Ferrocene-Based Compounds with Antimalaria/Anticancer Activity
Identifieur interne : 000757 ( Pmc/Checkpoint ); précédent : 000756; suivant : 000758Ferrocene-Based Compounds with Antimalaria/Anticancer Activity
Auteurs : Sijongesonke Peter ; Blessing Atim AderibigbeSource :
- Molecules [ 1420-3049 ] ; 2019.
Abstract
Malaria and cancer are chronic diseases. The challenge with drugs available for the treatment of these diseases is drug toxicity and resistance. Ferrocene is a potent organometallic which have been hybridized with other compounds resulting in compounds with enhanced biological activity such as antimalarial and anticancer. Drugs such as ferroquine were developed from ferrocene and chloroquine. It was tested in the 1990s as an antimalarial and is still an effective antimalarial. Many researchers have reported ferrocene compounds as potent compounds useful as anticancer and antimalarial agents when hybridized with other pharmaceutical scaffolds. This review will be focused on compounds with ferrocene moieties that exhibit either an anticancer or antimalarial activity.
Url:
DOI: 10.3390/molecules24193604
PubMed: 31591298
PubMed Central: 6804011
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Ferrocene-Based Compounds with Antimalaria/Anticancer Activity</title><author><name sortKey="Peter, Sijongesonke" sort="Peter, Sijongesonke" uniqKey="Peter S" first="Sijongesonke" last="Peter">Sijongesonke Peter</name></author><author><name sortKey="Aderibigbe, Blessing Atim" sort="Aderibigbe, Blessing Atim" uniqKey="Aderibigbe B" first="Blessing Atim" last="Aderibigbe">Blessing Atim Aderibigbe</name></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">31591298</idno><idno type="pmc">6804011</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6804011</idno><idno type="RBID">PMC:6804011</idno><idno type="doi">10.3390/molecules24193604</idno><date when="2019">2019</date><idno type="wicri:Area/Pmc/Corpus">000A68</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000A68</idno><idno type="wicri:Area/Pmc/Curation">000A68</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000A68</idno><idno type="wicri:Area/Pmc/Checkpoint">000757</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000757</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Ferrocene-Based Compounds with Antimalaria/Anticancer Activity</title><author><name sortKey="Peter, Sijongesonke" sort="Peter, Sijongesonke" uniqKey="Peter S" first="Sijongesonke" last="Peter">Sijongesonke Peter</name></author><author><name sortKey="Aderibigbe, Blessing Atim" sort="Aderibigbe, Blessing Atim" uniqKey="Aderibigbe B" first="Blessing Atim" last="Aderibigbe">Blessing Atim Aderibigbe</name></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>Malaria and cancer are chronic diseases. The challenge with drugs available for the treatment of these diseases is drug toxicity and resistance. Ferrocene is a potent organometallic which have been hybridized with other compounds resulting in compounds with enhanced biological activity such as antimalarial and anticancer. Drugs such as ferroquine were developed from ferrocene and chloroquine. It was tested in the 1990s as an antimalarial and is still an effective antimalarial. Many researchers have reported ferrocene compounds as potent compounds useful as anticancer and antimalarial agents when hybridized with other pharmaceutical scaffolds. This review will be focused on compounds with ferrocene moieties that exhibit either an anticancer or antimalarial activity. </p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Glennon, E K K" uniqKey="Glennon E">E.K.K. Glennon</name></author><author><name sortKey="Dankwa, S" uniqKey="Dankwa S">S. 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<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></journal-title-group><issn pub-type="epub">1420-3049</issn><publisher><publisher-name>MDPI</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">31591298</article-id><article-id pub-id-type="pmc">6804011</article-id><article-id pub-id-type="doi">10.3390/molecules24193604</article-id><article-id pub-id-type="publisher-id">molecules-24-03604</article-id><article-categories><subj-group subj-group-type="heading"><subject>Review</subject></subj-group></article-categories><title-group><article-title>Ferrocene-Based Compounds with Antimalaria/Anticancer Activity</article-title></title-group><contrib-group><contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-6935-905X</contrib-id><name><surname>Peter</surname><given-names>Sijongesonke</given-names></name></contrib><contrib contrib-type="author"><name><surname>Aderibigbe</surname><given-names>Blessing