The spermine-bisaryl conjugate as a potent inducer of B- to Z-DNA transition

Issei Doi, Genichiro Tsuji, Kyoko Kawakami, Osamu Nakagawa, Yosuke Taniguchi, Shigeki Sasaki

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Abstract

DNA containing alternating purine and pyrimidine repeats has the potential to adopt the Z-DNA structure, one of the well-studied structures besides A- and B-DNA. Despite a number of molecular models that have been proposed to explain the mechanism for B→Z transition, there is continued discussion on the mechanism and physiological role of this transition. In this study, we have found that the bis(2-naphthyl)-maleimide-spermine conjugate (3c) exhibits a remarkable ability to cause the B→Z transition of d(CGCGCG)2 at low salt concentrations. Using isothermal titration calorimetry (ITC) we show that the B→Z transition induced by 3c is both enthalpically and entropically favorable. The ligand might effect the dehydration of B-DNA, which leads to the B→Z transition. Interestingly, an intermediate CD between the B and Z forms was observed in the pH-dependent transition in the presence of the ligand. The unique structure and characteristics of the ligand designed in this investigation will be useful for the study of Z-DNA. From B to Z: The bis(2-naphthyl)maleimide-spermine conjugate shown in the figure exhibits a remarkable ability to cause the B→Z transition of d(CGCGCG)2 at low salt concentrations. A stable intermediate between the B and Z forms was observed in the presence of the ligand at about pH 8.

Original languageEnglish
Pages (from-to)11993-11999
Number of pages7
JournalChemistry - A European Journal
Volume16
Issue number39
DOIs
Publication statusPublished - Oct 18 2010

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Z-Form DNA
Spermine
DNA
Ligands
Salts
B-Form DNA
Calorimetry
Dehydration
Titration
tri(deoxycytidylic acid-deoxyguanylic acid)
maleimide
tri(cytidylic acid-guanidylic acid)

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

The spermine-bisaryl conjugate as a potent inducer of B- to Z-DNA transition. / Doi, Issei; Tsuji, Genichiro; Kawakami, Kyoko; Nakagawa, Osamu; Taniguchi, Yosuke; Sasaki, Shigeki.

In: Chemistry - A European Journal, Vol. 16, No. 39, 18.10.2010, p. 11993-11999.

Research output: Contribution to journalArticle

Doi, Issei ; Tsuji, Genichiro ; Kawakami, Kyoko ; Nakagawa, Osamu ; Taniguchi, Yosuke ; Sasaki, Shigeki. / The spermine-bisaryl conjugate as a potent inducer of B- to Z-DNA transition. In: Chemistry - A European Journal. 2010 ; Vol. 16, No. 39. pp. 11993-11999.
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