Cascade post-polymerization modification of single pentafluorophenyl ester-bearing homopolymer as a facile route to redox-responsive nanogels
[Display omitted] Poly(pentafluorophenyl methacrylate) (PPFPMA) was first subjected to post-polymerization modification with oligo(ethylene glycol) methyl ether amine (OEG-NH2) and yielded poly(pentafluorophenyl methacrylate)-co-poly(oligo(ethylene glycol methacrylamide)), PPFPMA-co-POEGMAM. These a...
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| Veröffentlicht in: | Journal of colloid and interface science 2017-09, Vol.501, p.94-102 |
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| container_title | Journal of colloid and interface science |
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| creator | Noree, Susita Tangpasuthadol, Varawut Kiatkamjornwong, Suda Hoven, Voravee P. |
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Poly(pentafluorophenyl methacrylate) (PPFPMA) was first subjected to post-polymerization modification with oligo(ethylene glycol) methyl ether amine (OEG-NH2) and yielded poly(pentafluorophenyl methacrylate)-co-poly(oligo(ethylene glycol methacrylamide)), PPFPMA-co-POEGMAM. These amphiphilic random copolymers can self-assemble into micellar nanoparticles in water having sizes less than 100nm. By tandemly reacting the pentafluorophenyl (PFP) groups in the copolymeric nanoparticles with a dithiol crosslinker, cystamine, redox-responsive nanogels can be formed. The last step of post functionalization with isopropylamine was introduced in order to remove the remaining PFP groups in the nanogels. Stepwise post functionalization can be monitored by FTIR and 19F NMR spectroscopy. Release of a model hydrophobic drug, nile red (NR) from the nanogels, simultaneously encapsulated during micelles formation, can be accelerated in the presence of glutathione (GSH) especially at 37°C. Results from cytocompatibility evaluation suggested that these developed redox-responsive nanogels strongly possessed a potential for applications in controlled delivery. |
| doi_str_mv | 10.1016/j.jcis.2017.04.030 |
| format | Article |
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Poly(pentafluorophenyl methacrylate) (PPFPMA) was first subjected to post-polymerization modification with oligo(ethylene glycol) methyl ether amine (OEG-NH2) and yielded poly(pentafluorophenyl methacrylate)-co-poly(oligo(ethylene glycol methacrylamide)), PPFPMA-co-POEGMAM. These amphiphilic random copolymers can self-assemble into micellar nanoparticles in water having sizes less than 100nm. By tandemly reacting the pentafluorophenyl (PFP) groups in the copolymeric nanoparticles with a dithiol crosslinker, cystamine, redox-responsive nanogels can be formed. The last step of post functionalization with isopropylamine was introduced in order to remove the remaining PFP groups in the nanogels. Stepwise post functionalization can be monitored by FTIR and 19F NMR spectroscopy. Release of a model hydrophobic drug, nile red (NR) from the nanogels, simultaneously encapsulated during micelles formation, can be accelerated in the presence of glutathione (GSH) especially at 37°C. Results from cytocompatibility evaluation suggested that these developed redox-responsive nanogels strongly possessed a potential for applications in controlled delivery.</description><identifier>ISSN: 0021-9797</identifier><identifier>EISSN: 1095-7103</identifier><identifier>DOI: 10.1016/j.jcis.2017.04.030</identifier><identifier>PMID: 28437702</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Active ester group ; Delayed-Action Preparations - chemistry ; Drug carrier ; Esterification ; Gels - chemistry ; Glutathione ; Glutathione - chemistry ; Methacrylates - chemistry ; Micelles ; Nanogel ; Nanoparticles - chemistry ; Oxazines - administration & dosage ; Oxidation-Reduction ; Pentafluorophenyl ester ; Polymerization ; Post-polymerization modification ; Redox responsive</subject><ispartof>Journal of colloid and interface science, 2017-09, Vol.501, p.94-102</ispartof><rights>2017 Elsevier Inc.