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

Kazunobu Toshima; Tomohiro Ozawa; Tomonori Kimura; Shuichi Matsumura

doi:10.1016/j.bmcl.2004.03.065

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

Kazunobu Toshima, Tomohiro Ozawa, Tomonori Kimura, Shuichi Matsumura

Department of Applied Chemistry

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

31 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 language	English
Pages (from-to)	2777-2779
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	14
Issue number	11
DOIs	https://doi.org/10.1016/j.bmcl.2004.03.065
Publication status	Published - 2004 Jun 7

Keywords

Carbohydrate
Cytotoxicity
DNA photocleavage
Oligosaccharide
Quinoxaline

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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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",

note = "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. ",

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AU - Toshima, Kazunobu

AU - Ozawa, Tomohiro

AU - Kimura, Tomonori

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.

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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.

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

Abstract

Keywords

ASJC Scopus subject areas

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