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A novel diclofenac-hydrogel conjugate system for intraarticular sustained release: Development of 2-pyridylamino-substituted 1-phenylethanol (PAPE) and its derivatives as tunable traceless linkers
[Display omitted] A local sustained-release drug delivery system, or depot, for intra-articular injection offers the opportunity to release a therapeutic agent directly to the joint with limited need for reinjection. A successful system would provide more consistent efficacy and minimize systemic si...
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Published in: | International journal of pharmaceutics 2020-07, Vol.585, p.119519-119519, Article 119519 |
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container_title | International journal of pharmaceutics |
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creator | Kawanami, Toshio LaBonte, Laura R. Amin, Jakal Thibodeaux, Stefan J. Lee, Cameron C. Argintaru, O. Andreea Adams, Christopher M. |
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A local sustained-release drug delivery system, or depot, for intra-articular injection offers the opportunity to release a therapeutic agent directly to the joint with limited need for reinjection. A successful system would provide more consistent efficacy and minimize systemic side effects. In this paper, we explore the potential use of diclofenac, a non-steroidal anti-inflammatory drug, for use in a polymer-conjugate depot system. During the course of our exploration it was determined that “conventional ester” conjugates of diclofenac were not appropriate as upon incubation in buffer (pH 7.4) or in bovine synovial fluid, a considerable amount of undesired diclofenac-lactam was released. Thus we developed a novel linker system for diclofenac in order to minimize the production of the lactam. This new linker enables a diclofenac conjugate system with tunable release rates and minimizes the production of undesired lactam side-products. |
doi_str_mv | 10.1016/j.ijpharm.2020.119519 |
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A local sustained-release drug delivery system, or depot, for intra-articular injection offers the opportunity to release a therapeutic agent directly to the joint with limited need for reinjection. A successful system would provide more consistent efficacy and minimize systemic side effects. In this paper, we explore the potential use of diclofenac, a non-steroidal anti-inflammatory drug, for use in a polymer-conjugate depot system. During the course of our exploration it was determined that “conventional ester” conjugates of diclofenac were not appropriate as upon incubation in buffer (pH 7.4) or in bovine synovial fluid, a considerable amount of undesired diclofenac-lactam was released. Thus we developed a novel linker system for diclofenac in order to minimize the production of the lactam. This new linker enables a diclofenac conjugate system with tunable release rates and minimizes the production of undesired lactam side-products.</description><identifier>ISSN: 0378-5173</identifier><identifier>EISSN: 1873-3476</identifier><identifier>DOI: 10.1016/j.ijpharm.2020.119519</identifier><identifier>PMID: 32535069</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>2-Pyridylamino substituted 1-phenylethanol (PAPE) ; Animals ; Anti-Inflammatory Agents, Non-Steroidal - administration & dosage ; Benzyl Alcohols - chemistry ; Cattle ; Chemistry, Pharmaceutical - methods ; Delayed-Action Preparations ; Diclofenac ; Diclofenac - administration & dosage ; Drug delivery system ; Drug Delivery Systems - methods ; Humans ; Hydrogel ; Hydrogels - chemistry ; Hydrogen-Ion Concentration ; Injections, Intra-Articular ; Osteoarthritis ; Polymeric prodrug ; Prodrugs ; Sustained release ; Synovial Fluid</subject><ispartof>International journal of pharmaceutics, 2020-07, Vol.585, p.119519-119519, Article 119519</ispartof><rights>2020 Elsevier B.V.