Molecular design, chemical synthesis and biological evaluation of quinoxaline-carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents

Kazunobu Toshima, Tomonori Kimura, Ryusuke Takano, Tomohiro Ozawa, Akiko Ariga, Yutaka Shima, Kazuo Umezawa, Shuichi Matsumura

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The quinoxaline moiety in antitumor quinoxaline antibiotics cleaved double stranded DNA at the 5′ side guanine of the 5′-GG-3′ site upon irradiation with UV light with a long wavelength and without any additive. The quinoxaline-carbohydrate hybrid system was very effective for the DNA cleavage. Furthermore, the quinoxaline-carbohydrate hybrids exhibited strong and selective cytotoxicity against cancer cells with photoirradiation.

Original languageEnglish
Pages (from-to)7057-7066
Number of pages10
JournalTetrahedron
Volume59
Issue number35
DOIs
Publication statusPublished - 2003 Aug 25

Fingerprint

Quinoxalines
Cytotoxins
Carbohydrates
DNA
DNA Cleavage
Guanine
Ultraviolet Rays
Cytotoxicity
Hybrid systems
Ultraviolet radiation
Cells
Irradiation
Anti-Bacterial Agents
Wavelength
Neoplasms

Keywords

  • Carbohydrate
  • Cytotoxicity
  • DNA photocleavage
  • Quinoxaline

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Molecular design, chemical synthesis and biological evaluation of quinoxaline-carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents. / Toshima, Kazunobu; Kimura, Tomonori; Takano, Ryusuke; Ozawa, Tomohiro; Ariga, Akiko; Shima, Yutaka; Umezawa, Kazuo; Matsumura, Shuichi.

In: Tetrahedron, Vol. 59, No. 35, 25.08.2003, p. 7057-7066.

Research output: Contribution to journalArticle

Toshima, Kazunobu ; Kimura, Tomonori ; Takano, Ryusuke ; Ozawa, Tomohiro ; Ariga, Akiko ; Shima, Yutaka ; Umezawa, Kazuo ; Matsumura, Shuichi. / Molecular design, chemical synthesis and biological evaluation of quinoxaline-carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents. In: Tetrahedron. 2003 ; Vol. 59, No. 35. pp. 7057-7066.
@article{a6f497c5a81f4366b80c75c1b6910202,
title = "Molecular design, chemical synthesis and biological evaluation of quinoxaline-carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents",
abstract = "The quinoxaline moiety in antitumor quinoxaline antibiotics cleaved double stranded DNA at the 5′ side guanine of the 5′-GG-3′ site upon irradiation with UV light with a long wavelength and without any additive. The quinoxaline-carbohydrate hybrid system was very effective for the DNA cleavage. Furthermore, the quinoxaline-carbohydrate hybrids exhibited strong and selective cytotoxicity against cancer cells with photoirradiation.",
keywords = "Carbohydrate, Cytotoxicity, DNA photocleavage, Quinoxaline",
author = "Kazunobu Toshima and Tomonori Kimura and Ryusuke Takano and Tomohiro Ozawa and Akiko Ariga and Yutaka Shima and Kazuo Umezawa and Shuichi Matsumura",
year = "2003",
month = "8",
day = "25",
doi = "10.1016/S0040-4020(03)00820-2",
language = "English",
volume = "59",
pages = "7057--7066",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "35",

}

TY - JOUR

T1 - Molecular design, chemical synthesis and biological evaluation of quinoxaline-carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents

AU - Toshima, Kazunobu

AU - Kimura, Tomonori

AU - Takano, Ryusuke

AU - Ozawa, Tomohiro

AU - Ariga, Akiko

AU - Shima, Yutaka

AU - Umezawa, Kazuo

AU - Matsumura, Shuichi

PY - 2003/8/25

Y1 - 2003/8/25

N2 - The quinoxaline moiety in antitumor quinoxaline antibiotics cleaved double stranded DNA at the 5′ side guanine of the 5′-GG-3′ site upon irradiation with UV light with a long wavelength and without any additive. The quinoxaline-carbohydrate hybrid system was very effective for the DNA cleavage. Furthermore, the quinoxaline-carbohydrate hybrids exhibited strong and selective cytotoxicity against cancer cells with photoirradiation.

AB - The quinoxaline moiety in antitumor quinoxaline antibiotics cleaved double stranded DNA at the 5′ side guanine of the 5′-GG-3′ site upon irradiation with UV light with a long wavelength and without any additive. The quinoxaline-carbohydrate hybrid system was very effective for the DNA cleavage. Furthermore, the quinoxaline-carbohydrate hybrids exhibited strong and selective cytotoxicity against cancer cells with photoirradiation.

KW - Carbohydrate

KW - Cytotoxicity

KW - DNA photocleavage

KW - Quinoxaline

UR - http://www.scopus.com/inward/record.url?scp=0043160197&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0043160197&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(03)00820-2

DO - 10.1016/S0040-4020(03)00820-2

M3 - Article

AN - SCOPUS:0043160197

VL - 59

SP - 7057

EP - 7066

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 35

ER -