JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 68 No 3 (2023): Journal of the Chilean Chemical Society
Original Research Papers

DOCKING SIMULATIONS OF STEROIDAL OXIMES TOWARD ESTROGEN RECEPTOR ALPHA. ANALYSIS OF THEIR POTENTIAL ANTICANCER ACTIVITY

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  • Dayana Alonso,
  • Dayana Mesa,
  • Giselle Hernández,
  • Andres F. Olea,
  • Luis Espinoza,
  • Yamilet Coll
Dayana Alonso
Laboratory of Synthetic and Biomolecular Chemistry, Faculty of Chemistry, University of Havana, Zapata and G, Havana 10400, Cuba.
Dayana Mesa
Center for Natural Product Research, Faculty of Chemistry, University of Havana, Zapata and G, Havana 10400, Cuba.
Giselle Hernández
Center for Natural Product Research, Faculty of Chemistry, University of Havana, Zapata and G, Havana 10400, Cuba.
Andres F. Olea
Grupo QBAB, Instituto de Ciencias Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, Llano Subercaseaux 2801, San Miguel, Santiago, Chile.
Luis Espinoza
Departamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, Valparaíso 2340000, Chile
Yamilet Coll
Center for Natural Product Research, Faculty of Chemistry, University of Havana, Zapata and G, Havana 10400, Cuba.
Published December 31, 2023
Keywords
  • breast cancer,
  • estrogen receptor,
  • docking,
  • hydroxyimino steroid
How to Cite
Alonso, D., Mesa, D., Hernández, G., Olea, A. F., Espinoza, L., & Coll, Y. (2023). DOCKING SIMULATIONS OF STEROIDAL OXIMES TOWARD ESTROGEN RECEPTOR ALPHA. ANALYSIS OF THEIR POTENTIAL ANTICANCER ACTIVITY. Journal of the Chilean Chemical Society, 68(3), 5918-5923. Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/2463

Copyright (c) 2023 SChQ

Creative Commons License

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Abstract

Breast cancer is the most common cause of cancer deaths in women. Normal breast cells and most breast cancer cells have receptors that attach to circulating estrogen and progesterone. Estrogen and progesterone bind to the receptors and may cause cancer cells to proliferate. Drugs, currently being used to treat this disease are not so effective and cause adverse effects. For this reason, the quest of new compounds that bind to the estrogen receptor (ER), activating or inhibiting ERs selectively, is a very active field of research. In this task, molecular docking plays a vital role in drug design, either as a tool in drug discovery and analysis of protein-ligand interactions. In this work, 26 steroidal oximes, which are derivatives of diosgenin, were analyzed using docking studies, and compared against the estrogen receptor (ERa). The 3D structures of ERa were downloaded from Protein Data Bank (3ERT) and optimized using pdb2pqr.py. Modifications in rings A and B were made, and both oxime configurations (E or Z) were considered. Results for hydroximino steroids were compared with those obtained for compounds exhibiting biological activity against this type of cancer, namely, 4-hydroxytamoxifen, diosgenin and 6,23-dihydroximino diosgenin derivative. Molecular docking studies on ERa revealed that three mono oximes were found to interact with the protein more efficiently and have the best docking score. Thus, modification of diosgenin with oxime groups could lead to antiproliferative steroidal compounds, and therefore they could be considered for further research and in vivo evaluations for breast cancer treatment and management strategies

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