Beta-cyclodextrin derivatives as carriers to enhance the antiviral activity of an antisense oligonucleotide directed toward a coronavirus intergenic consensus sequence

Archives of Virology

Volumn 142, Issue 8, 1997, Pages 1585-1602

  Abdou, S ^a   Collomb, J ^a   Sallas, F ^a   Marsura, A ^a   Finance, C ^a  

^a UNIVERSITÉ DE LORRAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTISENSE OLIGONUCLEOTIDE; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; CYCLODEXTRIN; DRUG CARRIER; VIRUS RNA;

ARTICLE; CELL CULTURE; CONSENSUS SEQUENCE; CORONAVIRUS; DRUG EFFECT; GENETICS; INTRON; PHYSIOLOGY; VIRUS REPLICATION;

BETA-CYCLODEXTRINS; CELLS, CULTURED; CONSENSUS SEQUENCE; CORONAVIRUS; CYCLODEXTRINS; DRUG CARRIERS; INTRONS; OLIGONUCLEOTIDES, ANTISENSE; RNA, VIRAL; VIRUS REPLICATION;

CORONAVIRUS; ENTERIC CORONAVIRUS;

EID: 0030849802     PISSN: 03048608     EISSN: None     Source Type: Journal    
DOI: 10.1007/s007050050182     Document Type: Article

References (65)

