Graphene-based hybrid for enantioselective sensing applications
Zor, Erhan (Institut Català de Nanociència i Nanotecnologia)
Morales-Narváez, Eden (Institut Català de Nanociència i Nanotecnologia)
Alpaydin, Sabri (Necmettin Erbakan University. Department of Chemistry)
Bingol, Haluk (Necmettin Erbakan University. Department of Chemistry)
Ersoz, Mustafa (Selcuk University)
Merkoçi, Arben (Institut Català de Nanociència i Nanotecnologia)

Data:	2017
Resum:	Chirality is a major field of research of chemical biology and is essential in pharmacology. Accordingly, approaches for distinguishing between different chiral forms of a compound are of great interest. We report on an efficient and generic enantioselective sensor that is achieved by coupling reduced graphene oxide with γ-cyclodextrin (rGO/γ-CD). The enantioselective sensing capability of the resulting structure was operated in both electrical and optical mode for of tryptophan enantiomers (D-/L-Trp). In this sense, voltammetric and photoluminescence measurements were conducted and the experimental results were compared to molecular docking method. We gain insight into the occurring recognition mechanism with selectivity toward D- and L-Trp as shown in voltammetric, photoluminescence and molecular docking responses. As an enantioselective solid phase on an electrochemical transducer, thanks to the different dimensional interaction of enantiomers with hybrid material, a discrepancy occurs in the Gibbs free energy leading to a difference in oxidation peak potential as observed in electrochemical measurements. The optical sensing principle is based on the energy transfer phenomenon that occurs between photoexcited D-/L-Trp enantiomers and rGO/γ-CD giving rise to an enantioselective photoluminescence quenching due to the tendency of chiral enantiomers to form complexes with γ-CD in different molecular orientations as demonstrated by molecular docking studies. The approach, which is the first demonstration of applicability of molecular docking to show both enantioselective electrochemical and photoluminescence quenching capabilities of a graphene-related hybrid material, is truly new and may have broad interest in combination of experimental and computational methods for enantiosensing of chiral molecules.
Ajuts:	Agència de Gestió d'Ajuts Universitaris i de Recerca 2014/SGR-260 Ministerio de Economía y Competitividad SEV-2013-0295 Ministerio de Economía y Competitividad MAT2014-52485-P
Drets:	Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, i la comunicació pública de l'obra, sempre que no sigui amb finalitats comercials, i sempre que es reconegui l'autoria de l'obra original. No es permet la creació d'obres derivades.
Llengua:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Matèria:	Graphene oxide ; Cyclodextrin ; Enantioselectivity ; Sensor ; Molecular docking
Publicat a:	Biosensors & bioelectronics, Vol. 87 (January 2017) , p. 410-416, ISSN 1873-4235

DOI: 10.1016/j.bios.2016.08.074

Postprint 23 p, 2.1 MB

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