Mimicking anaesthetic-receptor interaction: A combined spectroscopic and computational study of propofol⋯phenol

  1. León, I. 1
  2. Millán, J. 2
  3. Cocinero, E.J. 1
  4. Lesarri, A. 3
  5. Castaño, F. 1
  6. Fernández, J.A. 1
  1. 1 Universidad del País Vasco/Euskal Herriko Unibertsitatea

    Universidad del País Vasco/Euskal Herriko Unibertsitatea

    Lejona, España

    ROR https://ror.org/000xsnr85

  2. 2 Universidad de La Rioja

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  3. 3 Universidad de Valladolid

    Universidad de Valladolid

    Valladolid, España

    ROR https://ror.org/01fvbaw18

Physical Chemistry Chemical Physics

ISSN: 1463-9076

Year of publication: 2012

Volume: 14

Issue: 25

Pages: 8956-8963

Type: Article

DOI: 10.1039/C2CP40656J PMID: 22516915 SCOPUS: 2-s2.0-84862282466 WoS: WOS:000305006200020 GOOGLE SCHOLAR

More publications in: Physical Chemistry Chemical Physics

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Propofol is a general anaesthetic that exerts its action by interaction with the GABA A 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. © 2012 the Owner Societies.