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

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 inhibito...

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Главные авторы:	Aksenov, D. A., Аксенов, Д. А.
Формат:	Статья
Язык:	Russian
Опубликовано:	Springer 2025
Темы:	1-isocyanoadamantane Adamantane derivatives Cytotoxic activity Isoselenocyanates Isothiocyanates of adamantane series Oncology
Online-ссылка:	https://dspace.ncfu.ru/handle/123456789/30516
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id	ir-123456789-30516
record_format	dspace
spelling	ir-123456789-305162025-06-18T09:32:48Z Synthesis of isothio- and isoselenocyanates of adamantane series and their cytotoxic activity Aksenov, D. A. Аксенов, Д. А. 1-isocyanoadamantane Adamantane derivatives Cytotoxic activity Isoselenocyanates Isothiocyanates of adamantane series Oncology 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. 2025-06-18T09:31:48Z 2025-06-18T09:31:48Z 2025 Статья Pitushkin D.A., Danilov D.V., Kuznetsov Y.P., Aksenov D.A., Osipov V.N., Butov G.M., Novakov I.A. Synthesis of isothio- and isoselenocyanates of adamantane series and their cytotoxic activity // Russian Chemical Bulletin. - 2025. - 74 (4). - pp. 1169 - 1176. - DOI: 10.1007/s11172-025-4610-x https://dspace.ncfu.ru/handle/123456789/30516 ru Russian Chemical Bulletin application/pdf application/pdf Springer
institution	СКФУ
collection	Репозиторий
language	Russian
topic	1-isocyanoadamantane Adamantane derivatives Cytotoxic activity Isoselenocyanates Isothiocyanates of adamantane series Oncology
spellingShingle	1-isocyanoadamantane Adamantane derivatives Cytotoxic activity Isoselenocyanates Isothiocyanates of adamantane series Oncology Aksenov, D. A. Аксенов, Д. А. Synthesis of isothio- and isoselenocyanates of adamantane series and their cytotoxic activity
description	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.
format	Статья
author	Aksenov, D. A. Аксенов, Д. А.
author_facet	Aksenov, D. A. Аксенов, Д. А.
author_sort	Aksenov, D. A.
title	Synthesis of isothio- and isoselenocyanates of adamantane series and their cytotoxic activity
title_short	Synthesis of isothio- and isoselenocyanates of adamantane series and their cytotoxic activity
title_full	Synthesis of isothio- and isoselenocyanates of adamantane series and their cytotoxic activity
title_fullStr	Synthesis of isothio- and isoselenocyanates of adamantane series and their cytotoxic activity
title_full_unstemmed	Synthesis of isothio- and isoselenocyanates of adamantane series and their cytotoxic activity
title_sort	synthesis of isothio- and isoselenocyanates of adamantane series and their cytotoxic activity
publisher	Springer
publishDate	2025
url	https://dspace.ncfu.ru/handle/123456789/30516
work_keys_str_mv	AT aksenovda synthesisofisothioandisoselenocyanatesofadamantaneseriesandtheircytotoxicactivity AT aksenovda synthesisofisothioandisoselenocyanatesofadamantaneseriesandtheircytotoxicactivity
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Synthesis of isothio- and isoselenocyanates of adamantane series and their cytotoxic activity

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