Unraveling the benzocaine-receptor interaction at molecular level using mass-resolved spectroscopy.
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.
Departamento de Química Física, Facultad de Ciencia y Tecnología, Universidad del País Vasco (UPV/EHU) , B° Sarriena s/n, 48940 Leioa, Spain.
Edurne
E
Aguado
Iker
I
León
Judith
J
Millán
Emilio J
EJ
Cocinero
Sander
S
Jaeqx
Anouk M
AM
Rijs
Alberto
A
Lesarri
José A
JA
Fernández
D001566:Benzocaine / Q000737:chemistry*; D006860:Hydrogen Bonding; D007834:Lasers; D008958:Models, Molecular; D011789:Quantum Theory; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014050:Toluene / Q000737:chemistry*; D061566:Voltage-Gated Sodium Channels / Q000737:chemistry*
D061566:Voltage-Gated Sodium Channels; D014050:Toluene; D001566:Benzocaine