Unraveling the benzocaine-receptor interaction at molecular level using mass-resolved spectroscopy

  1. Aguado, Edurne . 2
  2. León, I. 2
  3. Millán, J. 1
  4. Cocinero, E.J. 2
  5. Jaeqx, S. 4
  6. Rijs, A.M. 4
  7. Lesarri, A. 3
  8. Fernández, J.A. 2
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Universidad del País Vasco/Euskal Herriko Unibertsitatea
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    Universidad del País Vasco/Euskal Herriko Unibertsitatea

    Lejona, España

    ROR https://ror.org/000xsnr85

  3. 3 Universidad de Valladolid
    info

    Universidad de Valladolid

    Valladolid, España

    ROR https://ror.org/01fvbaw18

  4. 4 Radboud University Nijmegen
    info

    Radboud University Nijmegen

    Nimega, Holanda

    ROR https://ror.org/016xsfp80

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Revista:
Journal of Physical Chemistry B

ISSN: 1520-6106

Año de publicación: 2013

Volumen: 117

Número: 43

Páginas: 13472-13480

Tipo: Artículo

DOI: 10.1021/JP4068944 SCOPUS: 2-s2.0-84887104644 WoS: WOS:000326608500009 GOOGLE SCHOLAR

Otras publicaciones en: Journal of Physical Chemistry B

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Resumen

The benzocaine-toluene cluster has been used as a model system to mimic the interaction between the local anesthetic benzocaine and the phenylalanine residue in Na+ channels. The cluster was generated in a supersonic expansion of benzocaine and toluene in helium. Using a combination of mass-resolved laser-based experimental techniques and computational methods, the complex was fully characterized, finding four conformational isomers in which the molecules are bound through N-H···π and π···π weak hydrogen bonds. The structures of the detected isomers closely resemble those predicted for benzocaine in the inner pore of the ion channels, giving experimental support to previously reported molecular chemistry models. © 2013 American Chemical Society.