{"created":"2023-05-15T14:53:01.042794+00:00","id":72334,"links":{},"metadata":{"_buckets":{"deposit":"f90cd77b-c4f9-44d2-ad71-b5d65c02de1b"},"_deposit":{"created_by":1,"id":"72334","owners":[1],"pid":{"revision_id":0,"type":"depid","value":"72334"},"status":"published"},"_oai":{"id":"oai:repo.qst.go.jp:00072334","sets":["10:28"]},"author_link":["712405","712408","712417","712414","712416","712410","712411","712406","712403","712412","712407","712409","712404","712415","712413","712418"],"item_10005_date_7":{"attribute_name":"発表年月日","attribute_value_mlt":[{"subitem_date_issued_datetime":"2017-05-15","subitem_date_issued_type":"Issued"}]},"item_10005_description_5":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"Objectives: 18F-Fluoroalkylation is a useful method for introduction of fluorine-18 into molecules containing NH, OH, and SH-groups, analogously to the 11C-methylation with [11C]CH3I. Moreover, introduction of [18F]fluoroalkyl group could sometimes lead to significant improvement of in vitro properties and in vivo behaviors. We have developed a 18F-fluoroalkylation route with [18F]FMeOTf, [18F]FEtBr or [18F]FPrBr etc., which could be purified by simple distillation using an automated synthesis system [1]. Furthermore, we have routinely produced clinically useful 18F-ligands, such as [18F]FMeNER-d2, [18F]FEDAC and [18F]FEtPE2I by using of these agents. To further extend application of this technique, here, we developed a simple method for introducing 3-[18F]fluoro-2-hydroxypropyl group into phenol precursors with [18F]epifluorohydrin ([18F]2) and applied the method to synthesize 18F-labeled ligands.\nMethods: Glycidyl tosylate 1 was synthesized by reaction of glycidol and tosyl chloride with K2CO3. Unlabeled 3 and 4 were prepared by reaction of corresponding phenol derivatives and 2 in the presence of base. [18F]3 and [18F]4 was synthesized by reacting with phenol precursors with [18F]2 using a homemade automated synthesis system.\nResults: We used 4-phenylphenol as a model substrate. After 18F-fluorination of 1 (10 L) with [18F]fluoride ion in 1,2-dichlorobenzene at 130 oC, [18F]2 (b.p. 85-86 oC) was formed and then purified by distillation into a DMF solution containing desmethyl precursor (1 mg) and NaOH for 2 min. The radiochemical yield of [18F]2 was estimated to be 80% (based on the [18F]fluoride ion, corrected for decay). After the trapping, this reaction mixture was heated at 130 oC for 20 min. By purification for the reaction mixture using semi-preparative HPLC, [18F]3 was obtained with a synthesis time of 68 min. As application of this reagent for development of 18F-labeled ligand, [18F]4 as a new TSPO ligand was synthesized by reaction of the corresponding precursor with [18F]2. After HPLC purification and formulation, [18F]4 was obtained with 5% radiochemical yield (isolated-yield).\nConclusion: We have successfully developed a convenient and reliable technique for producing [18F]2 using a home-made automated synthesis system. This reagent has been used to introduce 3-[18F]fluoro-2-hydroxypropyl group into PET ligand candidates, such as [18F]4.  This novel PET ligand is now available for evaluation in mice or rat and improvement for the radiochemical yield is on progress.\nAcknowledgements:\nReferences: [1] Zhang M-R, et al, Curr Top Med Chem., 2007, 7(18), 1817-1828.","subitem_description_type":"Abstract"}]},"item_10005_description_6":{"attribute_name":"会議概要（会議名, 開催地, 会期, 主催者等）","attribute_value_mlt":[{"subitem_description":"22nd International symposium on radiopharmaceutical science (ISRS)","subitem_description_type":"Other"}]},"item_access_right":{"attribute_name":"アクセス権","attribute_value_mlt":[{"subitem_access_right":"metadata only access","subitem_access_right_uri":"http://purl.org/coar/access_right/c_14cb"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Fujinaga, Masayuki"}],"nameIdentifiers":[{"nameIdentifier":"712403","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Ohkubo, Takayuki"}],"nameIdentifiers":[{"nameIdentifier":"712404","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Yamasaki, Tomoteru"}],"nameIdentifiers":[{"nameIdentifier":"712405","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Zhang, Yiding"}],"nameIdentifiers":[{"nameIdentifier":"712406","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Hatori, Akiko"}],"nameIdentifiers":[{"nameIdentifier":"712407","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Kumata, Katsushi"}],"nameIdentifiers":[{"nameIdentifier":"712408","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Nengaki, Nobuki"}],"nameIdentifiers":[{"nameIdentifier":"712409","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Zhang, Ming-Rong"}],"nameIdentifiers":[{"nameIdentifier":"712410","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"藤永 雅之","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"712411","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"大久保 崇之","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"712412","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"山崎 友照","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"712413","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"張 一鼎","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"712414","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"羽鳥 晶子","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"712415","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"熊田 勝志","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"712416","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"念垣 信樹","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"712417","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"張 明栄","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"712418","nameIdentifierScheme":"WEKO"}]}]},"item_language":{"attribute_name":"言語","attribute_value_mlt":[{"subitem_language":"eng"}]},"item_resource_type":{"attribute_name":"資源タイプ","attribute_value_mlt":[{"resourcetype":"conference object","resourceuri":"http://purl.org/coar/resource_type/c_c94f"}]},"item_title":"Simple method for introduction of 3-[18F]fluoro-2-hydroxypropyl group and application for synthesis of 18F-labeled ligand","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"Simple method for introduction of 3-[18F]fluoro-2-hydroxypropyl group and application for synthesis of 18F-labeled ligand"}]},"item_type_id":"10005","owner":"1","path":["28"],"pubdate":{"attribute_name":"公開日","attribute_value":"2017-05-24"},"publish_date":"2017-05-24","publish_status":"0","recid":"72334","relation_version_is_last":true,"title":["Simple method for introduction of 3-[18F]fluoro-2-hydroxypropyl group and application for synthesis of 18F-labeled ligand"],"weko_creator_id":"1","weko_shared_id":-1},"updated":"2023-05-15T19:41:03.902669+00:00"}