Dual antioxidant and cytotoxic activities of novel 1,2,3-triazole-decorated unsymmetrical monocarbonyl curcumin analogs

Q1 Environmental Science Case Studies in Chemical and Environmental Engineering Pub Date : 2024-11-26 DOI:10.1016/j.cscee.2024.101031

Bayu Ardiansah , Ahmad Farhan , Novita Sari Nurhasanah , Mochammad Arfin Fardiansyah Nasution , Noordini M. Salleh , Kenji Mizuguchi , Antonius Herry Cahyana , Lina Mardiana

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Abstract

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.

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