Synthesis and characterization of thiolated carboxymethyl chitosan-graft-cyclodextrin nanoparticles as a drug delivery vehicle for albendazole
A new strategy for the synthesis of thiolated carboxymethyl chitosan-g-cyclodextrin nanoparticles by an ionic-gelation method is presented. The synthetic approach was based on the utilization of 1,6-hexamethylene diisocyanate during cyclodextrin grafting onto carboxymethyl chitosan. The use of the 1...
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| Veröffentlicht in: | Journal of materials science. Materials in medicine 2013-08, Vol.24 (8), p.1939-1949 |
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| container_issue | 8 |
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| container_title | Journal of materials science. Materials in medicine |
| container_volume | 24 |
| creator | Alamdarnejad, Ghazaleh Sharif, Alireza Taranejoo, Shahrouz Janmaleki, Mohsen Kalaee, Mohammad Reza Dadgar, Mohsen Khakpour, Mazyar |
| description | A new strategy for the synthesis of thiolated carboxymethyl chitosan-g-cyclodextrin nanoparticles by an ionic-gelation method is presented. The synthetic approach was based on the utilization of 1,6-hexamethylene diisocyanate during cyclodextrin grafting onto carboxymethyl chitosan. The use of the 1,6-hexamethylene diisocyanate resulted in reactions between cyclodextrin and active sites at the C
6
-position of chitosan, and preserved amino groups of chitosan for subsequent reactions with thioglycolic acid, as the thiolating agent, and tripolyphosphate, as the gelling counterion. Various methods such as scanning electron microscopy, rheology and in vitro release studies were employed to exhibit significant features of the nanoparticles for mucosal albendazole delivery applications. It was found that the thiolated carboxymethyl chitosan-g-cyclodextrin nanoparticles prepared using an aqueous solution containing 1 wt% of tripolyphosphate and having 115.65 (μmol/g polymer) of grafted thiol groups show both the highest mucoadhesive properties and the highest albendazole entrapment efficiency. The latter was confirmed theoretically by calculating the enthalpy of mixing of albendazole in the above thiolated chitosan polymer. |
| doi_str_mv | 10.1007/s10856-013-4947-9 |
| format | Article |
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6
-position of chitosan, and preserved amino groups of chitosan for subsequent reactions with thioglycolic acid, as the thiolating agent, and tripolyphosphate, as the gelling counterion. Various methods such as scanning electron microscopy, rheology and in vitro release studies were employed to exhibit significant features of the nanoparticles for mucosal albendazole delivery applications. It was found that the thiolated carboxymethyl chitosan-g-cyclodextrin nanoparticles prepared using an aqueous solution containing 1 wt% of tripolyphosphate and having 115.65 (μmol/g polymer) of grafted thiol groups show both the highest mucoadhesive properties and the highest albendazole entrapment efficiency. The latter was confirmed theoretically by calculating the enthalpy of mixing of albendazole in the above thiolated chitosan polymer.</description><identifier>ISSN: 0957-4530</identifier><identifier>EISSN: 1573-4838</identifier><identifier>DOI: 10.1007/s10856-013-4947-9</identifier><identifier>PMID: 23665921</identifier><language>eng</language><publisher>Boston: Springer US</publisher><subject>Albendazole - administration & dosage ; Albendazole - pharmacokinetics ; Anthelmintics - administration & dosage ; Anthelmintics - pharmacokinetics ; Biological and medical sciences ; Biomaterials ; Biomedical Engineering and Bioengineering ; Biomedical materials ; Biosynthesis ; Biotechnology ; Body Fluids - metabolism ; Ceramics ; Chemistry and Materials Science ; Chitosan - analogs & derivatives ; Chitosan - chemistry ; Coated Materials, Biocompatible - chemical synthesis ; Coated Materials, Biocompatible - chemistry ; Composites ; Cyclodextrins - chemical synthesis ; Cyclodextrins - chemistry ; Drug Compounding - methods ; Drug delivery systems ; Glass ; Humans ; Intestinal Secretions - metabolism ; Materials Science ; Materials Testing ; Medical sciences ; Nanoparticles - chemistry ; Natural Materials ; Pharmaceutical Vehicles - chemical synthesis ; Pharmaceutical Vehicles - chemistry ; Polymer Sciences ; Polymers ; Regenerative Medicine/Tissue Engineering ; Sulfhydryl Compounds - chemical synthesis ; Sulfhydryl Compounds - chemistry ; Surfaces and Interfaces ; Surgery (general aspects). Transplantations, organ and tissue grafts. Graft diseases ; Technology. Biomaterials. Equipments ; Thin Films</subject><ispartof>Journal of materials science. Materials in medicine, 2013-08, Vol.24 (8), p.1939-1949</ispartof><rights>Springer Science+Business Media New York 2013</rights><rights>2014 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c472t-2663da7a8a6eb775fe1839104cca962130987cddfdb4a7e104f2d81ff37c3cba3</citedby><cites>FETCH-LOGICAL-c472t-2663da7a8a6eb775fe1839104cca962130987cddfdb4a7e104f2d81ff37c3cba3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10856-013-4947-9$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10856-013-4947-9$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=27572089$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23665921$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Alamdarnejad, Ghazaleh</creatorcontrib><creatorcontrib>Sharif, Alireza</creatorcontrib><creatorcontrib>Taranejoo, Shahrouz</creatorcontrib><creatorcontrib>Janmaleki, Mohsen</creatorcontrib><creatorcontrib>Kalaee, Mohammad Reza</creatorcontrib><creatorcontrib>Dadgar, Mohsen</creatorcontrib><creatorcontrib>Khakpour, Mazyar</creatorcontrib><title>Synthesis and characterization of thiolated carboxymethyl chitosan-graft-cyclodextrin nanoparticles as a drug delivery vehicle for albendazole</title><title>Journal of materials science. Materials in medicine</title><addtitle>J Mater Sci: Mater Med</addtitle><addtitle>J Mater Sci Mater Med</addtitle><description>A new strategy for the synthesis of thiolated carboxymethyl chitosan-g-cyclodextrin nanoparticles by an ionic-gelation method is presented. The synthetic approach was based on the utilization of 1,6-hexamethylene diisocyanate during cyclodextrin grafting onto carboxymethyl chitosan. The use of the 1,6-hexamethylene diisocyanate resulted in reactions between cyclodextrin and active sites at the C
6
-position of chitosan, and preserved amino groups of chitosan for subsequent reactions with thioglycolic acid, as the thiolating agent, and tripolyphosphate, as the gelling counterion. Various methods such as scanning electron microscopy, rheology and in vitro release studies were employed to exhibit significant features of the nanoparticles for mucosal albendazole delivery applications. It was found that the thiolated carboxymethyl chitosan-g-cyclodextrin nanoparticles prepared using an aqueous solution containing 1 wt% of tripolyphosphate and having 115.65 (μmol/g polymer) of grafted thiol groups show both the highest mucoadhesive properties and the highest albendazole entrapment efficiency. The latter was confirmed theoretically by calculating the enthalpy of mixing of albendazole in the above thiolated chitosan polymer.</description><subject>Albendazole - administration & dosage</subject><subject>Albendazole - pharmacokinetics</subject><subject>Anthelmintics - administration & dosage</subject><subject>Anthelmintics - pharmacokinetics</subject><subject>Biological and medical sciences</subject><subject>Biomaterials</subject><subject>Biomedical Engineering and Bioengineering</subject><subject>Biomedical materials</subject><subject>Biosynthesis</subject><subject>Biotechnology</subject><subject>Body Fluids - metabolism</subject><subject>Ceramics</subject><subject>Chemistry and Materials Science</subject><subject>Chitosan - analogs & derivatives</subject><subject>Chitosan - chemistry</subject><subject>Coated Materials, Biocompatible - chemical synthesis</subject><subject>Coated Materials, Biocompatible - chemistry</subject><subject>Composites</subject><subject>Cyclodextrins - chemical synthesis</subject><subject>Cyclodextrins - chemistry</subject><subject>Drug Compounding - methods</subject><subject>Drug delivery systems</subject><subject>Glass</subject><subject>Humans</subject><subject>Intestinal Secretions - metabolism</subject><subject>Materials Science</subject><subject>Materials Testing</subject><subject>Medical sciences</subject><subject>Nanoparticles - chemistry</subject><subject>Natural Materials</subject><subject>Pharmaceutical Vehicles - chemical synthesis</subject><subject>Pharmaceutical Vehicles - chemistry</subject><subject>Polymer Sciences</subject><subject>Polymers</subject><subject>Regenerative Medicine/Tissue Engineering</subject><subject>Sulfhydryl Compounds - chemical synthesis</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>Surfaces and Interfaces</subject><subject>Surgery (general aspects). Transplantations, organ and tissue grafts. Graft diseases</subject><subject>Technology. Biomaterials. 