Biodegradable Polycarbonate-b-polypeptide and Polyester-b-polypeptide Block Copolymers: Synthesis and Nanoparticle Formation Towards Biomaterials
The amino poly(trimethylene carbonate)-NHt-Boc (PTMC-NHt-Boc) and poly(ε-caprolactone)-NHt-Boc (PCL-NHt-Boc) were synthesized by ring-opening polymerization (ROP) of TMC or CL and subsequently deprotected into the corresponding PTMC-NH2 and PCL-NH2. These functional homopolymers were used as macroin...
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| Veröffentlicht in: | Biomacromolecules 2008-07, Vol.9 (7), p.1924-1933 |
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| container_title | Biomacromolecules |
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| creator | Le Hellaye, Maude Fortin, Nicolas Guilloteau, Julien Soum, Alain Lecommandoux, Sebastien Guillaume, Sophie M |
| description | The amino poly(trimethylene carbonate)-NHt-Boc (PTMC-NHt-Boc) and poly(ε-caprolactone)-NHt-Boc (PCL-NHt-Boc) were synthesized by ring-opening polymerization (ROP) of TMC or CL and subsequently deprotected into the corresponding PTMC-NH2 and PCL-NH2. These functional homopolymers were used as macroinitiators for the ROP of γ-benzyl-l-glutamate N-carboxyanhydride (BLG), consequently, giving the respective diblock copolymers PTMC-b-PBLG and PCL-b-PBLG in almost quantitative yields. The (co)polymers have been characterized by NMR and SEC analyses. DSC and IR studies confirmed the block structure of the copolymers and highlighted a phase separation between the rigid peptide (α-helix conformation) and the more flexible polyester segments. The self-assembly and the degradation behaviors of the copolymers depended on the nature of the polyester block and on the copolymer composition. Nanoparticles obtained from PBLG block copolymers were twice smaller (R H < 100 nm) than those formed from PTMC and PCL homopolymers. Finally, their enzymatic degradation revealed that PTMC nanoparticles degraded faster than those made of PCL. |
| doi_str_mv | 10.1021/bm8001792 |
| format | Article |
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These functional homopolymers were used as macroinitiators for the ROP of γ-benzyl-l-glutamate N-carboxyanhydride (BLG), consequently, giving the respective diblock copolymers PTMC-b-PBLG and PCL-b-PBLG in almost quantitative yields. The (co)polymers have been characterized by NMR and SEC analyses. DSC and IR studies confirmed the block structure of the copolymers and highlighted a phase separation between the rigid peptide (α-helix conformation) and the more flexible polyester segments. The self-assembly and the degradation behaviors of the copolymers depended on the nature of the polyester block and on the copolymer composition. Nanoparticles obtained from PBLG block copolymers were twice smaller (R H < 100 nm) than those formed from PTMC and PCL homopolymers. Finally, their enzymatic degradation revealed that PTMC nanoparticles degraded faster than those made of PCL.</description><identifier>ISSN: 1525-7797</identifier><identifier>EISSN: 1526-4602</identifier><identifier>DOI: 10.1021/bm8001792</identifier><identifier>PMID: 18529076</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aminoacid polymers ; Applied sciences ; Biocompatible Materials - chemical synthesis ; Carbonates - chemistry ; Chemical Sciences ; Dioxanes - chemistry ; Enzymes - metabolism ; Exact sciences and technology ; Molecular Conformation ; Nanoparticles - chemistry ; Peptides - chemistry ; Physicochemistry of polymers ; Polyesters - chemistry ; Polymers ; Polymers - chemical synthesis ; Polymers - chemistry ; Spectrum Analysis ; Synthetic biopolymers</subject><ispartof>Biomacromolecules, 2008-07, Vol.9 (7), p.1924-1933</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2009 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a408t-c4ee6b3247af2d74fa75393499bbeac2dbc1171809a6e0d8e03bb84c1fb09a223</citedby><cites>FETCH-LOGICAL-a408t-c4ee6b3247af2d74fa75393499bbeac2dbc1171809a6e0d8e03bb84c1fb09a223</cites><orcidid>0000-0003-0465-8603 ; 