Design and Synthesis of Amphiphilic Graft Polyphosphazene Micelles for Docetaxel Delivery
The structural versatility of polydichlorophosphazene derived from the inestimable possibilities to functionalize the two halogens, attached to each phosphazene main chain unit, attracted increasing attention in the last decade. This uncountable chemical derivatization is doubled by the amphiphilic...
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MDPI AG
2023-05-01
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| Series: | Pharmaceutics |
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| Online Access: | https://www.mdpi.com/1999-4923/15/5/1564 |
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| author | Diana Serbezeanu Tǎchițǎ Vlad-Bubulac Ana-Maria Macsim Vera Bǎlan |
| author_facet | Diana Serbezeanu Tǎchițǎ Vlad-Bubulac Ana-Maria Macsim Vera Bǎlan |
| author_sort | Diana Serbezeanu |
| collection | DOAJ |
| description | The structural versatility of polydichlorophosphazene derived from the inestimable possibilities to functionalize the two halogens, attached to each phosphazene main chain unit, attracted increasing attention in the last decade. This uncountable chemical derivatization is doubled by the amphiphilic roleplay demonstrated by polyphosphazenes containing twofold side-chained hydrophilic and hydrophobic moieties. Thus, it is able to encapsulate specific bioactive molecules for various targeted nanomedicine applications. A new amphiphilic graft, polyphosphazenes (PPP/PEG–NH/Hys/MAB), was synthesized via the thermal ring-opening polymerization of hexachlorocyclotriphosphazene, followed by a subsequent two-step substitution reaction of chlorine atoms with hydrophilic methoxypolyethylene glycol amine/histamine dihydrochloride adduct (PEG–NH<sub>2</sub>)/(Hys) and hydrophobic methyl-<i>p</i>-aminobenzoate (MAB), respectively. Fourier transform infrared spectroscopy (FTIR) and <sup>1</sup>H and <sup>31</sup>P-nuclear magnetic resonance spectroscopy (NMR) have been used to validate the expected architectural assembly of the copolymer. Docetaxel loaded micelles based on synthesized PPP/PEG–NH/Hys/MAB were designed by dialysis method. The micelles size was evaluated by dynamic light scattering (DLS) and transmission electron microscopy (TEM). The drug release profiles from the PPP/PEG–NH/Hys/MAB micelles were established. In vitro cytotoxicity tests of PPP/PEG–NH/Hys/MAB micelles loaded with Docetaxel revealed that designed polymeric micelles exhibited an increased cytotoxic effect on MCF-7 cells. |
| first_indexed | 2024-03-11T03:24:49Z |
| format | Article |
| id | doaj.art-df0ab5b3152846f38f946f1950e3eb81 |
| institution | Directory Open Access Journal |
| issn | 1999-4923 |
| language | English |
| last_indexed | 2024-03-11T03:24:49Z |
| publishDate | 2023-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceutics |
| spelling | doaj.art-df0ab5b3152846f38f946f1950e3eb812023-11-18T02:53:22ZengMDPI AGPharmaceutics1999-49232023-05-01155156410.3390/pharmaceutics15051564Design and Synthesis of Amphiphilic Graft Polyphosphazene Micelles for Docetaxel DeliveryDiana Serbezeanu0Tǎchițǎ Vlad-Bubulac1Ana-Maria Macsim2Vera Bǎlan3“Petru Poni” Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, Romania“Petru Poni” Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, Romania“Petru Poni” Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaFaculty of Medical Bioengineering, “Grigore T. Popa” University of Medicine and Pharmacy, 9-13 Kogalniceanu Street, 700454 Iasi, RomaniaThe structural versatility of polydichlorophosphazene derived from the inestimable possibilities to functionalize the two halogens, attached to each phosphazene main chain unit, attracted increasing attention in the last decade. This uncountable chemical derivatization is doubled by the amphiphilic roleplay demonstrated by polyphosphazenes containing twofold side-chained hydrophilic and hydrophobic moieties. Thus, it is able to encapsulate specific bioactive molecules for various targeted nanomedicine applications. A new amphiphilic graft, polyphosphazenes (PPP/PEG–NH/Hys/MAB), was synthesized via the thermal ring-opening polymerization of hexachlorocyclotriphosphazene, followed by a subsequent two-step substitution reaction of chlorine atoms with hydrophilic methoxypolyethylene glycol amine/histamine dihydrochloride adduct (PEG–NH<sub>2</sub>)/(Hys) and hydrophobic methyl-<i>p</i>-aminobenzoate (MAB), respectively. Fourier transform infrared spectroscopy (FTIR) and <sup>1</sup>H and <sup>31</sup>P-nuclear magnetic resonance spectroscopy (NMR) have been used to validate the expected architectural assembly of the copolymer. Docetaxel loaded micelles based on synthesized PPP/PEG–NH/Hys/MAB were designed by dialysis method. The micelles size was evaluated by dynamic light scattering (DLS) and transmission electron microscopy (TEM). The drug release profiles from the PPP/PEG–NH/Hys/MAB micelles were established. In vitro cytotoxicity tests of PPP/PEG–NH/Hys/MAB micelles loaded with Docetaxel revealed that designed polymeric micelles exhibited an increased cytotoxic effect on MCF-7 cells.https://www.mdpi.com/1999-4923/15/5/1564polyphosphazeneshistamine dihydrochloridemicellesdocetaxelcytotoxicity |
| spellingShingle | Diana Serbezeanu Tǎchițǎ Vlad-Bubulac Ana-Maria Macsim Vera Bǎlan Design and Synthesis of Amphiphilic Graft Polyphosphazene Micelles for Docetaxel Delivery Pharmaceutics polyphosphazenes histamine dihydrochloride micelles docetaxel cytotoxicity |
| title | Design and Synthesis of Amphiphilic Graft Polyphosphazene Micelles for Docetaxel Delivery |
| title_full | Design and Synthesis of Amphiphilic Graft Polyphosphazene Micelles for Docetaxel Delivery |
| title_fullStr | Design and Synthesis of Amphiphilic Graft Polyphosphazene Micelles for Docetaxel Delivery |
| title_full_unstemmed | Design and Synthesis of Amphiphilic Graft Polyphosphazene Micelles for Docetaxel Delivery |
| title_short | Design and Synthesis of Amphiphilic Graft Polyphosphazene Micelles for Docetaxel Delivery |
| title_sort | design and synthesis of amphiphilic graft polyphosphazene micelles for docetaxel delivery |
| topic | polyphosphazenes histamine dihydrochloride micelles docetaxel cytotoxicity |
| url | https://www.mdpi.com/1999-4923/15/5/1564 |
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