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

doi:10.1016/S0040-4020(03)00820-2

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

24 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 language	English
Pages (from-to)	7057-7066
Number of pages	10
Journal	Tetrahedron
Volume	59
Issue number	35
DOIs	https://doi.org/10.1016/S0040-4020(03)00820-2
Publication status	Published - 2003 Aug 25

Keywords

Carbohydrate
Cytotoxicity
DNA photocleavage
Quinoxaline

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/S0040-4020(03)00820-2

Cite this

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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",

note = "Funding Information: This research was partially supported by Grant-in-Aid for the 21st Century COE program {\textquoteleft}KEIO Life Conjugate Chemistry{\textquoteright} and for General Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan, and Takeda Science Foundation.",

year = "2003",

month = aug,

day = "25",

doi = "10.1016/S0040-4020(03)00820-2",

language = "English",

volume = "59",

pages = "7057--7066",

journal = "Tetrahedron",

issn = "0040-4020",

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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

N1 - Funding Information: This research was partially supported by Grant-in-Aid for the 21st Century COE program ‘KEIO Life Conjugate Chemistry’ and for General Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan, and Takeda Science Foundation.

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

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

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

M3 - Article

AN - SCOPUS:0043160197

SN - 0040-4020

VL - 59

SP - 7057

EP - 7066

JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

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