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      Structure-based design of a novel synthetic spiroketal pyran as a pharmacophore for the marine natural product spongistatin 1

      , , , ,
      Bioorganic & Medicinal Chemistry Letters
      Elsevier BV

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          Abstract

          SPIKET-P, a novel synthetic spiroketal pyran, was rationally designed as a pharmocophore for the tubulin depolymerizing marine natural product Spongistatin 1. SPIKET-P was prepared from the commercially available benzyl (R)-(-)-glycidyl ether using a versatile 11-step synthetic scheme in a stereocontrolled fashion. At nanomolar concentrations, SPIKET-P caused tubulin depolymerization in cell-free turbidity assays and exhibited potent cytotoxic activity against cancer cells as evidenced by destruction of microtubule organization, and prevention of mitotic spindle formation in human breast cancer cells.

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          Author and article information

          Journal
          Bioorganic & Medicinal Chemistry Letters
          Bioorganic & Medicinal Chemistry Letters
          Elsevier BV
          0960894X
          March 2000
          March 2000
          : 10
          : 6
          : 541-545
          Article
          10.1016/S0960-894X(00)00044-5
          10741549
          abe3c3fb-8e5d-45a5-80e1-908f9650513e
          © 2000

          https://www.elsevier.com/tdm/userlicense/1.0/

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