In Vitro Investigation of Thiolated Chitosan Derivatives as Mucoadhesive Coating Materials for Solid Lipid Nanoparticles
In the present study, chitosan (CS) was thiolated by introducing l-cysteine via amide bond formation. Free thiol groups were protected with highly reactive 6-mercaptonicotinic acid (6-MNA) and less-reactive l-cysteine, respectively, via thiol/disulfide-exchange reactions. Unmodified CS, l-cysteine-m...
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| Veröffentlicht in: | Biomacromolecules 2021-09, Vol.22 (9), p.3980-3991 |
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| creator | Wibel, Richard Braun, Doris E Hämmerle, Laurenz Jörgensen, Arne M Knoll, Patrick Salvenmoser, Willi Steinbring, Christian Bernkop-Schnürch, Andreas |
| description | In the present study, chitosan (CS) was thiolated by introducing l-cysteine via amide bond formation. Free thiol groups were protected with highly reactive 6-mercaptonicotinic acid (6-MNA) and less-reactive l-cysteine, respectively, via thiol/disulfide-exchange reactions. Unmodified CS, l-cysteine-modified thiolated CS (CS-Cys), 6-MNA-S-protected thiolated CS (CS-Cys-MNA), and l-cysteine-S-protected thiolated CS (CS-Cys-Cys) were applied as coating materials to solid lipid nanoparticles (SLN). The strength of mucus interaction followed the rank order plain < CS < CS-Cys-Cys < CS-Cys < CS-Cys-MNA, whereas mucus diffusion followed the rank order CS-Cys < CS-Cys-Cys < CS < CS-Cys-MNA < plain. In accordance with lower reactivity, CS-Cys-Cys-coated SLN were immobilized to a lower extent than CS-Cys-coated SLN, while CS-Cys-MNA-coated SLN dissociated from their coating material resulting in a similar diffusion behavior as plain SLN. Consequently, CS-Cys-Cys-coated SLN and CS-Cys-MNA-coated SLN showed the highest retention on porcine intestinal mucosa by enabling a synergism of efficient mucus diffusion and strong mucoadhesion. |
| doi_str_mv | 10.1021/acs.biomac.1c00776 |
| format | Article |
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Free thiol groups were protected with highly reactive 6-mercaptonicotinic acid (6-MNA) and less-reactive l-cysteine, respectively, via thiol/disulfide-exchange reactions. Unmodified CS, l-cysteine-modified thiolated CS (CS-Cys), 6-MNA-S-protected thiolated CS (CS-Cys-MNA), and l-cysteine-S-protected thiolated CS (CS-Cys-Cys) were applied as coating materials to solid lipid nanoparticles (SLN). The strength of mucus interaction followed the rank order plain < CS < CS-Cys-Cys < CS-Cys < CS-Cys-MNA, whereas mucus diffusion followed the rank order CS-Cys < CS-Cys-Cys < CS < CS-Cys-MNA < plain. In accordance with lower reactivity, CS-Cys-Cys-coated SLN were immobilized to a lower extent than CS-Cys-coated SLN, while CS-Cys-MNA-coated SLN dissociated from their coating material resulting in a similar diffusion behavior as plain SLN. Consequently, CS-Cys-Cys-coated SLN and CS-Cys-MNA-coated SLN showed the highest retention on porcine intestinal mucosa by enabling a synergism of efficient mucus diffusion and strong mucoadhesion.]]></description><identifier>ISSN: 1525-7797</identifier><identifier>EISSN: 1526-4602</identifier><identifier>DOI: 10.1021/acs.biomac.1c00776</identifier><identifier>PMID: 34459197</identifier><language>eng</language><publisher>WASHINGTON: American Chemical Society</publisher><subject>Biochemistry & Molecular Biology ; Chemistry ; Chemistry, Organic ; Life Sciences & Biomedicine ; Physical Sciences ; Polymer Science ; Science & Technology</subject><ispartof>Biomacromolecules, 2021-09, Vol.22 (9), p.3980-3991</ispartof><rights>2021 The Authors. Published by American Chemical Society</rights><rights>2021 The Authors. 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Free thiol groups were protected with highly reactive 6-mercaptonicotinic acid (6-MNA) and less-reactive l-cysteine, respectively, via thiol/disulfide-exchange reactions. Unmodified CS, l-cysteine-modified thiolated CS (CS-Cys), 6-MNA-S-protected thiolated CS (CS-Cys-MNA), and l-cysteine-S-protected thiolated CS (CS-Cys-Cys) were applied as coating materials to solid lipid nanoparticles (SLN). The strength of mucus interaction followed the rank order plain < CS < CS-Cys-Cys < CS-Cys < CS-Cys-MNA, whereas mucus diffusion followed the rank order CS-Cys < CS-Cys-Cys < CS < CS-Cys-MNA < plain. In accordance with lower reactivity, CS-Cys-Cys-coated SLN were immobilized to a lower extent than CS-Cys-coated SLN, while CS-Cys-MNA-coated SLN dissociated from their coating material resulting in a similar diffusion behavior as plain SLN. Consequently, CS-Cys-Cys-coated SLN and CS-Cys-MNA-coated SLN showed the highest retention on porcine intestinal mucosa by enabling a synergism of efficient mucus diffusion and strong mucoadhesion.]]