Sphaeropsidin A C15-C16 Cross-Metathesis Analogues with Potent Anticancer Activity.

ABSTRACT: We recently discovered that sphaeropsidin A (SphA), a fungal metabolite from Diplodia cupressi, overcomes apoptosis resistance in cancer cells by inducing cellular shrinkage by impairing regulatory volume increase. Previously, we prepared a pyrene-conjugated derivative of SphA by a cross-metathesis reaction involving the phytotoxin's C15,C16-alkene. This derivative's evaluation in a cancer cell panel revealed a significant increase in potency, with the IC₅₀ values 5-10× lower than those displayed by the original natural product. Herein, we describe the preparation and anticancer evaluation of fifteen novel C15,C16-alkene cross-metathesis analogues in which the pyrene moiety was replaced with other aromatic or non-aromatic hydrophobic groups. The idea for this replacement was to

SUBMITTER: Wagh SB 

PROVIDER: S-EPMC11645891 | biostudies-literature | 2024 Sep

REPOSITORIES: biostudies-literature