Evaluation of dicopper azacryptand complexes in aqueous CuAAC reactions and their tolerance toward biological thiols
A series of dicopper azacryptand complexes was evaluated in copper-catalysed azide-alkyne cycloaddition (CuAAC) in water at 37 °C. It was found that they showed high activity at concentrations as low as 5 μM. These dinuclear catalysts were more susceptible toward inhibition by cysteine rather than g...
Gespeichert in:
| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2019-07, Vol.48 (26), p.9751-9758 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 9758 |
|---|---|
| container_issue | 26 |
| container_start_page | 9751 |
| container_title | Dalton transactions : an international journal of inorganic chemistry |
| container_volume | 48 |
| creator | Tran, Thi V Couture, Garret Do, Loi H |
| description | A series of dicopper azacryptand complexes was evaluated in copper-catalysed azide-alkyne cycloaddition (CuAAC) in water at 37 °C. It was found that they showed high activity at concentrations as low as 5 μM. These dinuclear catalysts were more susceptible toward inhibition by cysteine rather than glutathione under the conditions tested. Interestingly, the mononuclear copper complexes that are ligated by tripodal amine ligands, also exhibited good catalytic activity in aqueous media and showed similar sensitivity toward biological thiols as that of the dinuclear complexes. Our results suggest that the azacryptand catalysts are too structurally flexible to adequately prevent interactions of their metal centres with external nucleophiles. However, further steric tuning of the ligand structure might enable more effective substrate gating in future studies.
The catalytic activity of dicopper azacryptands was evaluated in water and in the presence of biological thiols. |
| doi_str_mv | 10.1039/c9dt00724e |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_journals_2251158232</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2210012293</sourcerecordid><originalsourceid>FETCH-LOGICAL-c337t-a6a325fbb21dcee906178700774adea539342b93a03100dfc5cfc7b7257aed463</originalsourceid><addsrcrecordid>eNpd0UtLAzEQAOAgitbHxbsS8CJCNY_dpjmWtT6g4EXPy2wyq1u2mzXZVeuvN7VawVMG8s0wD0KOObvkTOoro23HmBIJbpEBT5QaaiGT7U0sRntkP4Q5Y0KwVOySPcn0OB0nbEC66RvUPXSVa6grqa2Ma1v0FD7B-GXbQWOpcYu2xg8MtGoovPbo-kCzfjLJqEcwq9xAV7B7wcrTztXooTEYo3fwlhaVq91zZaCOIsbhkOyUUAc8-nkPyNPN9DG7G84ebu-zyWxopFTdEEYgRVoWheDWIGo24mqs4qQqAYuQSi0TUWgJTHLGbGlSUxpVKJEqQJuM5AE5X9dtvYtthy5fVMFgXUOzmiEXIuZxIbSM9OwfnbveN7G7qFLO07GQIqqLtTLeheCxzFtfLcAvc87y1S3yTF8_ft9iGvHpT8m-WKDd0N_lR3CyBj6Yze_fMeUX8euPJA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2251158232</pqid></control><display><type>article</type><title>Evaluation of dicopper azacryptand complexes in aqueous CuAAC reactions and their tolerance toward biological thiols</title><source>Royal Society Of Chemistry Journals</source><source>Alma/SFX Local Collection</source><creator>Tran, Thi V ; Couture, Garret ; Do, Loi H</creator><creatorcontrib>Tran, Thi V ; Couture, Garret ; Do, Loi H</creatorcontrib><description>A series of dicopper azacryptand complexes was evaluated in copper-catalysed azide-alkyne cycloaddition (CuAAC) in water at 37 °C. It was found that they showed high activity at concentrations as low as 5 μM. These dinuclear catalysts were more susceptible toward inhibition by cysteine rather than glutathione under the conditions tested. Interestingly, the mononuclear copper complexes that are ligated by tripodal amine ligands, also exhibited good catalytic activity in aqueous media and showed similar sensitivity toward biological thiols as that of the dinuclear complexes. Our results suggest that the azacryptand catalysts are too structurally flexible to adequately prevent interactions of their metal centres with external nucleophiles. However, further steric tuning of the ligand structure might enable more effective substrate gating in future studies.
The catalytic activity of dicopper azacryptands was evaluated in water and in the presence of biological thiols.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/c9dt00724e</identifier><identifier>PMID: 30985840</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkynes ; Aqueous solutions ; Catalysis ; Catalysts ; Catalytic activity ; Coordination compounds ; Copper ; Copper compounds ; Cycloaddition ; Glutathione ; Ligands ; NMR ; Nuclear magnetic resonance ; Nucleophiles ; Substrates ; Thiols</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2019-07, Vol.48 (26), p.9751-9758</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-a6a325fbb21dcee906178700774adea539342b93a03100dfc5cfc7b7257aed463</citedby><cites>FETCH-LOGICAL-c337t-a6a325fbb21dcee906178700774adea539342b93a03100dfc5cfc7b7257aed463</cites><orcidid>0000-0002-8859-141X</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/30985840$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tran, Thi V</creatorcontrib><creatorcontrib>Couture, Garret</creatorcontrib><creatorcontrib>Do, Loi H</creatorcontrib><title>Evaluation of dicopper azacryptand complexes in aqueous CuAAC reactions and their tolerance toward biological thiols</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>A series of dicopper azacryptand complexes was evaluated in copper-catalysed azide-alkyne cycloaddition (CuAAC) in water at 37 °C. It was found that they showed high activity at concentrations as low as 5 μM. These dinuclear catalysts were more susceptible toward inhibition by cysteine rather than glutathione under the conditions tested. Interestingly, the mononuclear copper complexes that are ligated by tripodal amine ligands, also exhibited good catalytic activity in aqueous media and showed similar sensitivity toward biological thiols as that of the dinuclear complexes. Our results suggest that the azacryptand catalysts are too structurally flexible to adequately prevent interactions of their metal centres with external nucleophiles. However, further steric tuning of the ligand structure might enable more effective substrate gating in future studies.
