Biologically active oligodeoxyribonucleotides, 5. 5'-end-substituted d(TGGGAG) possesses anti-human immunodeficiency virus type 1 activity by forming a G-quadruplex structure

Journal of Medicinal Chemistry

Volumn 41, Issue 19, 1998, Pages 3655-3663

  Hotoda, Hitoshi ^a   Koizumi, Makoto ^a   Koga, Rika ^a   Kaneko, Masakatsu ^a   Momota, Kenji ^a   Ohmine, Toshinori ^a   Furukawa, Hidehiko ^a   Agatsuma, Toshinori ^a   Nishigaki, Takashi ^a   Sone, Junko ^a   Tsutsumi, Shinya ^a   Kosaka, Toshiyuki ^a   Abe, Koji ^a   Kimura, Satoshi ^b,c   Shimada, Kaoru ^b,d  

^a DAIICHI SANKYO CO   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c UNIVERSITY OF TOKYO HOSPITAL   (Japan)

^d Tokyo Senbai Hospital   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGODEOXYRIBONUCLEOTIDE;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG EFFECT; DRUG SCREENING; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; VIRUS INHIBITION;

ANTI-HIV AGENTS; CELL LINE, TRANSFORMED; CIRCULAR DICHROISM; DRUG STABILITY; HIV-1; HUMANS; MOLECULAR CONFORMATION; OLIGODEOXYRIBONUCLEOTIDES; SOLUTIONS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 15644384134     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970658w     Document Type: Article

References (33)