Atim</given-names></name><xref rid="c1-molecules-24-03604" ref-type="corresp">*</xref></contrib></contrib-group><contrib-group><contrib contrib-type="editor"><name><surname>Santini</surname><given-names>Carlo</given-names></name><role>Academic Editor</role></contrib><contrib contrib-type="editor"><name><surname>Pellei</surname><given-names>Maura</given-names></name><role>Academic Editor</role></contrib></contrib-group><aff id="af1-molecules-24-03604">Department of Chemistry, University of Fort Hare, Alice campus, Eastern Cape 5700, South Africa;<email>201414787@ufh.ac.za</email></aff><author-notes><corresp id="c1-molecules-24-03604"><label>*</label>Correspondence: <email>blessingaderibigbe@gmail.com</email>; Tel.: +27-40602-2266</corresp></author-notes><pub-date pub-type="epub"><day>07</day><month>10</month><year>2019</year></pub-date><pub-date pub-type="collection"><month>10</month><year>2019</year></pub-date><volume>24</volume><issue>19</issue><elocation-id>3604</elocation-id><history><date date-type="received"><day>11</day><month>7</month><year>2019</year></date><date date-type="accepted"><day>21</day><month>8</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>Malaria and cancer are chronic diseases. The challenge with drugs available for the treatment of these diseases is drug toxicity and resistance. Ferrocene is a potent organometallic which have been hybridized with other compounds resulting in compounds with enhanced biological activity such as antimalarial and anticancer. Drugs such as ferroquine were developed from ferrocene and chloroquine. It was tested in the 1990s as an antimalarial and is still an effective antimalarial. Many researchers have reported ferrocene compounds as potent compounds useful as anticancer and antimalarial agents when hybridized with other pharmaceutical scaffolds. This review will be focused on compounds with ferrocene moieties that exhibit either an anticancer or antimalarial activity. </p></abstract><kwd-group><kwd>organometallics</kwd><kwd>malaria</kwd><kwd>cancer</kwd><kwd>ferrocene compounds</kwd><kwd>ferroquine</kwd></kwd-group></article-meta></front><floats-group><fig id="molecules-24-03604-f001" orientation="portrait" position="float"><label>Figure 1</label><caption><p>Synthesis of ferroquine by Biot and co-partners.</p></caption><graphic xlink:href="molecules-24-03604-g001"></graphic></fig><fig id="molecules-24-03604-f002" orientation="portrait" position="float"><label>Figure 2</label><caption><p>Chemical structure of compound hydroxyferroquine derivatives (<bold>1a</bold>–<bold>c</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g002"></graphic></fig><fig id="molecules-24-03604-f003" orientation="portrait" position="float"><label>Figure 3</label><caption><p>Chemical structures of trioxaferroquine derivatives (<bold>2</bold>–<bold>5</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g003"></graphic></fig><fig id="molecules-24-03604-f004" orientation="portrait" position="float"><label>Figure 4</label><caption><p>Hybrid compounds <bold>6</bold>–<bold>10</bold>.</p></caption><graphic xlink:href="molecules-24-03604-g004"></graphic></fig><fig id="molecules-24-03604-f005" orientation="portrait" position="float"><label>Figure 5</label><caption><p>Chemical structures of quinolone-ferrocene hybrids (<bold>11</bold>–<bold>15</bold>). <bold>13</bold>-Z = CH<sub>3</sub>, <bold>14-Y</bold> = 1,2,3,5-diisopropylidene glucofuranose moiety, <bold>15a</bold>-X = diisopropylidene-protected 6-amino-deoxyglucofuranose, <bold>15b</bold>-X = 6-amino-6-deoxygalactopyranose.</p></caption><graphic xlink:href="molecules-24-03604-g005"></graphic></fig><fig id="molecules-24-03604-f006" orientation="portrait" position="float"><label>Figure 6</label><caption><p>Artemisinin and its derivatives.</p></caption><graphic xlink:href="molecules-24-03604-g006"></graphic></fig><fig id="molecules-24-03604-f007" orientation="portrait" position="float"><label>Figure 7</label><caption><p>Hybrid compound <bold>17</bold>.</p></caption><graphic xlink:href="molecules-24-03604-g007"></graphic></fig><fig id="molecules-24-03604-f008" orientation="portrait" position="float"><label>Figure 8</label><caption><p>Chemical structures of second generation dihydroartemisinin ferrocene derivatives (<bold>18</bold>–<bold>22</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g008"></graphic></fig><fig id="molecules-24-03604-f009" orientation="portrait" position="float"><label>Figure 9</label><caption><p>Synthesis of amino–artemisinin–ferrocene compound (<bold>23</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g009"></graphic></fig><fig id="molecules-24-03604-f010" orientation="portrait" position="float"><label>Figure 10</label><caption><p>Chemical structures of dihydroartemisinin ferrocene derivatives (<bold>24</bold>–<bold>27</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g010"></graphic></fig><fig id="molecules-24-03604-f011" orientation="portrait" position="float"><label>Figure 11</label><caption><p>Ferrocenyl–novobiocin derivatives (<bold>28a</bold>–<bold>b</bold> and <bold>29a</bold>–<bold>c</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g011"></graphic></fig><fig id="molecules-24-03604-f012" orientation="portrait" position="float"><label>Figure 12</label><caption><p>Structure of synthesized ferrocenyl pyrrolo[1,2-a]quinoxaline derivatives (<bold>30a</bold>–<bold>b</bold> and <bold>31a</bold>–<bold>b</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g012"></graphic></fig><fig id="molecules-24-03604-f013" orientation="portrait" position="float"><label>Figure 13</label><caption><p>Chemical structure of isatin–ferrocene-based derivative (<bold>32a</bold>–<bold>h</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g013"></graphic></fig><fig id="molecules-24-03604-f014" orientation="portrait" position="float"><label>Figure 14</label><caption><p>Schematic route showing the synthesis of ferrocene-pyrimidine conjugates (<bold>33a</bold>–<bold>f</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g014"></graphic></fig><fig id="molecules-24-03604-f015" orientation="portrait" position="float"><label>Figure 15</label><caption><p>Ferrocenyl chalcones derivatives (<bold>34</bold>–<bold>35</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g015"></graphic></fig><fig id="molecules-24-03604-f016" orientation="portrait" position="float"><label>Figure 16</label><caption><p>Chemical structures of <italic>O</italic>-alkyl azide ferrocenylchalcones (<bold>36</bold>); piperazine (<bold>37</bold>), phenyl (<bold>38</bold>), amino alcohol (<bold>39</bold>) –linked 7-chloroquinoline-ferrocenylchalcone derivatives.</p></caption><graphic xlink:href="molecules-24-03604-g016"></graphic></fig><fig id="molecules-24-03604-f017" orientation="portrait" position="float"><label>Figure 17</label><caption><p>Chemical structure of indole (<bold>40</bold>–<bold>46</bold>) and ferrocene–indole derivatives (<bold>47</bold>–<bold>55</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g017"></graphic></fig><fig id="molecules-24-03604-f018" orientation="portrait" position="float"><label>Figure 18</label><caption><p>Hybrids <bold>56a</bold> and <bold>56b</bold>.</p></caption><graphic xlink:href="molecules-24-03604-g018"></graphic></fig><fig id="molecules-24-03604-f019" orientation="portrait" position="float"><label>Figure 19</label><caption><p>Chemical structures of ferrociphenol compound (<bold>57a</bold>–<bold>c</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g019"></graphic></fig><fig id="molecules-24-03604-f020" orientation="portrait" position="float"><label>Figure 20</label><caption><p>Chemical structures of hydroxypropyl-ferrocephenol derivatives (<bold>58</bold>–<bold>60</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g020"></graphic></fig><fig id="molecules-24-03604-f021" orientation="portrait" position="float"><label>Figure 21</label><caption><p>Chemical structures of hydroxyphenyl–ferrocephenol derivatives (<bold>61</bold>–<bold>64</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g021"></graphic></fig><fig id="molecules-24-03604-f022" orientation="portrait" position="float"><label>Figure 22</label><caption><p>Chemical structures of 2-ferrocenyl-1-1-diphenyl-but-1-ene derivatives (<bold>65</bold>–<bold>67</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g022"></graphic></fig><fig id="molecules-24-03604-f023" orientation="portrait" position="float"><label>Figure 23</label><caption><p>Chemical structures of ferrocenyl- clotrimazole derivatives (<bold>68</bold>–<bold>69</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g023"></graphic></fig><fig id="molecules-24-03604-f024" orientation="portrait" position="float"><label>Figure 24</label><caption><p>Chemical structures of ferrocenyl–chalcogeno–triazole conjugates (<bold>70</bold>–<bold>71</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g024"></graphic></fig><fig id="molecules-24-03604-f025" orientation="portrait" position="float"><label>Figure 25</label><caption><p>Chemical structures of ferrocenyl–olefins (<bold>72</bold>–<bold>74</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g025"></graphic></fig><fig id="molecules-24-03604-f026" orientation="portrait" position="float"><label>Figure 26</label><caption><p>Chemical structures of ferrocene with 1,4-dihydropyrimidine derivatives (<bold>75a</bold>–<bold>j</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g026"></graphic></fig><fig id="molecules-24-03604-f027" orientation="portrait" position="float"><label>Figure 27</label><caption><p>Chemical structures of ferrocene–carboxylate derivatives (<bold>76</bold>–<bold>80</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g027"></graphic></fig><fig id="molecules-24-03604-f028" orientation="portrait" position="float"><label>Figure 28</label><caption><p>Chemical structures of ferrocene incorporated selenourea derivatives (<bold>81a</bold>–<bold>q</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g028"></graphic></fig><fig id="molecules-24-03604-f029" orientation="portrait" position="float"><label>Figure 29</label><caption><p>Hybrid compounds <bold>82a</bold>–<bold>c</bold>.</p></caption><graphic xlink:href="molecules-24-03604-g029"></graphic></fig><fig id="molecules-24-03604-f030" orientation="portrait" position="float"><label>Figure 30</label><caption><p>Hybrid compounds <bold>83a</bold>–<bold>c</bold>.</p></caption><graphic xlink:href="molecules-24-03604-g030"></graphic></fig><fig id="molecules-24-03604-f031" orientation="portrait" position="float"><label>Figure 31</label><caption><p>Hybrid compounds <bold>84a</bold>–<bold>c</bold>.</p></caption><graphic xlink:href="molecules-24-03604-g031"></graphic></fig><fig id="molecules-24-03604-f032" orientation="portrait" position="float"><label>Figure 32</label><caption><p>Chemical structures of ferrocene–steroids derivatives (<bold>85a</bold>–<bold>e</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g032"></graphic></fig><fig id="molecules-24-03604-f033" orientation="portrait" position="float"><label>Figure 33</label><caption><p>Chemical structure of aminoferrocene-based derivatives (<bold>86a</bold>–<bold>b</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g033"></graphic></fig><fig id="molecules-24-03604-f034" orientation="portrait" position="float"><label>Figure 34</label><caption><p>Chemical structures of ferrocene–Lawsone Mannich base derivatives (<bold>87a</bold>–<bold>d</bold>).</p></caption><graphic xlink:href="molecules-24-03604-g034"></graphic></fig><table-wrap id="molecules-24-03604-t001" orientation="portrait" position="float"><object-id pub-id-type="pii">molecules-24-03604-t001_Table 1</object-id><label>Table 1</label><caption><p>In vitro activities of compound <bold>1a</bold>–<bold>c</bold> against <italic>P. falciparum</italic> strains (3D7 and W2).</p></caption><table frame="hsides" rules="groups"><thead><tr><th colspan="3" align="center" valign="middle" style="border-top:solid thin;border-bottom:solid thin" rowspan="1">IC<sub>50</sub> Values (nM)</th></tr></thead><tbody><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>Compound</bold></td><td align="center" valign="middle" rowspan="1" colspan="1"><bold>3D7</bold></td><td align="center" valign="middle" rowspan="1" colspan="1"><bold>W2</bold></td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>1a</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">15.4</td><td align="center" valign="middle" rowspan="1" colspan="1">133.2
</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>1b</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">21.5
</td><td align="center" valign="middle" rowspan="1" colspan="1">30
</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1"><bold>1c</bold></td><td align="center" valign="middle" rowspan="1" colspan="1">11.7
</td><td align="center" valign="middle" rowspan="1" colspan="1">20.4
</td></tr><tr><td align="center" valign="middle" rowspan="1" colspan="1">Ferroquine</td><td align="center" valign="middle" rowspan="1" colspan="1">7.8
</td><td align="center" valign="middle" rowspan="1" colspan="1">9.7
</td></tr><tr><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">Chloroquine</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">10.6
</td><td align="center" valign="middle" style="border-bottom:solid thin" rowspan="1" colspan="1">138.9
</td></tr></tbody></table></table-wrap></floats-group></pmc><affiliations><list></list><tree><noCountry><name sortKey="Aderibigbe, Blessing Atim" sort="Aderibigbe, Blessing Atim" uniqKey="Aderibigbe B" first="Blessing Atim" last="Aderibigbe">Blessing Atim Aderibigbe</name><name sortKey="Peter, Sijongesonke" sort="Peter, Sijongesonke" uniqKey="Peter S" first="Sijongesonke" last="Peter">Sijongesonke Peter</name></noCountry></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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