Synthesis of Poly(<i>N</i>-vinylpyrrolidone)-Based Polymer Bottlebrushes by ATRPA and RAFT Polymerization: Toward Drug Delivery Application
Atom transfer radical polyaddition (ATRPA) was utilized herein to synthesize a specific functional polyester. We conducted ATRPA of 4-vinylbenzyl 2-bromo-2-phenylacetate (VBBPA) inimer and successfully obtained a linear type poly(VBBPA) (PVBBPA) polyester with benzylic bromides along the backbone. T...
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| Format: | Article |
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MDPI AG
2019-06-01
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| Series: | Polymers |
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| Online Access: | https://www.mdpi.com/2073-4360/11/6/1079 |
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| author | Yi-Shen Huang Jem-Kun Chen Shiao-Wei Kuo Ya-An Hsieh Shota Yamamoto Jun Nakanishi Chih-Feng Huang |
| author_facet | Yi-Shen Huang Jem-Kun Chen Shiao-Wei Kuo Ya-An Hsieh Shota Yamamoto Jun Nakanishi Chih-Feng Huang |
| author_sort | Yi-Shen Huang |
| collection | DOAJ |
| description | Atom transfer radical polyaddition (ATRPA) was utilized herein to synthesize a specific functional polyester. We conducted ATRPA of 4-vinylbenzyl 2-bromo-2-phenylacetate (VBBPA) inimer and successfully obtained a linear type poly(VBBPA) (PVBBPA) polyester with benzylic bromides along the backbone. To obtain a novel amphiphilic polymer bottlebrush, however, the lateral ATRP chain extension of PVBBPA with <i>N</i>-vinyl pyrrolidone (NVP) met the problem of quantitative dimerization. By replacing the bromides to xanthate moieties efficiently, we thus observed a pseudo linear first order reversible addition−fragmentation chain transfer (RAFT) polymerization to obtain novel poly(4-vinylbenzyl-2-phenylacetate)-<i>g</i>-poly(NVP) (PVBPA-<i>g</i>-PNVP) amphiphilic polymer bottlebrushes. The critical micelle concentration (CMC) and particle size of the amphiphilic polymer bottlebrushes were characterized by fluorescence spectroscopy, dynamic light scattering (DLS), and scanning electron microscopy (SEM) (CMCs < 0.5 mg/mL; particle sizes = ca. 100 nm). Toward drug delivery application, we examined release profiles using a model drug of Nile red at different pH environments (3, 5, and 7). Eventually, low cytotoxicity and well cell uptake of the Madin-Darby Canine Kidney Epithelial (MDCK) for the polymer bottlebrush micelles were demonstrated. |
| first_indexed | 2024-04-13T02:50:36Z |
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| id | doaj.art-7e45c9fe14174f10bb1e45791cdd32ed |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-04-13T02:50:36Z |
| publishDate | 2019-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-7e45c9fe14174f10bb1e45791cdd32ed2022-12-22T03:05:51ZengMDPI AGPolymers2073-43602019-06-01116107910.3390/polym11061079polym11061079Synthesis of Poly(<i>N</i>-vinylpyrrolidone)-Based Polymer Bottlebrushes by ATRPA and RAFT Polymerization: Toward Drug Delivery ApplicationYi-Shen Huang0Jem-Kun Chen1Shiao-Wei Kuo2Ya-An Hsieh3Shota Yamamoto4Jun Nakanishi5Chih-Feng Huang6Department of Chemical Engineering, National Chung Hsing University, 145 Xingda Road, Taichung 40227, TaiwanDepartment of Materials Science and Engineering, National Taiwan University of Science and Technology, Taipei 10607, TaiwanDepartment of Materials and Optoelectronic Science, Center of Crystal Research, National Sun Yat-Sen University, Kaohsiung 804, TaiwanDepartment of Chemical Engineering, National Chung Hsing University, 145 Xingda Road, Taichung 40227, TaiwanWorld Premier International Research Center for Materials Nanoarchitectonics (WPI-MANA), National