Functionalized head-to-head hairpin polyamides: Synthesis, double-stranded DNA-binding activity and affinity

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 16, 2005, Pages 3720-3724

  Halby, Ludovic ^a   Ryabinin, Vladimir A ^b,c   Sinyakov, Alexandre N ^b,c   Boutorine, Alexandre S ^a  

^a MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

^b INSTITUTE OF CHEMICAL BIOLOGY AND FUNDAMENTAL MEDICINE   (Russian Federation)

^c STATE RESEARCH CENTER OF VIROLOGY AND BIOTECHNOLOGY VECTOR   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

DOUBLE STRANDED DNA; POLYAMIDE;

ARTICLE; BASE PAIRING; BINDING AFFINITY; COMPARATIVE STUDY; DNA DRUG COMPLEX; DNA SEQUENCE; DRUG DNA BINDING; DRUG SYNTHESIS; NUCLEOTIDE SEQUENCE; SEQUENCE ANALYSIS;

BASE SEQUENCE; BINDING SITES; DNA; HEPARIN; HIV; HUMANS; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; NUCLEIC ACID CONFORMATION; NYLONS; PROVIRUSES;

EID: 22844438124     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.05.106     Document Type: Article

References (22)

1. P.B. Dervan, and B.S. Edelson Curr. Opin. Struct. Biol. 13 2003 284
2. P.B. Dervan, and R.W. Bürli Curr. Opin. Chem. Biol. 3 1999 688
3. J.W. Szewczyk, E.E. Baird, and P.B. Dervan Angew. Chem. Int. Ed. 35 1996 1487
4. P.B. Arimondo, C. Bailly, A.S. Boutorine, V.A. Ryabinin, A.N. Sinyakov, J.S. Sun, T. Garestier, and C. Hélène Angew. Chem. Int. Ed. 40 2001 3045
5. C.C.C. Wang, and P.B. Dervan J. Am. Chem. Soc. 123 2001 8657
6. M.A. Marques, R.M. Doss, S. Foister, and P.B. Dervan J. Am. Chem. Soc. 126 2004 10339
7. V.A. Ryabinin, A.Y. Denisov, D.V. Pyshnyi, T.V. Abramova, A.N. Sinyakov, and V.V. Vlasov Dokl. Akad. Nauk. 368 1999 836
8. A.N. Sinyakov, V.A. Ryabinin, G.N. Grimm, and A.S. Boutorine Mol. Biol. Engl. Tr. 35 2001 251
9. V.A. Ryabinin, A.S. Boutorine, C. Hélène, A.Y. Denisov, D.V. Pyshnyi, and A.N. Sinyakov Nucleosides Nucleotides Nucleic Acids 23 2004 953
10. A.S. Boutorine, V.A. Ryabinin, D.S. Novopashina, A.G. Venyaminova, C. Hé lène, and A.N. Sinyakov Nucleosides Nucleotides Nucleic Acids 22 2003 1267
11. Novopashina, D. S.; Sinyakov, A. N.; Ryabinin, V. A.; Venyaminova, A. G.; Halby, L.; Sun, J. S.; Boutorine, A. S. Chem. Biodiv. 2005, accepted for publication.
12. T. Mukaiyama, R. Matsueda, and M. Suzuki Tetrahedron Lett. 22 1970 1901
13. G.N. Grimm, A.S. Boutorine, and C. Hélène Nucleosides Nucleotides Nucleic Acids 19 2000 1943
14. C.R. Woods, T. Ishii, and D.L. Boger J. Am. Chem. Soc. 124 2002 10676
15. A.N. Sinyakov, M.V. Feshchenko, and V.A. Ryabinin Russ. J. Bioorg. Chem. 29 2003 402
16. V.A. Ryabinin, A.S. Boutorine, C. Hélène, D.V. Pyshnyi, and A.N. Sinyakov Nucleosides Nucleotides Nucleic Acids 23 2004 789
17. J.P. Genêt, J. Uziel, M. Port, A.M. Touzin, S. Roland, S. Thorimbert, and S. Tanier Tetrahedron Lett. 33 1992 77
18. The products (3), (6), (7), and (9) were purified by HPLC on a C-18 X-terra column (Waters, 7 μm, 7.8 × 300 mm) in a linear 0-80% water/acetonitrile gradient with 0.02 M ammonium acetate (products (3) and (6)), or 0.1% trifluoroacetic acid (products (7) and (9)). The flow rate was 2 ml/min.
19. 20 calculated: 2264.55.
20. C. Giovannangeli, S. Diviacco, V. Labrousse, S. Gryaznov, P. Charneau, and C. Hélène Proc. Natl. Acad. Sci. USA 94 1997 79
21. A.S. Boutorine, T. Le Doan, J.P. Battioni, D. Mansuy, D. Dupré, and C. Hélène Bioconjug. Chem. 1 1990 350
22. V.A. Ryabinin, A.S. Boutorine, C. Hélène, D.V. Pyshnyi, and A.N. Sinyakov Nucleosides Nucleotides Nucleic Acids 23 2004 789