Drug-polymer conjugates with dynamic cloud point temperatures based on poly(2-oxazoline) copolymers
A dynamic thermo-responsive drug delivery concept using poly(2-oxazoline) copolymers conjugated with a hydrophobic drug is presented. The novel strategy entails the synthesis of copolymers comprising 2- n -propyl-2-oxazoline and 2-methoxycarbonylpropyl-2-oxazoline to which the drug, benazepril is co...
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| Veröffentlicht in: | Polymer chemistry 2020-08, Vol.11 (32), p.5191-5199 |
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| container_title | Polymer chemistry |
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| creator | Park, Jong-Ryul Sarwat, Mariah Bolle, Eleonore C. L de Laat, Melody A Van Guyse, Joachim F. R Podevyn, Annelore Hoogenboom, Richard Dargaville, Tim R |
| description | A dynamic thermo-responsive drug delivery concept using poly(2-oxazoline) copolymers conjugated with a hydrophobic drug is presented. The novel strategy entails the synthesis of copolymers comprising 2-
n
-propyl-2-oxazoline and 2-methoxycarbonylpropyl-2-oxazoline to which the drug, benazepril is conjugated
via
an ester linkage. The polymer without drug is non-toxic and has a cloud point temperature in aqueous conditions around 50 °C meaning that it is soluble at body temperature. Yet, when conjugated with the drug, the cloud point temperature decreases to in between 0 and 30 °C, depending on the quantity of drug coupled to the polymer. Conversely, as the drug is cleaved
via
ester hydrolysis, the cloud point temperature shifts to higher temperature and the polymer becomes soluble. This shift in cloud point temperature from above to below body temperature upon modification of the polymer with the drug benazepril is hypothesized to make it suitable as an injectable soluble polymer-drug conjugate that forms an insoluble depot to slowly release the pristine drug followed by redissolution of the drug-free polymer.
A shift in cloud point temperatures of poly(2-oxazoline)/ACE inhibitor polymer drug conjugates occurs on release of the drug. |
| doi_str_mv | 10.1039/d0py00602e |
| format | Article |
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n
-propyl-2-oxazoline and 2-methoxycarbonylpropyl-2-oxazoline to which the drug, benazepril is conjugated
via
an ester linkage. The polymer without drug is non-toxic and has a cloud point temperature in aqueous conditions around 50 °C meaning that it is soluble at body temperature. Yet, when conjugated with the drug, the cloud point temperature decreases to in between 0 and 30 °C, depending on the quantity of drug coupled to the polymer. Conversely, as the drug is cleaved
via
ester hydrolysis, the cloud point temperature shifts to higher temperature and the polymer becomes soluble. This shift in cloud point temperature from above to below body temperature upon modification of the polymer with the drug benazepril is hypothesized to make it suitable as an injectable soluble polymer-drug conjugate that forms an insoluble depot to slowly release the pristine drug followed by redissolution of the drug-free polymer.
