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Efficient synthesis and chiral separation of 11C-labeled ibuprofen assisted by DMSO for imaging of in vivo behavior of the individual isomers by positron emission tomography
https://repo.qst.go.jp/records/46097
https://repo.qst.go.jp/records/460970cbd43a6-2c47-4dbd-b447-ac3175af82c5
Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2011-06-06 | |||||
タイトル | ||||||
タイトル | Efficient synthesis and chiral separation of 11C-labeled ibuprofen assisted by DMSO for imaging of in vivo behavior of the individual isomers by positron emission tomography | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
アクセス権 | ||||||
アクセス権 | metadata only access | |||||
アクセス権URI | http://purl.org/coar/access_right/c_14cb | |||||
著者 |
Kikuchi, Tatsuya
× Kikuchi, Tatsuya× Okada, Maki× Nengaki, Nobuki× Furutsuka, Kenji× Wakizaka, Hidekatsu× Okamura, Toshimitsu× Zhang, Ming-Rong× Kato, Koichi× 菊池 達矢× 岡田 真希× 念垣 信樹× 古塚 賢士× 脇坂 秀克× 岡村 敏充× 張 明栄× 加藤 孝一 |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | The pharmacological mechanisms focusing on chiral isomer of ibuprofen are not fully understood. Only the (S)-isomer of ibuprofen inhibits cyclooxygenases, which mediates the generation of prostanoids and thromboxanes. Consequently, (S)-isomers represent a major promoter of the anti-inflammatory effect,and the effects of the (R)-isomers have not been widely discussed. However, more recently, the cyclooxygenase-independent pharmacological effects of ibuprofen have been lucidated. Pharmacokinetic studies with individual isomers of ibuprofen by positron emission tomography should aid our understanding of the pharmacological mechanisms of ibuprofen. The efficient 11C-labeling of ibuprofen for chiral separation via the TBAF-promoted a-[11C]methylation was achieved by using DMSO rather than THF as the reaction solvent. The robust production of the radiochemically labile 11C-labeled ibuprofen ester was realized by the protective effect of DMSO on radiolysis. After intravenous injection of each enantiomer of [11C]ibuprofen, significantly high radioactivity was observed in the joints of arthritis mice when compared to the levels observed in normal mice. However, the high accumulation was equivalent between the enantiomers, indicating that ibuprofen is accumulated in the arthritic joints regardless of the expression of cyclooxygenases. |
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書誌情報 |
Bioorganic & Medicinal Chemistry 巻 19, 号 10, p. 3265-3273, 発行日 2011-05 |
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ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 0968-0896 |