Fragmentation of Golgi membranes by norrisolide and designed analogues

Bioorganic & Medicinal Chemistry Letters
Thomas P BradyEmmanuel A Theodorakis

Abstract

The effect of norrisolide (4) and designed analogues on the Golgi membranes is presented. We found that 4 is the first compound known to induce an irreversible vesiculation of these membranes. To investigate the chemical origins of this new effect we synthesized and evaluated a series of norrisolide analogues in which the chemical functionalities present in the parent structure were altered. Such structure/function studies suggest that the perhydroindane core of 4 is critical for binding to the target protein, while the C21 acetate unit is essential for the irreversible vesiculation of the Golgi membranes.

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Citations

Apr 20, 2006·Journal of the American Chemical Society·Brian C GoessMatthew D Shair
Nov 18, 2005·Organic Letters·Roland WeisserOliver Reiser
Nov 23, 2007·Natural Product Reports·Neil DixonJason Micklefield
Mar 25, 2010·Proceedings of the National Academy of Sciences of the United States of America·Martin J SchnermannLarry E Overman
Dec 25, 2015·Journal of Natural Products·Andrew M WhiteMary J Garson
Jul 12, 2014·Bioorganic & Medicinal Chemistry Letters·Michael P D'ErasmoRyan P Murelli
Sep 16, 2005·Chemistry : a European Journal·Thomas P BradyEmmanuel A Theodorakis
Feb 8, 2018·Journal of the American Chemical Society·Daniel J TaoLarry E Overman

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