Preparation of Oligoselenodiglutathiones and Their Suppressive Effects on Oxidative DNA Damage Induced by Catechol and Copper
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- Ando Motozumi
- Faculty of Pharmacy, Meijo University
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- Nishida Hiroyuki
- Faculty of Pharmacy, Meijo University
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- Ueda Koji
- Faculty of Pharmacy, Meijo University
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- Itoh Kazuo
- Faculty of Pharmacy, Meijo University
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- Okamoto Yoshinori
- Faculty of Pharmacy, Meijo University
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- Kojima Nakao
- Faculty of Pharmacy, Meijo University
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We previously reported that novel polyselenodithiols are produced along with selenotrisulfide when a thiol (penicillamine) is reacted with selenite (H2SeO3). Here, we report the production of oligoselenodiglutathiones and their suppressive effects on oxidative DNA damage. Oligoselenodiglutathiones were produced by exceeding the conventional reaction ratio of [H2SeO3]/[glutathione (GSH)]=1/4. In liquid chromatography-mass spectrometry (LC/MS) analysis, the observed isotope patterns showed good agreement with the calculated isotope patterns assuming that two, three, or four selenium (Se) atoms were incorporated in the molecules. Based on 1H NMR and MS data, the structures of oligoselenodiglutathiones were assumed to have a common symmetrical structure that was centered by linearly bound Se atoms “wedged” in the disulfide bond of two GSH molecules. At 8 μM, selenodiglutathione (GSSeSG) and diselenodiglutathione (GSSe2SG) showed 80% suppression of the formation of 8-oxo-7,8-dihydroxy-2'-deoxyguanosine (in calf thymus DNA) induced by carcinogenic catechol and copper. The suppressive effects of GSSeSG and GSSe2SG were around threefold higher than that of glutathione disulfide at the same concentration, and the suppressive effect was not observed for H2SeO3 or GSH. Thus, formation of oligoselenodiglutathiones is important for Se or GSH to exert its protective effects on biomolecules from oxidative damage.
収録刊行物
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- JOURNAL OF HEALTH SCIENCE
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JOURNAL OF HEALTH SCIENCE 57 (1), 72-77, 2011
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390001204498359296
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- NII論文ID
- 130000425125
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- NII書誌ID
- AA11316464
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- ISSN
- 13475207
- 13449702
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- NDL書誌ID
- 10952026
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
- CiNii Articles
- KAKEN
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- 使用不可