In Vitro Cytotoxicity of Oleanolic/Ursolic Acids-Loaded in PLGA Nanoparticles in Different Cell Lines
Identifieur interne : 000792 ( Pmc/Curation ); précédent : 000791; suivant : 000793In Vitro Cytotoxicity of Oleanolic/Ursolic Acids-Loaded in PLGA Nanoparticles in Different Cell Lines
Auteurs : Amélia M. Silva [Portugal] ; Helen L. Alvarado [Portugal, Espagne] ; Guadalupe Abrego [Portugal, Salvador] ; Carlos Martins-Gomes [Portugal] ; Maria L. Gardu O-Ramirez [Mexique] ; María L. García [Espagne] ; Ana C. Calpena [Espagne] ; Eliana B. Souto [Portugal]Source :
- Pharmaceutics [ 1999-4923 ] ; 2019.
Abstract
Oleanolic (OA) and ursolic (UA) acids are recognized triterpenoids with anti-cancer properties, showing cell-specific activity that can be enhanced when loaded into polymeric nanoparticles. The cytotoxic activity of OA and UA was assessed by Alamar Blue assay in three different cell lines, i.e., HepG2 (Human hepatoma cell line), Caco-2 (Human epithelial colorectal adenocarcinoma cell line) and Y-79 (Human retinoblastoma cell line). The natural and synthetic mixtures of these compounds were tested as free and loaded in polymeric nanoparticles in a concentration range from 2 to 32 µmol/L. The highest tested concentrations of the free triterpene mixtures produced statistically significant cell viability reduction in HepG2 and Caco-2 cells, compared to the control (untreated cells). When loaded in the developed PLGA nanoparticles, no differences were recorded for the tested concentrations in the same cell lines. However, in the Y-79 cell line, a decrease on cell viability was observed when testing the lowest concentration of both free triterpene mixtures, and after their loading into PLGA nanoparticles.
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DOI: 10.3390/pharmaceutics11080362
PubMed: 31344882
PubMed Central: 6723971
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Silva</name><affiliation wicri:level="1"><nlm:aff id="af1-pharmaceutics-11-00362">Centre for Research and Technology of Agro-Environmental and Biological Sciences (CITAB), University of Trás-os Montes e Alto Douro (UTAD), Quinta de Prados, 5001-801 Vila Real, Portugal</nlm:aff><country xml:lang="fr">Portugal</country><wicri:regionArea>Centre for Research and Technology of Agro-Environmental and Biological Sciences (CITAB), University of Trás-os Montes e Alto Douro (UTAD), Quinta de Prados, 5001-801 Vila Real</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="af2-pharmaceutics-11-00362">Department of Biology and Environment, UTAD, Quinta de Prados, 5001-801 Vila Real, Portugal</nlm:aff><country xml:lang="fr">Portugal</country><wicri:regionArea>Department of Biology and Environment, UTAD, Quinta de Prados, 5001-801 Vila Real</wicri:regionArea></affiliation></author><author><name sortKey="Alvarado, Helen L" sort="Alvarado, Helen L" uniqKey="Alvarado H" first="Helen L." last="Alvarado">Helen L. Alvarado</name><affiliation wicri:level="1"><nlm:aff id="af2-pharmaceutics-11-00362">Department of Biology and Environment, UTAD, Quinta de Prados, 5001-801 Vila Real, Portugal</nlm:aff><country xml:lang="fr">Portugal</country><wicri:regionArea>Department of Biology and Environment, UTAD, Quinta de Prados, 5001-801 Vila Real</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="af3-pharmaceutics-11-00362">Department of Pharmacy and Pharmaceutical Technology and Physical Chemistry, Faculty of Pharmacy, University of Barcelona, Ave. Joan XXIII s/n, 08028 Barcelona, Spain</nlm:aff><country xml:lang="fr">Espagne</country><wicri:regionArea>Department of Pharmacy and Pharmaceutical Technology and Physical Chemistry, Faculty of Pharmacy, University of Barcelona, Ave. Joan XXIII s/n, 08028 Barcelona</wicri:regionArea></affiliation></author><author><name sortKey="Abrego, Guadalupe" sort="Abrego, Guadalupe" uniqKey="Abrego