Exploration of cytotoxic potential and tubulin polymerization inhibition activity of <i>cis</i>-stilbene-1,2,3-triazole congeners

Bora, Darshana; Samir, Khan Mehtab; Sharma, Anamika; Chilvery, Shrilekha; Bansod, Sapana; John, Stephy Elza; Khan, Mursalim Ali; Godugu, Chandraiah; Shankaraiah, Nagula

doi:10.1039/d2md00400c

Cited by 5 publications

(3 citation statements)

References 28 publications

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“…This attribute is considered crucial for the effectiveness of anticancer drugs, as depicted in Figure . To fulfill our goal, we utilized the dual AO/EB staining technique and the DAPI method as qualitative approaches to explore apoptosis . By examining fluorescent images, we were able to classify cells into distinct categories, including live, early apoptotic, late apoptotic, or necrotic, based on observed alterations in nuclear morphology.…”

Section: Results and Discussionmentioning

confidence: 99%

Unraveling the Anticancer Efficacy and Biomolecular Properties of Ru(II)-Arene Complexes of Pyrene-Based Thiosemicarbazone Ligands: A Comprehensive In Silico/In Vitro Exploration

Vadakkedathu Palakkeezhillam,

Haribabu,

Kumar

et al. 2024

Organometallics

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We report the successful synthesis and comprehensive characterization of novel Ru(II)-arene complexes incorporating pyrene-based thiosemicarbazone (TSC) ligands. Utilizing a suite of advanced spectroscopic techniques including ultraviolet–visible (UV–visible), Fourier transform infrared (FT-IR), 1H NMR, 13C NMR, and high-resolution mass spectrometry (HRMS), the intricate structural and electronic nuances of these complexes were elucidated. X-ray crystallographic data unequivocally affirmed the ligands’ preferential coordination through the thionyl sulfur and imine nitrogen moieties with the Ru(II) ion. Rigorous density functional theory (DFT) computations reveal these complexes as exemplary electron donors, concomitantly hinting at their significant bioactive potential. Notably, molecular docking and molecular dynamic simulation studies suggest that they are potential SND1 protein inhibitors, which are essential proteins in the functioning of cancer cells. Furthermore, they have a strong affinity for binding to CT-DNA and bovine serum albumin (BSA), indicating DNA intercalation and a strong protein-binding ability. Intriguingly, the Ru-arene TSC complexes unveiled potent cytotoxic activity against an array of cancerous cell linesmost notably MDA-MB-231 (IC50 = 10.2 ± 0.02 μM), A549 (IC50 = 25.7 ± 0.07 μM), and HeLa (IC50 = 20.7 ± 0.05 μM) for RuP2P emerging as a standout agent.

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Section: Results and Discussionmentioning

confidence: 99%

Unraveling the Anticancer Efficacy and Biomolecular Properties of Ru(II)-Arene Complexes of Pyrene-Based Thiosemicarbazone Ligands: A Comprehensive In Silico/In Vitro Exploration

Vadakkedathu Palakkeezhillam,

Haribabu,

Kumar

et al. 2024

Organometallics

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“…Ethidium bromide (EB), on the other hand, is a counterstain that selectively enters cells that have damaged cytoplasmic membranes. It then stains the red nucleus and overshadowing AO …”

Section: Resultsmentioning

confidence: 99%

“…It then stains the red nucleus and overshadowing AO. 71 When AO and EB are combined in a dual AO/EB staining, viable cells are identifiable by a green nucleus, whereas early apoptotic cells are characterized by condensed chromatin and a nucleus showing a bright green-orange, and late apoptotic cells with an exclusively permeated damaged membrane presenting an orange-red nucleus are illuminated. 72 Notably, EB can penetrate damaged membranes in cells undergoing late apoptosis, whereas necrotic cells display a typical orange-red nucleus.…”

Section: Table 5 Electrochemical Titrations Parametersmentioning

confidence: 99%

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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N-phenethyl-2-(1H-1,2,3-triazol-1-yl)acetamide derivatives: Synthesis, crystal structure and molecular docking studies against SARS-CoV-2

Cedillo–Cruz,

Villalobos–López,

Cruz

et al. 2024

Journal of Molecular Structure

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Exploration of cytotoxic potential and tubulin polymerization inhibition activity of cis-stilbene-1,2,3-triazole congeners

Abstract: To scrutinize cis-stilbene based molecules with potential anticancer and tubulin polymerization inhibition activity, a new series of cis-stilbene-1,2,3-triazole congeners was designed and synthesized via a click chemistry protocol.

Cited by 5 publications

References 28 publications

Unraveling the Anticancer Efficacy and Biomolecular Properties of Ru(II)-Arene Complexes of Pyrene-Based Thiosemicarbazone Ligands: A Comprehensive In Silico/In Vitro Exploration

Unraveling the Anticancer Efficacy and Biomolecular Properties of Ru(II)-Arene Complexes of Pyrene-Based Thiosemicarbazone Ligands: A Comprehensive In Silico/In Vitro Exploration

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

N-phenethyl-2-(1H-1,2,3-triazol-1-yl)acetamide derivatives: Synthesis, crystal structure and molecular docking studies against SARS-CoV-2

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