Curcumin Derivatives Verify the Essentiality of ROS Upregulation in Tumor Suppression
Identifieur interne : 000921 ( Main/Exploration ); précédent : 000920; suivant : 000922Curcumin Derivatives Verify the Essentiality of ROS Upregulation in Tumor Suppression
Auteurs : Ikuko Nakamae ; Tsumoru Morimoto ; Hiroki Shima ; Masafumi Shionyu ; Hisayo Fujiki ; Noriko Yoneda-Kato ; Takashi Yokoyama ; Shigehiko Kanaya ; Kiyomi Kakiuchi ; Tsuyoshi Shirai ; Edy Meiyanto ; Jun-Ya KatoSource :
- Molecules [ 1420-3049 ] ; 2019.
Abstract
Background: Curcumin has been shown to exert pleiotropic biological effects, including anti-tumorigenic activity. We previously showed that curcumin controls reactive oxygen species (ROS) levels through the ROS metabolic enzymes, to prevent tumor cell growth. In this study, we synthesized 39 novel curcumin derivatives and examined their anti-proliferative and anti-tumorigenic properties. Methods and Results: Thirty-nine derivatives exhibited anti-proliferative activity toward human cancer cell lines, including CML-derived K562 leukemic cells, in a manner sensitive to an antioxidant,
Url:
DOI: 10.3390/molecules24224067
PubMed: 31717651
PubMed Central: 6891586
Affiliations:
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<affiliation><nlm:aff id="af1-molecules-24-04067">Laboratory of Tumor Cell Biology, Division of Biological Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>ikuko-n@bs.naist.jp</email>
(I.N.);<email>noriko-k@bs.naist.jp</email>
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<author><name sortKey="Morimoto, Tsumoru" sort="Morimoto, Tsumoru" uniqKey="Morimoto T" first="Tsumoru" last="Morimoto">Tsumoru Morimoto</name>
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(T.M.);<email>shima.hiroki.sz2@ms.naist.jp</email>
(H.S.);<email>f-hisayo@ad.naist.jp</email>
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<author><name sortKey="Shima, Hiroki" sort="Shima, Hiroki" uniqKey="Shima H" first="Hiroki" last="Shima">Hiroki Shima</name>
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<author><name sortKey="Shionyu, Masafumi" sort="Shionyu, Masafumi" uniqKey="Shionyu M" first="Masafumi" last="Shionyu">Masafumi Shionyu</name>
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<author><name sortKey="Fujiki, Hisayo" sort="Fujiki, Hisayo" uniqKey="Fujiki H" first="Hisayo" last="Fujiki">Hisayo Fujiki</name>
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(T.M.);<email>shima.hiroki.sz2@ms.naist.jp</email>
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<author><name sortKey="Yoneda Kato, Noriko" sort="Yoneda Kato, Noriko" uniqKey="Yoneda Kato N" first="Noriko" last="Yoneda-Kato">Noriko Yoneda-Kato</name>
<affiliation><nlm:aff id="af1-molecules-24-04067">Laboratory of Tumor Cell Biology, Division of Biological Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>ikuko-n@bs.naist.jp</email>
(I.N.);<email>noriko-k@bs.naist.jp</email>
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<author><name sortKey="Yokoyama, Takashi" sort="Yokoyama, Takashi" uniqKey="Yokoyama T" first="Takashi" last="Yokoyama">Takashi Yokoyama</name>
<affiliation><nlm:aff id="af1-molecules-24-04067">Laboratory of Tumor Cell Biology, Division of Biological Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>ikuko-n@bs.naist.jp</email>
(I.N.);<email>noriko-k@bs.naist.jp</email>
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<author><name sortKey="Kanaya, Shigehiko" sort="Kanaya, Shigehiko" uniqKey="Kanaya S" first="Shigehiko" last="Kanaya">Shigehiko Kanaya</name>
