V. P. Shevchenko, I. Yu. Nagaev, K. V. Shevchenko, N. F. Myasoedov
{"title":"多巴喹的氘标记","authors":"V. P. Shevchenko, I. Yu. Nagaev, K. V. Shevchenko, N. F. Myasoedov","doi":"10.1134/S1066362224060122","DOIUrl":null,"url":null,"abstract":"<p>The possibility of introducing deuterium into dopaquine, a compound consisting of quinone and dopamine fragments, was examined. The isotope exchange can be carried out with deuterated water in the presence of trifluoroacetic acid (TFA) and HCl. The best results were obtained with TFA at 80°С. To activate isotope exchange, catalysts based on iridium or palladium (5% Pd/Al<sub>2</sub>O<sub>3</sub>, cycloocta-1,5-dienyliridium(I) 1,1,1,5,5,5-hexafluoropentane-2,4-dionate) were added to the reaction mixture in addition to the acid component. The preparative synthesis of [D]dopaquine was carried out by isotope exchange with deuterated water (D<sub>2</sub>O : TFA 5 : 1, 80°С, 3 h). [D]Dopaquine was obtained in 20% yield with the deuterium content in the interval 1.2–1.4 atoms per molecule. The deuterium content in the dopamine fragment is 1.2–1.3 atoms per molecule. The quinone fragment contained approximately 4–7% of the isotope.</p>","PeriodicalId":747,"journal":{"name":"Radiochemistry","volume":"66 6","pages":"876 - 881"},"PeriodicalIF":0.9000,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Deuterium Labeling of Dopaquine\",\"authors\":\"V. P. Shevchenko, I. Yu. Nagaev, K. V. Shevchenko, N. F. Myasoedov\",\"doi\":\"10.1134/S1066362224060122\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>The possibility of introducing deuterium into dopaquine, a compound consisting of quinone and dopamine fragments, was examined. The isotope exchange can be carried out with deuterated water in the presence of trifluoroacetic acid (TFA) and HCl. The best results were obtained with TFA at 80°С. To activate isotope exchange, catalysts based on iridium or palladium (5% Pd/Al<sub>2</sub>O<sub>3</sub>, cycloocta-1,5-dienyliridium(I) 1,1,1,5,5,5-hexafluoropentane-2,4-dionate) were added to the reaction mixture in addition to the acid component. The preparative synthesis of [D]dopaquine was carried out by isotope exchange with deuterated water (D<sub>2</sub>O : TFA 5 : 1, 80°С, 3 h). [D]Dopaquine was obtained in 20% yield with the deuterium content in the interval 1.2–1.4 atoms per molecule. The deuterium content in the dopamine fragment is 1.2–1.3 atoms per molecule. The quinone fragment contained approximately 4–7% of the isotope.</p>\",\"PeriodicalId\":747,\"journal\":{\"name\":\"Radiochemistry\",\"volume\":\"66 6\",\"pages\":\"876 - 881\"},\"PeriodicalIF\":0.9000,\"publicationDate\":\"2025-02-17\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Radiochemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://link.springer.com/article/10.1134/S1066362224060122\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Radiochemistry","FirstCategoryId":"1085","ListUrlMain":"https://link.springer.com/article/10.1134/S1066362224060122","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
The possibility of introducing deuterium into dopaquine, a compound consisting of quinone and dopamine fragments, was examined. The isotope exchange can be carried out with deuterated water in the presence of trifluoroacetic acid (TFA) and HCl. The best results were obtained with TFA at 80°С. To activate isotope exchange, catalysts based on iridium or palladium (5% Pd/Al2O3, cycloocta-1,5-dienyliridium(I) 1,1,1,5,5,5-hexafluoropentane-2,4-dionate) were added to the reaction mixture in addition to the acid component. The preparative synthesis of [D]dopaquine was carried out by isotope exchange with deuterated water (D2O : TFA 5 : 1, 80°С, 3 h). [D]Dopaquine was obtained in 20% yield with the deuterium content in the interval 1.2–1.4 atoms per molecule. The deuterium content in the dopamine fragment is 1.2–1.3 atoms per molecule. The quinone fragment contained approximately 4–7% of the isotope.
期刊介绍:
Radiochemistry is a journal that covers the theoretical and applied aspects of radiochemistry, including basic nuclear physical properties of radionuclides; chemistry of radioactive elements and their compounds; the occurrence and behavior of natural and artificial radionuclides in the environment; nuclear fuel cycle; radiochemical analysis methods and devices; production and isolation of radionuclides, synthesis of labeled compounds, new applications of radioactive tracers; radiochemical aspects of nuclear medicine; radiation chemistry and after-effects of nuclear transformations.