G" first="Guadalupe" last="Abrego">Guadalupe Abrego</name><affiliation wicri:level="1"><nlm:aff id="af2-pharmaceutics-11-00362">Department of Biology and Environment, UTAD, Quinta de Prados, 5001-801 Vila Real, Portugal</nlm:aff><country xml:lang="fr">Portugal</country><wicri:regionArea>Department of Biology and Environment, UTAD, Quinta de Prados, 5001-801 Vila Real</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="af4-pharmaceutics-11-00362">Department of Chemical and Instrumental Analysis, Faculty of Chemistry and Pharmacy, University of El Salvador, Final 25 Ave. Norte, 3026 San Salvador, El Salvador</nlm:aff><country xml:lang="fr">Salvador</country><wicri:regionArea>Department of Chemical and Instrumental Analysis, Faculty of Chemistry and Pharmacy, University of El Salvador, Final 25 Ave. Norte, 3026 San Salvador</wicri:regionArea></affiliation></author><author><name sortKey="Martins Gomes, Carlos" sort="Martins Gomes, Carlos" uniqKey="Martins Gomes C" first="Carlos" last="Martins-Gomes">Carlos Martins-Gomes</name><affiliation wicri:level="1"><nlm:aff id="af1-pharmaceutics-11-00362">Centre for Research and Technology of Agro-Environmental and Biological Sciences (CITAB), University of Trás-os Montes e Alto Douro (UTAD), Quinta de Prados, 5001-801 Vila Real, Portugal</nlm:aff><country xml:lang="fr">Portugal</country><wicri:regionArea>Centre for Research and Technology of Agro-Environmental and Biological Sciences (CITAB), University of Trás-os Montes e Alto Douro (UTAD), Quinta de Prados, 5001-801 Vila Real</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="af2-pharmaceutics-11-00362">Department of Biology and Environment, UTAD, Quinta de Prados, 5001-801 Vila Real, Portugal</nlm:aff><country xml:lang="fr">Portugal</country><wicri:regionArea>Department of Biology and Environment, UTAD, Quinta de Prados, 5001-801 Vila Real</wicri:regionArea></affiliation></author><author><name sortKey="Gardu O Ramirez, Maria L" sort="Gardu O Ramirez, Maria L" uniqKey="Gardu O Ramirez M" first="Maria L." last="Gardu O-Ramirez">Maria L. Gardu O-Ramirez</name><affiliation wicri:level="1"><nlm:aff id="af5-pharmaceutics-11-00362">Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad No. 1001, Col Chamilpa, 62209 Cuernavaca, Mexico</nlm:aff><country xml:lang="fr">Mexique</country><wicri:regionArea>Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad No. 1001, Col Chamilpa, 62209 Cuernavaca</wicri:regionArea></affiliation></author><author><name sortKey="Garcia, Maria L" sort="Garcia, Maria L" uniqKey="Garcia M" first="María L." last="García">María L. García</name><affiliation wicri:level="1"><nlm:aff id="af3-pharmaceutics-11-00362">Department of Pharmacy and Pharmaceutical Technology and Physical Chemistry, Faculty of Pharmacy, University of Barcelona, Ave. Joan XXIII s/n, 08028 Barcelona, Spain</nlm:aff><country xml:lang="fr">Espagne</country><wicri:regionArea>Department of Pharmacy and Pharmaceutical Technology and Physical Chemistry, Faculty of Pharmacy, University of Barcelona, Ave. Joan XXIII s/n, 08028 Barcelona</wicri:regionArea></affiliation></author><author><name sortKey="Calpena, Ana C" sort="Calpena, Ana C" uniqKey="Calpena A" first="Ana C." last="Calpena">Ana C. Calpena</name><affiliation wicri:level="1"><nlm:aff id="af3-pharmaceutics-11-00362">Department of Pharmacy and Pharmaceutical Technology and Physical Chemistry, Faculty of Pharmacy, University of Barcelona, Ave. Joan XXIII s/n, 08028 Barcelona, Spain</nlm:aff><country xml:lang="fr">Espagne</country><wicri:regionArea>Department of Pharmacy and Pharmaceutical Technology and Physical Chemistry, Faculty of Pharmacy, University of Barcelona, Ave. Joan XXIII s/n, 08028 Barcelona</wicri:regionArea></affiliation></author><author><name sortKey="Souto, Eliana B" sort="Souto, Eliana B" uniqKey="Souto E" first="Eliana