</rights><rights>Copyright © 2020 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c365t-77bd893f5885ed11c5ab39723f1425dd32739d3c194e13150e4d01baf9001dd23</citedby><cites>FETCH-LOGICAL-c365t-77bd893f5885ed11c5ab39723f1425dd32739d3c194e13150e4d01baf9001dd23</cites><orcidid>0000-0001-7721-366X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32535069$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kawanami, Toshio</creatorcontrib><creatorcontrib>LaBonte, Laura R.</creatorcontrib><creatorcontrib>Amin, Jakal</creatorcontrib><creatorcontrib>Thibodeaux, Stefan J.</creatorcontrib><creatorcontrib>Lee, Cameron C.</creatorcontrib><creatorcontrib>Argintaru, O. Andreea</creatorcontrib><creatorcontrib>Adams, Christopher M.</creatorcontrib><title>A novel diclofenac-hydrogel conjugate system for intraarticular sustained release: Development of 2-pyridylamino-substituted 1-phenylethanol (PAPE) and its derivatives as tunable traceless linkers</title><title>International journal of pharmaceutics</title><addtitle>Int J Pharm</addtitle><description>[Display omitted]
A local sustained-release drug delivery system, or depot, for intra-articular injection offers the opportunity to release a therapeutic agent directly to the joint with limited need for reinjection. A successful system would provide more consistent efficacy and minimize systemic side effects. In this paper, we explore the potential use of diclofenac, a non-steroidal anti-inflammatory drug, for use in a polymer-conjugate depot system. During the course of our exploration it was determined that “conventional ester” conjugates of diclofenac were not appropriate as upon incubation in buffer (pH 7.4) or in bovine synovial fluid, a considerable amount of undesired diclofenac-lactam was released. Thus we developed a novel linker system for diclofenac in order to minimize the production of the lactam. This new linker enables a diclofenac conjugate system with tunable release rates and minimizes the production of undesired lactam side-products.</description><subject>2-Pyridylamino substituted 1-phenylethanol (PAPE)</subject><subject>Animals</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - administration & dosage</subject><subject>Benzyl Alcohols - chemistry</subject><subject>Cattle</subject><subject>Chemistry, Pharmaceutical - methods</subject><subject>Delayed-Action Preparations</subject><subject>Diclofenac</subject><subject>Diclofenac - administration & dosage</subject><subject>Drug delivery system</subject><subject>Drug Delivery Systems - methods</subject><subject>Humans</subject><subject>Hydrogel</subject><subject>Hydrogels - chemistry</subject><subject>Hydrogen-Ion Concentration</subject><subject>Injections, Intra-Articular</subject><subject>Osteoarthritis</subject><subject>Polymeric prodrug</subject><subject>Prodrugs</subject><subject>Sustained release</subject><subject>Synovial Fluid</subject><issn>0378-5173</issn><issn>1873-3476</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkU9v1DAQxSMEokvhI4B8LIcs_hNvNlzQqrSAVIke4Gw59qTrxbGDx1kp348PhqvdcuU00tN782b0q6q3jK4ZZZsPh7U7THudxjWnvGisk6x7Vq3YthW1aNrN82pFRbutJWvFRfUK8UAp3XAmXlYXgksh6aZbVX92JMQjeGKd8XGAoE29X2yKD0UzMRzmB52B4IIZRjLERFzISeuUnZm9TgRnzNoFsCSBB43wkXyGsjBOI4RM4kB4PS3J2cXr0YVY49xjdnnOJcLqaQ9h8ZD3OkRPru539zfviQ6WuIzEQnJHnd0RkGgkeQ6690BKvyldiMS78AsSvq5eDNojvDnPy-rn7c2P66_13fcv3653d7URG5nrtu3tthOD3G4lWMaM1L3oWi4G1nBpreCt6KwwrGuACSYpNJayXg8dpcxaLi6rq9PeKcXfM2BWo8NyitcB4oyKN6yhjAvKilWerCZFxASDmpIbdVoUo-oRoDqoM0D1CFCdAJbcu3PF3I9g_6WeiBXDp5MByqNHB0mhcRAMWJfAZGWj-0_FX_9Vs7Y</recordid><startdate>20200730</startdate><enddate>20200730</enddate><creator>Kawanami, Toshio</creator><creator>LaBonte, Laura R.</creator><creator>Amin, Jakal</creator><creator>Thibodeaux, Stefan J.</creator><creator>Lee, Cameron C.</creator><creator>Argintaru, O. Andreea</creator><creator>Adams, Christopher M.