A shift in cloud point temperatures of poly(2-oxazoline)/ACE inhibitor polymer drug conjugates occurs on release of the drug.</description><identifier>ISSN: 1759-9954</identifier><identifier>EISSN: 1759-9962</identifier><identifier>DOI: 10.1039/d0py00602e</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Body temperature ; Chemical synthesis ; Conjugates ; Copolymers ; Drug delivery systems ; Polymer chemistry ; Polymers</subject><ispartof>Polymer chemistry, 2020-08, Vol.11 (32), p.5191-5199</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c307t-d244dae1b11fb0618fccda35347f63909c55e66efaa226b675950938420ec4ea3</citedby><cites>FETCH-LOGICAL-c307t-d244dae1b11fb0618fccda35347f63909c55e66efaa226b675950938420ec4ea3</cites><orcidid>0000-0001-5725-6531 ; 0000-0001-7398-2058 ; 0000-0003-4665-9508 ; 0000-0001-7922-3642 ; 0000-0003-0682-6439</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids></links><search><creatorcontrib>Park, Jong-Ryul</creatorcontrib><creatorcontrib>Sarwat, Mariah</creatorcontrib><creatorcontrib>Bolle, Eleonore C. L</creatorcontrib><creatorcontrib>de Laat, Melody A</creatorcontrib><creatorcontrib>Van Guyse, Joachim F. R</creatorcontrib><creatorcontrib>Podevyn, Annelore</creatorcontrib><creatorcontrib>Hoogenboom, Richard</creatorcontrib><creatorcontrib>Dargaville, Tim R</creatorcontrib><title>Drug-polymer conjugates with dynamic cloud point temperatures based on poly(2-oxazoline) copolymers</title><title>Polymer chemistry</title><description>A dynamic thermo-responsive drug delivery concept using poly(2-oxazoline) copolymers conjugated with a hydrophobic drug is presented. The novel strategy entails the synthesis of copolymers comprising 2-
n
-propyl-2-oxazoline and 2-methoxycarbonylpropyl-2-oxazoline to which the drug, benazepril is conjugated
via
an ester linkage. The polymer without drug is non-toxic and has a cloud point temperature in aqueous conditions around 50 °C meaning that it is soluble at body temperature. Yet, when conjugated with the drug, the cloud point temperature decreases to in between 0 and 30 °C, depending on the quantity of drug coupled to the polymer. Conversely, as the drug is cleaved
via
ester hydrolysis, the cloud point temperature shifts to higher temperature and the polymer becomes soluble. This shift in cloud point temperature from above to below body temperature upon modification of the polymer with the drug benazepril is hypothesized to make it suitable as an injectable soluble polymer-drug conjugate that forms an insoluble depot to slowly release the pristine drug followed by redissolution of the drug-free polymer.
A shift in cloud point temperatures of poly(2-oxazoline)/ACE inhibitor polymer drug conjugates occurs on release of the drug.</description><subject>Body temperature</subject><subject>Chemical synthesis</subject><subject>Conjugates</subject><subject>Copolymers</subject><subject>Drug delivery systems</subject><subject>Polymer chemistry</subject><subject>Polymers</subject><issn>1759-9954</issn><issn>1759-9962</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kE1Lw0AQhhdRsNRevAsrXlSI7le2zVHa-gEFPejBU9jsTmpKko27CTb-ere21JtzmYF5eIZ5ETql5IYSntwa0vSESMLgAA3oOE6iJJHscD_H4hiNvF-RUJwKxuUA6ZnrllFjy74Ch7WtV91SteDxV9F-YNPXqio01qXtDG5sUbe4haoBp9rOBSpTHgy2Nd4YLllk1-rblkUNV8G1s_oTdJSr0sNo14fo7X7-On2MFs8PT9O7RaQ5GbeRYUIYBTSjNM-IpJNca6N4zMU4lzwhiY5jkBJypRiTmQxPxSThE8EIaAGKD9HF1ts4-9mBb9OV7VwdTqZMBAuVkrNAXW8p7az3DvK0cUWlXJ9Skm5yTGfk5f03x3mAz7aw83rP_eUc9uf_7dPG5PwHsjN7zg</recordid><startdate>20200828</startdate><enddate>20200828</enddate><creator>Park, Jong-Ryul</creator><creator>Sarwat, Mariah</creator><creator>Bolle, Eleonore C. L</creator><creator>de Laat, Melody A</creator><creator>Van Guyse, Joachim F. R</creator><creator>Podevyn, Annelore</creator><creator>Hoogenboom, Richard</creator><creator>Dargaville, Tim R</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0001-5725-6531</orcidid><orcidid>https://orcid.org/0000-0001-7398-2058</orcidid><orcidid>https://orcid.org/0000-0003-4665-9508</orcidid><orcidid>https://orcid.org/0000-0001-7922-3642</orcidid><orcidid>https://orcid.org/0000-0003-0682-6439</orcidid></search><sort><creationdate>20200828</creationdate><title>Drug-polymer