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

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

doi:10.1016/j.cscee.2024.101031

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

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Article number	101031
Journal	Case Studies in Chemical and Environmental Engineering
Volume	11
DOIs	https://doi.org/10.1016/j.cscee.2024.101031
Publication status	Published - Jun 2025

Keywords

1,2,3-triazole
Antioxidant
Curcumin analogs
Cytotoxic
Hybrid compounds

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10.1016/j.cscee.2024.101031

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Ardiansah, B., Farhan, A., Nurhasanah, N. S., Fardiansyah Nasution, M. A., Salleh, N. M., Mizuguchi, K., Cahyana, A. H., & Mardiana, L. (2025). Dual antioxidant and cytotoxic activities of novel 1,2,3-triazole-decorated unsymmetrical monocarbonyl curcumin analogs. Case Studies in Chemical and Environmental Engineering, 11, Article 101031. https://doi.org/10.1016/j.cscee.2024.101031

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

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.",

keywords = "1,2,3-triazole, Antioxidant, Curcumin analogs, Cytotoxic, Hybrid compounds",

author = "Bayu Ardiansah and Ahmad Farhan and Nurhasanah, {Novita Sari} and {Fardiansyah Nasution}, {Mochammad Arfin} and Salleh, {Noordini M.} and Kenji Mizuguchi and Cahyana, {Antonius Herry} and Lina Mardiana",

note = "Publisher Copyright: {\textcopyright} 2024 The Author(s)",

year = "2025",

month = jun,

doi = "10.1016/j.cscee.2024.101031",

language = "English",

volume = "11",

journal = "Case Studies in Chemical and Environmental Engineering",

issn = "2666-0164",

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T1 - Dual antioxidant and cytotoxic activities of novel 1,2,3-triazole-decorated unsymmetrical monocarbonyl curcumin analogs

AU - Ardiansah, Bayu

AU - Farhan, Ahmad

AU - Nurhasanah, Novita Sari

AU - Fardiansyah Nasution, Mochammad Arfin

AU - Salleh, Noordini M.

AU - Mizuguchi, Kenji

AU - Cahyana, Antonius Herry

AU - Mardiana, Lina

PY - 2025/6

Y1 - 2025/6

N2 - 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.

AB - 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.

KW - 1,2,3-triazole

KW - Antioxidant

KW - Curcumin analogs

KW - Cytotoxic

KW - Hybrid compounds

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U2 - 10.1016/j.cscee.2024.101031

DO - 10.1016/j.cscee.2024.101031

M3 - Article

AN - SCOPUS:85210405842

SN - 2666-0164

VL - 11

JO - Case Studies in Chemical and Environmental Engineering

JF - Case Studies in Chemical and Environmental Engineering

M1 - 101031

ER -

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

Abstract

Keywords

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