1. Agrawal S, Lyer RP (1995) Modified oligonucleotides as therapeutic and diagnostic agents. Curr Opin Biotechnol 6: 9-12
2. Agrawal S. (1996) Antisense oligonucleotides: towards clinical trials. Trends Biotechnol 14: 376-387
3. Archambault D, Stein CA, Cohen JS (1994) Phosphorothioate oligonucleotides inhibit the replication of lentiviruses and type D retroviruses, but not that of type C retroviruses. Arch Virol 139: 97-100
4. Attioui F, Al-Omar A, Leray E, Parrot-Lopez H, Finance C, Bonaly R (1994) Recognition ability and cytotoxicity of some oligosaccharidyl substituted β-cyclodextrins. Biol Cell 82: 161-167
5. Bennet CF, Chiang MY, Chan H, Shoemaker JEE, Mirabeli CK (1992) Cationic lipids enhance cellular uptake and activity of phosphorothioate antisense oligonucleotides. Mol Pharmacol 41: 1 023-1 033
6. Bergmann JF, Chassany O (1994) Piroxicam β-cyclodextrine: amélioration de la cinétique des médicaments par les cyclodextrines. Lett Pharmacol 8: 144-148
7. Block JC, Schwartzbrod L (1989) Viruses in water systems: detection and identification. VCH Publ., New York
8. Boiziau C, Toulmé JJ (1991) Modified oligonucleotides in rabbit reticulocytes: uptake, stability and antisense properties. Biochimie 73: 1 403-1 408
9. Brewster ME, Simpkins JW, Hora MS, Stern, WC, Bodor N (1989) The potential use of cyclodextrins in parenteral formulations. J Parent Sci Technol 43: 231-240
10. Budzilowick CJ, Wilczynki S, Weiss RS (1985) Three intergenic regions of nucleotide sequence that is homologous to the 3′ end of the viral mRNA leader sequence. J Virol 53: 834-840
11. Chang QY, Grill S, Egan W, Cheng YC (1993) Potent inhibition of Epstein-Barr virus by phosphorothioate oligodeoxynucleotides without sequence specification. Antimicrob Agents Chemother 37: 1 420-1 425
12. Chomczynski P, Sacchi N (1987) Single-step method for RNA isolation by acid guanidium thiocyanate-phenol-chloroform extraction. Anal Biochem 162: 156-159
13. Collomb J, Finance C, Alabouch S, Laporte J (1992) Radioactive and enzymatic cloned cDNA probes for bovine enteric coronavirus detection by molecular hybridation. Arch Virol 125: 25-37
14. Copple BL, Gmeiner WM Iversen PL (1995) Reaction between metabolically activated acetaminophen and phosphorothioate oligonucleotides. Toxicol Appl Pharmacol 133: 53-63
15. Crooke, R. M. (1991) In vitro toxicology and pharmacokinetics of antisense oligonucleotides. Anticancer Drug Des 6: 609-646
16. Czerny CP, Eichorn W (1989) Characterization of monoclonal and polyclonal antibodies of bovine enteric coronaviruses: establishment of an efficient Elisa for antigen detection in feces. Vet Microbiol 20: 111-122
17. De Robertis L, Lancelon-Pin C, Driguez H, Attioui F, Bonaly R, Marsura A (1994) Synthesis of new oligosacchridyl-thio-β-cyclodextrins (CDS): A novel family of potent drug-targetting vectors. Bioorg Med Chem Lett 4: 1 127-1 130
18. Farouqui F, Sarin PS, Sun D, Letsinger RL (1991) Effect of structural variations in cholesteryl conjugated oligonucleotides on inhibitory activity toward HIV-1. Bioconjugate Chem 2: 422-426
19. Higuchi T, Connors KA (1965) Phase-solubility techniques. In: Reilley CN (ed) Advances in analytical chemistry and instrumentation, vol. 4. J Wiley, New York, pp 117-212
20. Jacob A, Duval-Vallentin G, Ingrand D, Thuong N, Helene C (1993) Inhibition of viral growth by an α-oligonucleotide directed to the splice junction of herpes simplex virus type 1 immediate early pre-mRNA species 22 and 34. Eur J Biochem 216: 19-24
21. Jansen T, Xhonneux B, Mesens J, Borgers M (1990) Beta-cyclodextrins as vehicles in eye-drop formulations: an evaluation of their effects on rabbit corneal epithelium. Lens Eye Toxicity Res 7: 459-468
22. Jaroszewski JN, Cohen JS (1991) Cellular uptake of antisense oligodeoxynucleotides. Adv Drug Rev 6: 235-250
23. Juliano RL, Akhtar S (1992) Liposomes as a drug delivery system for antisense oligonucleotides. Antisense Res Dev 2: 165-176
24. Keck JG, Hogue BG, Brian DA, Lai MMC (1988) Temporal regulation of bovine coronavirus RNA synthesis. Virus Res 9: 343-356
25. Keller TH, Häner R (1993) Synthesis and hybridization properties of oligonucleotides containing 2′-O-modified ribonucleotides. Nucleic Acids Res 21: 4 499-4 505
26. Kierg AM, Tonkinson J, Matson S, Zhao Q, Saxen M, Zhang L, Bhanya U, Yakubov L, Stein CA (1993) Modification of antisense phosphodiester oligodeoxynucleotides by a 5′-cholesteryl moiety, increases cellular association and improves efficacy. Proc Natl Acad Sci USA 90: 1 048-1 052
27. Lai MMC, Baric RSS, Bray ton PR, Stohlman SA (1984) Characterization of leader RNA sequences on the virion and mRNAs of mouse hepatitis virus, a cytoplasmic RNA virus. Proc Natl Acad Sci USA 81: 3 626-3 630
28. Lai MMC, Patton CD, Baric RS, Stohlman SA (1983) Presence of leader sequences in the mRNA of mouse hepatitis virus. J Virol 46: 1 027-1 033
29. Lai MMC, Brayton PR, Armen RC, Patton CD, Pugh C, Stohlman SA (1981) Mouse hepatitis virus A59: mRNA structure and genetic localization of the sequence divergence from hepatotropic strain MHV-3. J Virol 39: 823-834
30. Laporte J, Bobulesco P, Rossi F (1980) Une lignée cellulaire particulièrement sensible à la réplication du Coronavirus entérique bovin : les cellules HRT- 18. CR Acad Sci Paris Série D 290: 623-626
31. Laporte J, L'Haridon R, Bobulesco P (1979) In vitro culture of bovine enteritic coronavirus (BEC). Les colloques de l'INSERM. Viral Enteritis 90: 99-102