conjugates with dynamic cloud point temperatures based on poly(2-oxazoline) copolymers</title><author>Park, Jong-Ryul ; Sarwat, Mariah ; Bolle, Eleonore C. L ; de Laat, Melody A ; Van Guyse, Joachim F. R ; Podevyn, Annelore ; Hoogenboom, Richard ; Dargaville, Tim R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c307t-d244dae1b11fb0618fccda35347f63909c55e66efaa226b675950938420ec4ea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Body temperature</topic><topic>Chemical synthesis</topic><topic>Conjugates</topic><topic>Copolymers</topic><topic>Drug delivery systems</topic><topic>Polymer chemistry</topic><topic>Polymers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Park, Jong-Ryul</creatorcontrib><creatorcontrib>Sarwat, Mariah</creatorcontrib><creatorcontrib>Bolle, Eleonore C. L</creatorcontrib><creatorcontrib>de Laat, Melody A</creatorcontrib><creatorcontrib>Van Guyse, Joachim F. R</creatorcontrib><creatorcontrib>Podevyn, Annelore</creatorcontrib><creatorcontrib>Hoogenboom, Richard</creatorcontrib><creatorcontrib>Dargaville, Tim R</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Polymer chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Park, Jong-Ryul</au><au>Sarwat, Mariah</au><au>Bolle, Eleonore C. L</au><au>de Laat, Melody A</au><au>Van Guyse, Joachim F. R</au><au>Podevyn, Annelore</au><au>Hoogenboom, Richard</au><au>Dargaville, Tim R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Drug-polymer conjugates with dynamic cloud point temperatures based on poly(2-oxazoline) copolymers</atitle><jtitle>Polymer chemistry</jtitle><date>2020-08-28</date><risdate>2020</risdate><volume>11</volume><issue>32</issue><spage>5191</spage><epage>5199</epage><pages>5191-5199</pages><issn>1759-9954</issn><eissn>1759-9962</eissn><abstract>A dynamic thermo-responsive drug delivery concept using poly(2-oxazoline) copolymers conjugated with a hydrophobic drug is presented. The novel strategy entails the synthesis of copolymers comprising 2-
n
-propyl-2-oxazoline and 2-methoxycarbonylpropyl-2-oxazoline to which the drug, benazepril is conjugated
via
an ester linkage. The polymer without drug is non-toxic and has a cloud point temperature in aqueous conditions around 50 °C meaning that it is soluble at body temperature. Yet, when conjugated with the drug, the cloud point temperature decreases to in between 0 and 30 °C, depending on the quantity of drug coupled to the polymer. Conversely, as the drug is cleaved
via
ester hydrolysis, the cloud point temperature shifts to higher temperature and the polymer becomes soluble. This shift in cloud point temperature from above to below body temperature upon modification of the polymer with the drug benazepril is hypothesized to make it suitable as an injectable soluble polymer-drug conjugate that forms an insoluble depot to slowly release the pristine drug followed by redissolution of the drug-free polymer.
A shift in cloud point temperatures of poly(2-oxazoline)/ACE inhibitor polymer drug conjugates occurs on release of the drug.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d0py00602e</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-5725-6531</orcidid><orcidid>https://orcid.org/0000-0001-7398-2058</orcidid><orcidid>https://orcid.org/0000-0003-4665-9508</orcidid><orcidid>https://orcid.org/0000-0001-7922-3642</orcidid><orcidid>https://orcid.org/0000-0003-0682-6439</orcidid></addata></record> |
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| identifier | ISSN: 1759-9954 |
| ispartof | Polymer chemistry, 2020-08, Vol.11 (32), p.5191-5199 |
| issn | 1759-9954 1759-9962 |
| language | eng |
| recordid | cdi_rsc_primary_d0py00602e |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Body temperature Chemical synthesis Conjugates Copolymers Drug delivery systems Polymer chemistry Polymers |
| title | Drug-polymer conjugates with dynamic cloud point temperatures based on poly(2-oxazoline) copolymers |
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