B." last="Souto">Eliana B. Souto</name><affiliation wicri:level="1"><nlm:aff id="af6-pharmaceutics-11-00362">Department of Pharmaceutical Technology, Faculty of Pharmacy, University of Coimbra (FFUC), Pólo das Ciências da Saúde, 3000-548 Coimbra, Portugal</nlm:aff><country xml:lang="fr">Portugal</country><wicri:regionArea>Department of Pharmaceutical Technology, Faculty of Pharmacy, University of Coimbra (FFUC), Pólo das Ciências da Saúde, 3000-548 Coimbra</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="af7-pharmaceutics-11-00362">CEB—Centre of Biological Engineering, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal</nlm:aff><country xml:lang="fr">Portugal</country><wicri:regionArea>CEB—Centre of Biological Engineering, University of Minho, Campus de Gualtar, 4710-057 Braga</wicri:regionArea></affiliation></author></analytic><series><title level="j">Pharmaceutics</title><idno type="eISSN">1999-4923</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>Oleanolic (OA) and ursolic (UA) acids are recognized triterpenoids with anti-cancer properties, showing cell-specific activity that can be enhanced when loaded into polymeric nanoparticles. The cytotoxic activity of OA and UA was assessed by Alamar Blue assay in three different cell lines, i.e., HepG2 (Human hepatoma cell line), Caco-2 (Human epithelial colorectal adenocarcinoma cell line) and Y-79 (Human retinoblastoma cell line). The natural and synthetic mixtures of these compounds were tested as free and loaded in polymeric nanoparticles in a concentration range from 2 to 32 µmol/L. The highest tested concentrations of the free triterpene mixtures produced statistically significant cell viability reduction in HepG2 and Caco-2 cells, compared to the control (untreated cells). When loaded in the developed PLGA nanoparticles, no differences were recorded for the tested concentrations in the same cell lines. However, in the Y-79 cell line, a decrease on cell viability was observed when testing the lowest concentration of both free triterpene mixtures, and after their loading into PLGA nanoparticles. </p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Jesus, J A" uniqKey="Jesus J">J.A. Jesus</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Valdes, K" uniqKey="Valdes K">K. Valdes</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Wo Niak, L" uniqKey="Wo Niak L">Ł. Woźniak</name></author><author><name sortKey="Sk Pska, S" uniqKey="Sk Pska S">S. Skąpska</name></author><author><name sortKey="Marszalek, K" uniqKey="Marszalek K">K. Marszałek</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Martins Gomes, C" uniqKey="Martins Gomes C">C. 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<front><journal-meta><journal-id journal-id-type="nlm-ta">Pharmaceutics</journal-id><journal-id journal-id-type="iso-abbrev">Pharmaceutics</journal-id><journal-id journal-id-type="publisher-id">pharmaceutics</journal-id><journal-title-group><journal-title>Pharmaceutics</journal-title></journal-title-group><issn pub-type="epub">1999-4923</issn><publisher><publisher-name>MDPI</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">31344882</article-id><article-id pub-id-type="pmc">6723971</article-id><article-id pub-id-type="doi">10.3390/pharmaceutics11080362</article-id><article-id pub-id-type="publisher-id">pharmaceutics-11-00362</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>In Vitro Cytotoxicity of Oleanolic/Ursolic Acids-Loaded in PLGA Nanoparticles in Different Cell Lines</article-title></title-group><contrib-group><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-7524-9914</contrib-id><name><surname>Silva</surname><given-names>Amélia M.</given-names></name><xref ref-type="aff" rid="af1-pharmaceutics-11-00362">1</xref><xref ref-type="aff" rid="af2-pharmaceutics-11-00362">2</xref><xref rid="c1-pharmaceutics-11-00362" ref-type="corresp">*</xref></contrib><contrib contrib-type="author"><name><surname>Alvarado</surname><given-names>Helen L.