New Antioxidant Triphenol-Derived Hydrazide-Hydrazone Thiazole: Formation and Analysis of Inclusion Complex with β-CD Using Experimental and Computational Approaches
A new water-soluble not-colored antioxidant (Z)-N'-(4-(3,4-dihydroxyphenyl)-3-ethylthiazol-2(3H)-ylidene)-4-hydroxybenzohydrazide hydrochloride (DHTH) was obtained and characterized. The interaction between DHTH and β-CD was studied by experimental thermodynamic methods such as isothermal titration calorimetry (ITC) and <sup>1</sup>H NMR spectroscopy and confirmed by in silico calculations. Thermodynamic data indicated that the inclusion process is driven by enthalpy, predominantly as a result of the guest-host hydrophobic interactions. <sup>1</sup>H NMR measurements were applied to study the interaction with β-CD by changing the studied compound concentration in the solution. UV-vis titration and in vitro antiradical assay were performed, to study the antioxidant activity of DHTH, free and included in β-CD. A molecular docking study added supplementary insight to the experimental analyses regarding the binding conformation of the new polyphenolic compound to β-CD.
Authors
- Laurian Vlase (ORCID: https://orcid.org/0000-0002-0664-3387)
- Mihaela Mic (ORCID: https://orcid.org/0000-0003-1236-4111)
- Smaranda Oniga (ORCID: https://orcid.org/0000-0002-0297-7697)
- Ovidiu Oniga
- Gabriel Marc (ORCID: https://orcid.org/0000-0001-9397-0388)
- Adrian Pı̂rnău (ORCID: https://orcid.org/0000-0002-2313-9350)
- O. Crisan (ORCID: https://orcid.org/0000-0002-7987-408X)
- Călin G. Floare
Institutions
- Iuliu Hațieganu University of Medicine and Pharmacy (RO)
- National Institute for Research and Development of Isotopic and Molecular Technologies (RO)
Publication Details
- Journal
- Molecules
- Published
- 2025-04-19
- DOI
- https://doi.org/10.3390/molecules30081842
- Citations
- 1
- Primary Topic
- Synthesis and biological activity
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Ministerio de Economía y Competitividad