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Free energy perturbation in the design of EED ligands as inhibitors of polycomb repressive complex 2 (PRC2) methyltransferase.

Authors :
O' Donovan DH
Gregson C
Packer MJ
Greenwood R
Pike KG
Kawatkar S
Bloecher A
Robinson J
Read J
Code E
Hsu JH
Shen M
Woods H
Barton P
Fillery S
Williamson B
Rawlins PB
Bagal SK
Source :
Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2021 May 01; Vol. 39, pp. 127904. Date of Electronic Publication: 2021 Mar 06.
Publication Year :
2021

Abstract

Free Energy Perturbation (FEP) calculations can provide high-confidence predictions of the interaction strength between a ligand and its protein target. We sought to explore a series of triazolopyrimidines which bind to the EED subunit of the PRC2 complex as potential anticancer therapeutics, using FEP calculations to inform compound design. Combining FEP predictions with a late-stage functionalisation (LSF) inspired synthetic approach allowed us to rapidly evaluate structural modifications in a previously unexplored region of the EED binding site. This approach generated a series of novel triazolopyrimidine EED ligands with improved physicochemical properties and which inhibit PRC2 methyltransferase activity in a cancer-relevant G401 cell line.<br /> (Copyright © 2021 Elsevier Ltd. All rights reserved.)

Details

Language :
English
ISSN :
1464-3405
Volume :
39
Database :
MEDLINE
Journal :
Bioorganic & medicinal chemistry letters
Publication Type :
Academic Journal
Accession number :
33684441
Full Text :
https://doi.org/10.1016/j.bmcl.2021.127904