Copper-mediated cyclization of thiosemicarbazones leading to 1,3,4-thiadiazoles: Structural elucidation, DFT calculations, in vitro biological evaluation and in silico evaluation studies

Manakkadan, Vipin; Haribabu, Jebiti; Palakkeezhillam, Vishnunarayanan Namboothiri Vadakkedathu; Rasin, Puthiyavalappil; Vediyappan, Ramesh; Kumar, Vaishnu Suresh; Garg, Mohit; Bhuvanesh, Nattamai; Sreekanth, Anandaram

doi:10.1016/j.saa.2024.124117

Cited by 1 publication

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“…In vitro testing is very important in the early stages of developing new drugs that might fight cancer. The MTT assay is one of the ways used to find the compounds half-maximal inhibitory concentration (IC 50 ) values for certain cells . This helps to find the compounds with the greatest activity and classify them, which sets their effectiveness ranking.…”

Section: Resultsmentioning

confidence: 99%

“…The MTT assay is one of the ways used to find the compounds half-maximal inhibitory concentration (IC 50 ) values for certain cells. 68 This helps to find the compounds with the greatest activity and classify them, which sets their effectiveness ranking. Our study was mostly about testing the activity of complexes in HeLa, MCF-7 and MDA-MB 231 cancer cell lines.…”

Section: Interaction Of Complexes With Bsamentioning

confidence: 99%

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Biomolecular Interactions and Anticancer Mechanisms of Ru(II)-Arene Complexes of Cinnamaldehyde-Derived Thiosemicarbazone Ligands: Analysis Combining In Silico and In Vitro Approaches

Vadakkedathu Palakkeezhillam,

Haribabu,

Kumar

et al. 2024

ACS Appl. Bio Mater.

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Our study focuses on synthesizing and exploring the potential of three N-(4) substituted thiosemicarbazones derived from cinnamic aldehyde, alongside their Ru(II)-(η 6 -p-cymene)/ (η 6 -benzene) complexes. The synthesized compounds were comprehensively characterized using a range of analytical techniques, including FT-IR, UV−visible spectroscopy, NMR ( 1 H, 13 C), and HRMS. We investigated their electronic and physicochemical properties via density functional theory (DFT). X-ray crystal structures validated structural differences identified by DFT. Molecular docking predicted promising bioactivities, supported by experimental observations. Notably, docking with EGFR suggested an inhibitory potential against this cancer-related protein. Spectroscopic titrations revealed significant DNA/BSA binding affinities, particularly with DNA intercalation and BSA hydrophobic interactions. RuPCAM displayed the strongest binding affinity with DNA (K b = 6.23 × 10 7 M −1 ) and BSA (K b = 9.75 × 10 5 M −1 ). Assessed the cytotoxicity of the complexes on cervical cancer cells (HeLa), and breast cancer cells (MCF-7 and MDA-MB 231), revealing remarkable potency. Additionally, selectivity was assessed by examining MCF-10a normal cell lines. The active complexes were found to trigger apoptosis, a vital cellular process crucial for evaluating their potential as anticancer agents utilizing staining assays and flow cytometry analysis. Intriguingly, complexation with Ru(II)-arene precursors significantly amplified the bioactivity of thiosemicarbazones, unveiling promising avenues toward the creation of powerful anticancer agents.

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Section: Resultsmentioning

confidence: 99%

Section: Interaction Of Complexes With Bsamentioning

confidence: 99%