Melatonin (MT) is a vital hormone controlling biorhythms, and optimizing its release in the human body is crucial. To address MTs unfavorable pharmacokinetics, we explored the inclusion complexes of MT with β-cyclodextrin (β-CD). Nano spray drying was applied to efficiently synthesize these complexes in three molar ratios (MT:β-CD = 1 : 1, 2 : 1, and 1 : 2), reducing reagent use and expediting inclusion. The complex powders were characterized through thermal analyses (TGA and DSC), Fourier transform infrared spectroscopy (FTIR), and in vitro MT release measurements via high-performance liquid chromatography (HPLC). In parallel, computational studies were conducted, examining the stability of MT:β-CD complexes by means of unbiased semi-empirical conformational searches refined by DFT, which produced a distribution of MT : β-CD binding enthalpies. Computational findings highlighted that these complexes are stabilized by specific hydrogen bonds and non-specific dispersive forces, with stronger binding in the 1 : 1 complex, which was corroborated by in vitro release data. Furthermore, the alignment between simulated and experimental FTIR spectra demonstrated the quality of both the structural model and computational methodology, which was crucial to enhance our comprehension of optimizing MTs release for therapeutic applications.

Unveiling the synergy: a combined experimental and theoretical study of β-cyclodextrin with melatonin / Ferrero, Riccardo; Pantaleone, Stefano; Gho, CECILIA IRENE; Hoti, Gjylije; Trotta, Francesco; Brunella, Valentina; Corno, Marta. - In: JOURNAL OF MATERIALS CHEMISTRY. B. - ISSN 2050-750X. - ELETTRONICO. - 12:16(2024), pp. 4004-4017. [10.1039/D3TB02795C]

Unveiling the synergy: a combined experimental and theoretical study of β-cyclodextrin with melatonin

Cecilia Irene Gho;
2024

Abstract

Melatonin (MT) is a vital hormone controlling biorhythms, and optimizing its release in the human body is crucial. To address MTs unfavorable pharmacokinetics, we explored the inclusion complexes of MT with β-cyclodextrin (β-CD). Nano spray drying was applied to efficiently synthesize these complexes in three molar ratios (MT:β-CD = 1 : 1, 2 : 1, and 1 : 2), reducing reagent use and expediting inclusion. The complex powders were characterized through thermal analyses (TGA and DSC), Fourier transform infrared spectroscopy (FTIR), and in vitro MT release measurements via high-performance liquid chromatography (HPLC). In parallel, computational studies were conducted, examining the stability of MT:β-CD complexes by means of unbiased semi-empirical conformational searches refined by DFT, which produced a distribution of MT : β-CD binding enthalpies. Computational findings highlighted that these complexes are stabilized by specific hydrogen bonds and non-specific dispersive forces, with stronger binding in the 1 : 1 complex, which was corroborated by in vitro release data. Furthermore, the alignment between simulated and experimental FTIR spectra demonstrated the quality of both the structural model and computational methodology, which was crucial to enhance our comprehension of optimizing MTs release for therapeutic applications.
File in questo prodotto:
File Dimensione Formato  
d3tb02795c.pdf

accesso aperto

Tipologia: 2a Post-print versione editoriale / Version of Record
Licenza: Creative commons
Dimensione 1.69 MB
Formato Adobe PDF
1.69 MB Adobe PDF Visualizza/Apri
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11583/2987594