<affiliation><nlm:aff id="af4-molecules-24-04067">Laboratory of Computational Systems Biology, Division of Information Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>skanaya@gtc.naist.jp</email>
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<author><name sortKey="Kakiuchi, Kiyomi" sort="Kakiuchi, Kiyomi" uniqKey="Kakiuchi K" first="Kiyomi" last="Kakiuchi">Kiyomi Kakiuchi</name>
<affiliation><nlm:aff id="af2-molecules-24-04067">Laboratory of Synthetic Organic Chemistry, Division of Materials Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>morimoto@ms.naist.jp</email>
(T.M.);<email>shima.hiroki.sz2@ms.naist.jp</email>
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<author><name sortKey="Shirai, Tsuyoshi" sort="Shirai, Tsuyoshi" uniqKey="Shirai T" first="Tsuyoshi" last="Shirai">Tsuyoshi Shirai</name>
<affiliation><nlm:aff id="af3-molecules-24-04067">Nagahama Institute of Bio-Science and Technology, Nagahama 526-0829, Shiga, Japan;<email>m_shionyu@nagahama-i-bio.ac.jp</email>
(M.S.);<email>t_shirai@nagahama-i-bio.ac.jp</email>
(T.S.)</nlm:aff>
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<author><name sortKey="Meiyanto, Edy" sort="Meiyanto, Edy" uniqKey="Meiyanto E" first="Edy" last="Meiyanto">Edy Meiyanto</name>
<affiliation><nlm:aff id="af5-molecules-24-04067">Cancer Chemoprevention Research Center, Faculty of Pharmacy, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia;<email>edy_meiyanto@ugm.ac.id</email>
</nlm:aff>
</affiliation>
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<author><name sortKey="Kato, Jun Ya" sort="Kato, Jun Ya" uniqKey="Kato J" first="Jun-Ya" last="Kato">Jun-Ya Kato</name>
<affiliation><nlm:aff id="af1-molecules-24-04067">Laboratory of Tumor Cell Biology, Division of Biological Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>ikuko-n@bs.naist.jp</email>
(I.N.);<email>noriko-k@bs.naist.jp</email>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Curcumin Derivatives Verify the Essentiality of ROS Upregulation in Tumor Suppression</title>
<author><name sortKey="Nakamae, Ikuko" sort="Nakamae, Ikuko" uniqKey="Nakamae I" first="Ikuko" last="Nakamae">Ikuko Nakamae</name>
<affiliation><nlm:aff id="af1-molecules-24-04067">Laboratory of Tumor Cell Biology, Division of Biological Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>ikuko-n@bs.naist.jp</email>
(I.N.);<email>noriko-k@bs.naist.jp</email>
(N.Y.-K.);<email>yokoyama-t@bs.naist.jp</email>
(T.Y.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Morimoto, Tsumoru" sort="Morimoto, Tsumoru" uniqKey="Morimoto T" first="Tsumoru" last="Morimoto">Tsumoru Morimoto</name>
<affiliation><nlm:aff id="af2-molecules-24-04067">Laboratory of Synthetic Organic Chemistry, Division of Materials Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>morimoto@ms.naist.jp</email>
(T.M.);<email>shima.hiroki.sz2@ms.naist.jp</email>
(H.S.);<email>f-hisayo@ad.naist.jp</email>
(H.F.);<email>kakiuchi@ms.naist.jp</email>
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<author><name sortKey="Shima, Hiroki" sort="Shima, Hiroki" uniqKey="Shima H" first="Hiroki" last="Shima">Hiroki Shima</name>
<affiliation><nlm:aff id="af2-molecules-24-04067">Laboratory of Synthetic Organic Chemistry, Division of Materials Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>morimoto@ms.naist.jp</email>
(T.M.);<email>shima.hiroki.sz2@ms.naist.jp</email>
(H.S.);<email>f-hisayo@ad.naist.jp</email>
(H.F.);<email>kakiuchi@ms.naist.jp</email>
(K.K.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Shionyu, Masafumi" sort="Shionyu, Masafumi" uniqKey="Shionyu M" first="Masafumi" last="Shionyu">Masafumi Shionyu</name>