0000-0003-2917-8657</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bm8001792$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bm8001792$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20870179$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18529076$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00338908$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Le Hellaye, Maude</creatorcontrib><creatorcontrib>Fortin, Nicolas</creatorcontrib><creatorcontrib>Guilloteau, Julien</creatorcontrib><creatorcontrib>Soum, Alain</creatorcontrib><creatorcontrib>Lecommandoux, Sebastien</creatorcontrib><creatorcontrib>Guillaume, Sophie M</creatorcontrib><title>Biodegradable Polycarbonate-b-polypeptide and Polyester-b-polypeptide Block Copolymers: Synthesis and Nanoparticle Formation Towards Biomaterials</title><title>Biomacromolecules</title><addtitle>Biomacromolecules</addtitle><description>The amino poly(trimethylene carbonate)-NHt-Boc (PTMC-NHt-Boc) and poly(ε-caprolactone)-NHt-Boc (PCL-NHt-Boc) were synthesized by ring-opening polymerization (ROP) of TMC or CL and subsequently deprotected into the corresponding PTMC-NH2 and PCL-NH2. These functional homopolymers were used as macroinitiators for the ROP of γ-benzyl-l-glutamate N-carboxyanhydride (BLG), consequently, giving the respective diblock copolymers PTMC-b-PBLG and PCL-b-PBLG in almost quantitative yields. The (co)polymers have been characterized by NMR and SEC analyses. DSC and IR studies confirmed the block structure of the copolymers and highlighted a phase separation between the rigid peptide (α-helix conformation) and the more flexible polyester segments. The self-assembly and the degradation behaviors of the copolymers depended on the nature of the polyester block and on the copolymer composition. Nanoparticles obtained from PBLG block copolymers were twice smaller (R H < 100 nm) than those formed from PTMC and PCL homopolymers. Finally, their enzymatic degradation revealed that PTMC nanoparticles degraded faster than those made of PCL.</description><subject>Aminoacid polymers</subject><subject>Applied sciences</subject><subject>Biocompatible Materials - chemical synthesis</subject><subject>Carbonates - chemistry</subject><subject>Chemical Sciences</subject><subject>Dioxanes - chemistry</subject><subject>Enzymes - metabolism</subject><subject>Exact sciences and technology</subject><subject>Molecular Conformation</subject><subject>Nanoparticles - chemistry</subject><subject>Peptides - chemistry</subject><subject>Physicochemistry of polymers</subject><subject>Polyesters - chemistry</subject><subject>Polymers</subject><subject>Polymers - chemical synthesis</subject><subject>Polymers - chemistry</subject><subject>Spectrum Analysis</subject><subject>Synthetic biopolymers</subject><issn>1525-7797</issn><issn>1526-4602</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc9u1DAQxi1ERUvhwAugXEDikGI7Tmxza1f0j7QCJMo5GtsT6pLEqZ0F7WPwxni3q10JIXEa-5uf5xvPEPKK0TNGOXtvBkUpk5o_ISes5k0pGsqfbs91KaWWx-R5SveUUl2J-hk5ZqrmmsrmhPy-8MHh9wgOTI_Fl9CvLUQTRpixNOWU7xNOs3dYwOi2eUwzxr9yF32wP4pF2GgDxvSh-Loe5ztMPm3ffYIxTBBnb7PJZYgDzD6MxW34BdGlIjeRFYwe-vSCHHU54MtdPCXfLj_eLq7L5eerm8X5sgRB1VxagdiYigsJHXdSdCDrKn9Pa2MQLHfGMiaZohoapE4hrYxRwrLOZInz6pS8e6x7B307RT9AXLcBfHt9vmw3GqVVpTRVP1lm3z6yUwwPqzyAdvDJYt_DiGGV2kZXrJFc_BfkVNVaqOrgbmNIKWK3b4HRdrPUdr_UzL7eFV2ZAd2B3G0xA292ACQLfRdhtD7tuWwqN5UOHNjU3odVHPOA_2H4Bzrwt5Y</recordid><startdate>20080701</startdate><enddate>20080701</enddate><creator>Le Hellaye, Maude</creator><creator>Fortin, Nicolas</creator><creator>Guilloteau, Julien</creator><creator>Soum, Alain</creator><creator>Lecommandoux, Sebastien</creator><creator>Guillaume, Sophie M</creator><general>American Chemical Society</general><scope>IQODW</scope><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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-0465-8603</orcidid><orcidid>https://orcid.org/0000-0003-2917-8657</orcidid></search><sort><creationdate>20080701</creationdate><title>Biodegradable Polycarbonate-b-polypeptide and Polyester-b-polypeptide Block Copolymers: Synthesis and Nanoparticle Formation Towards