Institute for Materials Science (NIMS), 1-1, Namiki, Tsukuba, Ibaraki 305-0044, JapanWorld Premier International Research Center for Materials Nanoarchitectonics (WPI-MANA), National Institute for Materials Science (NIMS), 1-1, Namiki, Tsukuba, Ibaraki 305-0044, JapanDepartment of Chemical Engineering, National Chung Hsing University, 145 Xingda Road, Taichung 40227, TaiwanAtom transfer radical polyaddition (ATRPA) was utilized herein to synthesize a specific functional polyester. We conducted ATRPA of 4-vinylbenzyl 2-bromo-2-phenylacetate (VBBPA) inimer and successfully obtained a linear type poly(VBBPA) (PVBBPA) polyester with benzylic bromides along the backbone. To obtain a novel amphiphilic polymer bottlebrush, however, the lateral ATRP chain extension of PVBBPA with <i>N</i>-vinyl pyrrolidone (NVP) met the problem of quantitative dimerization. By replacing the bromides to xanthate moieties efficiently, we thus observed a pseudo linear first order reversible addition−fragmentation chain transfer (RAFT) polymerization to obtain novel poly(4-vinylbenzyl-2-phenylacetate)-<i>g</i>-poly(NVP) (PVBPA-<i>g</i>-PNVP) amphiphilic polymer bottlebrushes. The critical micelle concentration (CMC) and particle size of the amphiphilic polymer bottlebrushes were characterized by fluorescence spectroscopy, dynamic light scattering (DLS), and scanning electron microscopy (SEM) (CMCs < 0.5 mg/mL; particle sizes = ca. 100 nm). Toward drug delivery application, we examined release profiles using a model drug of Nile red at different pH environments (3, 5, and 7). Eventually, low cytotoxicity and well cell uptake of the Madin-Darby Canine Kidney Epithelial (MDCK) for the polymer bottlebrush micelles were demonstrated.https://www.mdpi.com/2073-4360/11/6/1079atom transfer radical polyaddition (ATRPA)reversible addition–fragmentation chain transfer (RAFT) polymerizationfunctional polyesterspoly(<i>N</i>-vinylpyrrolidone)amphiphilic polymer bottlebrush |
| spellingShingle | Yi-Shen Huang Jem-Kun Chen Shiao-Wei Kuo Ya-An Hsieh Shota Yamamoto Jun Nakanishi Chih-Feng Huang Synthesis of Poly(<i>N</i>-vinylpyrrolidone)-Based Polymer Bottlebrushes by ATRPA and RAFT Polymerization: Toward Drug Delivery Application Polymers atom transfer radical polyaddition (ATRPA) reversible addition–fragmentation chain transfer (RAFT) polymerization functional polyesters poly(<i>N</i>-vinylpyrrolidone) amphiphilic polymer bottlebrush |
| title | Synthesis of Poly(<i>N</i>-vinylpyrrolidone)-Based Polymer Bottlebrushes by ATRPA and RAFT Polymerization: Toward Drug Delivery Application |
| title_full | Synthesis of Poly(<i>N</i>-vinylpyrrolidone)-Based Polymer Bottlebrushes by ATRPA and RAFT Polymerization: Toward Drug Delivery Application |
| title_fullStr | Synthesis of Poly(<i>N</i>-vinylpyrrolidone)-Based Polymer Bottlebrushes by ATRPA and RAFT Polymerization: Toward Drug Delivery Application |
| title_full_unstemmed | Synthesis of Poly(<i>N</i>-vinylpyrrolidone)-Based Polymer Bottlebrushes by ATRPA and RAFT Polymerization: Toward Drug Delivery Application |
| title_short | Synthesis of Poly(<i>N</i>-vinylpyrrolidone)-Based Polymer Bottlebrushes by ATRPA and RAFT Polymerization: Toward Drug Delivery Application |
| title_sort | synthesis of poly i n i vinylpyrrolidone based polymer bottlebrushes by atrpa and raft polymerization toward drug delivery application |
| topic | atom transfer radical polyaddition (ATRPA) reversible addition–fragmentation chain transfer (RAFT) polymerization functional polyesters poly(<i>N</i>-vinylpyrrolidone) amphiphilic polymer bottlebrush |
| url | https://www.mdpi.com/2073-4360/11/6/1079 |
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