<affiliation><nlm:aff id="af3-molecules-24-04067">Nagahama Institute of Bio-Science and Technology, Nagahama 526-0829, Shiga, Japan;<email>m_shionyu@nagahama-i-bio.ac.jp</email>
(M.S.);<email>t_shirai@nagahama-i-bio.ac.jp</email>
(T.S.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Fujiki, Hisayo" sort="Fujiki, Hisayo" uniqKey="Fujiki H" first="Hisayo" last="Fujiki">Hisayo Fujiki</name>
<affiliation><nlm:aff id="af2-molecules-24-04067">Laboratory of Synthetic Organic Chemistry, Division of Materials Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>morimoto@ms.naist.jp</email>
(T.M.);<email>shima.hiroki.sz2@ms.naist.jp</email>
(H.S.);<email>f-hisayo@ad.naist.jp</email>
(H.F.);<email>kakiuchi@ms.naist.jp</email>
(K.K.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Yoneda Kato, Noriko" sort="Yoneda Kato, Noriko" uniqKey="Yoneda Kato N" first="Noriko" last="Yoneda-Kato">Noriko Yoneda-Kato</name>
<affiliation><nlm:aff id="af1-molecules-24-04067">Laboratory of Tumor Cell Biology, Division of Biological Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>ikuko-n@bs.naist.jp</email>
(I.N.);<email>noriko-k@bs.naist.jp</email>
(N.Y.-K.);<email>yokoyama-t@bs.naist.jp</email>
(T.Y.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Yokoyama, Takashi" sort="Yokoyama, Takashi" uniqKey="Yokoyama T" first="Takashi" last="Yokoyama">Takashi Yokoyama</name>
<affiliation><nlm:aff id="af1-molecules-24-04067">Laboratory of Tumor Cell Biology, Division of Biological Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>ikuko-n@bs.naist.jp</email>
(I.N.);<email>noriko-k@bs.naist.jp</email>
(N.Y.-K.);<email>yokoyama-t@bs.naist.jp</email>
(T.Y.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Kanaya, Shigehiko" sort="Kanaya, Shigehiko" uniqKey="Kanaya S" first="Shigehiko" last="Kanaya">Shigehiko Kanaya</name>
<affiliation><nlm:aff id="af4-molecules-24-04067">Laboratory of Computational Systems Biology, Division of Information Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>skanaya@gtc.naist.jp</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Kakiuchi, Kiyomi" sort="Kakiuchi, Kiyomi" uniqKey="Kakiuchi K" first="Kiyomi" last="Kakiuchi">Kiyomi Kakiuchi</name>
<affiliation><nlm:aff id="af2-molecules-24-04067">Laboratory of Synthetic Organic Chemistry, Division of Materials Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>morimoto@ms.naist.jp</email>
(T.M.);<email>shima.hiroki.sz2@ms.naist.jp</email>
(H.S.);<email>f-hisayo@ad.naist.jp</email>
(H.F.);<email>kakiuchi@ms.naist.jp</email>
(K.K.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Shirai, Tsuyoshi" sort="Shirai, Tsuyoshi" uniqKey="Shirai T" first="Tsuyoshi" last="Shirai">Tsuyoshi Shirai</name>
<affiliation><nlm:aff id="af3-molecules-24-04067">Nagahama Institute of Bio-Science and Technology, Nagahama 526-0829, Shiga, Japan;<email>m_shionyu@nagahama-i-bio.ac.jp</email>
(M.S.);<email>t_shirai@nagahama-i-bio.ac.jp</email>
(T.S.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Meiyanto, Edy" sort="Meiyanto, Edy" uniqKey="Meiyanto E" first="Edy" last="Meiyanto">Edy Meiyanto</name>
<affiliation><nlm:aff id="af5-molecules-24-04067">Cancer Chemoprevention Research Center, Faculty of Pharmacy, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia;<email>edy_meiyanto@ugm.ac.id</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Kato, Jun Ya" sort="Kato, Jun Ya" uniqKey="Kato J" first="Jun-Ya" last="Kato">Jun-Ya Kato</name>
<affiliation><nlm:aff id="af1-molecules-24-04067">Laboratory of Tumor Cell Biology, Division of Biological Science, Graduate School of Science and Technology, Nara Institute of Science and Technology, Nara 630-0192, Ikoma, Japan;<email>ikuko-n@bs.naist.jp</email>
(I.N.);<email>noriko-k@bs.naist.jp</email>
