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 : 000718 ( Pmc/Curation ); précédent : 000717; suivant : 000719Novel 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
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">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</title>
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<author><name sortKey="Salomatina, Oksana V" sort="Salomatina, Oksana V" uniqKey="Salomatina O" first="Oksana V." last="Salomatina">Oksana V. Salomatina</name>
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<author><name sortKey="Logashenko, Evgeniya B" sort="Logashenko, Evgeniya B" uniqKey="Logashenko E" first="Evgeniya B." last="Logashenko">Evgeniya B. Logashenko</name>
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<author><name sortKey="Salakhutdinov, Nariman F" sort="Salakhutdinov, Nariman F" uniqKey="Salakhutdinov N" first="Nariman F." last="Salakhutdinov">Nariman F. Salakhutdinov</name>
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<author><name sortKey="Zenkova, Marina A" sort="Zenkova, Marina A" uniqKey="Zenkova M" first="Marina A." last="Zenkova">Marina A. Zenkova</name>
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<series><title level="j">Molecules</title>
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<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>
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<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Molecules</journal-id>
<journal-id journal-id-type="iso-abbrev">Molecules</journal-id>
<journal-id journal-id-type="publisher-id">molecules</journal-id>
<journal-title-group><journal-title>Molecules</journal-title>
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<issn pub-type="epub">1420-3049</issn>
<publisher><publisher-name>MDPI</publisher-name>
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</journal-meta>
<article-meta><article-id pub-id-type="pmid">31330911</article-id>
<article-id pub-id-type="pmc">6681416</article-id>
<article-id pub-id-type="doi">10.3390/molecules24142644</article-id>
<article-id pub-id-type="publisher-id">molecules-24-02644</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Article</subject>
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<title-group><article-title>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</article-title>
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<xref ref-type="aff" rid="af1-molecules-24-02644">1</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Salakhutdinov</surname>
<given-names>Nariman F.</given-names>
</name>
<xref ref-type="aff" rid="af2-molecules-24-02644">2</xref>
<xref ref-type="aff" rid="af3-molecules-24-02644">3</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Zenkova</surname>
<given-names>Marina A.</given-names>
</name>
<xref ref-type="aff" rid="af1-molecules-24-02644">1</xref>
</contrib>
</contrib-group>
<aff id="af1-molecules-24-02644"><label>1</label>
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 8, 630090 Novosibirsk, Russia</aff>
<aff id="af2-molecules-24-02644"><label>2</label>
Novosibirsk State University, Pirogova str. 2, 630090 Novosibirsk, Russia</aff>
<aff id="af3-molecules-24-02644"><label>3</label>
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrent’ev ave., 9, 630090 Novosibirsk, Russia</aff>
<author-notes><corresp id="c1-molecules-24-02644"><label>*</label>
Correspondence: <email>andmrkv@gmail.com</email>
; Tel.: +7-383-363-51-61</corresp>
</author-notes>
<pub-date pub-type="epub"><day>21</day>
<month>7</month>
<year>2019</year>
</pub-date>
<pub-date pub-type="collection"><month>7</month>
<year>2019</year>
</pub-date>
<volume>24</volume>
<issue>14</issue>
<elocation-id>2644</elocation-id>
<history><date date-type="received"><day>24</day>
<month>6</month>
<year>2019</year>
</date>
<date date-type="accepted"><day>15</day>
<month>7</month>
<year>2019</year>
</date>
</history>
<permissions><copyright-statement>© 2019 by the authors.</copyright-statement>
<copyright-year>2019</copyright-year>
<license license-type="open-access"><license-p>Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (<ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/4.0/">http://creativecommons.org/licenses/by/4.0/</ext-link>
).</license-p>
</license>
</permissions>
<abstract><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>
</abstract>
<kwd-group><kwd>deoxycholic acid derivatives</kwd>
<kwd>diamines</kwd>
<kwd>aminoalcohols</kwd>
<kwd>apoptosis</kwd>
<kwd>autophagy</kwd>
<kwd>VDR</kwd>
</kwd-group>
</article-meta>
</front>
</pmc>
</record>
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