</given-names></name><xref ref-type="aff" rid="af2-pharmaceutics-11-00362">2</xref><xref ref-type="aff" rid="af3-pharmaceutics-11-00362">3</xref></contrib><contrib contrib-type="author"><name><surname>Abrego</surname><given-names>Guadalupe</given-names></name><xref ref-type="aff" rid="af2-pharmaceutics-11-00362">2</xref><xref ref-type="aff" rid="af4-pharmaceutics-11-00362">4</xref></contrib><contrib contrib-type="author"><name><surname>Martins-Gomes</surname><given-names>Carlos</given-names></name><xref ref-type="aff" rid="af1-pharmaceutics-11-00362">1</xref><xref ref-type="aff" rid="af2-pharmaceutics-11-00362">2</xref></contrib><contrib contrib-type="author"><name><surname>Garduño-Ramirez</surname><given-names>Maria L.</given-names></name><xref ref-type="aff" rid="af5-pharmaceutics-11-00362">5</xref></contrib><contrib contrib-type="author"><name><surname>García</surname><given-names>María L.</given-names></name><xref ref-type="aff" rid="af3-pharmaceutics-11-00362">3</xref></contrib><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-4989-4821</contrib-id><name><surname>Calpena</surname><given-names>Ana C.</given-names></name><xref ref-type="aff" rid="af3-pharmaceutics-11-00362">3</xref></contrib><contrib contrib-type="author"><name><surname>Souto</surname><given-names>Eliana B.</given-names></name><xref ref-type="aff" rid="af6-pharmaceutics-11-00362">6</xref><xref ref-type="aff" rid="af7-pharmaceutics-11-00362">7</xref><xref rid="c1-pharmaceutics-11-00362" ref-type="corresp">*</xref></contrib></contrib-group><aff id="af1-pharmaceutics-11-00362"><label>1</label>Centre for Research and Technology of Agro-Environmental and Biological Sciences (CITAB), University of Trás-os Montes e Alto Douro (UTAD), Quinta de Prados, 5001-801 Vila Real, Portugal</aff><aff id="af2-pharmaceutics-11-00362"><label>2</label>Department of Biology and Environment, UTAD, Quinta de Prados, 5001-801 Vila Real, Portugal</aff><aff id="af3-pharmaceutics-11-00362"><label>3</label>Department of Pharmacy and Pharmaceutical Technology and Physical Chemistry, Faculty of Pharmacy, University of Barcelona, Ave. Joan XXIII s/n, 08028 Barcelona, Spain</aff><aff id="af4-pharmaceutics-11-00362"><label>4</label>Department of Chemical and Instrumental Analysis, Faculty of Chemistry and Pharmacy, University of El Salvador, Final 25 Ave. Norte, 3026 San Salvador, El Salvador</aff><aff id="af5-pharmaceutics-11-00362"><label>5</label>Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad No. 1001, Col Chamilpa, 62209 Cuernavaca, Mexico</aff><aff id="af6-pharmaceutics-11-00362"><label>6</label>Department of Pharmaceutical Technology, Faculty of Pharmacy, University of Coimbra (FFUC), Pólo das Ciências da Saúde, 3000-548 Coimbra, Portugal</aff><aff id="af7-pharmaceutics-11-00362"><label>7</label>CEB—Centre of Biological Engineering, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal</aff><author-notes><corresp id="c1-pharmaceutics-11-00362"><label>*</label>Correspondence: <email>amsilva@utad.pt</email> (A.M.S.); <email>ebsouto@ebsouto.pt</email> (E.B.S.); Tel.: +351-259-350-106 (A.M.S.); +351-239-488-400 (E.B.S.)</corresp></author-notes><pub-date pub-type="epub"><day>24</day><month>7</month><year>2019</year></pub-date><pub-date pub-type="collection"><month>8</month><year>2019</year></pub-date><volume>11</volume><issue>8</issue><elocation-id>362</elocation-id><history><date date-type="received"><day>10</day><month>6</month><year>2019</year></date><date date-type="accepted"><day>22</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>Oleanolic (OA) and ursolic (UA) acids are recognized triterpenoids with anti-cancer properties, showing cell-specific activity that can be enhanced when loaded into polymeric