Preparation and Physicochemical Characterization of Water-Soluble Pyrazole-Based Nanoparticles by Dendrimer Encapsulation of an Insoluble Bioactive Pyrazole Derivative
2-(4-Bromo-3,5-diphenyl-pyrazol-1-yl)-ethanol (BBB4) was synthetized and successfully evaluated concerning numerous biological activities, except for antimicrobial and cytotoxic effects. Due to the antimicrobial effects possessed by pyrazole nucleus, which have been widely reported, and the worldwid...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-10-01
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| Series: | Nanomaterials |
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| Online Access: | https://www.mdpi.com/2079-4991/11/10/2662 |
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| author | Silvana Alfei Chiara Brullo Debora Caviglia Guendalina Zuccari |
| author_facet | Silvana Alfei Chiara Brullo Debora Caviglia Guendalina Zuccari |
| author_sort | Silvana Alfei |
| collection | DOAJ |
| description | 2-(4-Bromo-3,5-diphenyl-pyrazol-1-yl)-ethanol (BBB4) was synthetized and successfully evaluated concerning numerous biological activities, except for antimicrobial and cytotoxic effects. Due to the antimicrobial effects possessed by pyrazole nucleus, which have been widely reported, and the worldwide need for new antimicrobial agents, we thought it would be interesting to test BBB4 and to evaluate its possible antibacterial effects. Nevertheless, since it is water-insoluble, the future clinical application of BBB4 will remain utopic unless water-soluble BBB4 formulations are developed. To this end, before implementing biological evaluations, BBB4 was herein re-synthetized and characterized, and a new water-soluble BBB4-based nano-formulation was developed by its physical entrapment in a biodegradable non-cytotoxic cationic dendrimer (G4K), without recovering harmful solvents as DMSO or surfactants. The obtained BBB4 nanoparticles (BBB4-G4K NPs) showed good drug loading (DL%), satisfying encapsulation efficiency (EE%), and a biphasic quantitative release profile governed by first-order kinetics after 24 h. Additionally, BBB4-G4K was characterized by ATR-FTIR spectroscopy, NMR, SEM, dynamic light scattering analysis (DLS), and potentiometric titration experiments. While, before the nanotechnological manipulation, BBB4 was completely water-insoluble, in the form of BBB4-G4K NPs, its water-solubility resulted in being 105-fold higher than that of the pristine form, thus establishing the feasibility of its clinical application. |
| first_indexed | 2024-03-10T06:19:07Z |
| format | Article |
| id | doaj.art-586f628f868e4a6c9adf5241dcd31c76 |
| institution | Directory Open Access Journal |
| issn | 2079-4991 |
| language | English |
| last_indexed | 2024-03-10T06:19:07Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Nanomaterials |
| spelling | doaj.art-586f628f868e4a6c9adf5241dcd31c762023-11-22T19:24:45ZengMDPI AGNanomaterials2079-49912021-10-011110266210.3390/nano11102662Preparation and Physicochemical Characterization of Water-Soluble Pyrazole-Based Nanoparticles by Dendrimer Encapsulation of an Insoluble Bioactive Pyrazole DerivativeSilvana Alfei0Chiara Brullo1Debora Caviglia2Guendalina Zuccari3Department of Pharmacy, University of Genoa, Viale Cembrano, 16148 Genoa, ItalyDepartment of Pharmacy, University of Genoa, Viale Cembrano, 16148 Genoa, ItalyDepartment of Surgical Sciences and Integrated Diagnostics (DISC), University of Genoa, Viale Benedetto XV 6, 16132 Genoa, ItalyDepartment of Pharmacy, University of Genoa, Viale Cembrano, 16148 Genoa, Italy2-(4-Bromo-3,5-diphenyl-pyrazol-1-yl)-ethanol (BBB4) was synthetized and successfully evaluated concerning numerous biological activities, except for antimicrobial and cytotoxic effects. Due to the antimicrobial effects possessed by pyrazole nucleus, which have been widely reported, and the worldwide need for new antimicrobial agents, we thought it would be interesting to test BBB4 and to evaluate its possible antibacterial effects. Nevertheless, since it is water-insoluble, the future clinical application of BBB4 will remain utopic unless water-soluble BBB4 formulations are developed. To this end, before implementing biological evaluations, BBB4 was herein re-synthetized and characterized, and a new water-soluble BBB4-based nano-formulation was developed by its physical entrapment in a biodegradable non-cytotoxic cationic dendrimer (G4K), without recovering harmful solvents as DMSO or surfactants. The obtained BBB4 nanoparticles (BBB4-G4K NPs) showed good drug loading (DL%), satisfying encapsulation efficiency (EE%), and a biphasic quantitative release profile governed by first-order kinetics after 24 h. Additionally, BBB4-G4K was characterized by ATR-FTIR spectroscopy, NMR, SEM, dynamic light scattering analysis (DLS), and potentiometric titration experiments. While, before the nanotechnological manipulation, BBB4 was completely water-insoluble, in the form of BBB4-G4K NPs, its water-solubility resulted in being 105-fold higher than that of the pristine form, thus establishing the feasibility of its clinical application.https://www.mdpi.com/2079-4991/11/10/2662fourth-generation polyester-based lysine-modified dendrimerphysical encapsulation2-(4-Bromo-3,5-diphenyl-pyrazol-1-yl)-ethanol (BBB4)water-soluble BBB4-loaded NPsspherical morphologybiphasic release profile |
| spellingShingle | Silvana Alfei Chiara Brullo Debora Caviglia Guendalina Zuccari Preparation and Physicochemical Characterization of Water-Soluble Pyrazole-Based Nanoparticles by Dendrimer Encapsulation of an Insoluble Bioactive Pyrazole Derivative Nanomaterials fourth-generation polyester-based lysine-modified dendrimer physical encapsulation 2-(4-Bromo-3,5-diphenyl-pyrazol-1-yl)-ethanol (BBB4) water-soluble BBB4-loaded NPs spherical morphology biphasic release profile |
| title | Preparation and Physicochemical Characterization of Water-Soluble Pyrazole-Based Nanoparticles by Dendrimer Encapsulation of an Insoluble Bioactive Pyrazole Derivative |
| title_full | Preparation and Physicochemical Characterization of Water-Soluble Pyrazole-Based Nanoparticles by Dendrimer Encapsulation of an Insoluble Bioactive Pyrazole Derivative |
| title_fullStr | Preparation and Physicochemical Characterization of Water-Soluble Pyrazole-Based Nanoparticles by Dendrimer Encapsulation of an Insoluble Bioactive Pyrazole Derivative |
| title_full_unstemmed | Preparation and Physicochemical Characterization of Water-Soluble Pyrazole-Based Nanoparticles by Dendrimer Encapsulation of an Insoluble Bioactive Pyrazole Derivative |
| title_short | Preparation and Physicochemical Characterization of Water-Soluble Pyrazole-Based Nanoparticles by Dendrimer Encapsulation of an Insoluble Bioactive Pyrazole Derivative |
| title_sort | preparation and physicochemical characterization of water soluble pyrazole based nanoparticles by dendrimer encapsulation of an insoluble bioactive pyrazole derivative |
| topic | fourth-generation polyester-based lysine-modified dendrimer physical encapsulation 2-(4-Bromo-3,5-diphenyl-pyrazol-1-yl)-ethanol (BBB4) water-soluble BBB4-loaded NPs spherical morphology biphasic release profile |
| url | https://www.mdpi.com/2079-4991/11/10/2662 |
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