</rights><rights>Copyright © 2017 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c459t-80a155e5e79e5e978d27b5719eeb9cad290343843f74722b1c54ee01c841f80d3</citedby><cites>FETCH-LOGICAL-c459t-80a155e5e79e5e978d27b5719eeb9cad290343843f74722b1c54ee01c841f80d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.jcis.2017.04.030$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28437702$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Noree, Susita</creatorcontrib><creatorcontrib>Tangpasuthadol, Varawut</creatorcontrib><creatorcontrib>Kiatkamjornwong, Suda</creatorcontrib><creatorcontrib>Hoven, Voravee P.</creatorcontrib><title>Cascade post-polymerization modification of single pentafluorophenyl ester-bearing homopolymer as a facile route to redox-responsive nanogels</title><title>Journal of colloid and interface science</title><addtitle>J Colloid Interface Sci</addtitle><description>[Display omitted]
Poly(pentafluorophenyl methacrylate) (PPFPMA) was first subjected to post-polymerization modification with oligo(ethylene glycol) methyl ether amine (OEG-NH2) and yielded poly(pentafluorophenyl methacrylate)-co-poly(oligo(ethylene glycol methacrylamide)), PPFPMA-co-POEGMAM. These amphiphilic random copolymers can self-assemble into micellar nanoparticles in water having sizes less than 100nm. By tandemly reacting the pentafluorophenyl (PFP) groups in the copolymeric nanoparticles with a dithiol crosslinker, cystamine, redox-responsive nanogels can be formed. The last step of post functionalization with isopropylamine was introduced in order to remove the remaining PFP groups in the nanogels. Stepwise post functionalization can be monitored by FTIR and 19F NMR spectroscopy. Release of a model hydrophobic drug, nile red (NR) from the nanogels, simultaneously encapsulated during micelles formation, can be accelerated in the presence of glutathione (GSH) especially at 37°C. Results from cytocompatibility evaluation suggested that these developed redox-responsive nanogels strongly possessed a potential for applications in controlled delivery.</description><subject>Active ester group</subject><subject>Delayed-Action Preparations - chemistry</subject><subject>Drug carrier</subject><subject>Esterification</subject><subject>Gels - chemistry</subject><subject>Glutathione</subject><subject>Glutathione - chemistry</subject><subject>Methacrylates - chemistry</subject><subject>Micelles</subject><subject>Nanogel</subject><subject>Nanoparticles - chemistry</subject><subject>Oxazines - administration & dosage</subject><subject>Oxidation-Reduction</subject><subject>Pentafluorophenyl ester</subject><subject>Polymerization</subject><subject>Post-polymerization modification</subject><subject>Redox responsive</subject><issn>0021-9797</issn><issn>1095-7103</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kc2O1DAQhC0EYoeFF-CAfOSS0HaStS1xQaPlR1qJC5wtx-nsepS4g52sGN6Bd8ajGThyccvSV6WuLsZeC6gFiJt3h_rgQ64lCFVDW0MDT9hOgOkqJaB5ynYAUlRGGXXFXuR8ABCi68xzdiV12ygFcsd-7132bkC-UF6rhabjjCn8cmugyGcawhj8-UMjzyHeTwXFuLpx2ijR8oDxOHHMK6aqR5cKwR9oposTd5k7Pjofii7RtiJfiScc6GeVMC8Uc3hEHl2ke5zyS_ZsdFPGV5d5zb5_vP22_1zdff30Zf_hrvJtZ9ZKgytBsENlymOUHqTqOyUMYm9KGmmgaZuScVStkrIXvmsRQXjdilHD0Fyzt2ffJdGPrWxv55A9TpOLSFu2QhuhtW66m4LKM-oT5ZxwtEsKs0tHK8CearAHe6rBnmqw0NpSQxG9ufhv_YzDP8nfuxfg_RkoofExYLLZB4weh5DQr3ag8D__P7AmnOc</recordid><startdate>20170901</startdate><enddate>20170901</enddate><creator>Noree, Susita</creator><creator>Tangpasuthadol, Varawut</creator><creator>Kiatkamjornwong, Suda</creator><creator>Hoven, Voravee P.