Issue 25, 2012
From the journal:

Physical Chemistry Chemical Physics

Mimicking anaesthetic–receptor interaction: a combined spectroscopic and computational study of propofol⋯phenol†

Iker León,a   Judith Millán,b   Emilio J. Cocinero,a   Alberto Lesarri,c   Fernando Castañoa  and  José A. Fernández*a  

* Corresponding authors

a Dpto. Química Física, Facultad de Ciencia y Tecnología, Universidad del País Vasco, Bo Sarriena s/n, Leioa 48940, Spain
E-mail: josea.fernandez@ehu.es
Web: https://sites.google.com/site/gesemupv/
Fax: +34 946013500
Tel: +34 946015387

b Dpto. Química, Facultad de Ciencias, Estudios Agroalimentarios e Informática, Universidad de La Rioja, Madre de Dios, 51, Logroño 26006, Spain

c Dpto. de Química Física y Química Inorgánica, Facultad de Ciencias, Universidad de Valladolid, E-47005 Valladolid, Spain

Abstract

Propofol is a general anaesthetic that exerts its action by interaction with the GABAA receptor. Crystallographic studies suggest that there is a direct interaction between propofol and the phenolic residue of a tyrosine in the channel. In this study we create propofol⋯phenol clusters by their co-expansion in jets. The complex is probed using a set of mass-resolved spectroscopic strategies: 2-color REMPI, UV/UV hole-burning, IR/UV double resonance and the novel technique IR/IR/UV triple resonance. The existence of at least six different isomers in the expansion is demonstrated. All the isomers are stabilized by interactions between their aromatic rings. Additionally, in some conformers the OH moieties form hydrogen bonds in some of the isomers, with propofol and phenol alternating their donor–acceptor roles, while in others the –OH⋯OH angle points to a dipole–dipole interaction. Interpretation of the data in the light of dispersion-corrected DFT calculations shows that shallow barriers separate all the isomers, both in the ground and excited electronic states. Comparison of the structures of the complex with the X-ray diffraction data is also offered.

Graphical abstract: Mimicking anaesthetic–receptor interaction: a combined spectroscopic and computational study of propofol⋯phenol

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Article information

DOI
https://doi.org/10.1039/C2CP40656J
Article type
Paper
Submitted
01 Mar 2012
Accepted
04 Apr 2012
First published
04 Apr 2012

Phys. Chem. Chem. Phys., 2012,14, 8956-8963

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Mimicking anaesthetic–receptor interaction: a combined spectroscopic and computational study of propofol⋯phenol

I. León, J. Millán, E. J. Cocinero, A. Lesarri, F. Castaño and J. A. Fernández, Phys. Chem. Chem. Phys., 2012, 14, 8956 DOI: 10.1039/C2CP40656J

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