Synthesis, Antimicrobial, and Anticancer Activities of Novel Nitrofuran Derivatives
Keeping in view the varying therapeutic attributes of 5-nitrofuran and isatin derivatives, novel 5-nitrofuran‒isatin molecular hybrids (2, 5–7) were synthesized by standard protocols, characterized by various spectroscopic techniques, and eventually evaluated against a group of pathogenic bacteria a...
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| Format: | Article |
| Language: | English |
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Wiley
2023-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2023/1481595 |
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| author | Malik Suliman Mohamed Khaled M. Elamin Rawaf Alenazy Eyman Mohamed Eltayib Mona Timan Idriss Noura A. A. Alhudaib Tilal Elsaman Magdi Awadalla Mohamed |
| author_facet | Malik Suliman Mohamed Khaled M. Elamin Rawaf Alenazy Eyman Mohamed Eltayib Mona Timan Idriss Noura A. A. Alhudaib Tilal Elsaman Magdi Awadalla Mohamed |
| author_sort | Malik Suliman Mohamed |
| collection | DOAJ |
| description | Keeping in view the varying therapeutic attributes of 5-nitrofuran and isatin derivatives, novel 5-nitrofuran‒isatin molecular hybrids (2, 5–7) were synthesized by standard protocols, characterized by various spectroscopic techniques, and eventually evaluated against a group of pathogenic bacteria and fungi. Greater potency against Methicillin-resistant Staphylococcus aureus (MRSA) was exhibited by hybrids 5 and 6 with minimum inhibitory concentration values of 8 and 1 μg/mL, respectively. Cytotoxicity against both human embryonic kidney cells (HEK-293) and human red blood cells (RBCs) was investigated for the hybrids in hand. All hybrids appeared to have good safety; all of them were devoid of cytotoxicity, and none displayed hemolytic activity at the highest test concentration (CC50 and HI10 > 32 μg/mL). To support the postulation that these hybrids would be analogous to drugs containing the 5-nitrofurn ring system, molecular docking was carried out to streamline the binding affinity of the investigated hybrids towards the E. coli nitroreductase (NTR). Compared to the standard drug nitrofurazone, hybrid 6 demonstrated a higher affinity and better binding interactions with the NTR binding pocket. Therefore, it could be concluded that 6 displays its antibacterial action through a mechanism similar to that of nitrofurazone. Nonetheless, further wet investigations are to be conducted to confirm this finding. Encouraged by the well-established anticancer activity of isatin derivatives, 2, 5–7 were assessed for their potential antitumor activity, and they well demonstrated potent inhibitory activity against the human colon cancer cell line HCT 116 (IC50 = 1.62–8.8 μM) with isatin hybrid 3 being the best (IC50 = 1.62 μM). Thus, it is herein reported that these 5-nitrofuran‒isatin molecular hybrids could represent an ideal starting point for future studies to develop potent antimicrobial agents. |
| format | Article |
| id | doaj-art-1e5cacc4bbcf43eaadd3a89cc7beb355 |
| institution | OA Journals |
| issn | 2090-9071 |
| language | English |
| publishDate | 2023-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-1e5cacc4bbcf43eaadd3a89cc7beb3552025-08-20T02:04:44ZengWileyJournal of Chemistry2090-90712023-01-01202310.1155/2023/1481595Synthesis, Antimicrobial, and Anticancer Activities of Novel Nitrofuran DerivativesMalik Suliman Mohamed0Khaled M. Elamin1Rawaf Alenazy2Eyman Mohamed Eltayib3Mona Timan Idriss4Noura A. A. Alhudaib5Tilal Elsaman6Magdi Awadalla Mohamed7Department of PharmaceuticsGraduate School of Pharmaceutical SciencesDepartment of Medical LaboratoryDepartment of PharmaceuticsDepartment of Medical Sciences and Preparation YearDepartment of Medical Sciences and Preparation YearDepartment of Pharmaceutical ChemistryDepartment of Pharmaceutical ChemistryKeeping in view the varying therapeutic attributes of 5-nitrofuran and isatin derivatives, novel 5-nitrofuran‒isatin molecular hybrids (2, 5–7) were synthesized by standard protocols, characterized by various spectroscopic techniques, and eventually evaluated against a group of pathogenic bacteria and fungi. Greater potency against Methicillin-resistant Staphylococcus aureus (MRSA) was exhibited by hybrids 5 and 6 with minimum inhibitory concentration values of 8 and 1 μg/mL, respectively. Cytotoxicity against both human embryonic kidney cells (HEK-293) and human red blood cells (RBCs) was investigated for the hybrids in hand. All hybrids appeared to have good safety; all of them were devoid of cytotoxicity, and none displayed hemolytic activity at the highest test concentration (CC50 and HI10 > 32 μg/mL). To support the postulation that these hybrids would be analogous to drugs containing the 5-nitrofurn ring system, molecular docking was carried out to streamline the binding affinity of the investigated hybrids towards the E. coli nitroreductase (NTR). Compared to the standard drug nitrofurazone, hybrid 6 demonstrated a higher affinity and better binding interactions with the NTR binding pocket. Therefore, it could be concluded that 6 displays its antibacterial action through a mechanism similar to that of nitrofurazone. Nonetheless, further wet investigations are to be conducted to confirm this finding. Encouraged by the well-established anticancer activity of isatin derivatives, 2, 5–7 were assessed for their potential antitumor activity, and they well demonstrated potent inhibitory activity against the human colon cancer cell line HCT 116 (IC50 = 1.62–8.8 μM) with isatin hybrid 3 being the best (IC50 = 1.62 μM). Thus, it is herein reported that these 5-nitrofuran‒isatin molecular hybrids could represent an ideal starting point for future studies to develop potent antimicrobial agents.http://dx.doi.org/10.1155/2023/1481595 |
| spellingShingle | Malik Suliman Mohamed Khaled M. Elamin Rawaf Alenazy Eyman Mohamed Eltayib Mona Timan Idriss Noura A. A. Alhudaib Tilal Elsaman Magdi Awadalla Mohamed Synthesis, Antimicrobial, and Anticancer Activities of Novel Nitrofuran Derivatives Journal of Chemistry |
| title | Synthesis, Antimicrobial, and Anticancer Activities of Novel Nitrofuran Derivatives |
| title_full | Synthesis, Antimicrobial, and Anticancer Activities of Novel Nitrofuran Derivatives |
| title_fullStr | Synthesis, Antimicrobial, and Anticancer Activities of Novel Nitrofuran Derivatives |
| title_full_unstemmed | Synthesis, Antimicrobial, and Anticancer Activities of Novel Nitrofuran Derivatives |
| title_short | Synthesis, Antimicrobial, and Anticancer Activities of Novel Nitrofuran Derivatives |
| title_sort | synthesis antimicrobial and anticancer activities of novel nitrofuran derivatives |
| url | http://dx.doi.org/10.1155/2023/1481595 |
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