Chemical modification of the naphthoyl 3-position of JWH-015: in search of a fluorescent probe to the cannabinoid CB2 receptor

Andrew S Yates; Stephen W Doughty; David A Kendall; Barrie Kellam

doi:10.1016/j.bmcl.2005.05.049

Chemical modification of the naphthoyl 3-position of JWH-015: in search of a fluorescent probe to the cannabinoid CB2 receptor

Bioorg Med Chem Lett. 2005 Aug 15;15(16):3758-62. doi: 10.1016/j.bmcl.2005.05.049.

Authors

Andrew S Yates¹, Stephen W Doughty, David A Kendall, Barrie Kellam

Affiliation

¹ School of Pharmacy, Centre for Biomolecular Sciences, University of Nottingham, University Park, Nottingham NG7 2RD, UK.

PMID: 15993070
DOI: 10.1016/j.bmcl.2005.05.049

Abstract

In silico modelling was used to guide the positioning of the fluorescent dye NBD-F on the cannabinoid CB2 receptor agonist JWH-015. While the ultimate fluorescent conjugate lost extensive binding affinity to the cannabinoid CB2 receptor, affinity and efficacy studies on the naphthoyl 3-position modified precursor molecules have provided new insight into structure-activity relationships associated with this position.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Binding, Competitive / drug effects
Crystallography, X-Ray
Fluorescent Dyes / chemical synthesis
Fluorescent Dyes / chemistry*
Fluorescent Dyes / pharmacology*
Humans
Indoles / chemical synthesis
Indoles / chemistry*
Indoles / pharmacology*
Models, Molecular
Molecular Structure
Protein Conformation
Receptor, Cannabinoid, CB2 / agonists*
Receptor, Cannabinoid, CB2 / metabolism
Structure-Activity Relationship

Substances

Fluorescent Dyes
Indoles
Receptor, Cannabinoid, CB2
JHW 015