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Abstract <p><b>Objective:</b> The aim of this study was to develop an efficient method for the preparation of 2-fluorocordycepin and to evaluate its anticancer activity <i>in vitro</i>. <b>Methods:</b> An approach to chemical synthesis of 2-fluorocordycepin was developed. The conditions of chemoenzymatic synthesis of this compound were optimized. <b>Results and Discussion:</b> 2-Fluorocordycepin was prepared chemically using α-acetoxyisobutyryl bromide in three steps with 34% yield and by enzymatic method using <i>E. coli</i> purine nucleoside phosphorylase and 1-alpha phosphate of 3-deoxyribose with 66% yield. The latter compound was synthesized in eight steps: the protected isopropylidene derivative of 3-deoxyribose was obtained in four steps, followed by an attempt at direct “one pot” phosphorylation. <b>Conclusions:</b> Two methods of 2-fluorocordycepin preparation were proposed and implemented: chemical synthesis from 2-fluoradenosine and chemoenzymatic synthesis, including preparation of 3-deoxyerythropentofuranoso-1-phosphate, followed by transglycosylation using <i>E. coli</i> purine nucleoside phosphorylase. The cytotoxic activity of 2-fluorocordycepin <i>in vitro</i> was evaluated. It was shown that 2-fluorocordycepin exhibits antimetabolic effect against a number of cancer 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 anticancer drugs.</p>

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2-Fluorocordycepin: Chemoenzymatic Synthesis and Study of Anticancer Activities In Vitro

  • 期刊论文

  • 发表日期：

    2025年6月3日

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  • A. O. Arnautova,
  • K. V. Antonov,
  • E. A. Zorina,
  • M. A. Simonova,
  • A. S. Paramonov,
  • O. S. Zhukova,
  • M. V. Kiselevskiy,
  • A. L. Kayushin,
  • I. V. Fateev,
  • E. V. Dorofeeva,
  • B. Z. Eletskaya,
  • M. Ya. Berzina,
  • O. S. Smirnova,
  • T. V. Egorova,
  • R. S. Esipov,
  • A. I. Miroshnikov,
  • I. D. Konstantinova

摘要

Abstract

Objective: The aim of this study was to develop an efficient method for the preparation of 2-fluorocordycepin and to evaluate its anticancer activity in vitro. Methods: An approach to chemical synthesis of 2-fluorocordycepin was developed. The conditions of chemoenzymatic synthesis of this compound were optimized. Results and Discussion: 2-Fluorocordycepin was prepared chemically using α-acetoxyisobutyryl bromide in three steps with 34% yield and by enzymatic method using E. coli purine nucleoside phosphorylase and 1-alpha phosphate of 3-deoxyribose with 66% yield. The latter compound was synthesized in eight steps: the protected isopropylidene derivative of 3-deoxyribose was obtained in four steps, followed by an attempt at direct “one pot” phosphorylation. Conclusions: Two methods of 2-fluorocordycepin preparation were proposed and implemented: chemical synthesis from 2-fluoradenosine and chemoenzymatic synthesis, including preparation of 3-deoxyerythropentofuranoso-1-phosphate, followed by transglycosylation using E. coli purine nucleoside phosphorylase. The cytotoxic activity of 2-fluorocordycepin in vitro was evaluated. It was shown that 2-fluorocordycepin exhibits antimetabolic effect against a number of cancer 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 anticancer drugs.