Triple helix stabilization by covalently linked DNA-bisbenzimidazole conjugate synthesized by maleimide-thiol coupling chemistry

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 18, 2006, Pages 6444-6452

  Jain, Akash K ^a   Awasthi, Satish Kumar ^b   Tandon, Vibha ^a  

^a UNIVERSITY OF DELHI   (India)

^b UNIVERSITY OF DELHI   (India)

Author keywords

Crosslinking reagent; Heterobifunctional; Induced CD signal; Maleimide conjugate; Minor groove binders; Triple helix

Indexed keywords

4 [5 (4 METHYL 1 PIPERAZINYL)[2,5' BI 1H BENZIMIDAZOL] 2' YL]PHENOL; DOUBLE STRANDED DNA; MALEIMIDE DERIVATIVE; N,N DIMETHYLFORMAMIDE; PIBENZIMOL; PURINE DERIVATIVE; PYRIMIDINE DERIVATIVE; SOLVENT; SUCCINIC ACID DERIVATIVE; SUCCINIMIDYL 4 (N MALEIMIDOMETHYL)CYCLOHEXANE 1 CARBOXYLATE; THIOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CIRCULAR DICHROISM; COVALENT BOND; CROSS LINKING; DNA SEQUENCE; FLUORESCENCE; HYBRIDIZATION; TEMPERATURE DEPENDENCE; THERMOSTABILITY; TRIPLE HELIX;

BENZIMIDAZOLES; BISBENZIMIDE; CIRCULAR DICHROISM; DNA; MALEIMIDES; MOLECULAR STRUCTURE; NUCLEIC ACID CONFORMATION; OLIGONUCLEOTIDES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS; TEMPERATURE;

EID: 33747095383     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.05.034     Document Type: Article

References (43)

1. Giovannongeli C., Perrouault L., Escude C., Thoung N., and Helene C. Biochemistry 35 (1996) 10539
2. Broitman S., Amosova O., Dolinnaya N.G., and Fresco J.R. J. Biol. Chem. 274 (1999) 21763
3. Wang G., Levy D.D., Seidman M.M., and Glazer P.M. Mol. Cell. Biol. 15 (1995) 1759
4. Murry J.A.H., and Crockett N. In: Murry J.A.H. (Ed). Antisense RNA and DNA Vol. II (1992), John Wiley & Sons, New York 1-48
5. Le Doan T., Perrouault L., Praueth D., Habhoub N., Decout J.L., Thoung N.T., Lhomme J., and Helene C. Nucleic Acids Res. 15 (1987) 7749
6. Pilch D.S., Levenson C., and Shafer R.H. Biochemistry 30 (1991) 6081
7. Svinarchuk F., Paoletti J., and Malvy C. J. Biol. Chem. 270 (1995) 14068
8. Singleton S.F., and Dervan P.B. Biochemistry 32 (1993) 13171
9. Mallkov V.A., Voloshin O.N., and Sayfer V.N. Nucleic Acids Res. 21 (1993) 585
10. Uhlman E., and Peyman A. Chem. Rev. 90 (1990) 543
11. Kurreck J. Eur. J. Biochem. 270 (2003) 1628
12. Mergny J.L., Duval-Velentin G., Nguyen C.H., Perrouault L., Faucon B., Rougee M., Moutenay-Garesteier T.M., Bisagaui E., and Helene C. Science 256 (1992) 1681
13. Lee J.S., Latimer L.J., and Hampel K.J. Biochemistry 32 (1993) 5591
14. Pilch S.D., and Breslauer K.J. Proc. Natl. Acad. Sci. U.S.A. 91 (1994) 9332
15. Pilch D.S., Kirolos M.A., and Breslauer K.J. Biochemistry 34 (1995) 16107
16. Fortisch I., Birch-Hirschfeld E., Schutz H., and Zinner C. J. Biomol. Struct. Dyn. 14 (1996) 317
17. Durand M., Thoung N.T., and Maurizot J.C. J. Biol. Chem. 267 (1992) 24394
18. Durand M., Thoung N.T., and Maurizot J.C. Biochimie 76 (1994) 181
19. Silver G.C., Sun J.S., Nauyae C.H., Boutorine A.S., and Helene C. J. Am. Chem. Soc. 119 (1997) 263
20. Stonehouse T.J., and Fox K.R. Biochim. Biophys. Acta 1218 (1994) 322
21. Tung C.H., Breslauer K.J., and Stein S. Nucleic Acids Res. 21 (1993) 5489
22. Szewcyk J.W., Baird E.E., and Dervan P.B. J. Am. Chem. Soc. 118 (1996) 6778
23. Gryaznov S.M., and Lloyd D.H. Nucleic Acids Res. 21 (1993) 5909
24. Robles J., and McLaughlin L.W.C. J. Am. Chem. Soc. 119 (1997) 6014
25. Reddy P.M., and Bruice T.C. J. Am. Chem. Soc. 126 (2004) 3736
26. Coiuzza A.J. Tetrahedron Lett. 30 (1989) 6287
27. Asselin U., Bonfils E., Kenfurst R., Chassignd M., Roij V., and Thung N.T. Tetrahedron 48 (1992) 1233
28. Brinkley M. Bioconjugate Chem. 3 (1992) 2
29. Youle R.J., and Neville D.M. Proc. Natl. Acad. Sci. U.S.A. 77 (1980) 5483
30. Ghosh S.S., Kao P.N., McCue A.W., and Chappelle H.L. Bioconjugate Chem. 1 (1990) 71
31. Harrison J.G., and Balasubramanian S. Nucleic Acids Res. 26 (1998) 3136
32. Koppelhus U., Awasthi S.K., Zacher V., Holst H.V., Ebbesen P., and Nielsen P.E. Antisense Nucleic Acid Drug Dev. 12 (2002) 51
33. Arndt-Jovin D.J., and Jovin T.M. Cytometry 11 (1990) 80
34. Arya D.P., and Willis B. J. Am. Chem. Soc. 125 (2003) 12398
35. Connolly B.A., and Ridev P. Nucleic Acids Res. 13 (1985) 4485
36. Connolly B.A. Nucleic Acids Res. 15 (1987) 3131
37. Rajur B.S., Robles J., Wiederholt K., Kuimelis R.G., and McLaughlin L.W. J. Org. Chem. 62 (1997) 523
38. Staz A.L., and Bruice T.C. Bioorg. Med. Chem. 8 (2000) 1871
39. Kelly D.P., Bateman S.A., Martin R.F., Reum M.E., Rose M., and Whittaker A.R.D. Aust. J. Chem. 47 (1994) 247
40. Behreus C., Harrit N., and Nielsen P.E. Bioconjugate Chem. 12 (2001) 1021
41. Chrisey U.A., Lee G.U., and Ferral G.U. Nucleic Acids Res. 24 (1996) 3031
42. Lee B.R., Hasemm D.B., and Reynolds C.D. Cytometry 10 (1989) 256
43. Tawar U., Jain A.K., Dwarkanath B.S., Chandra R., Singh Y., Chaudhary N.K., and Tandon V. J. Med. Chem. 46 (2003) 3785