Recognition of a 10 base pair sequence of DNA and stereochemical control of the binding affinity of chiral hairpin polyamide-Hoechst 33258 conjugates

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 24, 2005, Pages 5531-5536

  Reddy, Putta Mallikarjuna ^a   Toporowski, Joseph W ^a   Kahane, Alexandra L ^a   Bruice, Thomas C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Chiral hairpin polyamide Hoechst 33258 conjugates

Indexed keywords

4 [5 (4 METHYL 1 PIPERAZINYL)[2,5' BI 1H BENZIMIDAZOL] 2' YL]PHENOL; AMINO ACID; BENZIMIDAZOLE DERIVATIVE; DNA BASE; POLYAMIDE; PROTON;

AMINO TERMINAL SEQUENCE; ARTICLE; BASE PAIRING; BINDING AFFINITY; CHIRALITY; DNA SEQUENCE; DRUG CONJUGATION; DRUG DNA BINDING; DRUG SYNTHESIS; ENANTIOMER; HYDROGEN BOND; MOLECULAR MODEL; MOLECULAR RECOGNITION; SOLID; SPECTROFLUOROMETRY; STEREOCHEMISTRY;

BASE PAIRING; BASE SEQUENCE; BINDING SITES; BISBENZIMIDE; DNA; KINETICS; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION; NYLONS; PYRROLES; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 27644589596     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.08.076     Document Type: Article

References (40)

1. P.B. Dervan Bioorg. Med. Chem. 9 2001 2215
2. M. Mrksich, M.E. Parks, and P.B. Dervan J. Am. Chem. Soc. 116 1994 7983
3. M.E. Parks, E.E. Baird, and P.B. Dervan J. Am. Chem. Soc. 118 1996 6147
4. M.E. Parks, E.E. Baird, and P.B. Dervan J. Am. Chem. Soc. 118 1996 6153
5. J.W. Trauger, E.E. Baird, and P.B. Dervan Chem. Biol. 3 1996 369
6. S.E. Swalley, E.E. Baird, and P.B. Dervan J. Am. Chem. Soc. 118 1996 8198
7. D.S. Pilch, N.A. Pokar, C.A. Gelfand, S.M. Law, K.J. Breslauer, E.E. Baird, and P.B. Dervan Proc. Natl. Acad Sci. U.S.A. 93 1996 8306
8. R.P.L. de Claire, B.H. Geierstanger, M. Mrksich, P.B. Dervan, and D.E. Wemmer J. Am. Chem. Soc. 119 1997 7909
9. J.M. Gottesfeld, L. Neeley, J.W. Trauger, E.E. Baird, and P.B. Dervan Nature 387 1997 202
10. A.M. Mapp, A.Z. Ansari, M. Ptashne, and P.B. Dervan Proc. Natl. Acad Sci. U.S.A. 97 2000 3930
11. J.J. Kelly, E.E. Baird, and P.B. Dervan Proc. Natl. Acad. Sci. U.S.A. 93 1996 6981
12. C.L. Kielkopf, E.E. Baird, P.B. Dervan, and D.C. Rees Nat. Struct. Biol. 5 1998 104
13. S.Y. Chiang, R.W. Burli, C.C. Benz, L. Gawron, G.K. Scott, P.B. Dervan, and T.A. Beerman J. Biol. Chem. 275 2000 24246
14. A.L. Satz, and T.C. Bruice J. Am. Chem. Soc. 123 2001 2469
15. A.L. Satz, and T.C. Bruice Bioorg. Med. Chem. 10 2002 241
16. P.M. Reddy, P.T. Jindra, A.L. Satz, and T.C. Bruice J. Am. Chem. Soc. 125 2003 7843
17. C.M. White, A.L. Satz, T.C. Bruice, and T.A. Beerman Proc. Natl. Acad. Sci. U.S.A. 98 2001 10590
18. C.M. White, A.L. Satz, L.S. Gawron, T.C. Bruice, and T.A. Beerman Biochim. Biophys. Acta 1574 2001 100
19. P.M. Reddy, R. Dexter, and T.C. Bruice Bioorg. Med. Chem. Lett. 14 2004 3803
20. C.R. Woods, T. Ishii, B. Wu, K.W. Bair, and D.L. Boger J. Am. Chem. Soc. 124 2002 2148
21. D.M. Herman, E.E. Baird, and P.B. Dervan J. Am. Chem. Soc. 120 1998 1382
22. D.M. Herman, E.E. Baird, and P.B. Dervan Chem. Eur. J. 5 1999 975
23. J.W. Trauger, E.E. Baird, and P.B. Dervan Chem. Biol. 3 1996 369
24. N.R. Wurtz, J.M. Turner, E.E. Baird, and P.B. Dervan Org. Lett. 3 2001 1201
25. P.M. Reddy, and T.C. Bruice J. Am. Chem. Soc. 126 2004 3736
26. C. Park, and K. Burgess J. Comb. Chem. 3 2001 257
27. S.-Y. Chiang, T.C. Bruice, J.C. Azizkhan, L. Gawron, and T. Beerman Proc. Natl. Acad. Sci. U.S.A. 94 1997 2811
28. G.X. He, K.A. Browne, A. Blasko, and T.C. Bruice J. Am. Chem. Soc. 116 1994 3716
29. K.A. Browne, G.X. He, and T.C. Bruice J. Am. Chem. Soc. 115 1993 7072
30. F.G. Loontiens, P. Regenfuss, A. Zechel, L. Dumortier, and R.M. Clegg Biochemistry 29 1990 9029
31. C.E. Bostock-Smith, and M.S. Searle Nucleic Acids Res. 27 1999 1619
32. I. Haq, J.E. Ladbury, B.Z. Chowdhry, T.C. Jenkins, and J.B. Chaires J. Mol. Biol. 271 1997 244
33. F.G. Loontiens, L.W. McLaughlin, S. Diekmann, and R.M. Clegg Biochemistry 30 1991 182
34. The point of intersection of the two straight lines generated by fitting the pre- and post-saturation data points in the titration over x-axis provided the stoichiometry of conjugate:dsDNA complex.
35. K.A. Browne, G.X. He, and T.C. Bruice J. Am. Chem. Soc. 115 1993 7072
36. A.L. Satz, and T.C. Bruice Bioorg. Med. Chem. 8 2000 1871
37. Sybyl, version 6.8, 2001 Tripos, St. Louis, MO.
38. S.N. Mitra, M.C. Wahl, and M. Sundaralingam Acta Crystallogr. D55 1999 602
39. M.C. Vega, I.G. Saez, J. Aymami, R. Eritja, G.A. van deer Marel, J.H. van Boom, A. Rich, and M. Coll Eur. J. Biochem. 222 1994 721
40. Delano W. L, 'The PyMOL Graphics System.' version 0.97, 2004, Delano Scientific LLC, San Carlos, CA, USA. http://www.pymol.org.