nanoparticles. The cytotoxic activity of OA and UA was assessed by Alamar Blue assay in three different cell lines, i.e., HepG2 (Human hepatoma cell line), Caco-2 (Human epithelial colorectal adenocarcinoma cell line) and Y-79 (Human retinoblastoma cell line). The natural and synthetic mixtures of these compounds were tested as free and loaded in polymeric nanoparticles in a concentration range from 2 to 32 µmol/L. The highest tested concentrations of the free triterpene mixtures produced statistically significant cell viability reduction in HepG2 and Caco-2 cells, compared to the control (untreated cells). When loaded in the developed PLGA nanoparticles, no differences were recorded for the tested concentrations in the same cell lines. However, in the Y-79 cell line, a decrease on cell viability was observed when testing the lowest concentration of both free triterpene mixtures, and after their loading into PLGA nanoparticles. </p></abstract><kwd-group><kwd>oleanolic acid</kwd><kwd>ursolic acid</kwd><kwd>cytotoxicity</kwd><kwd>PLGA</kwd><kwd>polymeric nanoparticles</kwd><kwd>retinoblastoma cell line</kwd></kwd-group></article-meta></front><floats-group><fig id="pharmaceutics-11-00362-f001" orientation="portrait" position="float"><label>Figure 1</label><caption><p>The chemical structure of ursolic acid (UA) and oleanolic acid (OA).</p></caption><graphic xlink:href="pharmaceutics-11-00362-g001"></graphic></fig><fig id="pharmaceutics-11-00362-f002" orientation="portrait" position="float"><label>Figure 2</label><caption><p>The effect of OA/UA on HepG2 (human hepatoma) cells viability. HepG2 cells were exposed to the natural mixture of oleanolic and ursolic acids (NM-OA/UA) (<bold>A</bold>), NM-OA/UA nanoparticles (NPs) (<bold>B</bold>), the synthetic mixture of oleanolic acid and ursolic acids (SM-OA/UA) (<bold>C</bold>), SM-OA/UA NPs (<bold>D</bold>), for 24 and 48 h, as denoted. Statistically significant differences, <italic>p</italic> < 0.05, are denoted with * or **, in relation to respective control at 24 or 48 h, respectively; # denotes statistical differences for incubation periods at indicated concentration. The results are the mean ± S.D. of <italic>n</italic> = 4.</p></caption><graphic xlink:href="pharmaceutics-11-00362-g002"></graphic></fig><fig id="pharmaceutics-11-00362-f003" orientation="portrait" position="float"><label>Figure 3</label><caption><p>The effect of OA/UA on Caco-2 (human epithelial colorectal adenocarcinoma) cells viability. Caco-2 cells were exposed to NM-OA/UA (<bold>A</bold>), NM-OA/UA NPs (<bold>B</bold>), SM-OA/UA (<bold>C</bold>), SM-OA/UA NPs (<bold>D</bold>), for 24 and 48 h, as denoted. Statistically significant differences, <italic>p</italic> < 0.05 are denoted with * or **, in relation to respective control at 24 or 48 h, respectively; # denotes statistical differences for incubation periods at indicated concentration. The results are the mean ± S.D. of <italic>n</italic> = 4.</p></caption><graphic xlink:href="pharmaceutics-11-00362-g003"></graphic></fig><fig id="pharmaceutics-11-00362-f004" orientation="portrait" position="float"><label>Figure 4</label><caption><p>The effect of OA/UA on Y-79, human retinoblastoma cells viability. Y-79 cells were exposed to NM-OA/UA (<bold>A</bold>), NM-OA/UA NPs (<bold>B</bold>), SM-OA/UA (<bold>C</bold>), SM-OA/UA NPs (<bold>D</bold>), for 24 and 48 h, as denoted. Statistically significant differences, <italic>p</italic> < 0.05 are denoted with * or **, in relation to respective control at 24 or 48 h, respectively; # denotes statistical differences for incubation periods at indicated concentration. The results are the mean ± S.D. of <italic>n</italic> = 4.