Open Access
International Journal of Molecular Sciences, volume 22, issue 24, pages 13645
Designing Red-Shifted Molecular Emitters Based on the Annulated Locked GFP Chromophore Derivatives
Farkhutdinova Dilara A
1
,
Myasnyanko Ivan N
2, 3
,
Baleeva Nadezhda S
2, 3
,
Baranov Mikhail
2, 3
,
Publication type: Journal Article
Publication date: 2021-12-20
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.6
ISSN: 16616596, 14220067
PubMed ID:
34948442
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Computer Science Applications
Spectroscopy
Molecular Biology
General Medicine
Abstract
Bioimaging techniques require development of a wide variety of fluorescent probes that absorb and emit red light. One way to shift absorption and emission of a chromophore to longer wavelengths is to modify its chemical structure by adding polycyclic aromatic hydrocarbon (PAH) fragments, thus increasing the conjugation length of a molecule while maintaining its rigidity. Here, we consider four novel classes of conformationally locked Green Fluorescent Protein (GFP) chromophore derivatives obtained by extending their aromatic systems in different directions. Using high-level ab initio quantum chemistry calculations, we show that the alteration of their electronic structure upon annulation may unexpectedly result in a drastic change of their fluorescent properties. A flip of optically bright and dark electronic states is most prominent in the symmetric fluorene-based derivative. The presence of a completely dark lowest-lying excited state is supported by the experimentally measured extremely low fluorescence quantum yield of the newly synthesized compound. Importantly, one of the asymmetric modes of annulation provides a very promising strategy for developing red-shifted molecular emitters with an absorption wavelength of ∼600 nm, having no significant impact on the character of the bright S-S1 transition.
Citations by journals
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1
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Russian Journal of Bioorganic Chemistry
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Russian Journal of Bioorganic Chemistry
1 publication, 50%
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Liquid Crystals
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Liquid Crystals
1 publication, 50%
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1
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Citations by publishers
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1
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Pleiades Publishing
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Pleiades Publishing
1 publication, 50%
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Taylor & Francis
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Taylor & Francis
1 publication, 50%
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1
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Sinenko G. D. et al. Designing Red-Shifted Molecular Emitters Based on the Annulated Locked GFP Chromophore Derivatives // International Journal of Molecular Sciences. 2021. Vol. 22. No. 24. p. 13645.
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Sinenko G. D., Farkhutdinova D. A., Myasnyanko I. N., Baleeva N. S., Baranov M., Bochenkova A. V. Designing Red-Shifted Molecular Emitters Based on the Annulated Locked GFP Chromophore Derivatives // International Journal of Molecular Sciences. 2021. Vol. 22. No. 24. p. 13645.
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RIS
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TY - JOUR
DO - 10.3390/ijms222413645
UR - https://doi.org/10.3390%2Fijms222413645
TI - Designing Red-Shifted Molecular Emitters Based on the Annulated Locked GFP Chromophore Derivatives
T2 - International Journal of Molecular Sciences
AU - Farkhutdinova, Dilara A
AU - Myasnyanko, Ivan N
AU - Baleeva, Nadezhda S
AU - Sinenko, Gregory D
AU - Baranov, Mikhail
AU - Bochenkova, Anastasia V.
PY - 2021
DA - 2021/12/20 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 13645
IS - 24
VL - 22
PMID - 34948442
SN - 1661-6596
SN - 1422-0067
ER -
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BibTex
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@article{2021_Sinenko,
author = {Dilara A Farkhutdinova and Ivan N Myasnyanko and Nadezhda S Baleeva and Gregory D Sinenko and Mikhail Baranov and Anastasia V. Bochenkova},
title = {Designing Red-Shifted Molecular Emitters Based on the Annulated Locked GFP Chromophore Derivatives},
journal = {International Journal of Molecular Sciences},
year = {2021},
volume = {22},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {dec},
url = {https://doi.org/10.3390%2Fijms222413645},
number = {24},
pages = {13645},
doi = {10.3390/ijms222413645}
}
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MLA
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Sinenko, Gregory D., et al. “Designing Red-Shifted Molecular Emitters Based on the Annulated Locked GFP Chromophore Derivatives.” International Journal of Molecular Sciences, vol. 22, no. 24, Dec. 2021, p. 13645. https://doi.org/10.3390%2Fijms222413645.