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A synthesis strategy for tetracyclic terpenoids leads to agonists of ERβ

Author

Listed:
  • Wan Shin Kim

    (Burke Laboratory)

  • Zachary A. Shalit

    (Burke Laboratory)

  • Sidney M. Nguyen

    (Dartmouth College, Geisel School of Medicine, Department of Neurology)

  • Emmalie Schoepke

    (Washington University School of Medicine and St. Louis College of Pharmacy)

  • Alan Eastman

    (Dartmouth College, Geisel School of Medicine, Department of Molecular and Systems Biology)

  • Thomas P. Burris

    (Washington University School of Medicine and St. Louis College of Pharmacy)

  • Arti B. Gaur

    (Dartmouth College, Geisel School of Medicine, Department of Neurology)

  • Glenn C. Micalizio

    (Burke Laboratory)

Abstract

Natural product and natural product-like molecules continue to be important for the development of pharmaceutical agents, as molecules in this class play a vital role in the pipeline for new therapeutics. Among these, tetracyclic terpenoids are privileged, with >100 being FDA-approved drugs. Despite this significant pharmaceutical success, there remain considerable limitations to broad medicinal exploitation of the class due to lingering scientific challenges associated with compound availability. Here, we report a concise asymmetric route to forging natural and unnatural (enantiomeric) C19 and C20 tetracyclic terpenoid skeletons suitable to drive medicinal exploration. While efforts have been focused on establishing the chemical science, early investigations reveal that the emerging chemical technology can deliver compositions of matter that are potent and selective agonists of the estrogen receptor beta, and that are selectively cytotoxic in two different glioblastoma cell lines (U251 and U87).

Suggested Citation

  • Wan Shin Kim & Zachary A. Shalit & Sidney M. Nguyen & Emmalie Schoepke & Alan Eastman & Thomas P. Burris & Arti B. Gaur & Glenn C. Micalizio, 2019. "A synthesis strategy for tetracyclic terpenoids leads to agonists of ERβ," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-10415-6
    DOI: 10.1038/s41467-019-10415-6
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    Cited by:

    1. Yan Zou & Yajing Sun & Yibin Wang & Dongya Zhang & Huiqing Yang & Xin Wang & Meng Zheng & Bingyang Shi, 2023. "Cancer cell-mitochondria hybrid membrane coated Gboxin loaded nanomedicines for glioblastoma treatment," Nature Communications, Nature, vol. 14(1), pages 1-19, December.

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