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Intramolecular Proton and Charge Transfer of Pyrene-based trans-Stilbene Salicylic Acids Applied to Detection of Aggregated Proteins.
Zhang, Jun; Wang, Jun; Sandberg, Alexander; Wu, Xiongyu; Nyström, Sofie; LeVine, Harry; Konradsson, Peter; Hammarström, Per; Durbeej, Bo; Lindgren, Mikael.
Afiliação
  • Zhang J; Division of Chemistry Department of Physics, Chemistry and Biology, Linköping University, 581 83, Linköping, Sweden.
  • Wang J; Division of Theoretical Chemistry Department of Physics, Chemistry and Biology, Linköping University, 581 83, Linköping, Sweden.
  • Sandberg A; Division of Chemistry Department of Physics, Chemistry and Biology, Linköping University, 581 83, Linköping, Sweden.
  • Wu X; Division of Chemistry Department of Physics, Chemistry and Biology, Linköping University, 581 83, Linköping, Sweden.
  • Nyström S; Division of Chemistry Department of Physics, Chemistry and Biology, Linköping University, 581 83, Linköping, Sweden.
  • LeVine H; Sanders-Brown Center on Aging, University of Kentucky, KY 40536-0230, Lexington, USA.
  • Konradsson P; Division of Chemistry Department of Physics, Chemistry and Biology, Linköping University, 581 83, Linköping, Sweden.
  • Hammarström P; Division of Chemistry Department of Physics, Chemistry and Biology, Linköping University, 581 83, Linköping, Sweden.
  • Durbeej B; Division of Theoretical Chemistry Department of Physics, Chemistry and Biology, Linköping University, 581 83, Linköping, Sweden.
  • Lindgren M; Division of Chemistry Department of Physics, Chemistry and Biology, Linköping University, 581 83, Linköping, Sweden.
Chemphyschem ; 19(22): 3001-3009, 2018 11 19.
Article em En | MEDLINE | ID: mdl-30183138
ABSTRACT
Two analogues to the fluorescent amyloid probe 2,5-bis(4'-hydroxy-3'-carboxy-styryl)benzene (X-34) were synthesized based on the trans-stilbene pyrene scaffold (Py1SA and Py2SA). The compounds show strikingly different emission spectra when bound to preformed Aß1-42 fibrils. This remarkable emission difference is retained when bound to amyloid fibrils of four distinct proteins, suggesting a common binding configuration for each molecule. Density functional theory calculations show that Py1SA is twisted, while Py2SA is more planar. Still, an analysis of the highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) of the two compounds indicates that the degree of electronic coupling between the pyrene and salicylic acid (SA) moieties is larger in Py1SA than in Py2SA. Excited state intramolecular proton transfer (ESIPT) coupled-charge transfer (ICT) was observed for the anionic form in polar solvents. We conclude that ICT properties of trans-stilbene derivatives can be utilized for amyloid probe design with large changes in emission spectra and decay times from analogous chemical structures depending on the detailed physical nature of the binding site.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Fragmentos de Peptídeos / Prótons / Pirenos / Estilbenos / Salicilatos / Peptídeos beta-Amiloides Tipo de estudo: Diagnostic_studies Idioma: En Revista: Chemphyschem Assunto da revista: BIOFISICA / QUIMICA Ano de publicação: 2018 Tipo de documento: Article País de afiliação: Suécia

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Fragmentos de Peptídeos / Prótons / Pirenos / Estilbenos / Salicilatos / Peptídeos beta-Amiloides Tipo de estudo: Diagnostic_studies Idioma: En Revista: Chemphyschem Assunto da revista: BIOFISICA / QUIMICA Ano de publicação: 2018 Tipo de documento: Article País de afiliação: Suécia