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

応用化学科

研究成果: Article › 査読

30 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	2777-2779
ページ数	3
ジャーナル	Bioorganic and Medicinal Chemistry Letters
巻	14
号	11
DOI	https://doi.org/10.1016/j.bmcl.2004.03.065
出版ステータス	Published - 2004 6月 7

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ASJC Scopus subject areas

生化学
分子医療
分子生物学
薬科学
創薬
臨床生化学
有機化学

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10.1016/j.bmcl.2004.03.065

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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 - Ozawa, Tomohiro

AU - Kimura, Tomonori

AU - Matsumura, Shuichi

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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.

KW - Carbohydrate

KW - Cytotoxicity

KW - DNA photocleavage

KW - Oligosaccharide

KW - Quinoxaline

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

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UN SDG

ASJC Scopus subject areas

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