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Sphaerococcenol A Derivatives: Design, Synthesis, and Cytotoxicity. | LitMetric

AI Article Synopsis

  • Sphaerococcenol A is a potent cytotoxic compound derived from red algae, and its analogues were developed through chemical reactions to potentially enhance their effectiveness against cancer cells.
  • A total of six new analogues were tested on A549, DU-145, and MCF-7 cancer cell lines, revealing varying levels of cytotoxicity, with some compounds showing notably low IC values, indicating stronger effects.
  • The study highlights the potential of these analogues to further research on sphaerococcenol A as a framework for creating new therapeutic agents, although some modifications resulted in decreased cytotoxic activity.

Article Abstract

Sphaerococcenol A is a cytotoxic bromoditerpene biosynthesized by the red alga . A series of its analogues (-) was designed and semi-synthesized using thiol-Michael additions and enone reduction, and the structures of these analogues were characterized by spectroscopic methods. Cytotoxic analyses (1-100 µM; 24 h) were accomplished on A549, DU-145, and MCF-7 cells. The six novel sphaerococcenol A analogues displayed an IC range between 14.31 and 70.11 µM on A549, DU-145, and MCF-7 malignant cells. Compound , resulting from the chemical addition of 4-methoxybenzenethiol, exhibited the smallest IC values on the A549 (18.70 µM) and DU-145 (15.82 µM) cell lines, and compound , resulting from the chemical addition of propanethiol, exhibited the smallest IC value (14.31 µM) on MCF-7 cells. The highest IC values were exhibited by compound , suggesting that the chemical addition of benzylthiol led to a loss of cytotoxic activity. The remaining chemical modifications were not able to potentiate the cytotoxicity of the original compounds. Regarding A549 cell viability, analogue exhibited a marked effect on mitochondrial function, which was accompanied by an increase in ROS levels, Caspase-3 activation, and DNA fragmentation and condensation. This study opens new avenues for research by exploring sphaerococcenol A as a scaffold for the synthesis of novel bioactive molecules.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11432771PMC
http://dx.doi.org/10.3390/md22090408DOI Listing

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