></description><subject>Biochemistry & Molecular Biology</subject><subject>Chemistry</subject><subject>Chemistry, Organic</subject><subject>Life Sciences & Biomedicine</subject><subject>Physical Sciences</subject><subject>Polymer Science</subject><subject>Science & Technology</subject><issn>1525-7797</issn><issn>1526-4602</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>HGBXW</sourceid><recordid>eNqNkU1v1DAQhiMEoqXwBzj5iISytWPHHxcklFK60hYOFK6W13F2XWU9i-0s7b-v26wqcUFc7NHM886M5q2q9wQvCG7IubFpsfawM3ZBLMZC8BfVKWkbXjOOm5dPcVsLocRJ9SalW4yxoqx9XZ1QxlpFlDit7pYB_fI5AlqGg0vZb0z2EBAM6GbrYTTZ9ajb-gzJBHThoj8UoJDIJHQ9WTD91qWSQB2UQtig6yKJ3owJDRDRDxh9j1Z-X95vJsDexOzt6NLb6tVQIPfu-J9VPy-_3HRX9er712X3eVUbRmSuaY8ply1pKJOEGGkVdUL1GHMp-TAYZntHubKOKmrXLed0UE4wTMQgTG8EPas-zX3303rneutCjmbU--h3Jt5rMF7_XQl-qzdw0JKxciFZGnw4Nojweyon0jufrBtHExxMSTdlaNO2TOCCNjNqI6QU3fA8hmD9aJkulunZMn20rIjkLPrj1jAk612w7llYPOOKUyFJiSjufH7yp4Mp5CL9-P_SQi9m-nGJW5hiKHf_12YPpJu96g</recordid><startdate>20210913</startdate><enddate>20210913</enddate><creator>Wibel, Richard</creator><creator>Braun, Doris E</creator><creator>Hämmerle, Laurenz</creator><creator>Jörgensen, Arne M</creator><creator>Knoll, Patrick</creator><creator>Salvenmoser, Willi</creator><creator>Steinbring, Christian</creator><creator>Bernkop-Schnürch, Andreas</creator><general>American Chemical Society</general><general>Amer Chemical Soc</general><scope>BLEPL</scope><scope>DTL</scope><scope>HGBXW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-0503-4448</orcidid><orcidid>https://orcid.org/0000-0003-4187-8277</orcidid></search><sort><creationdate>20210913</creationdate><title>In Vitro Investigation of Thiolated Chitosan Derivatives as Mucoadhesive Coating Materials for Solid Lipid Nanoparticles</title><author>Wibel, Richard ; Braun, Doris E ; Hämmerle, Laurenz ; Jörgensen, Arne M ; Knoll, Patrick ; Salvenmoser, Willi ; Steinbring, Christian ; Bernkop-Schnürch, Andreas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a418t-3d036851234811a8c93e79d006886ffa4cde369ce393cb5663f9e74017f7ada73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Biochemistry & Molecular Biology</topic><topic>Chemistry</topic><topic>Chemistry, Organic</topic><topic>Life Sciences & Biomedicine</topic><topic>Physical Sciences</topic><topic>Polymer Science</topic><topic>Science & Technology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wibel, Richard</creatorcontrib><creatorcontrib>Braun, Doris E</creatorcontrib><creatorcontrib>Hämmerle, Laurenz</creatorcontrib><creatorcontrib>Jörgensen, Arne M</creatorcontrib><creatorcontrib>Knoll, Patrick</creatorcontrib><creatorcontrib>Salvenmoser, Willi</creatorcontrib><creatorcontrib>Steinbring, Christian</creatorcontrib><creatorcontrib>Bernkop-Schnürch, Andreas</creatorcontrib><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>Web of Science - Science Citation Index Expanded - 2021</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Biomacromolecules</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wibel, Richard</au><au>Braun, Doris E</au><au>Hämmerle, Laurenz</au><au>Jörgensen, Arne M</au><au>Knoll, Patrick</au><au>Salvenmoser, Willi</au><au>Steinbring, Christian</au><au>Bernkop-Schnürch, Andreas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>In Vitro Investigation of Thiolated Chitosan Derivatives as Mucoadhesive Coating Materials for Solid Lipid Nanoparticles</atitle><jtitle>Biomacromolecules</jtitle><stitle>BIOMACROMOLECULES</stitle><addtitle>Biomacromolecules</addtitle><date>2021-09-13</date><risdate>2021</risdate><volume>22</volume><issue>9</issue><spage>3980</spage><epage>3991</epage><pages>3980-3991</pages><issn>1525-7797</issn><eissn>1526-4602</eissn><abstract><![CDATA[In the present study, chitosan (CS) was thiolated by introducing l-cysteine via amide bond formation. Free thiol groups were protected with highly reactive 6-mercaptonicotinic acid (6-MNA) and less-reactive l-cysteine, respectively, via thiol/disulfide-exchange reactions. Unmodified CS, l-cysteine-modified thiolated CS (CS-Cys), 6-MNA-S-protected thiolated CS (CS-Cys-MNA), and l-cysteine-S-protected thiolated CS (CS-Cys-Cys) were applied as coating materials to solid lipid nanoparticles (SLN). The strength of mucus interaction followed the rank order plain < CS < CS-Cys-Cys < CS-Cys < CS-Cys-MNA, whereas mucus diffusion followed the rank order CS-Cys < CS-Cys-Cys < CS < CS-Cys-MNA < plain. In accordance with lower reactivity, CS-Cys-Cys-coated SLN were immobilized to a lower extent than CS-Cys-coated SLN, while CS-Cys-MNA-coated SLN dissociated from their coating material resulting in a similar diffusion behavior as plain SLN. 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| subjects | Biochemistry & Molecular Biology Chemistry Chemistry, Organic Life Sciences & Biomedicine Physical Sciences Polymer Science Science & Technology |
| title | In Vitro Investigation of Thiolated Chitosan Derivatives as Mucoadhesive Coating Materials for Solid Lipid Nanoparticles |
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