(N.Y.-K.);<email>yokoyama-t@bs.naist.jp</email>
(T.Y.)</nlm:aff>
</affiliation>
</author>
</analytic>
<series><title level="j">Molecules</title>
<idno type="eISSN">1420-3049</idno>
<imprint><date when="2019">2019</date>
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<front><div type="abstract" xml:lang="en"><p>Background: Curcumin has been shown to exert pleiotropic biological effects, including anti-tumorigenic activity. We previously showed that curcumin controls reactive oxygen species (ROS) levels through the ROS metabolic enzymes, to prevent tumor cell growth. In this study, we synthesized 39 novel curcumin derivatives and examined their anti-proliferative and anti-tumorigenic properties. Methods and Results: Thirty-nine derivatives exhibited anti-proliferative activity toward human cancer cell lines, including CML-derived K562 leukemic cells, in a manner sensitive to an antioxidant, <italic>N</italic>
-acetyl-cysteine (NAC). Some compounds exhibited lower GI<sub>50</sub>
values than curcumin, some efficiently induced cell senescence, and others markedly increased ROS levels, efficiently induced cell death and suppressed tumor formation in a xenograft mouse model, without any detectable side effects. A clustering analysis of the selected compounds and their measurement variables revealed that anti-tumorigenic activity was most well-correlated with an increase in ROS levels. Pulldown assays and a molecular docking analysis showed that curcumin derivatives competed with co-enzymes to bind to the respective ROS metabolic enzymes and inhibited their enzymatic activities. Conclusions: The analysis of novel curcumin derivatives established the importance of ROS upregulation in suppression of tumorigenesis, and these compounds are potentially useful for the development of an anti-cancer drug with few side effects.</p>
</div>
</front>
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</TEI>
<affiliations><list></list>
<tree><noCountry><name sortKey="Fujiki, Hisayo" sort="Fujiki, Hisayo" uniqKey="Fujiki H" first="Hisayo" last="Fujiki">Hisayo Fujiki</name>
<name sortKey="Kakiuchi, Kiyomi" sort="Kakiuchi, Kiyomi" uniqKey="Kakiuchi K" first="Kiyomi" last="Kakiuchi">Kiyomi Kakiuchi</name>
<name sortKey="Kanaya, Shigehiko" sort="Kanaya, Shigehiko" uniqKey="Kanaya S" first="Shigehiko" last="Kanaya">Shigehiko Kanaya</name>
<name sortKey="Kato, Jun Ya" sort="Kato, Jun Ya" uniqKey="Kato J" first="Jun-Ya" last="Kato">Jun-Ya Kato</name>
<name sortKey="Meiyanto, Edy" sort="Meiyanto, Edy" uniqKey="Meiyanto E" first="Edy" last="Meiyanto">Edy Meiyanto</name>
<name sortKey="Morimoto, Tsumoru" sort="Morimoto, Tsumoru" uniqKey="Morimoto T" first="Tsumoru" last="Morimoto">Tsumoru Morimoto</name>
<name sortKey="Nakamae, Ikuko" sort="Nakamae, Ikuko" uniqKey="Nakamae I" first="Ikuko" last="Nakamae">Ikuko Nakamae</name>
<name sortKey="Shima, Hiroki" sort="Shima, Hiroki" uniqKey="Shima H" first="Hiroki" last="Shima">Hiroki Shima</name>
<name sortKey="Shionyu, Masafumi" sort="Shionyu, Masafumi" uniqKey="Shionyu M" first="Masafumi" last="Shionyu">Masafumi Shionyu</name>
<name sortKey="Shirai, Tsuyoshi" sort="Shirai, Tsuyoshi" uniqKey="Shirai T" first="Tsuyoshi" last="Shirai">Tsuyoshi Shirai</name>
<name sortKey="Yokoyama, Takashi" sort="Yokoyama, Takashi" uniqKey="Yokoyama T" first="Takashi" last="Yokoyama">Takashi Yokoyama</name>
<name sortKey="Yoneda Kato, Noriko" sort="Yoneda Kato, Noriko" uniqKey="Yoneda Kato N" first="Noriko" last="Yoneda-Kato">Noriko Yoneda-Kato</name>
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</record>
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