Considerable Improvement of Ursolic Acid Water Solubility by Its Encapsulation in Dendrimer Nanoparticles: Design, Synthesis and Physicochemical Characterization
Ursolic acid (UA) is a pentacyclic triterpenoid found in many medicinal plants and aromas endowed with numerous in vitro pharmacological activities, including antibacterial effects. Unfortunately, UA is poorly administered in vivo, due to its water insolubility, low bioavailability, and residual sys...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-08-01
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| Series: | Nanomaterials |
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| Online Access: | https://www.mdpi.com/2079-4991/11/9/2196 |
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| author | Silvana Alfei Anna Maria Schito Guendalina Zuccari |
| author_facet | Silvana Alfei Anna Maria Schito Guendalina Zuccari |
| author_sort | Silvana Alfei |
| collection | DOAJ |
| description | Ursolic acid (UA) is a pentacyclic triterpenoid found in many medicinal plants and aromas endowed with numerous in vitro pharmacological activities, including antibacterial effects. Unfortunately, UA is poorly administered in vivo, due to its water insolubility, low bioavailability, and residual systemic toxicity, thus making urgent the development of water-soluble UA formulations. Dendrimers are nonpareil macromolecules possessing highly controlled size, shape, and architecture. In dendrimers with cationic surface, the contemporary presence of inner cavities and of hydrophilic peripheral functions, allows to encapsulate hydrophobic non-water-soluble drugs as UA, to enhance their water-solubility and stability, and to promote their protracted release, thus decreasing their systemic toxicity. In this paper, aiming at developing a new UA-based antibacterial agent administrable in vivo, we reported the physical entrapment of UA in a biodegradable not cytotoxic cationic dendrimer (G4K). UA-loaded dendrimer nanoparticles (UA-G4K) were obtained, which showed a drug loading (DL%) much higher than those previously reported, a protracted release profile governed by diffusion mechanisms, and no cytotoxicity. Also, UA-G4K was characterized by principal components analysis (PCA)-processed FTIR spectroscopy, by NMR and elemental analyses, and by dynamic light scattering experiments (DLS). The water solubility of UA-G4K was found to be 1868-fold times higher than that of pristine UA, thus making its clinical application feasible. |
| first_indexed | 2024-03-10T07:23:20Z |
| format | Article |
| id | doaj.art-89e3c92e82a44dedaecb98292a88e4f1 |
| institution | Directory Open Access Journal |
| issn | 2079-4991 |
| language | English |
| last_indexed | 2024-03-10T07:23:20Z |
| publishDate | 2021-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Nanomaterials |
| spelling | doaj.art-89e3c92e82a44dedaecb98292a88e4f12023-11-22T14:28:47ZengMDPI AGNanomaterials2079-49912021-08-01119219610.3390/nano11092196Considerable Improvement of Ursolic Acid Water Solubility by Its Encapsulation in Dendrimer Nanoparticles: Design, Synthesis and Physicochemical CharacterizationSilvana Alfei0Anna Maria Schito1Guendalina Zuccari2Department of Pharmacy, University of Genoa, Viale Cembrano, 4-16148 Genoa, ItalyDepartment of Surgical Sciences and Integrated Diagnostics (DISC), University of Genoa, Viale Benedetto XV, 6-16132 Genova, ItalyDepartment of Pharmacy, University of Genoa, Viale Cembrano, 4-16148 Genoa, ItalyUrsolic acid (UA) is a pentacyclic triterpenoid found in many medicinal plants and aromas endowed with numerous in vitro pharmacological activities, including antibacterial effects. Unfortunately, UA is poorly administered in vivo, due to its water insolubility, low bioavailability, and residual systemic toxicity, thus making urgent the development of water-soluble UA formulations. Dendrimers are nonpareil macromolecules possessing highly controlled size, shape, and architecture. In dendrimers with cationic surface, the contemporary presence of inner cavities and of hydrophilic peripheral functions, allows to encapsulate hydrophobic non-water-soluble drugs as UA, to enhance their water-solubility and stability, and to promote their protracted release, thus decreasing their systemic toxicity. In this paper, aiming at developing a new UA-based antibacterial agent administrable in vivo, we reported the physical entrapment of UA in a biodegradable not cytotoxic cationic dendrimer (G4K). UA-loaded dendrimer nanoparticles (UA-G4K) were obtained, which showed a drug loading (DL%) much higher than those previously reported, a protracted release profile governed by diffusion mechanisms, and no cytotoxicity. Also, UA-G4K was characterized by principal components analysis (PCA)-processed FTIR spectroscopy, by NMR and elemental analyses, and by dynamic light scattering experiments (DLS). The water solubility of UA-G4K was found to be 1868-fold times higher than that of pristine UA, thus making its clinical application feasible.https://www.mdpi.com/2079-4991/11/9/2196fourth-generation polyester-based lysine-modified dendrimerphysical encapsulationursolic acid (UA)water-soluble UA-loaded nanoparticleshigh negative zeta potentialprotracted release profile |
| spellingShingle | Silvana Alfei Anna Maria Schito Guendalina Zuccari Considerable Improvement of Ursolic Acid Water Solubility by Its Encapsulation in Dendrimer Nanoparticles: Design, Synthesis and Physicochemical Characterization Nanomaterials fourth-generation polyester-based lysine-modified dendrimer physical encapsulation ursolic acid (UA) water-soluble UA-loaded nanoparticles high negative zeta potential protracted release profile |
| title | Considerable Improvement of Ursolic Acid Water Solubility by Its Encapsulation in Dendrimer Nanoparticles: Design, Synthesis and Physicochemical Characterization |
| title_full | Considerable Improvement of Ursolic Acid Water Solubility by Its Encapsulation in Dendrimer Nanoparticles: Design, Synthesis and Physicochemical Characterization |
| title_fullStr | Considerable Improvement of Ursolic Acid Water Solubility by Its Encapsulation in Dendrimer Nanoparticles: Design, Synthesis and Physicochemical Characterization |
| title_full_unstemmed | Considerable Improvement of Ursolic Acid Water Solubility by Its Encapsulation in Dendrimer Nanoparticles: Design, Synthesis and Physicochemical Characterization |
| title_short | Considerable Improvement of Ursolic Acid Water Solubility by Its Encapsulation in Dendrimer Nanoparticles: Design, Synthesis and Physicochemical Characterization |
| title_sort | considerable improvement of ursolic acid water solubility by its encapsulation in dendrimer nanoparticles design synthesis and physicochemical characterization |
| topic | fourth-generation polyester-based lysine-modified dendrimer physical encapsulation ursolic acid (UA) water-soluble UA-loaded nanoparticles high negative zeta potential protracted release profile |
| url | https://www.mdpi.com/2079-4991/11/9/2196 |
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