The significant effect of the carbohydrate structures on the DNA photocleavage of the quinoxaline-carbohydrate hybrids

Kazunobu Toshima, Tomohiro Ozawa, Tomonori Kimura, Shuichi Matsumura

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The novel DNA interactive quinoxaline-carbohydrate hybrids possessing disaccharides as the carbohydrate moieties were designed and synthesized, and their DNA photocleaving abilities were evaluated in order to examine the effect of the disaccharide structures. The configurations of the glycosidic bonds in the disaccharide strongly affected the DNA photocleaving ability, and two β-glycosidic bond linkages were very effective for the DNA photocleavage. Furthermore, the quinoxaline-disaccharide hybrids exhibited selective cytotoxicity against cancer cells with photoirradiation.

Original languageEnglish
Pages (from-to)2777-2779
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume14
Issue number11
DOIs
Publication statusPublished - 2004 Jun 7

Fingerprint

Quinoxalines
Disaccharides
Carbohydrates
DNA
Cytotoxicity
Cells
Neoplasms

Keywords

  • Carbohydrate
  • Cytotoxicity
  • DNA photocleavage
  • Oligosaccharide
  • Quinoxaline

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

The significant effect of the carbohydrate structures on the DNA photocleavage of the quinoxaline-carbohydrate hybrids. / Toshima, Kazunobu; Ozawa, Tomohiro; Kimura, Tomonori; Matsumura, Shuichi.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 14, No. 11, 07.06.2004, p. 2777-2779.

Research output: Contribution to journalArticle

@article{2f2e0ac26f2640f4b63892128d13fecf,
title = "The significant effect of the carbohydrate structures on the DNA photocleavage of the quinoxaline-carbohydrate hybrids",
abstract = "The novel DNA interactive quinoxaline-carbohydrate hybrids possessing disaccharides as the carbohydrate moieties were designed and synthesized, and their DNA photocleaving abilities were evaluated in order to examine the effect of the disaccharide structures. The configurations of the glycosidic bonds in the disaccharide strongly affected the DNA photocleaving ability, and two β-glycosidic bond linkages were very effective for the DNA photocleavage. Furthermore, the quinoxaline-disaccharide hybrids exhibited selective cytotoxicity against cancer cells with photoirradiation.",
keywords = "Carbohydrate, Cytotoxicity, DNA photocleavage, Oligosaccharide, Quinoxaline",
author = "Kazunobu Toshima and Tomohiro Ozawa and Tomonori Kimura and Shuichi Matsumura",
year = "2004",
month = "6",
day = "7",
doi = "10.1016/j.bmcl.2004.03.065",
language = "English",
volume = "14",
pages = "2777--2779",
journal = "Bioorganic and Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Elsevier Limited",
number = "11",

}

TY - JOUR

T1 - The significant effect of the carbohydrate structures on the DNA photocleavage of the quinoxaline-carbohydrate hybrids

AU - Toshima, Kazunobu

AU - Ozawa, Tomohiro

AU - Kimura, Tomonori

AU - Matsumura, Shuichi

PY - 2004/6/7

Y1 - 2004/6/7

N2 - The novel DNA interactive quinoxaline-carbohydrate hybrids possessing disaccharides as the carbohydrate moieties were designed and synthesized, and their DNA photocleaving abilities were evaluated in order to examine the effect of the disaccharide structures. The configurations of the glycosidic bonds in the disaccharide strongly affected the DNA photocleaving ability, and two β-glycosidic bond linkages were very effective for the DNA photocleavage. Furthermore, the quinoxaline-disaccharide hybrids exhibited selective cytotoxicity against cancer cells with photoirradiation.

AB - The novel DNA interactive quinoxaline-carbohydrate hybrids possessing disaccharides as the carbohydrate moieties were designed and synthesized, and their DNA photocleaving abilities were evaluated in order to examine the effect of the disaccharide structures. The configurations of the glycosidic bonds in the disaccharide strongly affected the DNA photocleaving ability, and two β-glycosidic bond linkages were very effective for the DNA photocleavage. Furthermore, the quinoxaline-disaccharide hybrids exhibited selective cytotoxicity against cancer cells with photoirradiation.

KW - Carbohydrate

KW - Cytotoxicity

KW - DNA photocleavage

KW - Oligosaccharide

KW - Quinoxaline

UR - http://www.scopus.com/inward/record.url?scp=2342632050&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=2342632050&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2004.03.065

DO - 10.1016/j.bmcl.2004.03.065

M3 - Article

C2 - 15125931

AN - SCOPUS:2342632050

VL - 14

SP - 2777

EP - 2779

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 11

ER -