Water-Soluble Triarylborane Chromophores for One- and Two-Photon Excited Fluorescence Imaging of Mitochondria in Cells
Three water‐soluble tetracationic quadrupolar chromophores comprising two three‐coordinate boron π‐acceptor groups bridged by thiophene‐containing moieties were synthesised for biological imaging applications. Compound 3 containing the bulkier 5‐(3,5‐Me2C6H2)‐2,2′‐(C4H2S)2‐5′‐(3,5‐Me2C6H2) bridge is...
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| Veröffentlicht in: | Chemistry : a European journal 2016-10, Vol.22 (41), p.14701-14706 |
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| creator | Griesbeck, Stefanie Zhang, Zuolun Gutmann, Marcus Lühmann, Tessa Edkins, Robert M. Clermont, Guillaume Lazar, Adina N. Haehnel, Martin Edkins, Katharina Eichhorn, Antonius Blanchard-Desce, Mireille Meinel, Lorenz Marder, Todd B. |
| description | Three water‐soluble tetracationic quadrupolar chromophores comprising two three‐coordinate boron π‐acceptor groups bridged by thiophene‐containing moieties were synthesised for biological imaging applications. Compound 3 containing the bulkier 5‐(3,5‐Me2C6H2)‐2,2′‐(C4H2S)2‐5′‐(3,5‐Me2C6H2) bridge is stable over a long period of time, exhibits a high fluorescence quantum yield and strong one‐ and two‐photon absorption (TPA), and has a TPA cross section of 268 GM at 800 nm in water. Confocal laser scanning fluorescence microscopy studies in live cells indicated localisation of the chromophore at the mitochondria; moreover, cytotoxicity measurements proved biocompatibility. Thus, chromophore 3 has excellent potential for one‐ and two‐photon‐excited fluorescence imaging of mitochondrial function in cells.
Very positive image of boron: A new tetracationic, quadrupolar, three‐coordinate boron compound is water‐soluble and stable, and has a large two‐photon absorption cross section σ2 and fluorescence quantum yield, even in water. It localises at mitochondria and is non‐toxic to cells at concentrations required for one‐ and two‐photon excited fluorescence imaging of mitochondrial function (see figure). |
| doi_str_mv | 10.1002/chem.201602639 |
| format | Article |
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Very positive image of boron: A new tetracationic, quadrupolar, three‐coordinate boron compound is water‐soluble and stable, and has a large two‐photon absorption cross section σ2 and fluorescence quantum yield, even in water. It localises at mitochondria and is non‐toxic to cells at concentrations required for one‐ and two‐photon excited fluorescence imaging of mitochondrial function (see figure).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201602639</identifier><identifier>PMID: 27627995</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Absorption ; Bioengineering ; Boranes - chemical synthesis ; boron ; Boron compounds ; Chemical Sciences ; Chemistry ; Chromophores ; Confocal ; Cross sections ; Fluorescence ; Fluorescent Dyes - chemistry ; fluorescent probes ; HEK293 Cells ; Hep G2 Cells ; Humans ; Imaging ; imaging agents ; Life Sciences ; Microscopy, Fluorescence ; Mitochondria ; Mitochondria - metabolism ; Molecular Imaging - methods ; Molecular Structure ; nonlinear optics ; Optical Imaging ; or physical chemistry ; Organic chemistry ; Solubility ; Structure-Activity Relationship ; Theoretical and ; Thiophenes - chemistry ; Water</subject><ispartof>Chemistry : a European journal, 2016-10, Vol.22 (41), p.14701-14706</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6219-bd6be5909996d7e64a0f553a5302dda05db0cdfa96ba8454777f66d860fd172c3</citedby><cites>FETCH-LOGICAL-c6219-bd6be5909996d7e64a0f553a5302dda05db0cdfa96ba8454777f66d860fd172c3</cites><orcidid>0000-0002-9990-0169 ; 0000-0002-6885-5457 ; 0000-0002-1572-9545 ; 0000-0001-6117-5275</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%2Fchem.201602639$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201602639$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27627995$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-03572593$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Griesbeck, Stefanie</creatorcontrib><creatorcontrib>Zhang, Zuolun</creatorcontrib><creatorcontrib>Gutmann, Marcus</creatorcontrib><creatorcontrib>Lühmann, Tessa</creatorcontrib><creatorcontrib>Edkins, Robert M.</creatorcontrib><creatorcontrib>Clermont, Guillaume</creatorcontrib><creatorcontrib>Lazar, Adina N.</creatorcontrib><creatorcontrib>Haehnel, Martin</creatorcontrib><creatorcontrib>Edkins, Katharina</creatorcontrib><creatorcontrib>Eichhorn, Antonius</creatorcontrib><creatorcontrib>Blanchard-Desce, Mireille</creatorcontrib><creatorcontrib>Meinel, Lorenz</creatorcontrib><creatorcontrib>Marder, Todd B.</creatorcontrib><title>Water-Soluble Triarylborane Chromophores for One- and Two-Photon Excited Fluorescence Imaging of Mitochondria in Cells</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Three water‐soluble tetracationic quadrupolar chromophores comprising two three‐coordinate boron π‐acceptor groups bridged by thiophene‐containing moieties were synthesised for biological imaging applications. Compound 3 containing the bulkier 5‐(3,5‐Me2C6H2)‐2,2′‐(C4H2S)2‐5′‐(3,5‐Me2C6H2) bridge is stable over a long period of time, exhibits a high fluorescence quantum yield and strong one‐ and two‐photon absorption (TPA), and has a TPA cross section of 268 GM at 800 nm in water. Confocal laser scanning fluorescence microscopy studies in live cells indicated localisation of the chromophore at the mitochondria; moreover, cytotoxicity measurements proved biocompatibility. Thus, chromophore 3 has excellent potential for one‐ and two‐photon‐excited fluorescence imaging of mitochondrial function in cells.
Very positive image of boron: A new tetracationic, quadrupolar, three‐coordinate boron compound is water‐soluble and stable, and has a large two‐photon absorption cross section σ2 and fluorescence quantum yield, even in water. It localises at mitochondria and is non‐toxic to cells at concentrations required for one‐ and two‐photon excited fluorescence imaging of mitochondrial function (see figure).</description><subject>Absorption</subject><subject>Bioengineering</subject><subject>Boranes - chemical synthesis</subject><subject>boron</subject><subject>Boron compounds</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Chromophores</subject><subject>Confocal</subject><subject>Cross sections</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemistry</subject><subject>fluorescent probes</subject><subject>HEK293 Cells</subject><subject>Hep G2 Cells</subject><subject>Humans</subject><subject>Imaging</subject><subject>imaging agents</subject><subject>Life Sciences</subject><subject>Microscopy, Fluorescence</subject><subject>Mitochondria</subject><subject>Mitochondria - metabolism</subject><subject>Molecular Imaging - methods</subject><subject>Molecular Structure</subject><subject>nonlinear optics</subject><subject>Optical Imaging</subject><subject>or physical chemistry</subject><subject>Organic chemistry</subject><subject>Solubility</subject><subject>Structure-Activity Relationship</subject><subject>Theoretical