1. Hotoda, H.; Koizumi, M.; Koga, R.; Momota, K.; Ohmine, T.; Furukawa, H.; Nishigaki, T.; Kinoshita, T.; Kaneko, M.; Kimura, S.; Shimada, K. Biologically Active Oligodeoxyribonucleotides. 4: Anti-HIV-1 Activity of TGGGAG Having Hydrophobic Substituent at Its 5′-End via Phosphodiester Linkage. Nucleosides Nucleotides 1996, 15, 531-538.
2. Field, A. K.; Goodchild, J. Antisense Oligonucleotides: Rational Design for Genetic Pharmacology. Exp. Opin. Invest. Drugs 1995, 4, 799-821.
3. Bielinska, A.; Kukowska-Latallo, J. F.; Johnson, J.; Tomalia, D. A.; Baker, J. R., Jr. Regulation of In Vitro Gene Expression Using Antisense Oligonucleotides or Antisense Expression Plasmids Transfected Using Starburst PAMAM Dendrimers. Nucleic Acids Res. 1996, 24, 2176-2182.
4. Monia, B. P.; Johnston, J. F.; Sasmor, H.; Cummins, L. L. Nuclease Resistance and Antisense Activity of Modified Oligonucleotides Targeted to Ha-ras. J. Biol. Chem. 1996, 271, 14533-14540.
5. Taylor, M. F.; Paulauskis, J. D.; Weller, D. D.; Kobzik, L. In Vitro Efficacy of Morpholino-Modified Antisense Oligomers Directed Against Tumor Necrosis Factor a mRNA. J. Biol. Chem. 1996, 271, 17445-17452.
6. Shoji, Y.; Akhtar, S.; Periasamy, A.; Herman, B.; Juliano, R. L. Mechanism of Cellular Uptake of Modified Oligonucleotides Containing Methylphosphonate Linkages. Nucleic Acids Res. 1991, 19, 5543-5550.
7. Farrell, C. L.; Bready, J. V.; Kaufman, S. A.; Qian, Y. X.; Burgess, T. L. The Uptake and Distribution of Phosphorothioate Oligonucleotides into Vascular Smooth Muscle Cells In Vitro and Rabbit Arteries. Antisense Res. Dev. 1995, 5, 175-183.
8. Bock, L. C.; Griffin, L. C.; Latham, J. A.; Vermaas, E. H.; Toole, J. J. Selection of Single-Stranded DNA Molecules That Bind and Inhibit Human Thrombin. Nature 1992, 355, 564-566.
9. Ojwang, J. O.; Buckheit, R. W.; Pommier, Y.; Mazumder, A.; De Vreese, K.; Esté, J. A.; Reymen, D.; Pallansch, L. A.; Lackman-Smith, C.; Wallace, T. L.; De Clercq, E.; McGrath, M. S.; Rando, R. F. T30177, an Oligonucleotide Stabilized by an Intramolecular Guanosine Octet, Is a Potent Inhibitor of Laboratory Strains and Clinical Isolates of Human Immunodeficiency Virus Type 1. Antimicrob. Agents Chemother. 1995, 39, 2426-2435.
10. Rando, R. F.; Ojwang, J.; Elbaggari, A.; Reyes, G. R.; Tinder, R.; McGrath, M. S.; Hogan, M. E. Suppression of Human Immunodeficiency Virus Type 1 Activity In Vitro by Oligonucleotides Which Form Intramolecular Tetrads. J. Biol. Chem. 1995, 270, 1754-1760.
11. Bishop, J. S.; Guy-Caffey, J. K.; Ojwang, J. O.; Smith, S. R.; Hogan, M. E.; Cossum, P. A.; Rando, R. F.; Chaudhary, N. Intramolecular G-Quartet Motifs Confer Nuclease Resistance to a Potent Anti-HIV Oligonucleotide. J. Biol. Chem. 1996, 271, 5698-5703.
12. Wyatt, J. R.; Vickers, T. A.; Roberson, J. L.; Buckheit, R. W., Jr.; Klimkait, T.; DeBaets, E.; Davis, P. W.; Rayner, B.; Imbach, J. L.; Ecker, D. J. Combinatorially Selected Guanosine-Quartet Structure Is a Potent Inhibitor of Human Immunodeficiency Virus Envelope-Mediated Cell Fusion. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 1356-1360.
13. Wyatt, J. R.; Davis, P. W.; Freier, S. M. Kinetics of G-Quartet-Mediated Tetramer Formation. Biochemistry 1996, 35, 8002-8008.
14. Furukawa, H.; Momota, K.; Agatsuma, T.; Yamamoto, I.; Kimura, S.; Shimada, K. Mechanism of Inhibition of HIV-1 Infection In Vitro by Guanine-Rich Oligonucleotides Modified at the 5′ Terminal by Dimethoxytrityl Residue. Nucleic Acids Res. 1994, 22, 5621-5627.
15. Hotoda, H.; Momota, K.; Furukawa, H.; Nakamura, T.; Kaneko, M.; Kimura, S.; Shimada, K. Biologically Active Oligodeoxyribonucleotides. 2: Structure Activity Relationships of Anti-HIV-1 Pentadecadeoxyribonucleotides Bearing 5′-End-Modifications. Nucleosides Nucleotides 1994, 13, 1375-1395.
