Synthesis of N,N,O‐Schiff Base Mediated Cu(II) Complex for Anticancer and Catalytic Activities in the 3, 5‐DTBC and Dopamine Oxidation

Abstract Targeting cell growth‐regulatory proteins has emerged as a promising approach in cancer therapeutics. In this study, a copper(II) complex was synthesized using a Schiff base ligand derived from 5‐bromosalicylaldehyde and 3‐methyl‐6‐aminopyridine. The ligand formation occurred via condensation in methanol, followed by complexation with copper chloride under reflux conditions in the presence of triethylamine. Structural characterization was achieved through UV–visible spectroscopy, mass spectrometry, and powder X‐ray diffraction. Biological evaluation revealed potent cytotoxic activity against SiHa cervical cancer cells at a concentration of 50 µg/mL. Fluorescence microscopy using Acridine Orange and Ethidium Bromide staining demonstrated apoptotic progression, evidenced by a shift in cellular fluorescence from green to yellow. The complex also exhibited strong oxidative capabilities, efficiently catalyzing the transformation of catechol and dopamine, with turnover numbers of 5.02 × 10 3 and 1.35 × 10⁴, respectively. Molecular docking studies indicated high‐affinity binding to cyclin‐dependent kinase 4 (CDK4), particularly at tyrosine‐rich regions, with a calculated binding energy of −9.1 kcal/mol. This interaction suggests potential interference with cyclin D binding and modulation of tyrosine residues, underscoring the compound's promise as a cytotoxic agent with dual mechanistic roles—protein inhibition and oxidative stress induction.

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Journal
ChemistrySelect
Published
2025-10-01
DOI
https://doi.org/10.1002/slct.202500791
Primary Topic
Metal complexes synthesis and properties
Type
article
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article

Synthesis of N,N,O‐Schiff Base Mediated Cu(II) Complex for Anticancer and Catalytic Activities in the 3, 5‐DTBC and Dopamine Oxidation

Mohd Afzal, Shakti Prasad Pattanayak, Nayim Sepay, Kalyanmoy Jana et al.
ChemistrySelect
Metal complexes synthesis and properties
article

Synthesis of N,N,O‐Schiff Base Mediated Cu(II) Complex for Anticancer and Catalytic Activities in the 3, 5‐DTBC and Dopamine Oxidation

Mohd Afzal, Shakti Prasad Pattanayak, Nayim Sepay, Kalyanmoy Jana, Ribhu Maity, Tithi Maity, Nasim Sepay, Swapan Maity, Bidhan Chandra Samanta
article en

Abstract

Abstract Targeting cell growth‐regulatory proteins has emerged as a promising approach in cancer therapeutics. In this study, a copper(II) complex was synthesized using a Schiff base ligand derived from 5‐bromosalicylaldehyde and 3‐methyl‐6‐aminopyridine. The ligand formation occurred via condensation in methanol, followed by complexation with copper chloride under reflux conditions in the presence of triethylamine. Structural characterization was achieved through UV–visible spectroscopy, mass spectrometry, and powder X‐ray diffraction. Biological evaluation revealed potent cytotoxic activity against SiHa cervical cancer cells at a concentration of 50 µg/mL. Fluorescence microscopy using Acridine Orange and Ethidium Bromide staining demonstrated apoptotic progression, evidenced by a shift in cellular fluorescence from green to yellow. The complex also exhibited strong oxidative capabilities, efficiently catalyzing the transformation of catechol and dopamine, with turnover numbers of 5.02 × 10 3 and 1.35 × 10⁴, respectively. Molecular docking studies indicated high‐affinity binding to cyclin‐dependent kinase 4 (CDK4), particularly at tyrosine‐rich regions, with a calculated binding energy of −9.1 kcal/mol. This interaction suggests potential interference with cyclin D binding and modulation of tyrosine residues, underscoring the compound's promise as a cytotoxic agent with dual mechanistic roles—protein inhibition and oxidative stress induction.

ChemistrySelectVol. 10(40)
KPC Medical College and Hospital (IN), Soonchunhyang University (KR), Care Institute of Medical Sciences (IN), King Saud University (SA), Kanya Maha Vidyalaya (IN), Indian Institute of Technology BHU (IN), Banaras Hindu University (IN)
Openalex Percentile: Top 59%
Metal complexes synthesis and properties
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