Εξειδίκευση τύπου :	Άρθρο σε επιστημονικό περιοδικό
Τίτλος:	Comparative Interaction Studies of Quercetin with 2-Hydroxyl-propyl-β-cyclodextrin and 2,6-Methylated-β-cyclodextrin
Δημιουργός/Συγγραφέας:	Vakali, Vasiliki Papadourakis, Michail Georgiou, Nikitas Zoupanou, Nikoletta Diamantis, Dimitrios A Javornik, Uroš Papakyriakopoulou, Paraskevi Plavec, Janez Valsami, Georgia Tzakos, Andreas G [EL] Τζέλη, Δήμητρα[EN] Tzeli, Demeter Cournia, Zoe [EL] Μαυρομούστακος, Θωμάς[EN] Mavromoustakos, Thomas
Ημερομηνία:	2022-08-26
Γλώσσα:	Αγγλικά
ISSN:	1420-3049
DOI:	10.3390/molecules27175490
Άλλο:	36080258
Περίληψη:	Quercetin (QUE) is a well-known natural product that can exert beneficial properties on human health. However, due to its low solubility its bioavailability is limited. In the present study, we examine whether its formulation with two cyclodextrins (CDs) may enhance its pharmacological profile. Comparative interaction studies of quercetin with 2-hydroxyl-propyl-β-cyclodextrin (2HP-β-CD) and 2,6-methylated cyclodextrin (2,6Me-β-CD) were performed using NMR spectroscopy, DFT calculations, and in silico molecular dynamics (MD) simulations. Using T1 relaxation experiments and 2D DOSY it was illustrated that both cyclodextrin vehicles can host quercetin. Quantum mechanical calculations showed the formation of hydrogen bonds between QUE with 2HP-β-CD and 2,6Μe-β-CD. Six hydrogen bonds are formed ranging between 2 to 2.8 Å with 2HP-β-CD and four hydrogen bonds within 2.8 Å with 2,6Μe-β-CD. Calculations of absolute binding free energies show that quercetin binds favorably to both 2,6Me-β-CD and 2HP-β-CD. MM/GBSA results show equally favorable binding of quercetin in the two CDs. Fluorescence spectroscopy shows moderate binding of quercetin in 2HP-β-CD (520 M-1) and 2,6Me-β-CD (770 M-1). Thus, we propose that both formulations (2HP-β-CD:quercetin, 2,6Me-β-CD:quercetin) could be further explored and exploited as small molecule carriers in biological studies.
Τίτλος πηγής δημοσίευσης:	Molecules (Basel, Switzerland)
Τόμος/Κεφάλαιο:	27
Τεύχος:	17
Θεματική Κατηγορία:	[EL] Φυσική και θεωρητική χημεία[EN] Physical and theoretical chemistry [EL] Φασματοσκοπία[EN] Spectroscopy
Λέξεις-Κλειδιά:	2,6-methylated cyclodextrin 2-hydroxyl-propyl-β-cyclodextrin Density Functional Theory (DFT) FEP NMR spectroscopy absolute free energy calculation fluorescence spectroscopy molecular dynamics molecular interactions quercetin
EU Grant identifier:	IDs pa211102/CD-FEP Nos. P1-0242 Nos. J1-1704 Project Number: 991 No. 857645
Κάτοχος πνευματικών δικαιωμάτων:	© 2022 by the authors. Licensee MDPI, Basel, Switzerland.
Όροι και προϋποθέσεις δικαιωμάτων:	This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Ηλεκτρονική διεύθυνση στον εκδότη (link):	https://www.mdpi.com/1420-3049/27/17/5490
Σημειώσεις:	Data Availability Statement: Input files for MD simulations andabsolute free energy calculations using GROMACS 2021.4 are deposited in this link: https://doi.org/10.5281/zenodo.6967423 (accessed on 9 June 2022). Z.C. and M.P. acknowledge computational time granted from the Greek Research & Technology Network (GRNET) in the National HPC facility ARIS under project IDs pa211102/CD-FEP. Z.C. and M.P. thank Vytautas Gapsys for useful discussions; U.J. and J.P. acknowledge financial support of the Slovenian Research Agency [Grants Nos. P1-0242 and J1-1704]. The authors acknowledge the CERIC-ERIC consortium for the access to experimental facilities and financial support; M.P. acknowledges the Bodossaki Foundation Scholarships program for financially supporting his research. A.G.T acknowledges financial support of this research work by the Hellenic Foundation for Research and Innovation (H.F.R.I.) under the “First Call for H.F.R.I. Research Projects to support Faculty members and Researchers and the procurement of high-cost research equipment grant” (Project Number: 991, acronym PROTECT). Z.C. acknowledges funding by the European Union’s Horizon 2020 research and innovation programme under the grant agreement No. 857645 (project NI4OS-Europe).
Εμφανίζεται στις συλλογές:	Ινστιτούτο Θεωρητικής και Φυσικής Χημείας (ΙΘΦΧ) - Επιστημονικό έργο