The Spermine-Bisaryl Conjugate as a Potent Inducer of B- to Z-DNA Transition

被引：18

作者：

Doi, Issei ^{[1
]}

Tsuji, Genichiro ^{[1
]}

Kawakami, Kyoko ^{[1
]}

Nakagawa, Osamu ^{[1
]}

Taniguchi, Yosuke ^{[1
]}

Sasaki, Shigeki ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Higashi Ku, Fukuoka 8128582, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 39期

基金：

日本学术振兴会; 日本科学技术振兴机构;

关键词：

B-Z transition; circular dichroism; DNA; isothermal titration calorimetry; surface plasmon resonance; BINDING; CONDENSATION; HYDRATION; FORM;

D O I：

10.1002/chem.201000947

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：11993 / 11999

页数：7

共 29 条

[1] THE LOW-TEMPERATURE CRYSTAL-STRUCTURE OF THE PURE-SPERMINE FORM OF Z-DNA REVEALS BINDING OF A SPERMINE MOLECULE IN THE MINOR-GROOVE [J].

BANCROFT, D ;

WILLIAMS, LD ;

RICH, A ;

EGLI, M .

BIOCHEMISTRY, 1994, 33 (05) :1073-1086

[2]

BRITT M, 1986, MOL PHARMACOL, V29, P74

[3]

CHEN CW, 1983, BIOCHEMISTRY-US, V22, pA23

[4] EFFECTS OF A-T BASE-PAIRS ON THE B-Z CONFORMATIONAL TRANSITIONS OF DNA [J].

CHEN, FM .

NUCLEIC ACIDS RESEARCH, 1988, 16 (05) :2269-2281

[5] Interactions of a Tetraanionic Porphyrin with DNA: from a Z-DNA Sensor to a Versatile Supramolecular Device [J].

D'Urso, Alessandro ;

Mammana, Angela ;

Balaz, Milan ;

Holmes, Andrea E. ;

Berova, Nina ;

Lauceri, Rosaria ;

Purrello, Roberto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (06) :2046-+

[6] Enthalpy of the B-to-Z conformational transition of a DNA oligonucleotide determined by isothermal titration calorimetry [J].

Ferreira, Jaime M. ;

Sheardy, Richard D. .

BIOPHYSICAL JOURNAL, 2006, 91 (09) :3383-3389

[7] Molecular mechanisms for the B-Z transition in the example of poly[d(G-C)•d(G-C)] polymers.: A critical review [J].

Fuertes, Miguel A. ;

Cepeda, Victoria ;

Alonso, Carlos ;

Perez, Jose M. .

CHEMICAL REVIEWS, 2006, 106 (06) :2045-2064

[8] Synthesis of cholesterol-polyamine carbamates:: pKa studies and condensation of calf thymus DNA [J].

Geall, AJ ;

Taylor, RJ ;

Earll, ME ;

Eaton, MAW ;

Blagbrough, IS .

CHEMICAL COMMUNICATIONS, 1998, (13) :1403-1404

[9] INHIBITION OF THE B-TRANSITION TO Z-TRANSITION IN POLY(DGDC).POLY(DGDC) BY COVALENT ATTACHMENT OF ETHIDIUM - KINETIC-STUDIES [J].

GILBERT, PL ;

GRAVES, DE ;

BRITT, M ;

CHAIRES, JB .

BIOCHEMISTRY, 1991, 30 (45) :10931-10937

[10] HYDRATION OF METHYLATED AND NONMETHYLATED B-DNA AND Z-DNA [J].

HO, PS ;

QUIGLEY, GJ ;

TILTON, RF ;

RICH, A .

JOURNAL OF PHYSICAL CHEMISTRY, 1988, 92 (04) :939-945

← 1 2 3 →