Photochemical generation and reaction of 2'-substituted analogues of C4'-oxidized abasic lesion.

Eriko Tomi, Mariko Aso, Satoshi Inoue, Yukiko Toguchi, Kazuteru Usui, Mai Hamdy Azam, Akiko Jinnouchi, Hiroshi Suemune

研究成果: ジャーナルへの寄稿会談の抜粋

抄録

The C4'-oxidized abasic site (1) is one of the oxidatively damaged DNA lesions induced by antitumor bleomycins. The reactivity of 1 with amine under neutral conditions giving lactam 2 and its structural similarity to unmodified DNA suggested the possibility that ODN containing 1 could react with proteins which interact with DNA at lysine residue. In order to provide nucleic acid analogues with useful lysine modifying reactivity, we planned to study reaction of 2'-substituted analogues of 1, such as 3-5, with amine and their corresponding caged precursors 6-8 were synthesized. Uncaging reaction of 16 containing 6 proceeded efficiently. The reaction of obtained 17 containing 3 with Z-Lys-OH did not afford products corresponding to lactam. However, HPLC analysis of the reaction mixture suggested interaction of 3 with Z-Lys-OH.

元の言語英語
ページ(範囲)185-186
ページ数2
ジャーナルNucleic acids symposium series (2004)
発行部数53
出版物ステータス出版済み - 1 1 2009

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Lactams
Amines
DNA
Bleomycin
Nucleic Acids
Lysine
High Pressure Liquid Chromatography
Proteins
DNA-lysine adduct

All Science Journal Classification (ASJC) codes

  • Medicine(all)

これを引用

Tomi, E., Aso, M., Inoue, S., Toguchi, Y., Usui, K., Azam, M. H., ... Suemune, H. (2009). Photochemical generation and reaction of 2'-substituted analogues of C4'-oxidized abasic lesion. Nucleic acids symposium series (2004), (53), 185-186.

Photochemical generation and reaction of 2'-substituted analogues of C4'-oxidized abasic lesion. / Tomi, Eriko; Aso, Mariko; Inoue, Satoshi; Toguchi, Yukiko; Usui, Kazuteru; Azam, Mai Hamdy; Jinnouchi, Akiko; Suemune, Hiroshi.

:: Nucleic acids symposium series (2004), 番号 53, 01.01.2009, p. 185-186.

研究成果: ジャーナルへの寄稿会談の抜粋

Tomi, E, Aso, M, Inoue, S, Toguchi, Y, Usui, K, Azam, MH, Jinnouchi, A & Suemune, H 2009, 'Photochemical generation and reaction of 2'-substituted analogues of C4'-oxidized abasic lesion.', Nucleic acids symposium series (2004), 番号 53, pp. 185-186.
Tomi, Eriko ; Aso, Mariko ; Inoue, Satoshi ; Toguchi, Yukiko ; Usui, Kazuteru ; Azam, Mai Hamdy ; Jinnouchi, Akiko ; Suemune, Hiroshi. / Photochemical generation and reaction of 2'-substituted analogues of C4'-oxidized abasic lesion. :: Nucleic acids symposium series (2004). 2009 ; 番号 53. pp. 185-186.
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abstract = "The C4'-oxidized abasic site (1) is one of the oxidatively damaged DNA lesions induced by antitumor bleomycins. The reactivity of 1 with amine under neutral conditions giving lactam 2 and its structural similarity to unmodified DNA suggested the possibility that ODN containing 1 could react with proteins which interact with DNA at lysine residue. In order to provide nucleic acid analogues with useful lysine modifying reactivity, we planned to study reaction of 2'-substituted analogues of 1, such as 3-5, with amine and their corresponding caged precursors 6-8 were synthesized. Uncaging reaction of 16 containing 6 proceeded efficiently. The reaction of obtained 17 containing 3 with Z-Lys-OH did not afford products corresponding to lactam. However, HPLC analysis of the reaction mixture suggested interaction of 3 with Z-Lys-OH.",
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AU - Tomi, Eriko

AU - Aso, Mariko

AU - Inoue, Satoshi

AU - Toguchi, Yukiko

AU - Usui, Kazuteru

AU - Azam, Mai Hamdy

AU - Jinnouchi, Akiko

AU - Suemune, Hiroshi

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