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Cell Death Associated with Abnormal Mitosis Observed by Confocal Imaging in Live Cancer Cells
Published on: August 21, 2013
Novel benzofuran/pterostilbene hybrids trigger programmed cell death and impair migration in CRC cells
Angie Herrera-Ramírez1, Rubén Becerra-Quintana1, Andrés F Yepes1
1Química de Plantas Colombianas, Faculty of Exact and Natural Sciences, Institute of Chemistry, University of Antioquia (UdeA), Medellín, Colombia.
Abstract:
Colorectal cancer (CRC) remains one of the most prevalent and lethal malignancies worldwide, highlighting the urgent need for developing effective treatments. Molecular hybridization is a promising strategy for identifying new bioactive compounds. This study focused on designing and synthesizing a novel series of benzofuran-pterostilbene hybrid molecules. These compounds were successfully obtained, and their structures were elucidated by spectroscopic analysis. In addition, the activity of the hybrids was evaluated against colorectal adenocarcinoma cells. After the treatments, hybrids 6d and 6e exhibited the highest activity, with GI50 values of 11.93 ± 2.38 µM and 4.74 ± 0.38 µM, respectively, suggesting antiproliferative effects and measurable cytotoxicity under the tested conditions. Additionally, Hoechst 33342 fluorescence imaging revealed chromatin condensation and nuclear fragmentation, along with a diffuse DiOC₆ fluorescence pattern relative to the control, suggesting a form of programmed cell death, which was further supported by flow cytometric analysis showing an increased proportion of hypodiploid cells following propidium iodide staining. In parallel, wound-healing assays demonstrated impaired migration and cytotoxic effects that affected cell viability and structural integrity. Molecular docking simulations showed that compounds 6d and 6e bind strongly to mutant p53, CDK4, and PARP-1 proteins, which, in turn, may explain at the molecular level the in vitro cytotoxic effect of these compounds in SW480 colon cancer cells. Lastly, pharmacokinetic and toxicological modelling suggests that hybrids 6d and 6e possess optimal biopharmaceutical profiles with no major safety concerns. All these findings highlight the potential of the benzofuran-pterostilbene scaffold, with compounds 6d and 6e emerging as strong candidates for further evaluation against colorectal cancer.
Insights
Novel benzofuran-pterostilbene hybrids show potent anti-colorectal cancer activity. Compounds 6d and 6e effectively reduced cancer cell viability and migration, indicating promise for new colorectal cancer treatments.
Area of Science:
- Medicinal Chemistry
- Molecular Biology
- Pharmacology
Background:
- Colorectal cancer (CRC) is a leading cause of cancer mortality globally.
- There is a critical need for novel and effective CRC therapies.
- Molecular hybridization offers a strategy to discover new bioactive compounds.
Purpose of the Study:
- To design, synthesize, and evaluate a new series of benzofuran-pterostilbene hybrid molecules.
- To assess the antiproliferative and cytotoxic effects of these hybrids against colorectal adenocarcinoma cells.
- To investigate the molecular mechanisms underlying their efficacy and predict their drug-like properties.
Main Methods:
- Synthesis and structural elucidation of benzofuran-pterostilbene hybrids.
- In vitro cytotoxicity assays (GI50 determination) on colorectal cancer cells.
- Apoptosis assays (Hoechst staining, flow cytometry) and cell migration assays (wound-healing).
- Molecular docking simulations against key cancer targets (mutant p53, CDK4, PARP-1).
- Pharmacokinetic and toxicological modeling.
Main Results:
- Hybrids 6d and 6e demonstrated significant cytotoxicity, with GI50 values of 11.93 µM and 4.74 µM, respectively.
- Apoptosis induction was evidenced by chromatin condensation, nuclear fragmentation, and increased hypodiploid cell populations.
- Impaired cell migration and viability were observed, alongside cytotoxic effects on cell integrity.
- Molecular docking revealed strong binding of 6d and 6e to mutant p53, CDK4, and PARP-1.
- Computational modeling predicted favorable pharmacokinetic and toxicological profiles for 6d and 6e.
Conclusions:
- The benzofuran-pterostilbene scaffold is a promising platform for developing novel anti-colorectal cancer agents.
- Compounds 6d and 6e exhibit potent in vitro anticancer activity through apoptosis induction and inhibition of cell migration.
- These hybrids represent viable candidates for further preclinical development against colorectal cancer, supported by favorable predicted drug-like properties.
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