2-fluorocordycepin: chemoenzymatic synthesis and study of anticancer activities in vitro
- Authors: Arnautova A.O.1,2, Antonov K.V.1, Zorina E.A.1, Simonova М.A.1, Paramonov A.S.1, Zhukova О.S.3, Kiselevskiy M.V.3, Kayushin А.L.1, Fateev I.V.1, Dorofeeva Е.V.1, Eletskaya B.Z.1, Berzina М.Y.1, Smirnova О.S.1, Egorova Т.V.4, Esipov R.S.1, Miroshnikov А.I.1, Konstantinova I.D.1
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Affiliations:
- Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
- Engelhardt Institute of Molecular Biology RAS
- N.N. Blokhin National Medical Research Center of Oncology
- Moscow Pedagogical State University
- Issue: Vol 51, No 3 (2025)
- Pages: 469-485
- Section: ОБЗОРНАЯ СТАТЬЯ
- URL: https://journals.eco-vector.com/0132-3423/article/view/686992
- DOI: https://doi.org/10.31857/S0132342325030105
- EDN: https://elibrary.ru/KQZBWD
- ID: 686992
Cite item
Abstract
Two methods for obtaining 2-fluorocordycepin were proposed and implemented: chemical synthesis from 2-fluoroadenosine with a yield of 34% and chemical-enzymatic synthesis with a yield of 66%, including the production of 3-deoxyerythropentofuranose-1-phosphate and subsequent transglycosylation using E. coli purine nucleoside phosphorylase. The cytotoxic activity of 2-fluorocordycepin in vitro was assessed. It was shown that 2-fluorocordycepin exhibits an anti-metabolic effect on a number of tumor cell lines (Jurkat, Raji, MCF-7, THP-1, U937, A549, LS174T), which allows us to consider this compound as a promising candidate for the development of antitumor drugs.
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About the authors
A. O. Arnautova
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Engelhardt Institute of Molecular Biology RAS
Author for correspondence.
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Vavilova 32, Moscow, 119991
K. V. Antonov
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
E. A. Zorina
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
М. A. Simonova
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
A. S. Paramonov
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
О. S. Zhukova
N.N. Blokhin National Medical Research Center of Oncology
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Kosigina 4/1, Moscow, 119334
M. V. Kiselevskiy
N.N. Blokhin National Medical Research Center of Oncology
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Kosigina 4/1, Moscow, 119334
А. L. Kayushin
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
I. V. Fateev
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
Е. V. Dorofeeva
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
B. Z. Eletskaya
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
М. Ya. Berzina
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
О. S. Smirnova
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
Т. V. Egorova
Moscow Pedagogical State University
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Malaya Pirogovskaya 1/1, Moscow, 119991
R. S. Esipov
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
А. I. Miroshnikov
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
I. D. Konstantinova
Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS
Email: arnautova_ibch@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
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