Dual antioxidant and cytotoxic activities of novel 1,2,3-triazole-decorated unsymmetrical monocarbonyl curcumin analogs
Unsymmetrical monocarbonyl curcumin analogs containing 1,2,3-triazole scaffold (5a-5f) have been synthesized from vanillin. 5d, which contains a carboxylic group, exhibited the highest antioxidant and cytotoxic activities, with an IC50 of 0.56 mM against DPPH and an IC50 of 38.25 ± 4.79 μM against M...
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| Language: | English |
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Elsevier
2025-06-01
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| Series: | Case Studies in Chemical and Environmental Engineering |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666016424004250 |
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| author | Bayu Ardiansah Ahmad Farhan Novita Sari Nurhasanah Mochammad Arfin Fardiansyah Nasution Noordini M. Salleh Kenji Mizuguchi Antonius Herry Cahyana Lina Mardiana |
| author_facet | Bayu Ardiansah Ahmad Farhan Novita Sari Nurhasanah Mochammad Arfin Fardiansyah Nasution Noordini M. Salleh Kenji Mizuguchi Antonius Herry Cahyana Lina Mardiana |
| author_sort | Bayu Ardiansah |
| collection | DOAJ |
| description | Unsymmetrical monocarbonyl curcumin analogs containing 1,2,3-triazole scaffold (5a-5f) have been synthesized from vanillin. 5d, which contains a carboxylic group, exhibited the highest antioxidant and cytotoxic activities, with an IC50 of 0.56 mM against DPPH and an IC50 of 38.25 ± 4.79 μM against MCF-7 cells. Docking studies revealed that 5d has high binding affinity for the tubulin protein, with predicted binding value of −10.4 kcal/mol. Additionally, in silico ADME predictions indicated that 5d demonstrates high gastrointestinal absorption and moderate intrinsic clearance. These findings indicate that the designed compounds, particularly compound 5d, could be promising for developing a new drug candidate. |
| format | Article |
| id | doaj-art-b4589b6ce59f41c4b2ae4c4d5216dae0 |
| institution | OA Journals |
| issn | 2666-0164 |
| language | English |
| publishDate | 2025-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Case Studies in Chemical and Environmental Engineering |
| spelling | doaj-art-b4589b6ce59f41c4b2ae4c4d5216dae02025-08-20T02:38:23ZengElsevierCase Studies in Chemical and Environmental Engineering2666-01642025-06-011110103110.1016/j.cscee.2024.101031Dual antioxidant and cytotoxic activities of novel 1,2,3-triazole-decorated unsymmetrical monocarbonyl curcumin analogsBayu Ardiansah0Ahmad Farhan1Novita Sari Nurhasanah2Mochammad Arfin Fardiansyah Nasution3Noordini M. Salleh4Kenji Mizuguchi5Antonius Herry Cahyana6Lina Mardiana7Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Depok, 16424, Indonesia; Corresponding author.Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Depok, 16424, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Depok, 16424, IndonesiaInstitute for Protein Research, Osaka University, 3-2 Yamadaoka, Suita, Osaka, 565-0871, JapanDepartment of Chemistry, Faculty of Science, Universiti Malaya, 50603, Kuala Lumpur, MalaysiaInstitute for Protein Research, Osaka University, 3-2 Yamadaoka, Suita, Osaka, 565-0871, JapanDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Depok, 16424, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Depok, 16424, IndonesiaUnsymmetrical monocarbonyl curcumin analogs containing 1,2,3-triazole scaffold (5a-5f) have been synthesized from vanillin. 5d, which contains a carboxylic group, exhibited the highest antioxidant and cytotoxic activities, with an IC50 of 0.56 mM against DPPH and an IC50 of 38.25 ± 4.79 μM against MCF-7 cells. Docking studies revealed that 5d has high binding affinity for the tubulin protein, with predicted binding value of −10.4 kcal/mol. Additionally, in silico ADME predictions indicated that 5d demonstrates high gastrointestinal absorption and moderate intrinsic clearance. These findings indicate that the designed compounds, particularly compound 5d, could be promising for developing a new drug candidate.http://www.sciencedirect.com/science/article/pii/S2666016424004250Curcumin analogs1,2,3-triazoleHybrid compoundsCytotoxicAntioxidant |
| spellingShingle | Bayu Ardiansah Ahmad Farhan Novita Sari Nurhasanah Mochammad Arfin Fardiansyah Nasution Noordini M. Salleh Kenji Mizuguchi Antonius Herry Cahyana Lina Mardiana Dual antioxidant and cytotoxic activities of novel 1,2,3-triazole-decorated unsymmetrical monocarbonyl curcumin analogs Case Studies in Chemical and Environmental Engineering Curcumin analogs 1,2,3-triazole Hybrid compounds Cytotoxic Antioxidant |
| title | Dual antioxidant and cytotoxic activities of novel 1,2,3-triazole-decorated unsymmetrical monocarbonyl curcumin analogs |
| title_full | Dual antioxidant and cytotoxic activities of novel 1,2,3-triazole-decorated unsymmetrical monocarbonyl curcumin analogs |
| title_fullStr | Dual antioxidant and cytotoxic activities of novel 1,2,3-triazole-decorated unsymmetrical monocarbonyl curcumin analogs |
| title_full_unstemmed | Dual antioxidant and cytotoxic activities of novel 1,2,3-triazole-decorated unsymmetrical monocarbonyl curcumin analogs |
| title_short | Dual antioxidant and cytotoxic activities of novel 1,2,3-triazole-decorated unsymmetrical monocarbonyl curcumin analogs |
| title_sort | dual antioxidant and cytotoxic activities of novel 1 2 3 triazole decorated unsymmetrical monocarbonyl curcumin analogs |
| topic | Curcumin analogs 1,2,3-triazole Hybrid compounds Cytotoxic Antioxidant |
| url | http://www.sciencedirect.com/science/article/pii/S2666016424004250 |
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