Linked Life Data

21503302

Source:http://linkedlifedata.com/resource/pubmed/id/21503302

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pubmed-article:21503302pubmed:dateCreated2011-5-19lld:pubmed
pubmed-article:21503302pubmed:abstractTextPd(0)-mediated rapid couplings of CH(3)I (and then [(11)C]CH(3)I) with excess 5-tributylstannyl-2'-deoxyuridine and -4'-thio-2'-deoxyuridine were investigated for the syntheses of [methyl-(11)C]thymidine and its stable analogue, 4'-[methyl-(11)C]thiothymidine as PET probes for cancer diagnosis. The previously reported conditions were attempted using Pd(2)(dba)(3)/P(o-CH(3)C(6)H(4))(3) (1?:?4 in molar ratio) at 130 °C for 5 min in DMF, giving desired products only in 32 and 30% yields. Therefore, we adapted the current reaction conditions developed in our laboratory for heteroaromatic compounds. The reaction using CH(3)I/stannane/Pd(2)(dba)(3)/P(o-CH(3)C(6)H(4))(3)/CuCl/K(2)CO(3) (1?:?25?:?1?:?32?:?2?:?5) at 80 °C gave thymidine in 85% yield. Whereas, CH(3)I/stannane/Pd(2)(dba)(3)/P(o-CH(3)C(6)H(4))(3)/CuBr/CsF (1?:?25?:?1?:?32?:?2?:?5) including another CuBr/CsF system promoted the reaction at a milder temperature (60 °C), giving thymidine in 100% yield. Chemo-response of thiothymidine-precursor was different from thymidine system. Thus, the above optimized conditions including CuBr/CsF system gave 4'-thiothymidine only in 40% yield. The reaction using 5-fold amount of CuBr/CsF at 80 °C gave much higher yield (83%), but unexpectedly, the reaction was accompanied by a considerable amount of undesired destannylated product. Such destannylation was greatly suppressed by changing to a CuCl/K(2)CO(3) system using CH(3)I/stannane/Pd(2)(dba)(3)/P(o-CH(3)C(6)H(4))(3)/CuCl/K(2)CO(3) (1?:?25?:?1?:?32?:?2?:?5) at 80 °C, giving the 4'-thiothymidine in 98% yield. The each optimized conditions were successfully applied to the syntheses of the corresponding PET probes in 87 and 93% HPLC analytical yields. [(11)C]Compounds were isolated by preparative HPLC after the reaction conducted under slightly improved conditions, exhibiting sufficient radioactivity of 3.7-3.8 GBq and specific radioactivity of 89-200 GBq µmol(-1) with radiochemical purity of ?99.5% for animal and human PET studies.lld:pubmed
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pubmed-article:21503302pubmed:authorpubmed-author:SuzukiMasaaki...lld:pubmed
pubmed-article:21503302pubmed:authorpubmed-author:Siqinlld:pubmed
pubmed-article:21503302pubmed:authorpubmed-author:DoiHisashiHlld:pubmed
pubmed-article:21503302pubmed:authorpubmed-author:SumiKengoKlld:pubmed
pubmed-article:21503302pubmed:authorpubmed-author:ZhangZhouenZlld:pubmed
pubmed-article:21503302pubmed:authorpubmed-author:KoyamaHirokoHlld:pubmed
pubmed-article:21503302pubmed:authorpubmed-author:NagataHirokoHlld:pubmed
pubmed-article:21503302pubmed:authorpubmed-author:HattaYumaYlld:pubmed
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pubmed-article:21503302pubmed:year2011lld:pubmed
pubmed-article:21503302pubmed:articleTitleHighly efficient syntheses of [methyl-11C]thymidine and its analogue 4'-[methyl-11C]thiothymidine as nucleoside PET probes for cancer cell proliferation by Pd(0)-mediated rapid C-[11C]methylation.lld:pubmed
pubmed-article:21503302pubmed:affiliationDivision of Regeneration and Advanced Medical Science, Gifu University Graduate School of Medicine, Yanagido 1-1, Gifu, 501-1193, Japan.lld:pubmed
pubmed-article:21503302pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:21503302pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed