Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents
A series of 18 aminochalcone derivatives were obtained in yields of 21.5−88.6% by applying the classical Claisen-Schmidt reaction. Compounds <b>4</b>−<b>9</b>, <b>14</b> and <b>16</b>−<b>18</b> with 4-ethyl, 4-...
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MDPI AG
2019-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/22/4129 |
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| author | Joanna Kozłowska Bartłomiej Potaniec Dagmara Baczyńska Barbara Żarowska Mirosław Anioł |
| author_facet | Joanna Kozłowska Bartłomiej Potaniec Dagmara Baczyńska Barbara Żarowska Mirosław Anioł |
| author_sort | Joanna Kozłowska |
| collection | DOAJ |
| description | A series of 18 aminochalcone derivatives were obtained in yields of 21.5−88.6% by applying the classical Claisen-Schmidt reaction. Compounds <b>4</b>−<b>9</b>, <b>14</b> and <b>16</b>−<b>18</b> with 4-ethyl, 4-carboxy-, 4-benzyloxy- and 4-benzyloxy-3-methoxy groups were novel, not previously described in the scientific literature. To determine the biological properties of the synthesized compounds, anticancer and antimicrobial activity assays were performed. Antiproliferative potential was evaluated on four different human colon cancer cell lines—HT-29, LS180, LoVo and LoVo/DX —using the SRB assay and compared with green monkey kidney fibroblasts COS7. Anticancer activity was described as the IC<sub>50</sub> value. The best results were observed for 2′-aminochalcone (<b>1</b>), 3′-aminochalcone (<b>2</b>) and 4′-aminochalcone (<b>3</b>) (IC<sub>50</sub> = 1.43−1.98 µg·mL<sup>−1</sup>) against the HT-29 cell line and for amino-nitrochalcones <b>10</b>−<b>12</b> (IC<sub>50</sub> = 2.77−3.42 µg·mL<sup>−1</sup>) against the LoVo and LoVo/DX cell lines. Moreover, the antimicrobial activity of all derivatives was evaluated on two strains of bacteria: <i>Escherichia coli</i> ATCC10536 and <i>Staphylococcus aureus</i> DSM799, the yeast strain <i>Candida albicans</i> DSM1386 and three strains of fungi: <i>Alternaria alternata</i> CBS1526, <i>Fusarium linii</i> KB-F1 and <i>Aspergillus niger</i> DSM1957. In the case of <i>E.</i> <i>coli</i> ATCC10536 almost all derivatives hindered the bacterial growth (∆OD = 0). Furthermore, the best results were observed in the presence of 4′-aminochalcone (<b>3</b>), that completely limited the growth of all tested strains at the concentration range of 0.25−0.5 mg·mL<sup>−1</sup>. The strongest bacteriostatic activity was exhibited by novel 3′-amino-4-benzyloxychalcone (<b>14</b>), that prevented the growth of <i>E. coli</i> ATCC10536 with MIC = 0.0625 mg·mL<sup>−1</sup>. |
| first_indexed | 2024-12-20T02:05:58Z |
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| id | doaj.art-c59604fc5c654867ad0e8c5c5adce95c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-20T02:05:58Z |
| publishDate | 2019-11-01 |
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| series | Molecules |
| spelling | doaj.art-c59604fc5c654867ad0e8c5c5adce95c2022-12-21T19:57:11ZengMDPI AGMolecules1420-30492019-11-012422412910.3390/molecules24224129molecules24224129Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial AgentsJoanna Kozłowska0Bartłomiej Potaniec1Dagmara Baczyńska2Barbara Żarowska3Mirosław Anioł4Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Molecular and Cellular Biology, Faculty of Pharmacy with Division of Laboratory Diagnostics, Wroclaw Medical University, Borowska 211A, 50-556 Wrocław, PolandDepartment of Biotechnology and Food Microbiology, Wrocław University of Environmental and Life Sciences, Chełmońskiego 37, 51-630 Wrocław, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandA series of 18 aminochalcone derivatives were obtained in yields of 21.5−88.6% by applying the classical Claisen-Schmidt reaction. Compounds <b>4</b>−<b>9</b>, <b>14</b> and <b>16</b>−<b>18</b> with 4-ethyl, 4-carboxy-, 4-benzyloxy- and 4-benzyloxy-3-methoxy groups were novel, not previously described in the scientific literature. To determine the biological properties of the synthesized compounds, anticancer and antimicrobial activity assays were performed. Antiproliferative potential was evaluated on four different human colon cancer cell lines—HT-29, LS180, LoVo and LoVo/DX —using the SRB assay and compared with green monkey kidney fibroblasts COS7. Anticancer activity was described as the IC<sub>50</sub> value. The best results were observed for 2′-aminochalcone (<b>1</b>), 3′-aminochalcone (<b>2</b>) and 4′-aminochalcone (<b>3</b>) (IC<sub>50</sub> = 1.43−1.98 µg·mL<sup>−1</sup>) against the HT-29 cell line and for amino-nitrochalcones <b>10</b>−<b>12</b> (IC<sub>50</sub> = 2.77−3.42 µg·mL<sup>−1</sup>) against the LoVo and LoVo/DX cell lines. Moreover, the antimicrobial activity of all derivatives was evaluated on two strains of bacteria: <i>Escherichia coli</i> ATCC10536 and <i>Staphylococcus aureus</i> DSM799, the yeast strain <i>Candida albicans</i> DSM1386 and three strains of fungi: <i>Alternaria alternata</i> CBS1526, <i>Fusarium linii</i> KB-F1 and <i>Aspergillus niger</i> DSM1957. In the case of <i>E.</i> <i>coli</i> ATCC10536 almost all derivatives hindered the bacterial growth (∆OD = 0). Furthermore, the best results were observed in the presence of 4′-aminochalcone (<b>3</b>), that completely limited the growth of all tested strains at the concentration range of 0.25−0.5 mg·mL<sup>−1</sup>. The strongest bacteriostatic activity was exhibited by novel 3′-amino-4-benzyloxychalcone (<b>14</b>), that prevented the growth of <i>E. coli</i> ATCC10536 with MIC = 0.0625 mg·mL<sup>−1</sup>.https://www.mdpi.com/1420-3049/24/22/4129aminochalconeanticancer activityantimicrobial activity |
| spellingShingle | Joanna Kozłowska Bartłomiej Potaniec Dagmara Baczyńska Barbara Żarowska Mirosław Anioł Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents Molecules aminochalcone anticancer activity antimicrobial activity |
| title | Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents |
| title_full | Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents |
| title_fullStr | Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents |
| title_full_unstemmed | Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents |
| title_short | Synthesis and Biological Evaluation of Novel Aminochalcones as Potential Anticancer and Antimicrobial Agents |
| title_sort | synthesis and biological evaluation of novel aminochalcones as potential anticancer and antimicrobial agents |
| topic | aminochalcone anticancer activity antimicrobial activity |
| url | https://www.mdpi.com/1420-3049/24/22/4129 |
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