Novel Derivatives of Deoxycholic Acid Bearing Linear Aliphatic Diamine and Aminoalcohol Moieties and their Cyclic Analogs at the C3 Position: Synthesis and Evaluation of Their In Vitro Antitumor Potential
Identifieur interne : 000582 ( Main/Exploration ); précédent : 000581; suivant : 000583Novel Derivatives of Deoxycholic Acid Bearing Linear Aliphatic Diamine and Aminoalcohol Moieties and their Cyclic Analogs at the C3 Position: Synthesis and Evaluation of Their In Vitro Antitumor Potential
Auteurs : Andrey V. Markov [Russie] ; Valeriya O. Babich [Russie] ; Irina I. Popadyuk [Russie] ; Oksana V. Salomatina [Russie] ; Evgeniya B. Logashenko [Russie] ; Nariman F. Salakhutdinov [Russie] ; Marina A. Zenkova [Russie]Source :
- Molecules [ 1420-3049 ] ; 2019.
Abstract
A series of novel deoxycholic acid (DCA) derivatives containing aliphatic diamine and aminoalcohol or morpholine moieties at the C3 position were synthesized by 3,26-epoxide ring-opening reactions. These compounds were investigated for their cytotoxicity in four human tumor cell lines and murine macrophages and for inhibitory activity against macrophage-mediated NO synthesis in vitro. Obtained data revealed that: (i) all amine-containing substituents significantly increased the cytotoxicity of the novel compounds (IC50
Url:
DOI: 10.3390/molecules24142644
PubMed: 31330911
PubMed Central: 6681416
Affiliations:
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Markov</name><affiliation wicri:level="1"><nlm:aff id="af1-molecules-24-02644">Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk, Russia</nlm:aff><country xml:lang="fr">Russie</country><wicri:regionArea>Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk</wicri:regionArea><wicri:noRegion>630090 Novosibirsk</wicri:noRegion></affiliation></author><author><name sortKey="Babich, Valeriya O" sort="Babich, Valeriya O" uniqKey="Babich V" first="Valeriya O." last="Babich">Valeriya O. 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Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 9, 630090 Novosibirsk</wicri:regionArea><wicri:noRegion>630090 Novosibirsk</wicri:noRegion></affiliation></author><author><name sortKey="Zenkova, Marina A" sort="Zenkova, Marina A" uniqKey="Zenkova M" first="Marina A." last="Zenkova">Marina A. 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Markov</name><affiliation wicri:level="1"><nlm:aff id="af1-molecules-24-02644">Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk, Russia</nlm:aff><country xml:lang="fr">Russie</country><wicri:regionArea>Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk</wicri:regionArea><wicri:noRegion>630090 Novosibirsk</wicri:noRegion></affiliation></author><author><name sortKey="Babich, Valeriya O" sort="Babich, Valeriya O" uniqKey="Babich V" first="Valeriya O." last="Babich">Valeriya O. Babich</name><affiliation wicri:level="1"><nlm:aff id="af1-molecules-24-02644">Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk, Russia</nlm:aff><country xml:lang="fr">Russie</country><wicri:regionArea>Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk</wicri:regionArea><wicri:noRegion>630090 Novosibirsk</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:aff id="af2-molecules-24-02644">Novosibirsk State University, Pirogova str. 2, 630090 Novosibirsk, Russia</nlm:aff><country xml:lang="fr">Russie</country><wicri:regionArea>Novosibirsk State University, Pirogova str. 2, 630090 Novosibirsk</wicri:regionArea><wicri:noRegion>630090 Novosibirsk</wicri:noRegion></affiliation></author><author><name sortKey="Popadyuk, Irina I" sort="Popadyuk, Irina I" uniqKey="Popadyuk I" first="Irina I." last="Popadyuk">Irina I. Popadyuk</name><affiliation wicri:level="1"><nlm:aff id="af3-molecules-24-02644">N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 9, 630090 Novosibirsk, Russia</nlm:aff><country xml:lang="fr">Russie</country><wicri:regionArea>N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 9, 630090 Novosibirsk</wicri:regionArea><wicri:noRegion>630090 Novosibirsk</wicri:noRegion></affiliation></author><author><name sortKey="Salomatina, Oksana V" sort="Salomatina, Oksana V" uniqKey="Salomatina O" first="Oksana V." last="Salomatina">Oksana V. Salomatina</name><affiliation wicri:level="1"><nlm:aff id="af1-molecules-24-02644">Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk, Russia</nlm:aff><country xml:lang="fr">Russie</country><wicri:regionArea>Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk</wicri:regionArea><wicri:noRegion>630090 Novosibirsk</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:aff id="af3-molecules-24-02644">N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 9, 630090 Novosibirsk, Russia</nlm:aff><country xml:lang="fr">Russie</country><wicri:regionArea>N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 9, 630090 Novosibirsk</wicri:regionArea><wicri:noRegion>630090 Novosibirsk</wicri:noRegion></affiliation></author><author><name sortKey="Logashenko, Evgeniya B" sort="Logashenko, Evgeniya B" uniqKey="Logashenko E" first="Evgeniya B." last="Logashenko">Evgeniya