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題名 | 鎝環丁基丙烯胺肟非鏡像立體異構物合成路徑與影響因子之探討=Study on the Synthetical Routes and Influence Factors of Tc(V)O-cyclobutyl Propyl Amine Oxine Diastereoisomers |
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作者姓名(中文) | 蔡長書; | 書刊名 | 慈濟技術學院學報 |
卷期 | 16 2011.03[民100.03] |
頁次 | 頁417-429 |
分類號 | 414.93 |
關鍵詞 | 核醫藥物; 鎝-99錯合物; 非鏡像立體異構物; 鎝核構形; 取代途徑; 還原途徑; Technetium-99-complexes; Diastereoisomers; TcO-core configulation; Reduction route; Substitution route; |
語文 | 中文(Chinese) |
中文摘要 | 本研究以六甲基丙烯胺肟(propyl amine oxine)之6,6-環丁基取代基之鎝-99 氧錯合物,探討放射性鎝核醫藥物(radiopharmaceuticals)配位子不同丙烯胺肟衍生物之非鏡 像立體異構物之配位子合成路徑及其立體化學品質。首先利用有機合成法製備環丁基丙烯胺肟系列衍生物(propyl amine oxine derivatives)非鏡像立體異構物,並以多次分步再結晶法作有效分離d,l-型、meso-型及非晶成份之立體異構物,另以熱分析法之微差掃瞄卡計(DSC)進行熔點之測定。在鎝錯合物製備方面,以取代途徑、還原途徑兩種不同合成路徑(synthetical route)評估鎝核醫藥物不同環丁基丙烯胺肟衍生物配位子非鏡像立體異構物之相關品質與影響因子。評估因素包含合成產率、立體化學純度、鎝錯合反應及鎝核構形等。由實驗結果可知,以取代途徑(substitution route)合成路徑法合成99 TcO-d,1-CB-PAO 與99 TcO-meso-CB-PAO 兩者產率約為0 %(n=10)與傳統鎝核醫藥物或丙烯胺肟相關製備法大異其趣,推測原因可能與鎝核的構形及分子大小與形狀,及其立體化學結構有關,尤其CB-PAO 配位子在有機溶劑中顯現其高脂溶性,而較不具離子性質,故無法利用傳統離子交換方式形式有效進行鎝錯合反應。以還原途徑(reduction route)合成路徑法合成99 TcO-d,1-CB-PAO 與99 TcO-meso-CB-PAO 兩者產率分別為30~40 %及60~80 %(n=10)。以不同立體異構物樣品0.5~3.0 mg 進行熱分析法之微差掃瞄卡計測定結果得知,經純化之d,1-CB-PAO 熔點約為116.7±1℃,而由純度推估,約含3~5 % meso-CB-PAO 不純物;經純化之meso-CB-PAO 熔點約為159.7±1℃。經1H-NMR 及13C-NMR 鑑定,99TcO-d,1-CB-PAO 與99 TcO-meso-CB-PAO 兩者皆具有高立體化學純度。 |
英文摘要 | Propylene amine oxine oxo-technetium(V) complexes [Tc(V)O-cyclobutyl propylene amine oxine ;Tc(V)O-CB-PAO] were prepared and their characteristic properties of synthetic routes and influence factors were studied thoroughly. The CB-PAO diastereoisomers were synthesized and separated by recrystallization. The melting points of ligands were measured by DSC. Synthesis of 99Tc(V)O-CB-PAO through reduction route were compared with that of substitution route. The influence factors of Tc(V)O-cyclobutyl propyl amine oxine diastereoisomers were also evaluated by chemical yield, stereochemical purity, Tc-complexes reaction and TcO-core configulations. All compounds obtained in this study were examined by EA, FAB-MASS spectrometry, NMR spectroscopy to insure the qualities. Both 99Tc(V)O-d,l-CB-PAO and 99Tc(V)O-meso-CB-PAO are high stereochemical purities by 1H-NMR and 13C-NMR spectroscopy. They are also electrically neutral, and highly lipophilic. The chemical yieldis about 60~80 % for meso-form TcO-CB-PAO,and 30~40 % for d,l-form TcO-CB-PAO. However, it must be pointed out that the chemical yields for both TcO-CB-PAO complexes are ca. 0 % by substitution routes. The reasons may be related with some influence factors including TcO-core configulation, Tc-complexes size and their stereochemical structures. Expecially, the properties of CB-PAO ligands are more lipophilic, it may be difficult to form Tc-complexes through the ion-exchange reaction as conventional preparation. |
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