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Materials in medicine</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Alamdarnejad, Ghazaleh</au><au>Sharif, Alireza</au><au>Taranejoo, Shahrouz</au><au>Janmaleki, Mohsen</au><au>Kalaee, Mohammad Reza</au><au>Dadgar, Mohsen</au><au>Khakpour, Mazyar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and characterization of thiolated carboxymethyl chitosan-graft-cyclodextrin nanoparticles as a drug delivery vehicle for albendazole</atitle><jtitle>Journal of materials science. Materials in medicine</jtitle><stitle>J Mater Sci: Mater Med</stitle><addtitle>J Mater Sci Mater Med</addtitle><date>2013-08-01</date><risdate>2013</risdate><volume>24</volume><issue>8</issue><spage>1939</spage><epage>1949</epage><pages>1939-1949</pages><issn>0957-4530</issn><eissn>1573-4838</eissn><abstract>A new strategy for the synthesis of thiolated carboxymethyl chitosan-g-cyclodextrin nanoparticles by an ionic-gelation method is presented. The synthetic approach was based on the utilization of 1,6-hexamethylene diisocyanate during cyclodextrin grafting onto carboxymethyl chitosan. The use of the 1,6-hexamethylene diisocyanate resulted in reactions between cyclodextrin and active sites at the C
6
-position of chitosan, and preserved amino groups of chitosan for subsequent reactions with thioglycolic acid, as the thiolating agent, and tripolyphosphate, as the gelling counterion. Various methods such as scanning electron microscopy, rheology and in vitro release studies were employed to exhibit significant features of the nanoparticles for mucosal albendazole delivery applications. It was found that the thiolated carboxymethyl chitosan-g-cyclodextrin nanoparticles prepared using an aqueous solution containing 1 wt% of tripolyphosphate and having 115.65 (μmol/g polymer) of grafted thiol groups show both the highest mucoadhesive properties and the highest albendazole entrapment efficiency. The latter was confirmed theoretically by calculating the enthalpy of mixing of albendazole in the above thiolated chitosan polymer.</abstract><cop>Boston</cop><pub>Springer US</pub><pmid>23665921</pmid><doi>10.1007/s10856-013-4947-9</doi><tpages>11</tpages></addata></record> |
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| ispartof | Journal of materials science. Materials in medicine, 2013-08, Vol.24 (8), p.1939-1949 |
| issn | 0957-4530 1573-4838 |
| language | eng |
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| source | MEDLINE; SpringerNature Journals |
| subjects | Albendazole - administration & dosage Albendazole - pharmacokinetics Anthelmintics - administration & dosage Anthelmintics - pharmacokinetics Biological and medical sciences Biomaterials Biomedical Engineering and Bioengineering Biomedical materials Biosynthesis Biotechnology Body Fluids - metabolism Ceramics Chemistry and Materials Science Chitosan - analogs & derivatives Chitosan - chemistry Coated Materials, Biocompatible - chemical synthesis Coated Materials, Biocompatible - chemistry Composites Cyclodextrins - chemical synthesis Cyclodextrins - chemistry Drug Compounding - methods Drug delivery systems Glass Humans Intestinal Secretions - metabolism Materials Science Materials Testing Medical sciences Nanoparticles - chemistry Natural Materials Pharmaceutical Vehicles - chemical synthesis Pharmaceutical Vehicles - chemistry Polymer Sciences Polymers Regenerative Medicine/Tissue Engineering Sulfhydryl Compounds - chemical synthesis Sulfhydryl Compounds - chemistry Surfaces and Interfaces Surgery (general aspects). Transplantations, organ and tissue grafts. Graft diseases Technology. Biomaterials. Equipments Thin Films |
| title | Synthesis and characterization of thiolated carboxymethyl chitosan-graft-cyclodextrin nanoparticles as a drug delivery vehicle for albendazole |
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