J. Biol. Chem. 276:2001;15042-15050
148. Brewis N.D., Phelan A., Normand N., Choolun E., O'Hare P. Particle assembly incorporating a VP22-BH3 fusion protein, facilitating intracellular delivery, regulated release, and apoptosis 1. Mol. Ther. 7:2003;262-270
149. Escriou V., Carriere M., Scherman D., Wils P. NLS bioconjugate for targeting therapeutic genes to the nucleus. Adv. Drug Delivery Rev. 55:2003;295-306
150. Cartier R., Reszka R. Utilization of synthetic peptides containing nuclear localization signals for nonviral gene transfer systems. Gene Ther. 9:2002;157-167
151. Tanimoto M., Kamiya H., Minakawa N., Matsuda A., Harashima H. No enhancement of nuclear entry by direct conjugation of a nuclear localization signal peptide to linearized DNA. Bioconj. Chem. 14:2003;1197-1202
152. Garcia de la Torre B., Albericio F., Saison-Behmoaras E., Bachi A., Eritja R. Synthesis and binding properties of oligonucleotides carrying nuclear localizing sequences. Bioconj. Chem. 10:1999;1005-1012
153. Ragin A.D., Morgan R.A., Chmielewski J. Cellular import mediated by nuclear localization signal peptide sequences. Chem. Biol. 9:2002;943-948
154. Schirmbeck R., Riedl P., Zurbriggen R., Akira S., Reimann J. Antigenic epitopes fused to cationic peptide bound to oligonucleotides facilitate toll-like receptor 9-dependent, but CD4+T cell help-independent, priming of CD8+T cells. J. Immunol. 171:2003;5198-5207
155. Futaki S., Nakase I., Suzuki T., Youjun Z., Sugiura Y. Translocation of branched-chain arginine peptides through cell membranes: flexibility in the spatial disposition of positive charges in membrane-permeable peptides. Biochemistry. 41:2002;7925-7930
156. Colotto A., Martin I., Ruysschaert J.-M., Sen A., Hui S.W., Epand R.M. Structural study of the interaction between the SIV fusion peptide and model membranes. Biochemistry. 35:1996;980-989
157. Lundberg M., Johansson M. Positively charged DNA-binding proteins cause apparent cell membrane translocation 1. Biochem. Biophys. Res. Commun. 291:2002;367-371
158. Vives E. Cellular uptake of the Tat peptide: an endocytosis mechanism following ionic interactions. J. Mol. Recogn. 16:2003;265-271
159. Astriab-Fisher A., Sergueev D.S., Fisher M., Shaw B.R., Juliano R.L. Conjugates of antisense oligonucleotides with the Tat and antennapedia cell-penetrating peptides: effects on cellular uptake, binding to target sequences, and biologic actions. Pharmaceut. Res. 19:2002;744-754
160. Peyrottes S., Mestre B., Burlina F., Gait M.J. The synthesis of peptide-oligonucleotide conjugates by a fragment coupling approach. Tetrahedron. 54:1998;12513-12522
161. Chico D.E., Given R.L., Miller B.T. Binding of cationic cell-permeable peptides to plastic and glass. Peptides. 24:2003;3-9
162. Derossi D., Joliot A., Chassaing G., Prochiantz A. The third helix of the Antennapedia homeodomain translocates through biological membranes. J. Biol. Chem. 269:1994;10444-10450
163. Derossi D., Calvet S., Trembleau A., Brunissen A., Chassaing G., Prochiantz A. Cell internalization of the third helix of the Antennapedia homeodomain is receptor-independent. J. Biol. Chem. 271:1996;18188-18193
164. Allinquant B., Hantraye P., Mailleux P., Moya K., Bouillot C., Prochiantz A. Downregulation of amyloid precursor protein inhibits neurite outgrowth in vitro. J. Cell Biol. 128:1995;919-927
165. Astriab-Fisher A., Ye D., Sergueev D.S., Fisher M.H., Shaw B.R., Juliano R.L. Evaluating the specifity of antisense oligonucleotide conjugates. J. Biol. Chem. 277:2002;22980-22984
166. Rothbard J.B., Garlington S., Lin Q., Kirschberg T., Kreider E., McGrane L., Wender P.A., Khavari P.A. Conjugation of arginine oligomers to cyclosporin A facilitates topical delivery and inhibition of inflammation. Nat. Med. 6:2000;1253-1257
167. Morris M., Vidal P., Chaloin L., Heitz F., Divita G. A new peptide vector for efficient delivery of oligonucleotides into mammalian cells. Nucl. Acids. Res. 25:1997;2730-2736
168. Toth J., Boszormenyi I., Majer Z.S., Laczko I., Malvy C., Hollosi M., Bertrand J.-R. A two step model aimed at delivering antisense oligonucleotides in targeted cells. Biochem. Biophys. Res. Commun. 293:2002;18-22
169. Kubo T., Rumiana B., Ohba H., Fujii M. Antisense effects of DNA-peptide conjugates. Nucl. Acids Res. Suppl. 2003;179-180
170. Yano M., Kubo T., Yokoyama K., Ueki R., Sasaki K., Anno Y., Ohba H., Fujii M. Control of intracellular delivery of oligonucleotides by conjugation with signal peptides. Nucleosides, Nucleotides Nucl. Acids. 22:2003;1367-1369
171. Ladokhin A.S., White S.H. Detergent-like permeabilization of anionic lipid vesicles by melittin. Biochim. Biophys. Acta (BBA)-Biomembr. 1514:2001;253-260
172. Legendre J.Y., Trzeciak A., Bohrmann B., Deuschle U., Kitas E., Supersaxo A. Dioleoylmelittin as a novel serum-insensitive reagent for efficient transfection of mammalian cells. Bioconj. Chem. 8:1997;57-63
173. Rozema D.B., Ekena K., Lewis D.L., Loomis A.G., Wolff J.A. Endosomolysis by masking of a membrane-active agent (EMMA) for cytoplasmatic release of macromolecules. Bioconj. Chem. 14:2003;51-57
174. Oehlke J., Scheller A., Wiesner B., Krause E., Beyermann M., Klauschenz E., Melzig M., Bienert M. Cellular uptake of an [alpha]-helical amphipathic model peptide with the potential to deliver polar compounds into the cell interior non-endocytically. Biochim. et Biophys. Acta (BBA)-Biomembr. 1414:1998;127-139
175. Lear J., DeGrado W. Membrane binding and conformational properties of peptides representing the NH2 terminus of influenza HA-2. J. Biol. Chem. 262:1987;6500-6505
176. Murata M., Kagiwada S., Takahashi S. Membrane fusion induced by mutual interaction of the two charge-reversed amphiphilic peptides at neutral pH. J. Biologic. Chem. 266:1991;14353-14358
177. Lin Y.-Z., Yao S., Veach R.A., Torgerson T.R., Hawiger J. Inhibition of nuclear translocation of transcription factor NF-[IMAGE]B by a synthetic peptide containing a cell membrane-permeable motif and nuclear localization sequence. J. Biol. Chem. 270:1995;14255-14258