Synthesis of novel, DNA binding heterocyclic dehydroabietylamine derivatives as potential antiproliferative and apoptosis-inducing agents
Identifieur interne : 000495 ( Pmc/Curation ); précédent : 000494; suivant : 000496Synthesis of novel, DNA binding heterocyclic dehydroabietylamine derivatives as potential antiproliferative and apoptosis-inducing agents
Auteurs : Fengyi Zhao [République populaire de Chine] ; Xu Sun [République populaire de Chine] ; Wen Lu [République populaire de Chine] ; Li Xu [République populaire de Chine] ; Jiuzhou Shi [République populaire de Chine] ; Shilong Yang [République populaire de Chine] ; Mengyi Zhou [République populaire de Chine] ; Fan Su [République populaire de Chine] ; Feng Lin [République populaire de Chine] ; Fuliang Cao [République populaire de Chine]Source :
- Drug Delivery [ 1071-7544 ] ; 2020.
Abstract
Several dehydroabietylamine derivatives containing heterocyclic moieties such as
thiophene and pyrazine ring were successfully synthesized. The antiproliferative
activities of these thiophene-based Schiff-bases, thiophene amides, and pyrazine amides
were investigated
Url:
DOI: 10.1080/10717544.2020.1716879
PubMed: 31984809
PubMed Central: 7034089
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<country xml:lang="fr">République populaire de Chine</country>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Synthesis of novel, DNA binding heterocyclic dehydroabietylamine derivatives
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<author><name sortKey="Zhao, Fengyi" sort="Zhao, Fengyi" uniqKey="Zhao F" first="Fengyi" last="Zhao">Fengyi Zhao</name>
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<country xml:lang="fr">République populaire de Chine</country>
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<country xml:lang="fr">République populaire de Chine</country>
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<author><name sortKey="Shi, Jiuzhou" sort="Shi, Jiuzhou" uniqKey="Shi J" first="Jiuzhou" last="Shi">Jiuzhou Shi</name>
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<country xml:lang="fr">République populaire de Chine</country>
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<author><name sortKey="Yang, Shilong" sort="Yang, Shilong" uniqKey="Yang S" first="Shilong" last="Yang">Shilong Yang</name>
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<author><name sortKey="Zhou, Mengyi" sort="Zhou, Mengyi" uniqKey="Zhou M" first="Mengyi" last="Zhou">Mengyi Zhou</name>
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</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
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<author><name sortKey="Su, Fan" sort="Su, Fan" uniqKey="Su F" first="Fan" last="Su">Fan Su</name>
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</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
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<author><name sortKey="Lin, Feng" sort="Lin, Feng" uniqKey="Lin F" first="Feng" last="Lin">Feng Lin</name>
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, Nanjing,<country>PR China</country>
</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
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<author><name sortKey="Cao, Fuliang" sort="Cao, Fuliang" uniqKey="Cao F" first="Fuliang" last="Cao">Fuliang Cao</name>
<affiliation wicri:level="1"><nlm:aff id="AF0001"><institution>Co-Innovation Center for Sustainable Forestry in Southern China, Nanjing Forestry University</institution>
, Nanjing,<country>PR China</country>
;</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
<affiliation wicri:level="1"><nlm:aff id="AF0002"><institution>College of Forestry, Nanjing Forestry University</institution>
, Nanjing,<country>PR China</country>
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<country xml:lang="fr">République populaire de Chine</country>
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<series><title level="j">Drug Delivery</title>
<idno type="ISSN">1071-7544</idno>
<idno type="eISSN">1521-0464</idno>
<imprint><date when="2020">2020</date>
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<front><div type="abstract" xml:lang="en"><title>Abstract</title>
<p>Several dehydroabietylamine derivatives containing heterocyclic moieties such as
thiophene and pyrazine ring were successfully synthesized. The antiproliferative
activities of these thiophene-based Schiff-bases, thiophene amides, and pyrazine amides
were investigated <italic>in vitro</italic>
against Hela (cervix), MCF-7 (breast), A549
(lung), HepG2 (liver), and HUVEC (umbilical vein) cells by MTT assay. The toxicity of
<bold>L<sup>1</sup>
</bold>
−<bold>L<sup>10</sup>
</bold>
(IC<sub>50</sub>
