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Peer-reviewedCC BYInternational journal of molecular sciences

Microwave-Assisted Synthesis, Cytotoxic Profile, and Cellular Mechanism Analysis of Carveoylphenol Derivatives

  • Evelyn Muñoz1
  • Constanza Reyes2
  • Joan Villena3
  • Rut Vergara3
  • Guillermo Bravo4
  • Alejandro Madrid2
4 affiliations
  1. 1Facultad de Ciencias Químicas, Departamento de Química Orgánica, Universidad de Concepción, Concepción 4030000, Chile
  2. 2Laboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, Chile
  3. 3Center of Interdisciplinary Biomedical and Engineering Research for Health (MEDING), Escuela de Medicina, Universidad de Valparaíso, Angamos 655, Reñaca, Viña del Mar 2340000, Chile
  4. 4Departamento de Química y Medio Ambiente, Universidad Técnica Federico Santa Maria, Avenida Federico Santa Maria 6090, Viña del Mar 2520000, Chile
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Abstract

A series of carveoylphenol derivatives (1–12) was synthesized using a microwave-assisted approach and evaluated through an integrated in vitro and in silico strategy. Cytotoxicity was assessed against PC-3, MCF-7, and HT-29 human cancer lines, using non-tumorigenic CoN CCD841 cells as a reference. Derivatives 1, 2, 5, 6, 7, 8, and 11 exhibited activity (IC50 < 100 µM) against at least one cancer line, with 2 showing the highest potency (IC50 = 23.2 µM). Flow cytometry of compounds 1, 2, and 5 revealed structure-dependent cellular responses, where 2 at 40 µM induced maximum intracellular ROS generation (39.6%), 1 reduced mitochondrial membrane integrity to 42.1% intact cells, and 5 produced peak caspase activation (34.5%). Molecular docking against caspase-3 yielded predicted binding energies for all three molecules, with 5 scoring −6.4 kcal/mol. SwissADME analysis indicated comparable physicochemical profiles, high predicted gastrointestinal absorption, and potential blood–brain barrier permeability for these three derivatives. Overall, carveoylphenols, particularly compound 2, represent promising scaffolds for further structural optimization and mechanistic investigation.

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Cite

BibTeXRIS
BibTeX
@article{munoz2026microwaveassisted,
  title = {{Microwave-Assisted Synthesis, Cytotoxic Profile, and Cellular Mechanism Analysis of Carveoylphenol Derivatives}},
  author = {Evelyn Muñoz and Constanza Reyes and Joan Villena and Rut Vergara and Guillermo Bravo and Alejandro Madrid},
  journal = {International journal of molecular sciences},
  year = {2026},
  month = sep,
  doi = {10.3390/ijms27198749},
  url = {https://europepmc.org/article/PMC/PMC13665034},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Microwave-Assisted Synthesis, Cytotoxic Profile, and Cellular Mechanism Analysis of Carveoylphenol Derivatives
AU  - Evelyn Muñoz
AU  - Constanza Reyes
AU  - Joan Villena
AU  - Rut Vergara
AU  - Guillermo Bravo
AU  - Alejandro Madrid
PY  - 2026
DA  - 2026/09/30
JO  - International journal of molecular sciences
DO  - 10.3390/ijms27198749
UR  - https://europepmc.org/article/PMC/PMC13665034
AB  - A series of carveoylphenol derivatives (1–12) was synthesized using a microwave-assisted approach and evaluated through an integrated in vitro and in silico strategy. Cytotoxicity was assessed against PC-3, MCF-7, and HT-29 human cancer lines, using non-tumorigenic CoN CCD841 cells as a reference. Derivatives 1, 2, 5, 6, 7, 8, and 11 exhibited activity (IC50 < 100 µM) against at least one cancer line, with 2 showing the highest potency (IC50 = 23.2 µM). Flow cytometry of compounds 1, 2, and 5 revealed structure-dependent cellular responses, where 2 at 40 µM induced maximum intracellular ROS generation (39.6%), 1 reduced mitochondrial membrane integrity to 42.1% intact cells, and 5 produced peak caspase activation (34.5%). Molecular docking against caspase-3 yielded predicted binding energies for all three molecules, with 5 scoring −6.4 kcal/mol. SwissADME analysis indicated comparable physicochemical profiles, high predicted gastrointestinal absorption, and potential blood–brain barrier permeability for these three derivatives. Overall, carveoylphenols, particularly compound 2, represent promising scaffolds for further structural optimization and mechanistic investigation.
SN  - 1422-0067
ER  -