Biomaterials</title><author>Le Hellaye, Maude ; Fortin, Nicolas ; Guilloteau, Julien ; Soum, Alain ; Lecommandoux, Sebastien ; Guillaume, Sophie M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a408t-c4ee6b3247af2d74fa75393499bbeac2dbc1171809a6e0d8e03bb84c1fb09a223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Aminoacid polymers</topic><topic>Applied sciences</topic><topic>Biocompatible Materials - chemical synthesis</topic><topic>Carbonates - chemistry</topic><topic>Chemical Sciences</topic><topic>Dioxanes - chemistry</topic><topic>Enzymes - metabolism</topic><topic>Exact sciences and technology</topic><topic>Molecular Conformation</topic><topic>Nanoparticles - chemistry</topic><topic>Peptides - chemistry</topic><topic>Physicochemistry of polymers</topic><topic>Polyesters - chemistry</topic><topic>Polymers</topic><topic>Polymers - chemical synthesis</topic><topic>Polymers - chemistry</topic><topic>Spectrum Analysis</topic><topic>Synthetic biopolymers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Le Hellaye, Maude</creatorcontrib><creatorcontrib>Fortin, Nicolas</creatorcontrib><creatorcontrib>Guilloteau, Julien</creatorcontrib><creatorcontrib>Soum, Alain</creatorcontrib><creatorcontrib>Lecommandoux, Sebastien</creatorcontrib><creatorcontrib>Guillaume, Sophie M</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Biomacromolecules</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Le Hellaye, Maude</au><au>Fortin, Nicolas</au><au>Guilloteau, Julien</au><au>Soum, Alain</au><au>Lecommandoux, Sebastien</au><au>Guillaume, Sophie M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biodegradable Polycarbonate-b-polypeptide and Polyester-b-polypeptide Block Copolymers: Synthesis and Nanoparticle Formation Towards Biomaterials</atitle><jtitle>Biomacromolecules</jtitle><addtitle>Biomacromolecules</addtitle><date>2008-07-01</date><risdate>2008</risdate><volume>9</volume><issue>7</issue><spage>1924</spage><epage>1933</epage><pages>1924-1933</pages><issn>1525-7797</issn><eissn>1526-4602</eissn><abstract>The amino poly(trimethylene carbonate)-NHt-Boc (PTMC-NHt-Boc) and poly(ε-caprolactone)-NHt-Boc (PCL-NHt-Boc) were synthesized by ring-opening polymerization (ROP) of TMC or CL and subsequently deprotected into the corresponding PTMC-NH2 and PCL-NH2. These functional homopolymers were used as macroinitiators for the ROP of γ-benzyl-l-glutamate N-carboxyanhydride (BLG), consequently, giving the respective diblock copolymers PTMC-b-PBLG and PCL-b-PBLG in almost quantitative yields. The (co)polymers have been characterized by NMR and SEC analyses. DSC and IR studies confirmed the block structure of the copolymers and highlighted a phase separation between the rigid peptide (α-helix conformation) and the more flexible polyester segments. The self-assembly and the degradation behaviors of the copolymers depended on the nature of the polyester block and on the copolymer composition. Nanoparticles obtained from PBLG block copolymers were twice smaller (R H < 100 nm) than those formed from PTMC and PCL homopolymers. Finally, their enzymatic degradation revealed that PTMC nanoparticles degraded faster than those made of PCL.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18529076</pmid><doi>10.1021/bm8001792</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-0465-8603</orcidid><orcidid>https://orcid.org/0000-0003-2917-8657</orcidid></addata></record> |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Aminoacid polymers Applied sciences Biocompatible Materials - chemical synthesis Carbonates - chemistry Chemical Sciences Dioxanes - chemistry Enzymes - metabolism Exact sciences and technology Molecular Conformation Nanoparticles - chemistry Peptides - chemistry Physicochemistry of polymers Polyesters - chemistry Polymers Polymers - chemical synthesis Polymers - chemistry Spectrum Analysis Synthetic biopolymers |
| title | Biodegradable Polycarbonate-b-polypeptide and Polyester-b-polypeptide Block Copolymers: Synthesis and Nanoparticle Formation Towards Biomaterials |
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