Multiscale time-resolved fluorescence study of a glycogen phosphorylase inhibitor combined with quantum chemistry calculations

Valentin Maffeis 1, 2 Konstantinos Mavreas 3 Filippo Monti 4 Michael Mamais 3, 2 Thomas Gustavsson 2, 5 Evangelia Chrysina 6 Dimitra Markovitsi 2, 5 Thanasis Gimisis 3 Alessandro Venturini 7
1 LICSEN - Laboratoire Innovation en Chimie des Surfaces et NanoSciences
NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)
2 LIDyl - Laboratoire Interactions, Dynamiques et Lasers (ex SPAM)
3 National and Kapodistrian University of Athens
4 ISOF-CNR - Istituto per la Sintesi Organica e la Fotoreattività
5 DICO - Biomolécules Excitées
IRAMIS - Institut Rayonnement Matière de Saclay, LIDyl - Laboratoire Interactions, Dynamiques et Lasers (ex SPAM)
6 National Hellenic Research Foundation [Athens]
7 ISOF - Istituto CNR per la Sintesi Organica e Fotoreattivita
Abstract : A fluorescence study of N1-(β-D-glucopyranosyl)-N4-[2-acridin-9(10H)-onyl]-cytosine (GLAC), the first fluorescent potent inhibitor of glycogen phosphorylase (GP), in neutral aqueous solution, is presented herein. Quantum chemistry (TD-DFT) calculations show the existence of several conformers both in the ground and first excited states. They result from rotations of the acridone and cytosine moieties around an NH bridge which may lead to the formation of non-emitting charge-transfer states. The fingerprints of various conformers have been detected by time-resolved fluorescence spectroscopy (fluorescence upconversion and time-correlated single photon counting) and identified using as criteria their energy, polarization and relative population resulting from computations. Such an analysis should contribute to the design of new GP inhibitors with better fluorescence properties, suitable for imaging applications.
Document type :
Journal articles
Complete list of metadatas

Cited literature [49 references]  Display  Hide  Download
https://hal-cea.archives-ouvertes.fr/cea-02096313
Contributor : Caroline Lebe <>
Submitted on : Wednesday, October 23, 2019 - 10:34:21 AM
Last modification on : Friday, October 25, 2019 - 1:18:41 AM

File

2019_PCCP GLAC fluorescence.pd...
Files produced by the author(s)

Identifiers

Collections

CEA | UNIV-PARIS-SACLAY | CEA-UPSAY | IRAMIS-LIDYL | IRAMIS-NIMBE | INC-CNRS | PUBNIMBE | DSM-IRAMIS | CNRS | CEA-DRF

Citation

Valentin Maffeis, Konstantinos Mavreas, Filippo Monti, Michael Mamais, Thomas Gustavsson, et al.. Multiscale time-resolved fluorescence study of a glycogen phosphorylase inhibitor combined with quantum chemistry calculations. Physical Chemistry Chemical Physics, Royal Society of Chemistry, 2019, 21 (14), pp.7685-7696. ⟨10.1039/C8CP07538G⟩. ⟨cea-02096313⟩

Export

BibTeX TEI DC DCterms EndNote

Share

Metrics

Record views

71

Files downloads

35

Contact

CCSD