</p></caption><graphic xlink:href="pharmaceutics-11-00362-g004"></graphic></fig><fig id="pharmaceutics-11-00362-f005" orientation="portrait" position="float"><label>Figure 5</label><caption><p>The effect of blank NPs on Y-79 cell viability. Y-79 cells were exposed to blank NPs, for 24 and 48 h, as denoted. Statistically significant differences, <italic>p</italic> < 0.05, are denoted with * or **, in relation to respective control at 24 or 48 h, respectively. The results are the mean ± S.D. of <italic>n</italic> = 4.</p></caption><graphic xlink:href="pharmaceutics-11-00362-g005"></graphic></fig><table-wrap id="pharmaceutics-11-00362-t001" orientation="portrait" position="float"><object-id pub-id-type="pii">pharmaceutics-11-00362-t001_Table 1</object-id><label>Table 1</label><caption><p>The values of IC<sub>50</sub> (µmol/L), (half maximal inhibitory concentration) obtained for HepG2, Caco-2 and Y-79 cells exposed NM-OA/UA, SM-OA/UA, NM-OA/UA NPs and SM-OA/UA NPs. The results are expressed as the mean ± SD, <italic>n</italic> = 4.</p></caption><table frame="hsides" rules="groups"><thead><tr><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1"></th><th align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1" colspan="1"></th><th colspan="4" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1">IC<sub>50</sub> (µmol/L)</th></tr><tr><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">NM-AO/UA</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">SM-AO/UA</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">NM-AO/UA NPs</th><th align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">SM-AO/UA NPs</th></tr></thead><tbody><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>HepG2</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">24 h</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">>32.0</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">>32.0</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">>>32.0</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">>>32.0</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">48 h</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">>32.0</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">24.3 ± 1.8</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">>>32.0</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">>>32.0</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>Caco-2</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">24 h</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">>32.0</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">32.4 ± 0.9</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">>32.0</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">>32.0</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">48 h</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">24.3 ± 0.9</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">16.3 ± 0.6</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">>32.0</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">>32.0</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"><bold>Y-79</bold></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">24 h</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">6.4 ± 0.9</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">6.5 ± 0.9</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">82.0 ± 10.2</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">16.6 ± 1.3</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1"></td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">48 h</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">2.6 ± 0.4</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">2.9 ± 0.3</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">19.1 ± 2.2</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">11.1 ± 0.8</td></tr></tbody></table><table-wrap-foot><fn><p>Abbreviation: IC<sub>50</sub>, half maximal inhibitory concentration. 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