Regenerative Biomaterials that “Click”: Simple, Aqueous-Based Protocols for Hydrogel Synthesis, Surface Immobilization, and 3D Patterning

The click chemistry era has generated a library of versatile “spring-loaded” reactions that offer high yields, regio- and stereospecificity, and outstanding functional group tolerance. These powerful transformations are particularly advantageous for the design of sophisticated biomaterials that requ...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Bioconjugate chemistry 2011-11, Vol.22 (11), p.2199-2209
Hauptverfasser: Nimmo, Chelsea M, Shoichet, Molly S
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2209
container_issue 11
container_start_page 2199
container_title Bioconjugate chemistry
container_volume 22
creator Nimmo, Chelsea M
Shoichet, Molly S
description The click chemistry era has generated a library of versatile “spring-loaded” reactions that offer high yields, regio- and stereospecificity, and outstanding functional group tolerance. These powerful transformations are particularly advantageous for the design of sophisticated biomaterials that require high levels of precision and control, namely, materials that promote tissue regeneration such as hydrogels, 2D functionalized substrates, and 3D biomimetic scaffolds. In this review, the synthesis and application of regenerative biomaterials via click chemistry are summarized. Particular emphasis is placed on the copper­(I)-catalyzed alkyne–azide cycloaddition, Diels–Alder cycloadditions, and thiol–click coupling.
doi_str_mv 10.1021/bc200281k
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_905666863</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>905666863</sourcerecordid><originalsourceid>FETCH-LOGICAL-a341t-f64dc48e8e66788710be77a5c3c1654aa18406f569d7fc8320b266fb50e0b20c3</originalsourceid><addsrcrecordid>eNplkcFu1DAQhi0EoqVw4AWQhYQQ0gbGTuw43NoF2kqVqFg4R44z2bpN4q3tIC2nvkDfoLxcn6RebSkSnGYO3_z__PoJecngPQPOPjSGA3DFLh6RXSY4ZIVi_HHaocgzpoDvkGchnANAxRR_SnY4qypRCLVLrr_hEkf0OtqfSA-sG3REb3UfaDzTkd5e3cx7ay5ur35_pAs7rHqc0f3LCd0UsgMdsKWn3kVnXLronKdH69a7JfZ0sR7jGQYbZnQx-U4bpMfD4Brb21_JzY0zqseW5p_oqY7Jc7Tj8jl50iVrfHE_98iPL5-_z4-yk6-Hx_P9k0znBYtZJ4vWFAoVSlkqVTJosCy1MLlhUhRaM1WA7ISs2rIzKufQcCm7RgCmDUy-R95udVfepSwh1oMNBvtej5tgdQVCSqlknsjX_5DnbvJjem4DgaqYKBP0bgsZ70Lw2NUrbwft1zWDetNQ_dBQYl_dC07NgO0D-aeSBLzZAtqEv2b_C90BfviZfA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>905089157</pqid></control><display><type>article</type><title>Regenerative Biomaterials that “Click”: Simple, Aqueous-Based Protocols for Hydrogel Synthesis, Surface Immobilization, and 3D Patterning</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Nimmo, Chelsea M ; Shoichet, Molly S</creator><creatorcontrib>Nimmo, Chelsea M ; Shoichet, Molly S</creatorcontrib><description>The click chemistry era has generated a library of versatile “spring-loaded” reactions that offer high yields, regio- and stereospecificity, and outstanding functional group tolerance. These powerful transformations are particularly advantageous for the design of sophisticated biomaterials that require high levels of precision and control, namely, materials that promote tissue regeneration such as hydrogels, 2D functionalized substrates, and 3D biomimetic scaffolds. In this review, the synthesis and application of regenerative biomaterials via click chemistry are summarized. Particular emphasis is placed on the copper­(I)-catalyzed alkyne–azide cycloaddition, Diels–Alder cycloadditions, and thiol–click coupling.