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

A. Jancsó, Ervin Kovács, Levente Cseri, B. Rózsa, G. Galbács, I. Csizmadia, Zoltán Mucsi

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)161-170
Number of pages10
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume218
DOIs
Publication statusPublished - Jul 5 2019

Fingerprint

Chromophores
chromophores
Fluorescence
analogs
Derivatives
fluorescence
Thiohydantoins
synthesis
Quantum yield
Green Fluorescent Proteins
Functional groups
Molecular structure
Charge transfer
molecular structure
charge transfer
proteins
Proteins

Keywords

  • Aromaticity
  • Fluorescence
  • GFP
  • Hammet constant
  • ICT

ASJC Scopus subject areas

  • Analytical Chemistry
  • Atomic and Molecular Physics, and Optics
  • Instrumentation
  • Spectroscopy

Cite this

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title = "Synthesis and spectroscopic characterization of novel GFP chromophore analogues based on aminoimidazolone derivatives",
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",
author = "A. Jancs{\'o} and Ervin Kov{\'a}cs and Levente Cseri and B. R{\'o}zsa and G. Galb{\'a}cs and I. Csizmadia and Zolt{\'a}n Mucsi",
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T1 - Synthesis and spectroscopic characterization of novel GFP chromophore analogues based on aminoimidazolone derivatives

AU - Jancsó, A.

AU - Kovács, Ervin

AU - Cseri, Levente

AU - Rózsa, B.

AU - Galbács, G.

AU - Csizmadia, I.

AU - Mucsi, Zoltán

PY - 2019/7/5

Y1 - 2019/7/5

N2 - 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.

AB - 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.

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KW - Fluorescence

KW - GFP

KW - Hammet constant

KW - ICT

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U2 - 10.1016/j.saa.2019.03.111

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JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

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