= 5.92− >100 μM) was lower than <bold>L<sup>0</sup>
</bold>
(1.27 μM) and DOX (4.40 μM) in every case. Compound <bold>L<sup>1</sup>
</bold>
had higher
anti-HepG2 <bold>(</bold>
0.66 μM), anti-MCF-7 (5.33 μM), and anti-A549 (2.11 μM) and
compound <bold>L<sup>3</sup>
</bold>
had higher anti-HepG2 (1.63 μM) and anti-MCF-7
(2.65 μM) activities. Both of these compounds were recognized with high efficiency in
apoptosis induction in HepG2 cells and intercalated binding modes with DNA. Moreover, with
average IC<sub>50</sub>
values of 0.66 and 5.98 μM, <bold>L<sup>1</sup>
</bold>
was nine
times more effective at suppressing cultured HepG2 cells viability than normal cells (SI =
9). The relative tumor proliferation rate (T/C) was 38.6%, the tumor inhibition rate was
up to 61.2%, which indicated that <bold>L<sup>1</sup>
</bold>
had no significant toxicity
but high anti-HepG2 activity <italic>in vivo</italic>
. Thus, it may be a potential
antiproliferation drug with nontoxic side effects.</p>
</div>
</front>
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</TEI>
<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Drug Deliv</journal-id>
<journal-id journal-id-type="iso-abbrev">Drug Deliv</journal-id>
<journal-id journal-id-type="publisher-id">IDRD</journal-id>
<journal-id journal-id-type="publisher-id">idrd20</journal-id>
<journal-title-group><journal-title>Drug Delivery</journal-title>
</journal-title-group>
<issn pub-type="ppub">1071-7544</issn>
<issn pub-type="epub">1521-0464</issn>
<publisher><publisher-name>Taylor & Francis</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">31984809</article-id>
<article-id pub-id-type="pmc">7034089</article-id>
<article-id pub-id-type="doi">10.1080/10717544.2020.1716879</article-id>
<article-id pub-id-type="publisher-id">1716879</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Research Article</subject>
</subj-group>
</article-categories>
<title-group><article-title>Synthesis of novel, DNA binding heterocyclic dehydroabietylamine derivatives
as potential antiproliferative and apoptosis-inducing agents</article-title>
<alt-title alt-title-type="running-authors">F. Zhao et al.</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Zhao</surname>
<given-names>Fengyi</given-names>
</name>
<xref ref-type="aff" rid="AF0001"><sup>a</sup>
</xref>
<xref ref-type="aff" rid="AF0002"><sup>b</sup>
</xref>
<xref ref-type="aff" rid="AF0003"><sup>c</sup>
</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Sun</surname>
<given-names>Xu</given-names>
</name>
<xref ref-type="aff" rid="AF0003"><sup>c</sup>
</xref>
<xref ref-type="aff" rid="AF0004"><sup>d</sup>
</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Lu</surname>
<given-names>Wen</given-names>
</name>
<xref ref-type="aff" rid="AF0003"><sup>c</sup>
</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Xu</surname>
<given-names>Li</given-names>
</name>
<xref ref-type="aff" rid="AF0001"><sup>a</sup>
</xref>
<xref ref-type="aff" rid="AF0003"><sup>c</sup>
</xref>
<xref ref-type="corresp" rid="AN0001"></xref>
</contrib>
<contrib contrib-type="author"><name><surname>Shi</surname>
<given-names>Jiuzhou</given-names>
</name>
<xref ref-type="aff" rid="AF0003"><sup>c</sup>
</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Yang</surname>
<given-names>Shilong</given-names>
</name>
<xref ref-type="aff" rid="AF0005"><sup>e</sup>
</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Zhou</surname>
<given-names>Mengyi</given-names>
</name>
<xref ref-type="aff" rid="AF0005"><sup>e</sup>
</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Su</surname>
<given-names>Fan</given-names>
</name>
<xref ref-type="aff" rid="AF0005"><sup>e</sup>
</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Lin</surname>
<given-names>Feng</given-names>
</name>
<xref ref-type="aff" rid="AF0005"><sup>e</sup>
</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Cao</surname>
<given-names>Fuliang</given-names>
</name>
<xref ref-type="aff" rid="AF0001"><sup>a</sup>
</xref>
<xref ref-type="aff" rid="AF0002"><sup>b</sup>
</xref>
</contrib>
<aff id="AF0001"><label>a</label>
<institution>Co-Innovation Center for Sustainable Forestry in Southern China, Nanjing Forestry University</institution>
, Nanjing,<country>PR China</country>
;</aff>
<aff id="AF0002"><label>b</label>
<institution>College of Forestry, Nanjing Forestry University</institution>
, Nanjing,<country>PR China</country>
;</aff>
<aff id="AF0003"><label>c</label>
<institution>College of Science, Nanjing Forestry University</institution>
, Nanjing,<country>PR China</country>
;</aff>
<aff id="AF0004"><label>d</label>
<institution>College of Information Science and Technology, Nanjing Forestry University</institution>
, Nanjing,<country>PR China</country>
;</aff>
