Deuterium labeling of dopaquine

V. P. Shevchenko; Шевченко В. П.; I. Yu. Nagaev; Нагаев И. Ю.; K. V. Shevchenko; Шевченко К. В.; N. F. Myasoedov; Мясоедов Н. Ф.

doi:10.31857/S0033831124060101

Deuterium labeling of dopaquine

Авторлар: Shevchenko V.P.¹, Nagaev I.Y.¹, Shevchenko K.V.¹, Myasoedov N.F.¹
Мекемелер:
1. National Research Centre Kurchatov Institute
Шығарылым: Том 66, № 6 (2024)
Беттер: 589-595
Бөлім: Articles
URL: https://gynecology.orscience.ru/0033-8311/article/view/681273
DOI: https://doi.org/10.31857/S0033831124060101
ID: 681273

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Аннотация

The possibility of introducing deuterium into dopaquine, a compound consisting of quinone and dopamine fragments, has been studied. It has been established that isotope exchange can be carried out with deuterated water in the presence of trifluoroacetic acid (TFA) and HCl. Optimal conditions are the use of TFA at a temperature of 80°С. To activate isotope exchange, catalysts based on iridium or palladium (5%Pd/Al₂O₃, cycloocta-1,5-dienylyridium(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 of 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.

Негізгі сөздер

deuterium, dopaquine, isotope exchange

Толық мәтін

Авторлар туралы

V. Shevchenko

National Research Centre Kurchatov Institute

Email: nagaev.img@yandex.ru
Ресей, Moscow

I. Nagaev

National Research Centre Kurchatov Institute

Хат алмасуға жауапты Автор.
Email: nagaev.img@yandex.ru
Ресей, Moscow

K. Shevchenko

National Research Centre Kurchatov Institute

Email: nagaev.img@yandex.ru
Ресей, Moscow

N. Myasoedov

National Research Centre Kurchatov Institute

Email: nagaev.img@yandex.ru
Ресей, Moscow

Әдебиет тізімі

Гюнтер Х. Введение в курс спектроскопии ЯМР. М.: Мир, 1984. 478 с.
Pajak M., Kanska M. // J. Label. Compd. Radiopharm. 2006. Vol. 49. N 12. P. 1061–1067. https://doi.org/10.1002/jlcr.1123
Kozlowska M., Kanski R., Kanska M. // J. Label. Compd. Radiopharm. 2005. Vol. 48. N 3. P. 235–240. https://doi.org/10.1002/jlcr.919
Gerdes G., Chen P. // Organometallics. 2004. Vol. 23. N 12. P. 3031–3036. https://doi.org/10.1021/om030685m
Ziatdinov V.R., Oxgaard J., Mironov O.A., Young K.J.H., Goddard W.A., Periana R.A. // J. Am. Chem. Soc. 2006. Vol. 128. N 23. P. 7404–7405. https://doi.org/10.1021/ja060973k
Lockley W.J.S. // J. Label. Compd. Radiopharm. 2010. Vol. 53. N 11–12. P. 668–673. https://doi.org/10.1002/jlcr.1806
Kingston L.P., Lockley W.J.S., Mather A.N., Spink E., Thompson S.P., Wilkinson D.J. // Tetrahedron Lett. 2000. Vol. 41. N 15. P. 2705–2708. https://doi.org/10.1016/S0040-4039(00)00244-6
Di Giuseppe A., Castarlenas R., Perez-Torrente J.J., Lahoz F.J., Polo V., Oro L.A. // Angew. Chem. Int. Ed. 2011. Vol. 50. N 17. P. 3938–3942. https://doi.org/10.1002/anie.201007238
Di Giuseppe A., Castarlenas R., Perez-Torrente J.J., Lahoz F.J., Oro L.A. // Chem. Eur. J. 2014. Vol. 20. N 27. P. 8391–8403. https://doi.org/10.1002/chem.201402499
Evchenko S.V., Kamounah F.S., Schaumburg K. // J. Label. Compd. Radiopharm. 2005. Vol. 48. N 3. P. 209–218. https://doi.org/10.1002/jlcr.916
Куликова О.И., Стволинский С.Л., Федорова Т.Н., Адаева О.И., Демчук Д.В., Семенов В.В. Патент RU 2814111. Опубл. 22.02.2024 // Б.И. 2024. № 6.
Shevchenko V.P., Nagaev I.Yu., Myasoedov N.F. // Radiochemistry. 2024. Vol. 66. N 3. P. 372–376. https://doi.org/10.1134/S1066362224030111

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Жүктеу

2. Fig. 1. Isotopomeric composition of dopaquine depending on temperature (a, b, d), D2O : TFA ratio (a, c) and reaction time (b, d, f). a – 70°C, 3 h, D2O : TFA 5 : 1; b – 80°C, 3 h, D2O : TFA 5 : 1; c – 70°C, 3 h, D2O : TFA 1 : 1; d – 90°C, 3 h, D2O : TFA 5 : 1; d – 80°C, 0.5 h, D2O : TFA 5 : 1; f – 80°C, 1 h, D2O : TFA 5 : 1.

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3. Fig. 2. Isotopomer spectrum upon introduction of deuterium into dopaquine (80°C, D2O : TFA 5 : 1): a – without catalyst; b – in the presence of CODIrF6Acac; c – in the presence of 5% Pd/Al2O3–Al2O3.

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4. Fig. 3. Analysis of the reaction mixture on a Milichrom A-02 chromatograph (the first peak indicated is the retention time of dopamine, the second is dopaquine).