Email this article Synthesis of isotopically modified derivatives of dopamine, serotonin and doxorubicine with Boc-Pro and Boc-[2H]Pro
- Authors: Shevchenko V.P.1, Andreeva L.A.1, Nagaev I.Y.1, Myasoedov N.F.1
-
Affiliations:
- Institute of Molecular Genetics of the Russian Academy of Sciences
- Issue: Vol 485, No 2 (2019)
- Pages: 182-185
- Section: Chemistry
- URL: https://journals.eco-vector.com/0869-5652/article/view/12842
- DOI: https://doi.org/10.31857/S0869-56524852182-185
- ID: 12842
Cite item
Full Text
Abstract
The synthesis of Boc-Pro-Dox, Boc-Pro-DOPA, Boc-Pro-Srt, Pro-Dox, Pro-DOPA, and Pro-Srt, as well as Boc-[2H]Pro-Dox, Boc-[2H]Pro-DOPA, Boc-[2H]Pro-Srt and [2H]Pro-Dox, [2H]Pro-DOPA, and [2H]Pro-Srt were performed for the first time. It was established that Boc-[2H]Pro is the most promising for obtaining deuterated compounds. It was shown that hydrogenation of Boc-APro in ethyl acetate on a palladium catalyst allows 1.6-1.65 times more deuterium to be introduced than for hydrogenation of an unsaturated proline bound to serotonin and three times more than hydrogenating an unsaturated proline bound to dopamine. Due to the instability of doxorubicin under the conditions of the reduction of unsaturated proline, its condensation with Boc- [2H]Pro is the only possibility for obtaining Boc-[2H]Pro-Dox. Mass spectrometric methods determined the content of isotopomers in deuterated products.
About the authors
V. P. Shevchenko
Institute of Molecular Genetics of the Russian Academy of Sciences
Author for correspondence.
Email: nagaev@img.ras.ru
Russian Federation, Moscow
L. A. Andreeva
Institute of Molecular Genetics of the Russian Academy of Sciences
Email: nagaev@img.ras.ru
Russian Federation, Moscow
I. Yu. Nagaev
Institute of Molecular Genetics of the Russian Academy of Sciences
Email: nagaev@img.ras.ru
Russian Federation, Moscow
N. F. Myasoedov
Institute of Molecular Genetics of the Russian Academy of Sciences
Email: nagaev@img.ras.ru
academician of the RAS
Russian Federation, MoscowReferences
- Шевченко В. П., Нагаев И. Ю., Мясоедов Н. Ф. Меченные тритием липофильные соединения. М.: Наука, 2003. 246 с.
- Voges R., Heys J. R., Moenius Th. Preparation of Compounds Labeled with Tritium and Carbon-14. Chichester: Wiley, 2009. P. 664.
- Shevchenko V. P., Nagaev I.Yu., Myasoedov N. F. // J. Label. Comp. Radiopharm. 2010. V. 53. № 11/12. Р 693-703.
- Huang S., Fang R., Xu J., Qiu Sh., Zhang H., Du J., Cai Sh. // J. Drug Targeting. 2011. V. 19. № 7. Р. 487-496.
- Радченко Е. В., Карпов П. В., Соснин С. Б., Дя- бина А. С., Соснина Е. А., Палюлин В. А., Зефиров Н. С. // XX Менделеевский съезд по общей и прикладной химии. 26-30 сентября 2016 г. Екатеринбург, 2016. С. 432.
- Дябина А. С., Радченко Е. В., Палюлин В. А., Зефиров Н. С. // ДАН. 2016. Т. 470. № 6. С. 720-723.
- Гринштейн Дж., Виниц М. Химия аминокислот и пептидов. М.: Мир, 1965. 826 с.
- Гершкович А. А., Кибирев В. К. Химический синтез пептидов. Киев: Наук. думка, 1992. 360 с.
Supplementary files