16. Agatsuma, T.; Yamamoto, I.; Furukawa, H.; Nishigaki, T. Guanine-Rich Oligonucleotide Modified at the 5′ Terminal by Dimethoxytrityl Residue Inhibits HIV-1 Replication by Specific Interaction with the Envelope Glycoprotein. Antiviral Res. 1996, 31, 137-148.
17. Furukawa, H.; Momota, K.; Agatsuma, T.; Yamamoto, I.; Kimura, S.; Shimada, K. Inhibition of HIV-1 Infection In Vitro by Short Guanine-Rich Oligonucleotides Modified at the 5′-Terminal with Dimethoxytrityl Residue. Antisense Res. Dev. 1995, 5, 89.
18. Furukawa, H.; Momota, K.; Agatsuma, T.; Yamamoto, I.; Kimura, S.; Shimada, K. Identification of a Phosphodiester Hexanucleotide That Inhibits HIV-1 Infection In Vitro on Covalent Linkage of Its 5′-End with a Dimethoxytrityl Residue. Antisense Nucleic Acid Drug Dev. 1997, 7, 167-175.
19. Matsuzaki, J.; Hotoda, H.; Sekine, M.; Hata, T.; Higuchi, S.; Nishimura, Y.; Tsuboi, M. Self-complementary Tetradeoxyribonucleoside Triphosphates: Convenient Chemical Preparation and Spectroscopic Studies in Solution. Tetrahedron 1986, 42, 501-513.
20. Kamimura, T.; Tsuchiya, M.; Urakami, K.; Koura, K.; Sekine, M.; Shinozuka, K.; Miura, K.; Hata, T. Synthesis of a Dodecaribonucleotide, GUAUCAAUAAUG, by Use of "Fully" Protected Ribonucleotide Building Blocks. J. Am. Chem. Soc. 1984, 106, 4552-4557.
21. Grotjahn, L. In Mass Spectroscopy in Biomedical Research; Gaskell, S., Ed.; John Wiley & Sons: Chichester, 1986; pp 215-234.
22. Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Shols, D.; Herdewijn, P.; Desmyter, J.; DeClercq, E. Rapid and Automated Tetrazolium-Based Colorimetric Assay for the Detection of Anti-HIV Compounds. J. Virol. Methods 1988, 20, 309-321.
23. Wang, Y.; Patel, D. J. Solution Structure of a Parallel-Stranded G-Quadruplex DNA. J. Mol. Biol. 1993, 234, 1171-1183.
24. 4. J. Biol. Chem. 1995, 270, 23090-23096.
25. Kim, J.; Cheong, C.; Moore, P. B. Tetramerization of an RNA Oligonucleotide Containing a GGGG Sequence. Nature 1991, 351, 331-332.
26. Cantor, C. R.; Warshaw, M. M.; Shapiro, H. Oligonucleotides Interactions. 3. Circular Dichroism Studies of the Conformation of Deoxyoligonucleotides. Biopolymers 1970, 9, 1059-1077.
27. Giraldo, R.; Suzuki, M.; Chapman, L.; Rhodes, D. Promotion of Parallel DNA Quadruplexes by a Yeast Telomere Binding Protein: A Circular Dichroism Study. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7658-7662.
28. Hotoda, H.; Koizumi, M.; Koga, R.; Momota, K.; Ohmine, T.; Furukawa, T.; Nishigaki, T.; Kinoshita, T.; Kaneko, M.; Kimura, S.; Shimada, K. Biologically Active Oligodeoxyribonucleotides. 3: Structure-Activity Relationships of Anti-HIV-1 Hexadeoxyribonucleotides Bearing 5′-End-Modifications. Antisense Res. Dev. 1995, 5, 85.
29. Fujihashi, T.; Sakata, T.; Kaji, A.; Kaji, H. Short, Terminally Phosphorylated Oligoriboguanylic Acids Effectively Inhibit Cytopathicity Caused by Human Immunodeficiency Virus. Biochem. Biophys. Res. Commun. 1994, 203, 1244-1250.
30. Crooke, S. T.; Bennett, C. F. Progress in Antisense Oligonucleotide Therapeutics. Annu. Rev. Pharmacol. Toxicol. 1996, 36, 107-1029.
31. Lacoste, J.; Francois, J.-C.; Hélène, C. Triple Helix Formation with Purine-Rich Phosphorothioate-Containing Oligonucleotides Covalently Linked to an Acridine Derivative. Nucleic Acids Res. 1997, 25, 1991-1998.
32. Bates, P. J.; Laughton, C. A.; Jenkins, T. C.; Capaldi, D. C.; Roselt, P. D.; Reese, C. B.; Neidle, S. Efficient Triple Helix Formation By Oligodeoxyribonucleotides Containing α-or β-2-Amino-5-(2-deoxy-D-ribofuranosyl)pyridine Residues. Nucleic Acids Res. 1996, 24, 4176-4184.
33. 4-Containing Phosphorothioate Oligonucleotide. J. Am. Chem. Soc. 1996, 118, 6301-6302.