(P)-helicene displays chiral selection in binding to Z-DNA

Journal of the American Chemical Society

Volumn 126, Issue 21, 2004, Pages 6566-6567

  Xu, Yan ^a   Zhang, You Xin ^b   Sugiyama, Hiroshi ^a,c   Umano, Tomoko ^d   Osuga, Hideji ^d   Tanaka, Kazuhiko ^d  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^b JINZHOU MEDICAL UNIVERSITY   (China)

^c KYOTO UNIVERSITY   (Japan)

^d WAKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; DNA Z; HELICENE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; DNA BINDING; ENANTIOMER; ENANTIOSELECTIVITY; OPTICAL ROTATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

BASE SEQUENCE; CIRCULAR DICHROISM; DNA; DNA, Z-FORM; KINETICS; LIGANDS; MOLECULAR STRUCTURE; NUCLEIC ACID CONFORMATION; POLYCYCLIC COMPOUNDS; STEREOISOMERISM;

EID: 2542516862     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0499748     Document Type: Article

References (19)

1. (a) Rich, A.; Nordheim, A.; Wang, A. H.-J. Annu. Rev. Biochem. 1984, 53, 791-846.
2. (b) Liu, R.; Liu, H.; Chen, X.; Kirby, M.; Brown, P. O.; Zhao, K. Cell 2001, 106, 309-318.
3. (a) Herbert, A.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 12132-12136.
4. (b) Schwartz, T.; Rould, M. A.; Lowenhaupt, K.; Herbert, A.; Rich, A. Science 1999, 284, 1841-1845.
5. (c) Schwartz, T.; Behlke, J.; Lowenhaupt, K.; Heinemann, U.; Rich, A. Nat. Struct. Biol. 2001, 8, 761-765.
6. (a) Hurley, L. H. J. Med. Chem. 1989, 32, 2027-2033.
7. (b) Mergny, J. L.; Helene, C. Nat. Med. 1998, 4, 1366-1367.
8. (c) Qu, X. G.; Trent, J. O.; Fokt, I.; Priebe, W.; Chaires, J. B. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 12032-12037.
9. (d) Perry, P. J.; Jenkins, T. C. Exp. Opin. Invest. Drug. 1999, 8, 1981-2008.
10. Norden, B.; Tjerneld, F. FEBS Lett. 1976, 67, 368-370.
11. (a) Barton, J. K. J. Biomol. Struct. Dyn. 1983, 1, 621-632
12. (b) Chow, C. S.; Barton, J. K. Methods Enzymol. 1992, 212, 219-242
13. (c) Norden, B.; Lincoln, P.; Akerman, B.; Tuite, E. Met. Ions Biol. Syst. 1996, 33, 177-252.
14. 2 (ODN 2) were used. ODN 2 retains a B conformation in 100 mM NaCl, and ODN 1 adopts a Z conformation in the same solution.
15. Sugiyama, H.; Kawai, K.; Matsunaga, A.; Fujimoto, K.; Saito, I.; Robinson, H.; Wang, A. H.-J. Nucleic Acids Res. 1996, 24, 1272-1278.
16. McGhee, J.; von Hippel, P. H. J. Mol. Biol. 1974, 86, 469-68.
17. Enantioselective binding of other helicenes to B-DNA is reported. Honzawa, S.; Okubo, H.; Anzai, S.; Yamaguch, M.; Tsumoto, K.: Kumagai, I. Bioorg. Med. Chem. 2002, 10, 3213-3218.
18. Rich, A.; Zhang, S. Nat. Rev. Genet. 2003, 4, 566-572.
19. Kim, Y. G.; Muralinath, M.; Brandt, T.; Pearcy, M.; Hauns, K.; Lowenhaupt, K.; Jacobs, B. L.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 6974-6979.