<aff id="AF0005"><label>e</label>
<institution>Advanced Analysis and Testing Center, Nanjing Forestry University</institution>
, Nanjing,<country>PR China</country>
</aff>
</contrib-group>
<author-notes><fn id="AUFN1"><p>Supplemental data for this article can be accessed <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1080/10717544.2020.1716879"><underline>here</underline>
</ext-link>
.</p>
</fn>
<corresp id="AN0001">CONTACT Li Xu <email>2016qlsz@njfu.edu.cn</email>
<institution>Co-Innovation Center for Sustainable Forestry in Southern China, Nanjing
Forestry University</institution>
, Nanjing, 210037, <country>PR
China</country>
</corresp>
</author-notes>
<pub-date pub-type="collection"><year>2020</year>
</pub-date>
<pub-date pub-type="epub"><day>27</day>
<month>1</month>
<year>2020</year>
</pub-date>
<volume>27</volume>
<issue>1</issue>
<fpage seq="19">216</fpage>
<lpage>227</lpage>
<history><date date-type="received"><day>27</day>
<month>11</month>
<year>2019</year>
</date>
<date date-type="rev-recd"><day>05</day>
<month>1</month>
<year>2020</year>
</date>
<date date-type="accepted"><day>13</day>
<month>1</month>
<year>2020</year>
</date>
</history>
<permissions><copyright-statement>© 2020 The Author(s). Published by Informa UK Limited, trading as
Taylor & Francis Group.</copyright-statement>
<copyright-year>2020</copyright-year>
<copyright-holder>The Author(s)</copyright-holder>
<license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/4.0/"><license-p>This is an Open Access article distributed under the terms of the Creative
Commons Attribution 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>
), which permits unrestricted
use, distribution, and reproduction in any medium, provided the original work is
properly cited.</license-p>
</license>
</permissions>
<self-uri content-type="pdf" xlink:href="IDRD_27_1716879.pdf"></self-uri>
<abstract><title>Abstract</title>
<p>Several dehydroabietylamine derivatives containing heterocyclic moieties such as
thiophene and pyrazine ring were successfully synthesized. The antiproliferative
activities of these thiophene-based Schiff-bases, thiophene amides, and pyrazine amides
were investigated <italic>in vitro</italic>
against Hela (cervix), MCF-7 (breast), A549
(lung), HepG2 (liver), and HUVEC (umbilical vein) cells by MTT assay. The toxicity of
<bold>L<sup>1</sup>
</bold>
−<bold>L<sup>10</sup>
</bold>
(IC<sub>50</sub>
= 5.92− >100 μM) was lower than <bold>L<sup>0</sup>
</bold>
(1.27 μM) and DOX (4.40 μM) in every case. Compound <bold>L<sup>1</sup>
</bold>
had higher
anti-HepG2 <bold>(</bold>
0.66 μM), anti-MCF-7 (5.33 μM), and anti-A549 (2.11 μM) and
compound <bold>L<sup>3</sup>
</bold>
had higher anti-HepG2 (1.63 μM) and anti-MCF-7
(2.65 μM) activities. Both of these compounds were recognized with high efficiency in
apoptosis induction in HepG2 cells and intercalated binding modes with DNA. Moreover, with
average IC<sub>50</sub>
values of 0.66 and 5.98 μM, <bold>L<sup>1</sup>
</bold>
was nine
times more effective at suppressing cultured HepG2 cells viability than normal cells (SI =
9). The relative tumor proliferation rate (T/C) was 38.6%, the tumor inhibition rate was
up to 61.2%, which indicated that <bold>L<sup>1</sup>
</bold>
had no significant toxicity
but high anti-HepG2 activity <italic>in vivo</italic>
. Thus, it may be a potential
antiproliferation drug with nontoxic side effects.</p>
</abstract>
<kwd-group kwd-group-type="author"><title>Keywords</title>
<kwd>Dehydroabietylamine derivatives</kwd>
<kwd>antiproliferative</kwd>
<kwd>lower toxicity</kwd>
<kwd>apoptosis</kwd>
</kwd-group>
<funding-group><award-group><funding-source><named-content content-type="funder-name">National Key Research and Development Program
of China</named-content>
<named-content content-type="funderidentifier">10.13039/501100002852</named-content>
</funding-source>
<award-id>706</award-id>
</award-group>
<award-group><funding-source><named-content content-type="funder-name">Sate Key Laboratory for Chemistry and
Molecular Engineering of Medicinal Resources (Guangxi Normal
University)</named-content>
</funding-source>
<award-id>-B06</award-id>
</award-group>
<funding-statement>This work was supported by the National Key Research and Development
Program of China [grant number 2017YFD0600706] and Sate Key Laboratory for Chemistry and
Molecular Engineering of Medicinal Resources (Guangxi Normal University) [grant number
CMEMR2017-B06].</funding-statement>
</funding-group>
<counts><fig-count count="7"></fig-count>
<table-count count="4"></table-count>
<page-count count="12"></page-count>
<word-count count="8137"></word-count>
</counts>
</article-meta>
</front>
</pmc>
</record>
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