Syntheses of nucleic acid mimics designed for metal-induced strand formation on DNA

Akihiko Hatano, Kentaro Tanaka, Motoo Shiro, Mitsuhiko Shionoya

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

This paper describes design and syntheses of a new class of chelator-type nucleic acid mimics. Four nucleic acid mimics 7, 11, 15, 17 possess a nucleobase and two ethylenediamine moieties for intermolecular metal coordination. We expected that chelator-type nucleic acid mimics formed a strand in the presence of metal ion and then interacted with a single-stranded DNA. Efficient synthetic routes leading to the four nucleic acid analogues have been achieved via the key intermediate compound 5 which was derived from 3,5-dimethylphenol in five steps. Compound 7 was treated with zinc nitrate and Zn complex 8 was isolated as crystals. 1H NMR study of Zn complex 8 in D2O showed the single-strand formation. Job plots showed that mixture of (dT)70 with Zn complex 8 at 5°C reached a minimum absorbance at a mole ratio of 2:1, and the hypochromic effect showed the π-π stacking interaction between the nucleobases. Thermal denaturation study at 2:1 mole ratio of complexes between (dT)70 and Zn complex 8 showed melting point at 27°C.

Original languageEnglish
Pages (from-to)2965-2972
Number of pages8
JournalTetrahedron
Volume58
Issue number15
DOIs
Publication statusPublished - 2002 Apr 8
Externally publishedYes

Fingerprint

Nucleic Acids
Metals
ethylenediamine
DNA
Chelating Agents
Denaturation
Single-Stranded DNA
Metal ions
Melting point
Nuclear magnetic resonance
Crystals

Keywords

  • Chelator-type nucleic acid mimics
  • DNA
  • Intermolecular metal coordination

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Syntheses of nucleic acid mimics designed for metal-induced strand formation on DNA. / Hatano, Akihiko; Tanaka, Kentaro; Shiro, Motoo; Shionoya, Mitsuhiko.

In: Tetrahedron, Vol. 58, No. 15, 08.04.2002, p. 2965-2972.

Research output: Contribution to journalArticle

Hatano, Akihiko ; Tanaka, Kentaro ; Shiro, Motoo ; Shionoya, Mitsuhiko. / Syntheses of nucleic acid mimics designed for metal-induced strand formation on DNA. In: Tetrahedron. 2002 ; Vol. 58, No. 15. pp. 2965-2972.
@article{b1897b39db1c4fe99eba3ab5a6166e49,
title = "Syntheses of nucleic acid mimics designed for metal-induced strand formation on DNA",
abstract = "This paper describes design and syntheses of a new class of chelator-type nucleic acid mimics. Four nucleic acid mimics 7, 11, 15, 17 possess a nucleobase and two ethylenediamine moieties for intermolecular metal coordination. We expected that chelator-type nucleic acid mimics formed a strand in the presence of metal ion and then interacted with a single-stranded DNA. Efficient synthetic routes leading to the four nucleic acid analogues have been achieved via the key intermediate compound 5 which was derived from 3,5-dimethylphenol in five steps. Compound 7 was treated with zinc nitrate and Zn complex 8 was isolated as crystals. 1H NMR study of Zn complex 8 in D2O showed the single-strand formation. Job plots showed that mixture of (dT)70 with Zn complex 8 at 5°C reached a minimum absorbance at a mole ratio of 2:1, and the hypochromic effect showed the π-π stacking interaction between the nucleobases. Thermal denaturation study at 2:1 mole ratio of complexes between (dT)70 and Zn complex 8 showed melting point at 27°C.",
keywords = "Chelator-type nucleic acid mimics, DNA, Intermolecular metal coordination",
author = "Akihiko Hatano and Kentaro Tanaka and Motoo Shiro and Mitsuhiko Shionoya",
year = "2002",
month = "4",
day = "8",
doi = "10.1016/S0040-4020(02)00203-X",
language = "English",
volume = "58",
pages = "2965--2972",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "15",

}

TY - JOUR

T1 - Syntheses of nucleic acid mimics designed for metal-induced strand formation on DNA

AU - Hatano, Akihiko

AU - Tanaka, Kentaro

AU - Shiro, Motoo

AU - Shionoya, Mitsuhiko

PY - 2002/4/8

Y1 - 2002/4/8

N2 - This paper describes design and syntheses of a new class of chelator-type nucleic acid mimics. Four nucleic acid mimics 7, 11, 15, 17 possess a nucleobase and two ethylenediamine moieties for intermolecular metal coordination. We expected that chelator-type nucleic acid mimics formed a strand in the presence of metal ion and then interacted with a single-stranded DNA. Efficient synthetic routes leading to the four nucleic acid analogues have been achieved via the key intermediate compound 5 which was derived from 3,5-dimethylphenol in five steps. Compound 7 was treated with zinc nitrate and Zn complex 8 was isolated as crystals. 1H NMR study of Zn complex 8 in D2O showed the single-strand formation. Job plots showed that mixture of (dT)70 with Zn complex 8 at 5°C reached a minimum absorbance at a mole ratio of 2:1, and the hypochromic effect showed the π-π stacking interaction between the nucleobases. Thermal denaturation study at 2:1 mole ratio of complexes between (dT)70 and Zn complex 8 showed melting point at 27°C.

AB - This paper describes design and syntheses of a new class of chelator-type nucleic acid mimics. Four nucleic acid mimics 7, 11, 15, 17 possess a nucleobase and two ethylenediamine moieties for intermolecular metal coordination. We expected that chelator-type nucleic acid mimics formed a strand in the presence of metal ion and then interacted with a single-stranded DNA. Efficient synthetic routes leading to the four nucleic acid analogues have been achieved via the key intermediate compound 5 which was derived from 3,5-dimethylphenol in five steps. Compound 7 was treated with zinc nitrate and Zn complex 8 was isolated as crystals. 1H NMR study of Zn complex 8 in D2O showed the single-strand formation. Job plots showed that mixture of (dT)70 with Zn complex 8 at 5°C reached a minimum absorbance at a mole ratio of 2:1, and the hypochromic effect showed the π-π stacking interaction between the nucleobases. Thermal denaturation study at 2:1 mole ratio of complexes between (dT)70 and Zn complex 8 showed melting point at 27°C.

KW - Chelator-type nucleic acid mimics

KW - DNA

KW - Intermolecular metal coordination

UR - http://www.scopus.com/inward/record.url?scp=0037041488&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037041488&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(02)00203-X

DO - 10.1016/S0040-4020(02)00203-X

M3 - Article

VL - 58

SP - 2965

EP - 2972

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 15

ER -