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

Valentin Maffeis; Konstantinos Mavreas; Filippo Monti; Michael Mamais; Thomas Gustavsson; Evangelia Chrysina; Dimitra Markovitsi; Thanasis Gimisis; Alessandro Venturini

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 ⁵ Thomas Gustavsson ^{2, 6} Evangelia Chrysina ⁷ Dimitra Markovitsi ^{2, 6} Thanasis Gimisis ⁵ Alessandro Venturini ⁸

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, Dynamique et Lasers (ex SPAM)

3 UCA - Université Côte d'Azur

4 ISOF-CNR - Istituto per la Sintesi Organica e la Fotoreattività

5 National and Kapodistrian University of Athens

6 DICO - Biomolécules Excitées

IRAMIS - Institut Rayonnement Matière de Saclay, LIDyl - Laboratoire Interactions, Dynamique et Lasers (ex SPAM)

7 National Hellenic Research Foundation [Athens]

8 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

Domain :

Chemical Sciences / Theoretical and/or physical chemistry

Physics [physics] / Physics [physics] / Chemical Physics [physics.chem-ph]

Complete list of metadatas

https://hal-cea.archives-ouvertes.fr/cea-02096313
Contributor : Caroline Lebe <>
Submitted on : Thursday, April 11, 2019 - 11:40:21 AM
Last modification on : Wednesday, June 5, 2019 - 10:32:21 AM

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

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

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