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Chemistry and Biology of Ophiobolin A and Its Congeners

Chemistry and Biology of Ophiobolin A and Its Congeners

Marco Masi, Ramesh Dasari, Antonio Evidente, Veronique Mathieu, Alexander Kornienko

Bioorg Med Chem Lett. 2019 Apr 1;29(7):859-869.

PMID: 30765189

Abstract:

Ophiobolin A is a fungal secondary metabolite that was found to have significant activity against apoptosis-resistant glioblastoma cells through the induction of a non-apoptotic cell death, offering an innovative strategy to combat this aggressive cancer. The current article aims to make the bridge between the anti-cancer effects of ophiobolin A and its unique reaction with primary amines and suggests that pyrrolylation of lysine residues on its intracellular target protein(s) and/or phosphatidylethanolamine lipid is responsible for its biological effects. The article also discusses chemical derivatization of ophiobolin A to establish first synthetically generated structure-activity relationship. Finally, the reported total synthesis efforts toward the ophiobolin class of sesterterpenes are discussed and identified as a fertile area for improvement in pursuit of these molecules as anticancer agents.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP4611056	Ophiobolin A		4611-05-6	Price

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