</description><identifier>ISSN: 1043-1802</identifier><identifier>EISSN: 1520-4812</identifier><identifier>DOI: 10.1021/bc200281k</identifier><identifier>PMID: 21995458</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkynes - chemistry ; Azides - chemistry ; Biocompatible Materials - chemical synthesis ; Biocompatible Materials - chemistry ; Biomaterials ; Biomedical materials ; Biomimetics ; Chemical reactions ; Chemical synthesis ; Click Chemistry - methods ; Copper - chemistry ; Drug Delivery Systems ; Humans ; Hydrogels ; Hydrogels - chemical synthesis ; Hydrogels - chemistry ; Maleimides - chemistry ; Molecular Structure ; Regeneration ; Regenerative Medicine - methods ; Sulfhydryl Compounds - chemistry ; Surface Properties ; Tissue Engineering - methods ; Water - chemistry</subject><ispartof>Bioconjugate chemistry, 2011-11, Vol.22 (11), p.2199-2209</ispartof><rights>Copyright © 2011 American Chemical Society</rights><rights>Copyright American Chemical Society Nov 16, 2011</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a341t-f64dc48e8e66788710be77a5c3c1654aa18406f569d7fc8320b266fb50e0b20c3</citedby><cites>FETCH-LOGICAL-a341t-f64dc48e8e66788710be77a5c3c1654aa18406f569d7fc8320b266fb50e0b20c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bc200281k$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bc200281k$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21995458$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nimmo, Chelsea M</creatorcontrib><creatorcontrib>Shoichet, Molly S</creatorcontrib><title>Regenerative Biomaterials that “Click”: Simple, Aqueous-Based Protocols for Hydrogel Synthesis, Surface Immobilization, and 3D Patterning</title><title>Bioconjugate chemistry</title><addtitle>Bioconjugate Chem</addtitle><description>The click chemistry era has generated a library of versatile “spring-loaded” reactions that offer high yields, regio- and stereospecificity, and outstanding functional group tolerance. These powerful transformations are particularly advantageous for the design of sophisticated biomaterials that require high levels of precision and control, namely, materials that promote tissue regeneration such as hydrogels, 2D functionalized substrates, and 3D biomimetic scaffolds. In this review, the synthesis and application of regenerative biomaterials via click chemistry are summarized. Particular emphasis is placed on the copper­(I)-catalyzed alkyne–azide cycloaddition, Diels–Alder cycloadditions, and thiol–click coupling.</description><subject>Alkynes - chemistry</subject><subject>Azides - chemistry</subject><subject>Biocompatible Materials - chemical synthesis</subject><subject>Biocompatible Materials - chemistry</subject><subject>Biomaterials</subject><subject>Biomedical materials</subject><subject>Biomimetics</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Click Chemistry - methods</subject><subject>Copper - chemistry</subject><subject>Drug Delivery Systems</subject><subject>Humans</subject><subject>Hydrogels</subject><subject>Hydrogels - chemical synthesis</subject><subject>Hydrogels - chemistry</subject><subject>Maleimides - chemistry</subject><subject>Molecular Structure</subject><subject>Regeneration</subject><subject>Regenerative Medicine - methods</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>Surface Properties</subject><subject>Tissue Engineering - methods</subject><subject>Water - chemistry</subject><issn>1043-1802</issn><issn>1520-4812</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNplkcFu1DAQhi0EoqVw4AWQhYQQ0gbGTuw43NoF2kqVqFg4R44z2bpN4q3tIC2nvkDfoLxcn6RebSkSnGYO3_z__PoJecngPQPOPjSGA3DFLh6RXSY4ZIVi_HHaocgzpoDvkGchnANAxRR_SnY4qypRCLVLrr_hEkf0OtqfSA-sG3REb3UfaDzTkd5e3cx7ay5ur35_pAs7rHqc0f3LCd0UsgMdsKWn3kVnXLronKdH69a7JfZ0sR7jGQYbZnQx-U4bpMfD4Brb21_JzY0zqseW5p_oqY7Jc7Tj8jl50iVrfHE_98iPL5-_z4-yk6-Hx_P9k0znBYtZJ4vWFAoVSlkqVTJosCy1MLlhUhRaM1WA7ISs2rIzKufQcCm7RgCmDUy-R95udVfepSwh1oMNBvtej5tgdQVCSqlknsjX_5DnbvJjem4DgaqYKBP0bgsZ70Lw2NUrbwft1zWDetNQ_dBQYl_dC07NgO0D-aeSBLzZAtqEv2b_C90BfviZfA</recordid><startdate>20111116</startdate><enddate>20111116</enddate><creator>Nimmo, Chelsea M</creator><creator>Shoichet, Molly S</creator><general>American Chemical Society</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>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20111116</creationdate><title>Regenerative Biomaterials that “Click”: Simple, Aqueous-Based Protocols for Hydrogel Synthesis, Surface Immobilization, and 3D Patterning</title><author>Nimmo, Chelsea M ; Shoichet, Molly S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a341t-f64dc48e8e66788710be77a5c3c1654aa18406f569d7fc8320b266fb50e0b20c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Alkynes - chemistry</topic><topic>Azides - chemistry</topic><topic>Biocompatible Materials - chemical synthesis</topic><topic>Biocompatible Materials - chemistry</topic><topic>Biomaterials</topic><topic>Biomedical materials</topic><topic>Biomimetics</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Click Chemistry - methods</topic><topic>Copper - chemistry</topic><topic>Drug Delivery Systems</topic><topic>Humans</topic><topic>Hydrogels</topic><topic>Hydrogels - chemical synthesis</topic><topic>Hydrogels - chemistry</topic><topic>Maleimides - chemistry</topic><topic>Molecular Structure</topic><topic>Regeneration</topic><topic>Regenerative Medicine - methods</topic><topic>Sulfhydryl Compounds - chemistry</topic><topic>Surface Properties</topic><topic>Tissue Engineering - methods</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nimmo, Chelsea M</creatorcontrib><creatorcontrib>Shoichet, Molly S</creatorcontrib><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>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioconjugate chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nimmo, Chelsea M</au><au>Shoichet, Molly S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regenerative Biomaterials that “Click”: Simple, Aqueous-Based Protocols for Hydrogel Synthesis, Surface Immobilization, and 3D Patterning</atitle><jtitle>Bioconjugate chemistry</jtitle><addtitle>Bioconjugate Chem</addtitle><date>2011-11-16</date><risdate>2011</risdate><volume>22</volume><issue>11</issue><spage>2199</spage><epage>2209</epage><pages>2199-2209</pages><issn>1043-1802</issn><eissn>1520-4812</eissn><abstract>The click chemistry era has generated a library of versatile “spring-loaded” reactions that offer high yields, regio- and stereospecificity, and outstanding functional group tolerance. These powerful transformations are particularly advantageous for the design of sophisticated biomaterials that require high levels of precision and control, namely, materials that promote tissue regeneration such as hydrogels, 2D functionalized substrates, and 3D biomimetic scaffolds. In this review, the synthesis and application of regenerative biomaterials via click chemistry are summarized. Particular emphasis is placed on the copper­(I)-catalyzed alkyne–azide cycloaddition, Diels–Alder cycloadditions, and thiol–click coupling.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>21995458</pmid><doi>10.1021/bc200281k</doi><tpages>11</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1043-1802
ispartof Bioconjugate chemistry, 2011-11, Vol.22 (11), p.2199-2209
issn 1043-1802
1520-4812
language eng
recordid cdi_proquest_miscellaneous_905666863
source MEDLINE; American Chemical Society Journals
subjects Alkynes - chemistry
Azides - chemistry
Biocompatible Materials - chemical synthesis
Biocompatible Materials - chemistry
Biomaterials
Biomedical materials
Biomimetics
Chemical reactions
Chemical synthesis
Click Chemistry - methods
Copper - chemistry
Drug Delivery Systems
Humans
Hydrogels
Hydrogels - chemical synthesis
Hydrogels - chemistry
Maleimides - chemistry
Molecular Structure
Regeneration
Regenerative Medicine - methods
Sulfhydryl Compounds - chemistry
Surface Properties
Tissue Engineering - methods
Water - chemistry
title Regenerative Biomaterials that “Click”: Simple, Aqueous-Based Protocols for Hydrogel Synthesis, Surface Immobilization, and 3D Patterning
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-02T22%3A48%3A24IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Regenerative%20Biomaterials%20that%20%E2%80%9CClick%E2%80%9D:%20Simple,%20Aqueous-Based%20Protocols%20for%20Hydrogel%20Synthesis,%20Surface%20Immobilization,%20and%203D%20Patterning&rft.jtitle=Bioconjugate%20chemistry&rft.au=Nimmo,%20Chelsea%20M&rft.date=2011-11-16&rft.volume=22&rft.issue=11&rft.spage=2199&rft.epage=2209&rft.pages=2199-2209&rft.issn=1043-1802&rft.eissn=1520-4812&rft_id=info:doi/10.1021/bc200281k&rft_dat=%3Cproquest_cross%3E905666863%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=905089157&rft_id=info:pmid/21995458&rfr_iscdi=true