The catalytic activity of dicopper azacryptands was evaluated in water and in the presence of biological thiols.</description><subject>Alkynes</subject><subject>Aqueous solutions</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Catalytic activity</subject><subject>Coordination compounds</subject><subject>Copper</subject><subject>Copper compounds</subject><subject>Cycloaddition</subject><subject>Glutathione</subject><subject>Ligands</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Nucleophiles</subject><subject>Substrates</subject><subject>Thiols</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpd0UtLAzEQAOAgitbHxbsS8CJCNY_dpjmWtT6g4EXPy2wyq1u2mzXZVeuvN7VawVMG8s0wD0KOObvkTOoro23HmBIJbpEBT5QaaiGT7U0sRntkP4Q5Y0KwVOySPcn0OB0nbEC66RvUPXSVa6grqa2Ma1v0FD7B-GXbQWOpcYu2xg8MtGoovPbo-kCzfjLJqEcwq9xAV7B7wcrTztXooTEYo3fwlhaVq91zZaCOIsbhkOyUUAc8-nkPyNPN9DG7G84ebu-zyWxopFTdEEYgRVoWheDWIGo24mqs4qQqAYuQSi0TUWgJTHLGbGlSUxpVKJEqQJuM5AE5X9dtvYtthy5fVMFgXUOzmiEXIuZxIbSM9OwfnbveN7G7qFLO07GQIqqLtTLeheCxzFtfLcAvc87y1S3yTF8_ft9iGvHpT8m-WKDd0N_lR3CyBj6Yze_fMeUX8euPJA</recordid><startdate>20190702</startdate><enddate>20190702</enddate><creator>Tran, Thi V</creator><creator>Couture, Garret</creator><creator>Do, Loi H</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8859-141X</orcidid></search><sort><creationdate>20190702</creationdate><title>Evaluation of dicopper azacryptand complexes in aqueous CuAAC reactions and their tolerance toward biological thiols</title><author>Tran, Thi V ; Couture, Garret ; Do, Loi H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-a6a325fbb21dcee906178700774adea539342b93a03100dfc5cfc7b7257aed463</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alkynes</topic><topic>Aqueous solutions</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Catalytic activity</topic><topic>Coordination compounds</topic><topic>Copper</topic><topic>Copper compounds</topic><topic>Cycloaddition</topic><topic>Glutathione</topic><topic>Ligands</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Nucleophiles</topic><topic>Substrates</topic><topic>Thiols</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tran, Thi V</creatorcontrib><creatorcontrib>Couture, Garret</creatorcontrib><creatorcontrib>Do, Loi H</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tran, Thi V</au><au>Couture, Garret</au><au>Do, Loi H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Evaluation of dicopper azacryptand complexes in aqueous CuAAC reactions and their tolerance toward biological thiols</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2019-07-02</date><risdate>2019</risdate><volume>48</volume><issue>26</issue><spage>9751</spage><epage>9758</epage><pages>9751-9758</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>A series of dicopper azacryptand complexes was evaluated in copper-catalysed azide-alkyne cycloaddition (CuAAC) in water at 37 °C. It was found that they showed high activity at concentrations as low as 5 μM. These dinuclear catalysts were more susceptible toward inhibition by cysteine rather than glutathione under the conditions tested. Interestingly, the mononuclear copper complexes that are ligated by tripodal amine ligands, also exhibited good catalytic activity in aqueous media and showed similar sensitivity toward biological thiols as that of the dinuclear complexes. Our results suggest that the azacryptand catalysts are too structurally flexible to adequately prevent interactions of their metal centres with external nucleophiles. However, further steric tuning of the ligand structure might enable more effective substrate gating in future studies.
The catalytic activity of dicopper azacryptands was evaluated in water and in the presence of biological thiols.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>30985840</pmid><doi>10.1039/c9dt00724e</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-8859-141X</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2019-07, Vol.48 (26), p.9751-9758 |
| issn | 1477-9226 1477-9234 |
| language | eng |
| recordid | cdi_proquest_journals_2251158232 |
| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Alkynes Aqueous solutions Catalysis Catalysts Catalytic activity Coordination compounds Copper Copper compounds Cycloaddition Glutathione Ligands NMR Nuclear magnetic resonance Nucleophiles Substrates Thiols |
| title | Evaluation of dicopper azacryptand complexes in aqueous CuAAC reactions and their tolerance toward biological thiols |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-01T15%3A29%3A57IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Evaluation%20of%20dicopper%20azacryptand%20complexes%20in%20aqueous%20CuAAC%20reactions%20and%20their%20tolerance%20toward%20biological%20thiols&rft.jtitle=Dalton%20transactions%20:%20an%20international%20journal%20of%20inorganic%20chemistry&rft.au=Tran,%20Thi%20V&rft.date=2019-07-02&rft.volume=48&rft.issue=26&rft.spage=9751&rft.epage=9758&rft.pages=9751-9758&rft.issn=1477-9226&rft.eissn=1477-9234&rft_id=info:doi/10.1039/c9dt00724e&rft_dat=%3Cproquest_pubme%3E2210012293%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2251158232&rft_id=info:pmid/30985840&rfr_iscdi=true |