Synthesis and spectroscopic characterization of novel GFP chromophore analogues based on aminoimidazolone derivatives

Attila Jancsó; Ervin Kovács; Levente Cseri; Balázs J Rózsa; Gábor Galbács; Imre G Csizmadia; Zoltán Mucsi

doi:10.1016/j.saa.2019.03.111

Synthesis and spectroscopic characterization of novel GFP chromophore analogues based on aminoimidazolone derivatives

Spectrochim Acta A Mol Biomol Spectrosc. 2019 Jul 5:218:161-170. doi: 10.1016/j.saa.2019.03.111. Epub 2019 Apr 6.

Authors

Attila Jancsó¹, Ervin Kovács², Levente Cseri³, Balázs J Rózsa⁴, Gábor Galbács¹, Imre G Csizmadia⁵, Zoltán Mucsi⁶

Affiliations

¹ Department of Inorganic and Analytical Chemistry, University of Szeged, Szeged H-6720, Hungary.
² Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, H-1117 Budapest, Hungary; Department of Chemistry, Femtonics Inc., H-1094 Budapest, Hungary.
³ Department of Chemistry, Femtonics Inc., H-1094 Budapest, Hungary; School of Chemical Engineering & Analytical Science, The University of Manchester, Manchester, United Kingdom.
⁴ Two-Photon Measurement Technology Research Group, The Faculty of Information Technology, Pázmány Péter Catholic University, Budapest H-1083, Hungary; Laboratory of 3D Functional Imaging of Neuronal Networks and Dendritic Integration, Institute of Experimental Medicine, Hungarian Academy of Sciences, Budapest H-1083, Hungary.
⁵ Department of Chemistry, University of Toronto, Toronto, ON M5S 3H6, Canada.
⁶ Department of Chemistry, Femtonics Inc., H-1094 Budapest, Hungary; Two-Photon Measurement Technology Research Group, The Faculty of Information Technology, Pázmány Péter Catholic University, Budapest H-1083, Hungary. Electronic address: zmucsi@femtonics.eu.

PMID: 30986708
DOI: 10.1016/j.saa.2019.03.111

Abstract

In order to improve the fluorescence properties of the green fluorescent protein chromophore, p‑HOBDI ((5‑(4‑hydroxybenzylidene)‑2,3‑dimethyl‑3,5‑dihydro‑4H‑imidazol‑4‑one), sixteen dihydroimidazolone derivates were synthesized from thiohydantoin and arylaldehydes. The synthesis developed is an efficient, novel, one-pot procedure. The study provides a detailed description of the spectroscopic characteristics of the newly synthesized compounds, using p‑HOBDI as a reference. The new compounds all exhibited significantly stronger fluorescence than p‑HOBDI, up to 28 times higher quantum yields. An experimental and theoretical investigation of the relationship of the fluorescence properties with the molecular structure was also carried out. A good correlation was found between the emission wavenumber and the Hammett constant of the functional group, which suggests the intermolecular charge transfer (ICT) mechanism between the aromatic groups.

Keywords: Aromaticity; Fluorescence; GFP; Hammet constant; ICT.

MeSH terms

Amination
Combinatorial Chemistry Techniques
Fluorescence
Fluorescent Dyes / chemical synthesis
Fluorescent Dyes / chemistry*
Green Fluorescent Proteins / chemistry*
Imidazoles / chemical synthesis
Imidazoles / chemistry*
Models, Molecular
Spectrometry, Fluorescence

Substances

Fluorescent Dyes
Imidazoles
imidazolone
Green Fluorescent Proteins