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<p>Isothio- and isoselenocyanates of the adamantane series were synthesized in 45–88% yields and were shown to inhibit the growth of the cancer cells lines HCT-116 (colorectal carcinoma), MCF-7 (breast adenocarcinoma), PC-3 (prostate adenocarcinoma), and A549 (lung carcinoma) with half-maximal inhibitory concentrations (IC<sub>50</sub>) in the range of 1.7–67 µmol L<sup>−1</sup>. The following structure—activity relationship was established: the inhibitory activity of adamantyl-containing isoselenocyanates <b>2a–f</b> against the growth of the HCT-116, MCF-7, PC-3, and A549 cancer cell lines decreases with increasing length of the spacer between the adamantane moiety and the isoselenocyanate group, showing a saw-tooth decrease in the activity. The isosteric replacement of a sulfur atom by selenium leads to an increase in the inhibitory activity. Thus, 1-isoselenocyanatoadamantane <b>2c</b> proved to be three times more active against the growth of the MCF-7 cancer cell line (IC<sub>50</sub> = 8.2 µmol L<sup>−1</sup>) compared to its sulfur-containing analog. This effect noticeably decreases with increasing length of the spacer between the adamantane moiety and the isoselenocyanate group. 1-Isocyanoadamantane <b>3c</b>, which does not contain a sulfur or selenium atom, inhibits the growth of the HCT-116 cancer cell line (IC<sub>50</sub> = 40 µmol L<sup>−1</sup>) and is not active against the MCF-7, PC-3, and A549 cancer cell lines.</p>

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Synthesis of isothio- and isoselenocyanates of adamantane series and their cytotoxic activity

  • 期刊论文

  • 发表日期：

    2025年4月1日

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  • D. A. Pitushkin,
  • D. V. Danilov,
  • Ya. P. Kuznetsov,
  • D. A. Aksenov,
  • V. N. Osipov,
  • G. M. Butov,
  • I. A. Novakov

摘要

Isothio- and isoselenocyanates of the adamantane series were synthesized in 45–88% yields and were shown to inhibit the growth of the cancer cells lines HCT-116 (colorectal carcinoma), MCF-7 (breast adenocarcinoma), PC-3 (prostate adenocarcinoma), and A549 (lung carcinoma) with half-maximal inhibitory concentrations (IC50) in the range of 1.7–67 µmol L−1. The following structure—activity relationship was established: the inhibitory activity of adamantyl-containing isoselenocyanates 2a–f against the growth of the HCT-116, MCF-7, PC-3, and A549 cancer cell lines decreases with increasing length of the spacer between the adamantane moiety and the isoselenocyanate group, showing a saw-tooth decrease in the activity. The isosteric replacement of a sulfur atom by selenium leads to an increase in the inhibitory activity. Thus, 1-isoselenocyanatoadamantane 2c proved to be three times more active against the growth of the MCF-7 cancer cell line (IC50 = 8.2 µmol L−1) compared to its sulfur-containing analog. This effect noticeably decreases with increasing length of the spacer between the adamantane moiety and the isoselenocyanate group. 1-Isocyanoadamantane 3c, which does not contain a sulfur or selenium atom, inhibits the growth of the HCT-116 cancer cell line (IC50 = 40 µmol L−1) and is not active against the MCF-7, PC-3, and A549 cancer cell lines.