Europium(III) Macrocyclic Chelates Appended with Tyrosine‐based Chromophores and Di‐(2‐picolyl)amine‐based Receptors: Turn‐On Luminescent Chemosensors Selective to Zinc(II) Ions
Zinc ions play an important role in many biological processes in the human body. To selectively detect Zn2+, two EuDO3A‐based complexes (DO3A=1,4,7,10‐tetraazacyclododecane‐1,4,7‐tricarboxylic acid) appended with tyrosine as a chromophore and di‐(2‐picolyl)amine (DPA) as the Zn2+ recognition moiety...
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| Veröffentlicht in: | ChemPlusChem (Weinheim, Germany) Germany), 2020-05, Vol.85 (5), p.806-814 |
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| creator | Wang, Gaoji Platas‐Iglesias, Carlos Angelovski, Goran |
| description | Zinc ions play an important role in many biological processes in the human body. To selectively detect Zn2+, two EuDO3A‐based complexes (DO3A=1,4,7,10‐tetraazacyclododecane‐1,4,7‐tricarboxylic acid) appended with tyrosine as a chromophore and di‐(2‐picolyl)amine (DPA) as the Zn2+ recognition moiety were developed as suitable luminescent sensors. Their luminescence intensity is affected by the photoinduced electron transfer mechanism. Upon addition of Zn2+, both probes display an up to sevenfold enhancement in Eu3+ emission. Competition experiments demonstrated their specificity toward Zn2+ over other metal ions, while also revealing the nonspecificity of the derivatives lacking the DPA‐moiety, thus confirming the essential role of the DPA for the recognition of Zn2+. The induced emission changes of Eu3+ allow for precise quantitative analysis of Zn2+, establishing these lanthanide‐based complexes as viable chemosensors for biological applications.
Highly selective: Two EuDO3A‐based complexes, appended with tyrosine as a chromophore and DPA as a Zn2+ recognition moiety were developed as suitable luminescent sensors. Both probes exhibit strong luminescence enhancement in response to zinc over other studied metal ions. |
| doi_str_mv | 10.1002/cplu.201900731 |
| format | Article |
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Highly selective: Two EuDO3A‐based complexes, appended with tyrosine as a chromophore and DPA as a Zn2+ recognition moiety were developed as suitable luminescent sensors. Both probes exhibit strong luminescence enhancement in response to zinc over other studied metal ions.</description><identifier>ISSN: 2192-6506</identifier><identifier>EISSN: 2192-6506</identifier><identifier>DOI: 10.1002/cplu.201900731</identifier><identifier>PMID: 31967740</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Amines - chemistry ; Biological activity ; Chelates ; Chelating Agents - chemistry ; Chemical sensors ; Chemistry ; Chemoreceptors ; Chromophores ; Coordination Complexes - chemistry ; Density Functional Theory ; Electron transfer ; Emission analysis ; Europium ; Europium - chemistry ; Hydrogen-Ion Concentration ; Ions - chemistry ; lanthanides ; Ligands ; luminescence ; Luminescent Measurements - methods ; photoinduced electron transfer ; Recognition ; Tyrosine ; Tyrosine - chemistry ; Zinc ; Zinc - analysis</subject><ispartof>ChemPlusChem (Weinheim, Germany), 2020-05, Vol.85 (5), p.806-814</ispartof><rights>2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2020. This article is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4131-c657754e8a01f27ef8ad2973af283df908a3f2fcc50e5b67eae503c48492b2983</citedby><cites>FETCH-LOGICAL-c4131-c657754e8a01f27ef8ad2973af283df908a3f2fcc50e5b67eae503c48492b2983</cites><orcidid>0000-0002-6989-9654 ; 0000-0002-8883-2631</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcplu.201900731$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcplu.201900731$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31967740$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Gaoji</creatorcontrib><creatorcontrib>Platas‐Iglesias, Carlos</creatorcontrib><creatorcontrib>Angelovski, Goran</creatorcontrib><title>Europium(III) Macrocyclic Chelates Appended with Tyrosine‐based Chromophores and Di‐(2‐picolyl)amine‐based Receptors: Turn‐On Luminescent Chemosensors Selective to Zinc(II) Ions</title><title>ChemPlusChem (Weinheim, Germany)</title><addtitle>Chempluschem</addtitle><description>Zinc ions play an important role in many biological processes in the human body. To selectively detect Zn2+, two EuDO3A‐based complexes (DO3A=1,4,7,10‐tetraazacyclododecane‐1,4,7‐tricarboxylic acid) appended with tyrosine as a chromophore and di‐(2‐picolyl)amine (DPA) as the Zn2+ recognition moiety were developed as suitable luminescent sensors. Their luminescence intensity is affected by the photoinduced electron transfer mechanism. Upon addition of Zn2+, both probes display an up to sevenfold enhancement in Eu3+ emission. Competition experiments demonstrated their specificity toward Zn2+ over other metal ions, while also revealing the nonspecificity of the derivatives lacking the DPA‐moiety, thus confirming the essential role of the DPA for the recognition of Zn2+. The induced emission changes of Eu3+ allow for precise quantitative analysis of Zn2+, establishing these lanthanide‐based complexes as viable chemosensors for biological applications.