</creator><general>Elsevier B.V</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><orcidid>https://orcid.org/0000-0001-7721-366X</orcidid></search><sort><creationdate>20200730</creationdate><title>A novel diclofenac-hydrogel conjugate system for intraarticular sustained release: Development of 2-pyridylamino-substituted 1-phenylethanol (PAPE) and its derivatives as tunable traceless linkers</title><author>Kawanami, Toshio ; LaBonte, Laura R. ; Amin, Jakal ; Thibodeaux, Stefan J. ; Lee, Cameron C. ; Argintaru, O. Andreea ; Adams, Christopher M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c365t-77bd893f5885ed11c5ab39723f1425dd32739d3c194e13150e4d01baf9001dd23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>2-Pyridylamino substituted 1-phenylethanol (PAPE)</topic><topic>Animals</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - administration & dosage</topic><topic>Benzyl Alcohols - chemistry</topic><topic>Cattle</topic><topic>Chemistry, Pharmaceutical - methods</topic><topic>Delayed-Action Preparations</topic><topic>Diclofenac</topic><topic>Diclofenac - administration & dosage</topic><topic>Drug delivery system</topic><topic>Drug Delivery Systems - methods</topic><topic>Humans</topic><topic>Hydrogel</topic><topic>Hydrogels - chemistry</topic><topic>Hydrogen-Ion Concentration</topic><topic>Injections, Intra-Articular</topic><topic>Osteoarthritis</topic><topic>Polymeric prodrug</topic><topic>Prodrugs</topic><topic>Sustained release</topic><topic>Synovial Fluid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kawanami, Toshio</creatorcontrib><creatorcontrib>LaBonte, Laura R.</creatorcontrib><creatorcontrib>Amin, Jakal</creatorcontrib><creatorcontrib>Thibodeaux, Stefan J.</creatorcontrib><creatorcontrib>Lee, Cameron C.</creatorcontrib><creatorcontrib>Argintaru, O. Andreea</creatorcontrib><creatorcontrib>Adams, Christopher M.</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>International journal of pharmaceutics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kawanami, Toshio</au><au>LaBonte, Laura R.</au><au>Amin, Jakal</au><au>Thibodeaux, Stefan J.</au><au>Lee, Cameron C.</au><au>Argintaru, O. Andreea</au><au>Adams, Christopher M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A novel diclofenac-hydrogel conjugate system for intraarticular sustained release: Development of 2-pyridylamino-substituted 1-phenylethanol (PAPE) and its derivatives as tunable traceless linkers</atitle><jtitle>International journal of pharmaceutics</jtitle><addtitle>Int J Pharm</addtitle><date>2020-07-30</date><risdate>2020</risdate><volume>585</volume><spage>119519</spage><epage>119519</epage><pages>119519-119519</pages><artnum>119519</artnum><issn>0378-5173</issn><eissn>1873-3476</eissn><abstract>[Display omitted]
A local sustained-release drug delivery system, or depot, for intra-articular injection offers the opportunity to release a therapeutic agent directly to the joint with limited need for reinjection. A successful system would provide more consistent efficacy and minimize systemic side effects. In this paper, we explore the potential use of diclofenac, a non-steroidal anti-inflammatory drug, for use in a polymer-conjugate depot system. During the course of our exploration it was determined that “conventional ester” conjugates of diclofenac were not appropriate as upon incubation in buffer (pH 7.4) or in bovine synovial fluid, a considerable amount of undesired diclofenac-lactam was released. Thus we developed a novel linker system for diclofenac in order to minimize the production of the lactam. This new linker enables a diclofenac conjugate system with tunable release rates and minimizes the production of undesired lactam side-products.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>32535069</pmid><doi>10.1016/j.ijpharm.2020.119519</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0001-7721-366X</orcidid></addata></record> |
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subjects | 2-Pyridylamino substituted 1-phenylethanol (PAPE) Animals Anti-Inflammatory Agents, Non-Steroidal - administration & dosage Benzyl Alcohols - chemistry Cattle Chemistry, Pharmaceutical - methods Delayed-Action Preparations Diclofenac Diclofenac - administration & dosage Drug delivery system Drug Delivery Systems - methods Humans Hydrogel Hydrogels - chemistry Hydrogen-Ion Concentration Injections, Intra-Articular Osteoarthritis Polymeric prodrug Prodrugs Sustained release Synovial Fluid |
title | A novel diclofenac-hydrogel conjugate system for intraarticular sustained release: Development of 2-pyridylamino-substituted 1-phenylethanol (PAPE) and its derivatives as tunable traceless linkers |
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