Enantioselective binding of chiral 1,14-dimethyl[5]helicene-spermine ligands with B- and Z-DNA

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 19, 2013, Pages 6063-6068

  Tsuji, Genichiro ^a   Kawakami, Kyoko ^a   Sasaki, Shigeki ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Chiral recognition; DNA binding ligand; Helicene; Isothermal titration calorimetry; Surface plasmon resonance

Indexed keywords

1 BENZYL 3,4 DIBROMOPYRROLE 2,5 DIONE; 1 METHYLNAPHTHALENE 7 BORONIC ACID; 1,14 DIMETHYL[5]HELICENE SPERMINE; DNA B; DNA Z; DOUBLE STRANDED DNA; LIGAND; OLIGOMER; SPERMINE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHIRALITY; CIRCULAR DICHROISM; DNA BINDING; DNA CONFORMATION; DNA HELIX; DNA STRUCTURE; DNA SYNTHESIS; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTHERMAL TITRATION CALORIMETRY; RECOGNITION; STATIC ELECTRICITY; SURFACE PLASMON RESONANCE; THERMODYNAMICS;

CHIRAL RECOGNITION; DNA BINDING LIGAND; HELICENE; ISOTHERMAL TITRATION CALORIMETRY; SURFACE PLASMON RESONANCE;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA, B-FORM; DNA, Z-FORM; HYDROGEN-ION CONCENTRATION; LIGANDS; MODELS, MOLECULAR; SPERMINE; STATIC ELECTRICITY; STEREOISOMERISM; THERMODYNAMICS;

EID: 84883444983     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.07.022     Document Type: Article

References (21)

1. A. Rich, and S. Zhang Nat. Rev. Genet. 4 2003 566
2. M.A. Fuertes, V. Cepeda, C. Alonso, and J.M. Pérez Chem. Rev. 106 2006 2045
3. C. Mao, W. Sun, Z. Shen, and N.C. Seeman Nature 397 1999 144
4. N.C. Seeman, and A.M. Belcher Proc. Natl. Acad. Sci. U.S.A 99 Suppl 2 2002 6451 6455
5. S.C. Ha, K. Lowenhaupt, A. Rich, Y.-G. Kim, and K.K. Kim Nature 437 2005 1183
6. E.M. Lafer, A. Möller, A Nordheim, B.D. Stollar, and A. Rich Proc. Natl. Acad. Sci. U.S.A. 78 1981 3546
7. J.-A. Kwon, and A. Rich Proc. Natl. Acad. Sci. U.S.A. 102 2005 12759
8. Z. Wu, T. Tian, J. Yu, X. Weng, Y. Liu, and X. Zhou Angew. Chem., Int. Ed. 50 2011 11962
9. K.E. Erkkila, D.T. Odom, and J.K. Barton Chem. Rev. 1999 2777
10. X. Qu, J.O. Trent, I. Fokt, W. Priebe, and J.B. Chaires Proc. Natl. Acad. Sci. U.S.A. 97 2000 12032
11. Y. Xu, Y.X. Zhang, H. Sugiyama, T. Umano, H. Osuga, and K. Tanaka J. Am. Chem. Soc. 126 2004 6566
12. S. Honzawa, H. Okubo, S. Anzai, M. Yamaguchi, K. Tsumoto, and I. Kumagai Bioorg. Med. Chem. 10 2002 3213
13. I. Doi, G. Tsuji, K. Kawakami, O. Nakagawa, Y. Taniguchi, and S. Sasaki Chem-Eur. J. 16 2010 11993
14. J.K. Barton, L.A. Basile, A. Danishefsky, and A. Alexandrescu Proc. Natl. Acad. Sci. U.S.A. 81 1984 1961
15. C. Goedicke, and H. Stegemeyer Tetrahedron Lett. 11 1970 937
16. R.H. Janke, E. Wu, and J.H. Borkent J. Am. Chem. Soc. 118 1996 6031
17. I. Singh, and O. Seitz Organic Lett. 8 2006 4319
18. R.Talele Harish, J.Gohil Monik, and V.Bedekar Ashutosh Bull. Chem. Soc. Jpn. 82 2009 1182
19. Y. Xu, R. Ikeda, and H. Sugiyama J. Am. Chem. Soc. 125 2003 13519
20. B. Pan, C. Ban, M.C. Wahl, and M. Sundaralingam Biophys. J. 73 1997 1553
21. H. Ohishi, M. Odoko, D.-Y. Zhou, Y. Tozuka, N. Okabe, K. Nakatani, T. Ishida, and K. Grzeskowiak Biochem. Biophy. Res. Commun. 368 2008 382