Highly selective: Two EuDO3A‐based complexes, appended with tyrosine as a chromophore and DPA as a Zn2+ recognition moiety were developed as suitable luminescent sensors. Both probes exhibit strong luminescence enhancement in response to zinc over other studied metal ions.</description><subject>Amines - chemistry</subject><subject>Biological activity</subject><subject>Chelates</subject><subject>Chelating Agents - chemistry</subject><subject>Chemical sensors</subject><subject>Chemistry</subject><subject>Chemoreceptors</subject><subject>Chromophores</subject><subject>Coordination Complexes - chemistry</subject><subject>Density Functional Theory</subject><subject>Electron transfer</subject><subject>Emission analysis</subject><subject>Europium</subject><subject>Europium - chemistry</subject><subject>Hydrogen-Ion Concentration</subject><subject>Ions - chemistry</subject><subject>lanthanides</subject><subject>Ligands</subject><subject>luminescence</subject><subject>Luminescent Measurements - methods</subject><subject>photoinduced electron transfer</subject><subject>Recognition</subject><subject>Tyrosine</subject><subject>Tyrosine - chemistry</subject><subject>Zinc</subject><subject>Zinc - analysis</subject><issn>2192-6506</issn><issn>2192-6506</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><sourceid>EIF</sourceid><recordid>eNqFkc1u1DAUhS0EotXQLUtkic10MYN_kjhhV4VCIw0qgumGTeRxbjSuHDvYCVV2PALvw9vwJHU0pa3Y1Avbuv7u8bEPQq8pWVNC2DvVm3HNCC0IEZw-Q8eMFmyVpSR7_mh_hE5CuCZxZCRlgr9ER5wWmRAJOUZ_zkfvej12y6qqTvFnqbxTkzJa4XIPRg4Q8Fnfg22gwTd62OPt5F3QFv7--r2TIVbLvXed6_fOR1baBn_Q8WzJ4tRr5cxkTmX3uOErKOgH58N7vB29jfVLizfjzAQFdphv7lwAGyKDv4EBNeifgAeHv2urlrPRytnwCr1opQlwcrcu0NXH8215sdpcfqrKs81KJZTTlcpSIdIEckloywS0uWxYIbhsWc6btiC55C1rlUoJpLtMgISUcJXkScF2rMj5Ai0Pur13P0YIQ93paNQYacGNoWY84UkULGhE3_6HXrv4xOiuZgkRKRUzvEDrAxU_OwQPbd173Uk_1ZTUc7L1nGx9n2xseHMnO-46aO7xfzlGoDgAN9rA9IRcXX7ZXD2I3wKI_7ZS</recordid><startdate>202005</startdate><enddate>202005</enddate><creator>Wang, Gaoji</creator><creator>Platas‐Iglesias, Carlos</creator><creator>Angelovski, Goran</creator><general>Blackwell Publishing Ltd</general><scope>24P</scope><scope>WIN</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>4T-</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6989-9654</orcidid><orcidid>https://orcid.org/0000-0002-8883-2631</orcidid></search><sort><creationdate>202005</creationdate><title>Europium(III) Macrocyclic Chelates Appended with Tyrosine‐based Chromophores and Di‐(2‐picolyl)amine‐based Receptors: Turn‐On Luminescent Chemosensors Selective to Zinc(II) Ions</title><author>Wang, Gaoji ; Platas‐Iglesias, Carlos ; Angelovski, Goran</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4131-c657754e8a01f27ef8ad2973af283df908a3f2fcc50e5b67eae503c48492b2983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Amines - chemistry</topic><topic>Biological activity</topic><topic>Chelates</topic><topic>Chelating Agents - chemistry</topic><topic>Chemical sensors</topic><topic>Chemistry</topic><topic>Chemoreceptors</topic><topic>Chromophores</topic><topic>Coordination Complexes - chemistry</topic><topic>Density Functional Theory</topic><topic>Electron transfer</topic><topic>Emission analysis</topic><topic>Europium</topic><topic>Europium - chemistry</topic><topic>Hydrogen-Ion Concentration</topic><topic>Ions - chemistry</topic><topic>lanthanides</topic><topic>Ligands</topic><topic>luminescence</topic><topic>Luminescent Measurements - methods</topic><topic>photoinduced electron transfer</topic><topic>Recognition</topic><topic>Tyrosine</topic><topic>Tyrosine - chemistry</topic><topic>Zinc</topic><topic>Zinc - analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Gaoji</creatorcontrib><creatorcontrib>Platas‐Iglesias, Carlos</creatorcontrib><creatorcontrib>Angelovski, Goran</creatorcontrib><collection>Wiley-Blackwell Open Access Titles</collection><collection>Wiley Free Content</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Docstoc</collection><collection>MEDLINE - Academic</collection><jtitle>ChemPlusChem (Weinheim, Germany)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Gaoji</au><au>Platas‐Iglesias, Carlos</au><au>Angelovski, Goran</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Europium(III) Macrocyclic Chelates Appended with Tyrosine‐based Chromophores and Di‐(2‐picolyl)amine‐based Receptors: Turn‐On Luminescent Chemosensors Selective to Zinc(II) Ions</atitle><jtitle>ChemPlusChem (Weinheim, Germany)</jtitle><addtitle>Chempluschem</addtitle><date>2020-05</date><risdate>2020</risdate><volume>85</volume><issue>5</issue><spage>806</spage><epage>814</epage><pages>806-814</pages><issn>2192-6506</issn><eissn>2192-6506</eissn><abstract>Zinc ions play an important role in many biological processes in the human body. To selectively detect Zn2+, two EuDO3A‐based complexes (DO3A=1,4,7,10‐tetraazacyclododecane‐1,4,7‐tricarboxylic acid) appended with tyrosine as a chromophore and di‐(2‐picolyl)amine (DPA) as the Zn2+ recognition moiety were developed as suitable luminescent sensors. Their luminescence intensity is affected by the photoinduced electron transfer mechanism. Upon addition of Zn2+, both probes display an up to sevenfold enhancement in Eu3+ emission. Competition experiments demonstrated their specificity toward Zn2+ over other metal ions, while also revealing the nonspecificity of the derivatives lacking the DPA‐moiety, thus confirming the essential role of the DPA for the recognition of Zn2+. The induced emission changes of Eu3+ allow for precise quantitative analysis of Zn2+, establishing these lanthanide‐based complexes as viable chemosensors for biological applications.
Highly selective: Two EuDO3A‐based complexes, appended with tyrosine as a chromophore and DPA as a Zn2+ recognition moiety were developed as suitable luminescent sensors. Both probes exhibit strong luminescence enhancement in response to zinc over other studied metal ions.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>31967740</pmid><doi>10.1002/cplu.201900731</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-6989-9654</orcidid><orcidid>https://orcid.org/0000-0002-8883-2631</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Amines - chemistry Biological activity Chelates Chelating Agents - chemistry Chemical sensors Chemistry Chemoreceptors Chromophores Coordination Complexes - chemistry Density Functional Theory Electron transfer Emission analysis Europium Europium - chemistry Hydrogen-Ion Concentration Ions - chemistry lanthanides Ligands luminescence Luminescent Measurements - methods photoinduced electron transfer Recognition Tyrosine Tyrosine - chemistry Zinc Zinc - analysis |
| title | Europium(III) Macrocyclic Chelates Appended with Tyrosine‐based Chromophores and Di‐(2‐picolyl)amine‐based Receptors: Turn‐On Luminescent Chemosensors Selective to Zinc(II) Ions |
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