32. Leiter JME, Agrawal S, Palese P, Zamecnik PC (1990) Inhibition of influenza virus replication by phophorothioate oligodeoxynucleotides. Proc Natl Acad Sci USA 87: 3430-3434
33. Lisziewicz J, Sun D, Klotman M, Agrawal S, Zamecnik P, Robert G (1992) Specific inhibition of human immunodeficiency virus type 1 replication by antisense oligonucleotides: an in vitro model for treatment. Proc Natl Acad Sci USA 89: 11 209-11 213
34. Loke SL, Stein C, Zhang Xh, Mori K, Nakanishi M, Subasinghe C, Cohen JS, Neckers LM (1989) Characterization of oligonucleotide transport into living cells. Proc Natl Acad Sci USA 86: 3 474-3 478
35. Lund OS, Nielsen JO, Hansen JE (1995) Inhibition of HIV-1 in vitro by C-5 propyne phosphorothioate antisense to rev. Antiviral Res 28: 81-91
36. Makino S, Joo M (1993) Effect of intergenic consensus sequence flanking sequences on coronavirus transcription. J Virol 67: 3304-3311
37. Makino S, Joo M, Makino JK (1991) A system for study of coronavirus mRNA results from intergenic site insertion. J Virol 65: 6 031-6 041
38. Manzoni GC, Zamfferrani C, Granella F (1989) Piroxicam β-cyclodextrin in the symptomatic treatment of primary headache. Meeting of the Interdisciplinare di Cardiologia e Neurologia Selecta Neurologia 449-453
39. Matsui Y, Yokoi T, Mochida K (1976) Catalytic Properties of Cu (II) complex with a modified cyclodextrin. Chem Lett 1 037-1 040
40. Nakada Y, Fattal E, Foulquier M, Couvreur P (1996) Pharmacokinetics and biodistribution of oligonucleotide adsorbed onto poly (isobutylcyanoacrylate) nano particles after intravenous administration in mice. Pharm Res 13: 38-43
41. Onisk DV, Srikumaran S, Kelling CL, Frey ML (1991) Bovine viral diarrhoea virus-specific bovine monoclonal antibody. Arch Virol 121: 219-225
42. Otake T, Schols M, Witvouw L, Naesens L, Nakashima H, Moriya T, Kurita H, Matsumoto K, Ueba N, De Clercq E (1994) Modified cyclodextrin sulphates (mCDS11) have potent inhibitory activity against HIV and high oral bioavailability. Antivir Chem Chemother 5: 155-161
43. Pari GS, Kirkfield A, Smith J (1995) Potent antiviral activity of an antisense oligonucleotide complementary to the intron-exon boundary oxon boundary of human cytomegalovirus genes UL 36 and UL 37. Antimicrob Agents Chemother 39: 1 157-1 161
44. Phillips NC, Emili A (1991) Immunogenicity of immunoliposomes. Immunol Lett 30: 291-296
45. Potgieter LND, McCrachen MD, Hopkins FM, Walker RD, Guy JS (1984) Experimental production of bovine respiratory tract disease with bovine diarrhea virus. Am J Vet Res 45: 1 582-1 585
46. 3H-labelled oligonucleotides. Comparison of a phosphodiester and phosphorothioate. Mol Pharmacol 45: 932-943
47. Savoysky E, Boireau P, Finance C, Laporte J (1990) Sequence and analysis of BECV F15 matrix protein. Res Virol 141: 411-425
48. Sawiki SG, Sawiki DL (1990) Coronavirus transcription: subgenomic mouse hepatitis virus replicative intermediates function in RNA synthesis. J Virol 64: 1 050-1 056
49. Sethna PB, Hofmann MA, Brian DA (1991) Minus-strand copies of replicating coronavirus mRNA contain anti-leaders. J Virol 65: 320-325
50. Shien CK, Soe LH, Makino S, Chang MF, Stohlman SA, Lai MMC (1987) The 5′-end sequence of the murine coronavirus genome implications for multiple fusion sites in leader-primed transcription. Virology 156: 321-330
51. Simpkins JW (1991) Solubilization of ovine growth hormone with 2-hydroxypropyl-β-cyclodextrin. J Parent Sci Technol 45: 266-269
52. Spaan W, Cavanagh D, Horzinek MC (1988) Coronavirus: structure and genome expression. J Gen Virol 69: 2 939-2 952
53. Stein CA, Matsukura M, Subasinghe C, Broder S, Cohen JS (1989) Phosphorothioate oligodeoxynucleotides are potent sequence non-specific inhibitors of de novo infection by HIV. Aids Res Hum Retroviruses 5: 639-645
54. Stein CA (1995) Does antisense exist? Nature Med 1: 1 119-1 121
55. Stein CA (1996) Phosphorothioate antisense oligodeoxynucleotides: questions of specificity. Trends Biotechnol 14: 147-149
56. Stern DF, Kennedy SIT (1980) Coronavirus multiplication strategy. II. Mapping the avian infectious bronchitis virus intracellular RNA species to the genome. J Virol 36: 440-449
57. Stewart AJ, Canitrot Y, Barrachini E, Dean NN, Daly RG, Cole SPC (1996) Reduction of expression of the multidrug resistance protein (MRP) in human tumor cells by antisense phosphorothioate oligonucleotides. Biochem Pharmacol 51: 461-469
58. Sturman LS, Holmes K (1983) The molecular biology of coronaviruses. Adv Virus Res 28: 35-112
59. Temsamani J, Tang JY, Padimapriya A, Kubert M, Agrawal S (1993) Pharmacokinetics, biodistribution and stability of capped oligodeoxynucleotide phosphorothioates in mice. Antisense Res Dev 3: 277-284
60. Tonkinson JL, Stein CA (1993) Antisense nucleic-acids. Prospects for antiviral intervention. Antivir Chem Chemother 4: 193-200
61. Vautherot JF (1981) Plaque assay for titration of bovine enteric coronavirus. J Gen Virol 56: 451-455
62. Vlassov VV, Balakireva LA, Yakubov LA (1994) Transport of oligonucleotides across natural and model membranes. Biochem Biophys Acta 1197: 95-108
63. Weiner DB, Williams WV, Weisz PB, Greene MI (1992) Synthetic cyclodextrin derivatives inhibit HIV infection in vitro. Pathobiology 60: 206-212
64. Wenz G (1994) Cyclodextrin as building blocks for supramolecular structures and functional units. Angew Chem Int Edit 33: 803-822
65. Zhao Q, Temsamani J, Agrawal S (1995) Use of cyclodextrins and its derivatives as carriers for oligonucleotide delivery. Antisense Res Dev 5: 185