Uncoupling the structure–activity relationships of β2 adrenergic receptor ligands from membrane binding

Ligand binding to membrane proteins may be significantly influenced by the interaction of ligands with the membrane. In particular, the microscopic ligand concentration within the membrane surface solvation layer may exceed that in bulk solvent, resulting in overestimation of the intrinsic protein−l...

Full description

Bibliographic Details
Main Authors: Dickson, Callum J., Hornak, Victor, Velez-Vega, Camilo, McKay, Daniel J.J., Reilly, John, Sandham, David A., Shaw, Duncan, Fairhurst, Robin A., Charlton, Steven J., Sykes, David A., Pearlstein, Robert, Duca, Jose S.
Format: Article
Published: American Chemical Society 2016
Online Access:https://eprints.nottingham.ac.uk/38577/
_version_ 1848795644069675008
author Dickson, Callum J.
Hornak, Victor
Velez-Vega, Camilo
McKay, Daniel J.J.
Reilly, John
Sandham, David A.
Shaw, Duncan
Fairhurst, Robin A.
Charlton, Steven J.
Sykes, David A.
Pearlstein, Robert
Duca, Jose S.
author_facet Dickson, Callum J.
Hornak, Victor
Velez-Vega, Camilo
McKay, Daniel J.J.
Reilly, John
Sandham, David A.
Shaw, Duncan
Fairhurst, Robin A.
Charlton, Steven J.
Sykes, David A.
Pearlstein, Robert
Duca, Jose S.
author_sort Dickson, Callum J.
building Nottingham Research Data Repository
collection Online Access
description Ligand binding to membrane proteins may be significantly influenced by the interaction of ligands with the membrane. In particular, the microscopic ligand concentration within the membrane surface solvation layer may exceed that in bulk solvent, resulting in overestimation of the intrinsic protein−ligand binding contribution to the apparent/measured affinity. Using published binding data for a set of small molecules with the β2 adrenergic receptor, we demonstrate that deconvolution of membrane and protein binding contributions allows for improved structure−activity relationship analysis and structure-based drug design. Molecular dynamics simulations of ligand bound membrane protein complexes were used to validate binding poses, allowing analysis of key interactions and binding site solvation to develop structure−activity relationships of β2 ligand binding. The resulting relationships are consistent with intrinsic binding affinity (corrected for membrane interaction). The successful structure-based design of ligands targeting membrane proteins may require an assessment of membrane affinity to uncouple protein binding from membrane interactions.
first_indexed 2025-11-14T19:35:21Z
format Article
id nottingham-38577
institution University of Nottingham Malaysia Campus
institution_category Local University
last_indexed 2025-11-14T19:35:21Z
publishDate 2016
publisher American Chemical Society
recordtype eprints
repository_type Digital Repository
spelling nottingham-385772020-05-04T17:49:27Z https://eprints.nottingham.ac.uk/38577/ Uncoupling the structure–activity relationships of β2 adrenergic receptor ligands from membrane binding Dickson, Callum J. Hornak, Victor Velez-Vega, Camilo McKay, Daniel J.J. Reilly, John Sandham, David A. Shaw, Duncan Fairhurst, Robin A. Charlton, Steven J. Sykes, David A. Pearlstein, Robert Duca, Jose S. Ligand binding to membrane proteins may be significantly influenced by the interaction of ligands with the membrane. In particular, the microscopic ligand concentration within the membrane surface solvation layer may exceed that in bulk solvent, resulting in overestimation of the intrinsic protein−ligand binding contribution to the apparent/measured affinity. Using published binding data for a set of small molecules with the β2 adrenergic receptor, we demonstrate that deconvolution of membrane and protein binding contributions allows for improved structure−activity relationship analysis and structure-based drug design. Molecular dynamics simulations of ligand bound membrane protein complexes were used to validate binding poses, allowing analysis of key interactions and binding site solvation to develop structure−activity relationships of β2 ligand binding. The resulting relationships are consistent with intrinsic binding affinity (corrected for membrane interaction). The successful structure-based design of ligands targeting membrane proteins may require an assessment of membrane affinity to uncouple protein binding from membrane interactions. American Chemical Society 2016-05-30 Article PeerReviewed Dickson, Callum J., Hornak, Victor, Velez-Vega, Camilo, McKay, Daniel J.J., Reilly, John, Sandham, David A., Shaw, Duncan, Fairhurst, Robin A., Charlton, Steven J., Sykes, David A., Pearlstein, Robert and Duca, Jose S. (2016) Uncoupling the structure–activity relationships of β2 adrenergic receptor ligands from membrane binding. Journal of Medicinal Chemistry, 59 (12). pp. 5780-5789. ISSN 1520-4804 http://pubs.acs.org/doi/abs/10.1021/acs.jmedchem.6b00358 doi:10.1021/acs.jmedchem.6b00358 doi:10.1021/acs.jmedchem.6b00358
spellingShingle Dickson, Callum J.
Hornak, Victor
Velez-Vega, Camilo
McKay, Daniel J.J.
Reilly, John
Sandham, David A.
Shaw, Duncan
Fairhurst, Robin A.
Charlton, Steven J.
Sykes, David A.
Pearlstein, Robert
Duca, Jose S.
Uncoupling the structure–activity relationships of β2 adrenergic receptor ligands from membrane binding
title Uncoupling the structure–activity relationships of β2 adrenergic receptor ligands from membrane binding
title_full Uncoupling the structure–activity relationships of β2 adrenergic receptor ligands from membrane binding
title_fullStr Uncoupling the structure–activity relationships of β2 adrenergic receptor ligands from membrane binding
title_full_unstemmed Uncoupling the structure–activity relationships of β2 adrenergic receptor ligands from membrane binding
title_short Uncoupling the structure–activity relationships of β2 adrenergic receptor ligands from membrane binding
title_sort uncoupling the structure–activity relationships of β2 adrenergic receptor ligands from membrane binding
url https://eprints.nottingham.ac.uk/38577/
https://eprints.nottingham.ac.uk/38577/
https://eprints.nottingham.ac.uk/38577/