</creator><general>Elsevier Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20170901</creationdate><title>Cascade post-polymerization modification of single pentafluorophenyl ester-bearing homopolymer as a facile route to redox-responsive nanogels</title><author>Noree, Susita ; Tangpasuthadol, Varawut ; Kiatkamjornwong, Suda ; Hoven, Voravee P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c459t-80a155e5e79e5e978d27b5719eeb9cad290343843f74722b1c54ee01c841f80d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Active ester group</topic><topic>Delayed-Action Preparations - chemistry</topic><topic>Drug carrier</topic><topic>Esterification</topic><topic>Gels - chemistry</topic><topic>Glutathione</topic><topic>Glutathione - chemistry</topic><topic>Methacrylates - chemistry</topic><topic>Micelles</topic><topic>Nanogel</topic><topic>Nanoparticles - chemistry</topic><topic>Oxazines - administration & dosage</topic><topic>Oxidation-Reduction</topic><topic>Pentafluorophenyl ester</topic><topic>Polymerization</topic><topic>Post-polymerization modification</topic><topic>Redox responsive</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Noree, Susita</creatorcontrib><creatorcontrib>Tangpasuthadol, Varawut</creatorcontrib><creatorcontrib>Kiatkamjornwong, Suda</creatorcontrib><creatorcontrib>Hoven, Voravee P.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of colloid and interface science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Noree, Susita</au><au>Tangpasuthadol, Varawut</au><au>Kiatkamjornwong, Suda</au><au>Hoven, Voravee P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cascade post-polymerization modification of single pentafluorophenyl ester-bearing homopolymer as a facile route to redox-responsive nanogels</atitle><jtitle>Journal of colloid and interface science</jtitle><addtitle>J Colloid Interface Sci</addtitle><date>2017-09-01</date><risdate>2017</risdate><volume>501</volume><spage>94</spage><epage>102</epage><pages>94-102</pages><issn>0021-9797</issn><eissn>1095-7103</eissn><abstract>[Display omitted]
Poly(pentafluorophenyl methacrylate) (PPFPMA) was first subjected to post-polymerization modification with oligo(ethylene glycol) methyl ether amine (OEG-NH2) and yielded poly(pentafluorophenyl methacrylate)-co-poly(oligo(ethylene glycol methacrylamide)), PPFPMA-co-POEGMAM. These amphiphilic random copolymers can self-assemble into micellar nanoparticles in water having sizes less than 100nm. By tandemly reacting the pentafluorophenyl (PFP) groups in the copolymeric nanoparticles with a dithiol crosslinker, cystamine, redox-responsive nanogels can be formed. The last step of post functionalization with isopropylamine was introduced in order to remove the remaining PFP groups in the nanogels. Stepwise post functionalization can be monitored by FTIR and 19F NMR spectroscopy. Release of a model hydrophobic drug, nile red (NR) from the nanogels, simultaneously encapsulated during micelles formation, can be accelerated in the presence of glutathione (GSH) especially at 37°C. Results from cytocompatibility evaluation suggested that these developed redox-responsive nanogels strongly possessed a potential for applications in controlled delivery.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>28437702</pmid><doi>10.1016/j.jcis.2017.04.030</doi><tpages>9</tpages></addata></record> |
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| subjects | Active ester group Delayed-Action Preparations - chemistry Drug carrier Esterification Gels - chemistry Glutathione Glutathione - chemistry Methacrylates - chemistry Micelles Nanogel Nanoparticles - chemistry Oxazines - administration & dosage Oxidation-Reduction Pentafluorophenyl ester Polymerization Post-polymerization modification Redox responsive |
| title | Cascade post-polymerization modification of single pentafluorophenyl ester-bearing homopolymer as a facile route to redox-responsive nanogels |
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