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Open AccessArticle

Physicochemical Characterization and Antioxidant Activity Evaluation of Idebenone/Hydroxypropyl-β-Cyclodextrin Inclusion Complex

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Dipartimento di Scienze Matematiche e Informatiche, Scienze Fisiche e Scienze della Terra, Università degli Studi di Messina, V.le F. Stagno D’Alcontres, 31-98166 Messina, Italy
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Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche e Ambientali, Università degli Studi di Messina, V.le F. Stagno D’Alcontrés, 31-98166 Messina, Italy
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CNR-IPCF Istituto per i Processi Chimico Fisici, V.le F. Stagno d’Alcontres, 37-98158 Faro Superiore, Messina, Italy
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Dipartimento di Scienze Biomediche, Odontoiatriche, e delle Immagini Morfologiche e Funzionali, Università degli Studi di Messina, c/o A.O.U. Policlinico “G. Martino” Via Consolare Valeria, 1-98125 Messina, Italy
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Dipartimento di Medicina Clinica e Sperimentale, Università degli Studi di Catanzaro “Magna Græcia”, Campus Universitario “S. Venuta”, Viale S. Venuta-88100 Germaneto, Catanzaro, Italy
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Dipartimento di Scienze del Farmaco, Università degli Studi di Catania, V.le A. Doria, 6-95125 Catania, Italy
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Authors to whom correspondence should be addressed.
In memory of Professor Carmela Spatafora, friend, colleague and distinguished scientist, on the third anniversary of her premature death.
Biomolecules 2019, 9(10), 531; https://doi.org/10.3390/biom9100531
Received: 26 July 2019 / Revised: 21 September 2019 / Accepted: 22 September 2019 / Published: 25 September 2019
(This article belongs to the Special Issue Perspectives of Cyclodextrins)
Idebenone (IDE) is an antioxidant drug active at the level of the central nervous system (CNS), whose poor water solubility limits its clinical application. An IDE/2-hydroxypropyl-β-cyclodextrin (IDE/HP-β-CD) inclusion complex was investigated by combining experimental methods and theoretical approaches. Furthermore, biological in vitro/ex vivo assays were performed. Phase solubility studies showed an AL type diagram, suggesting the presence of a 1:1 complex with high solubility. Scanning electron microscopy (SEM) allowed us to detect the morphological changes upon complexation. The intermolecular interactions stabilizing the inclusion complex were experimentally characterized by exploring the complementarity of Fourier-transform infrared spectroscopy in attenuated total reflectance geometry (FTIR-ATR) with mid-infrared light, Fourier-transform near-infrared (FT-NIR) spectroscopy, and Raman spectroscopy. From the temperature evolution of the O–H stretching band of the complex, the average enthalpy ΔHHB of the hydrogen bond scheme upon inclusion was obtained. Two-dimensional (2D) rotating frame Overhauser effect spectroscopy (ROESY) analysis and computational studies involving molecular modeling and molecular dynamics (MD) simulation demonstrated the inclusion of the quinone ring of IDE inside the CD ring. In vitro/ex vivo studies evidenced that complexation produces a protective effect of IDE against the H2O2-induced damage on human glioblastoma astrocytoma (U373) cells and increases IDE permeation through the excised bovine nasal mucosa. View Full-Text
Keywords: idebenone; (2-hydroxypropyl)-β-cyclodextrin; inclusion complex; physicochemical characterization; antioxidant activity; U373 cells; excised bovine nasal mucosa idebenone; (2-hydroxypropyl)-β-cyclodextrin; inclusion complex; physicochemical characterization; antioxidant activity; U373 cells; excised bovine nasal mucosa
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MDPI and ACS Style

Venuti, V.; Crupi, V.; Fazio, B.; Majolino, D.; Acri, G.; Testagrossa, B.; Stancanelli, R.; De Gaetano, F.; Gagliardi, A.; Paolino, D.; Floresta, G.; Pistarà, V.; Rescifina, A.; Ventura, C.A. Physicochemical Characterization and Antioxidant Activity Evaluation of Idebenone/Hydroxypropyl-β-Cyclodextrin Inclusion Complex . Biomolecules 2019, 9, 531. https://doi.org/10.3390/biom9100531

AMA Style

Venuti V, Crupi V, Fazio B, Majolino D, Acri G, Testagrossa B, Stancanelli R, De Gaetano F, Gagliardi A, Paolino D, Floresta G, Pistarà V, Rescifina A, Ventura CA. Physicochemical Characterization and Antioxidant Activity Evaluation of Idebenone/Hydroxypropyl-β-Cyclodextrin Inclusion Complex . Biomolecules. 2019; 9(10):531. https://doi.org/10.3390/biom9100531

Chicago/Turabian Style

Venuti, Valentina; Crupi, Vincenza; Fazio, Barbara; Majolino, Domenico; Acri, Giuseppe; Testagrossa, Barbara; Stancanelli, Rosanna; De Gaetano, Federica; Gagliardi, Agnese; Paolino, Donatella; Floresta, Giuseppe; Pistarà, Venerando; Rescifina, Antonio; Ventura, Cinzia A. 2019. "Physicochemical Characterization and Antioxidant Activity Evaluation of Idebenone/Hydroxypropyl-β-Cyclodextrin Inclusion Complex " Biomolecules 9, no. 10: 531. https://doi.org/10.3390/biom9100531

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