PH-sensitive fluorophores from locked GFP chromophores by a non-alternant analogue of the photochemical meta effect

Olsen, Seth, Baranov, Mikhail S., Baleeva, Nadezhda S., Antonova, Maria M., Johnson, Kenneth A. and Solntsev, Kyril M. (2016) PH-sensitive fluorophores from locked GFP chromophores by a non-alternant analogue of the photochemical meta effect. Physical Chemistry Chemical Physics, 18 38: 26703-26711. doi:10.1039/c6cp02423h


Author Olsen, Seth
Baranov, Mikhail S.
Baleeva, Nadezhda S.
Antonova, Maria M.
Johnson, Kenneth A.
Solntsev, Kyril M.
Title PH-sensitive fluorophores from locked GFP chromophores by a non-alternant analogue of the photochemical meta effect
Formatted title
PH-sensitive fluorophores from locked GFP chromophores by a non-alternant analogue of the photochemical meta effect
Journal name Physical Chemistry Chemical Physics   Check publisher's open access policy
ISSN 1463-9076
1463-9084
Publication date 2016-10-14
Year available 2016
Sub-type Article (original research)
DOI 10.1039/c6cp02423h
Open Access Status Not yet assessed
Volume 18
Issue 38
Start page 26703
End page 26711
Total pages 9
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Language eng
Abstract We report the synthesis and characterization of a pH-sensitive fluorescence switch based on a conformationally-locked green fluorescent protein (GFP) chromophore. The chromophore differs from difluoroboryl-locked parent by the addition of a titratable alcohol group on the imidazolinone ring. The chromophore is fluorescent at pH <= 5, but becomes non-fluorescent at higher pH, where the substituent is ionized. We use a quantum chemical model to show that the mechanism of the fluorescence turn-off is electronically analogous to photochemical meta effects in aryl-containing systems.
Formatted abstract
We report the synthesis and characterization of a pH-sensitive fluorescence switch based on a conformationally-locked green fluorescent protein (GFP) chromophore. The chromophore differs from difluoroboryl-locked parent by the addition of a titratable alcohol group on the imidazolinone ring. The chromophore is fluorescent at pH ≤ 5, but becomes non-fluorescent at higher pH, where the substituent is ionized. We use a quantum chemical model to show that the mechanism of the fluorescence turn-off is electronically analogous to photochemical meta effects in aryl-containing systems.
Keyword Chemistry, Physical
Physics, Atomic, Molecular & Chemical
Chemistry
Physics
Q-Index Code C1
Q-Index Status Provisional Code
Grant ID 15-03-02856-a
CHE-1213047
DP110101580
m03
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: School of Mathematics and Physics
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