B. Logashenko</name><affiliation wicri:level="1"><nlm:aff id="af1-molecules-24-02644">Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk, Russia</nlm:aff><country xml:lang="fr">Russie</country><wicri:regionArea>Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk</wicri:regionArea><wicri:noRegion>630090 Novosibirsk</wicri:noRegion></affiliation></author><author><name sortKey="Salakhutdinov, Nariman F" sort="Salakhutdinov, Nariman F" uniqKey="Salakhutdinov N" first="Nariman F." last="Salakhutdinov">Nariman F. Salakhutdinov</name><affiliation wicri:level="1"><nlm:aff id="af2-molecules-24-02644">Novosibirsk State University, Pirogova str. 2, 630090 Novosibirsk, Russia</nlm:aff><country xml:lang="fr">Russie</country><wicri:regionArea>Novosibirsk State University, Pirogova str. 2, 630090 Novosibirsk</wicri:regionArea><wicri:noRegion>630090 Novosibirsk</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:aff id="af3-molecules-24-02644">N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 9, 630090 Novosibirsk, Russia</nlm:aff><country xml:lang="fr">Russie</country><wicri:regionArea>N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 9, 630090 Novosibirsk</wicri:regionArea><wicri:noRegion>630090 Novosibirsk</wicri:noRegion></affiliation></author><author><name sortKey="Zenkova, Marina A" sort="Zenkova, Marina A" uniqKey="Zenkova M" first="Marina A." last="Zenkova">Marina A. Zenkova</name><affiliation wicri:level="1"><nlm:aff id="af1-molecules-24-02644">Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk, Russia</nlm:aff><country xml:lang="fr">Russie</country><wicri:regionArea>Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk</wicri:regionArea><wicri:noRegion>630090 Novosibirsk</wicri:noRegion></affiliation></author></analytic><series><title level="j">Molecules</title><idno type="eISSN">1420-3049</idno><imprint><date when="2019">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>A series of novel deoxycholic acid (DCA) derivatives containing aliphatic diamine and aminoalcohol or morpholine moieties at the C3 position were synthesized by 3,26-epoxide ring-opening reactions. These compounds were investigated for their cytotoxicity in four human tumor cell lines and murine macrophages and for inhibitory activity against macrophage-mediated NO synthesis in vitro. Obtained data revealed that: (i) all amine-containing substituents significantly increased the cytotoxicity of the novel compounds (IC<sub>50</sub><bold><sup>2–10</sup></bold> = 1.0–36.0 μM) in comparison with DCA (IC<sub>50</sub><bold><sup>DCA</sup></bold> ≥ 82.9 μM); (ii) aminoalcohol moieties were more preferable than diamine moieties due to the fact they imparted better selectivity for tumor cells of the novel derivatives; (iii) the susceptibility of tested cell lines to derivatives diminished in the following order: HuTu-80 (duodenal carcinoma) ≈ HepG2 (hepatocarcinoma) > KB-3-1 (cervical carcinoma) > RAW264.7 (macrophages) > A549 (lung carcinoma); (iv) compounds <bold>8</bold> and <bold>9</bold>, bearing aminoethanol and aminopropanol moieties, respectively, exhibited high cytotoxic selectivity indexes (SI<sup>HuTu-80</sup> = 7.9 and 8.3, respectively) and good drug-likeness parameters; (v) the novel compounds do not display anti-NO activity. Mechanistic study revealed that compound <bold>9</bold> induces ROS-dependent cell death by activation of intrinsic caspase-dependent apoptosis and cytodestructive autophagy in HuTu-80 cells and vitamin D receptor can be considered as its primary target.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Hofmann, A F" uniqKey="Hofmann A">A.F. Hofmann</name></author><author><name sortKey="Hagey, L R" uniqKey="Hagey L">L.R. Hagey</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Arlia Ciommo, A" uniqKey="Arlia Ciommo A">A. Arlia-Ciommo</name></author><author><name sortKey="Piano, A" uniqKey="Piano A">A. Piano</name></author><author><name sortKey="Svistkova, V" uniqKey="Svistkova V">V. Svistkova</name></author><author><name sortKey="Mohtashami, S" uniqKey="Mohtashami S">S. Mohtashami</name></author><author><name sortKey="Titorenko, V I" uniqKey="Titorenko V">V.I. 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Popadyuk</name><name sortKey="Salakhutdinov, Nariman F" sort="Salakhutdinov, Nariman F" uniqKey="Salakhutdinov N" first="Nariman F." last="Salakhutdinov">Nariman F. Salakhutdinov</name><name sortKey="Salakhutdinov, Nariman F" sort="Salakhutdinov, Nariman F" uniqKey="Salakhutdinov N" first="Nariman F." last="Salakhutdinov">Nariman F. Salakhutdinov</name><name sortKey="Salomatina, Oksana V" sort="Salomatina, Oksana V" uniqKey="Salomatina O" first="Oksana V." last="Salomatina">Oksana V. Salomatina</name><name sortKey="Salomatina, Oksana V" sort="Salomatina, Oksana V" uniqKey="Salomatina O" first="Oksana V." last="Salomatina">Oksana V. Salomatina</name><name sortKey="Zenkova, Marina A" sort="Zenkova, Marina A" uniqKey="Zenkova M" first="Marina A." last="Zenkova">Marina A. Zenkova</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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