and</subject><subject>Thiophenes - chemistry</subject><subject>Water</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkUtv1DAUhS0EokNhyxJZYgOLDH6M7XhZommn0gytxEDZWU7sNClOPNhJH_8eDykjxAZWlq6-c67PPQC8xmiOESIfqsZ2c4IwR4RT-QTMMCM4o4Kzp2CG5EJknFF5BF7EeIMQkpzS5-CICE6ElGwGbq_0YEP22buxdBZuQ6vDgyt90L2FRRN853eNDzbC2gd40dsM6t7A7Z3PLhs_-B4u76t2sAaeunHPVbavLDzv9HXbX0Nfw007-KrxvUnWsO1hYZ2LL8GzWrtoXz2-x-DL6XJbrLL1xdl5cbLOKk6wzErDS8skklJyIyxfaFQzRjWjiBijETMlqkytJS91vmALIUTNuck5qg0WpKLH4P3k22indqHtUjrldatWJ2u1nyHKBGGS3uLEvpvYXfA_RhsH1bUpjnPpFH6MCqcNOUm3zv8DJVSiHOcioW__Qm_8GPoU-heFcorwIlHziaqCjzHY-vBZjNS-aLUvWh2KToI3j7Zj2VlzwH83mwA5AXetsw__sFPFarn50zybtG0c7P1Bq8N3xQUVTF19OlN4-3XDv30U6pL-BJbgwqo</recordid><startdate>20161004</startdate><enddate>20161004</enddate><creator>Griesbeck, Stefanie</creator><creator>Zhang, Zuolun</creator><creator>Gutmann, Marcus</creator><creator>Lühmann, Tessa</creator><creator>Edkins, Robert M.</creator><creator>Clermont, Guillaume</creator><creator>Lazar, Adina N.</creator><creator>Haehnel, Martin</creator><creator>Edkins, Katharina</creator><creator>Eichhorn, Antonius</creator><creator>Blanchard-Desce, Mireille</creator><creator>Meinel, Lorenz</creator><creator>Marder, Todd B.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><scope>BSCLL</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-9990-0169</orcidid><orcidid>https://orcid.org/0000-0002-6885-5457</orcidid><orcidid>https://orcid.org/0000-0002-1572-9545</orcidid><orcidid>https://orcid.org/0000-0001-6117-5275</orcidid></search><sort><creationdate>20161004</creationdate><title>Water-Soluble Triarylborane Chromophores for One- and Two-Photon Excited Fluorescence Imaging of Mitochondria in Cells</title><author>Griesbeck, Stefanie ; Zhang, Zuolun ; Gutmann, Marcus ; Lühmann, Tessa ; Edkins, Robert M. ; Clermont, Guillaume ; Lazar, Adina N. ; Haehnel, Martin ; Edkins, Katharina ; Eichhorn, Antonius ; Blanchard-Desce, Mireille ; Meinel, Lorenz ; Marder, Todd B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6219-bd6be5909996d7e64a0f553a5302dda05db0cdfa96ba8454777f66d860fd172c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Absorption</topic><topic>Bioengineering</topic><topic>Boranes - chemical synthesis</topic><topic>boron</topic><topic>Boron compounds</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Chromophores</topic><topic>Confocal</topic><topic>Cross sections</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemistry</topic><topic>fluorescent probes</topic><topic>HEK293 Cells</topic><topic>Hep G2 Cells</topic><topic>Humans</topic><topic>Imaging</topic><topic>imaging agents</topic><topic>Life Sciences</topic><topic>Microscopy, Fluorescence</topic><topic>Mitochondria</topic><topic>Mitochondria - metabolism</topic><topic>Molecular Imaging - methods</topic><topic>Molecular Structure</topic><topic>nonlinear optics</topic><topic>Optical Imaging</topic><topic>or physical chemistry</topic><topic>Organic chemistry</topic><topic>Solubility</topic><topic>Structure-Activity Relationship</topic><topic>Theoretical and</topic><topic>Thiophenes - chemistry</topic><topic>Water</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Griesbeck, Stefanie</creatorcontrib><creatorcontrib>Zhang, Zuolun</creatorcontrib><creatorcontrib>Gutmann, Marcus</creatorcontrib><creatorcontrib>Lühmann, Tessa</creatorcontrib><creatorcontrib>Edkins, Robert M.</creatorcontrib><creatorcontrib>Clermont, Guillaume</creatorcontrib><creatorcontrib>Lazar, Adina N.</creatorcontrib><creatorcontrib>Haehnel, Martin</creatorcontrib><creatorcontrib>Edkins, Katharina</creatorcontrib><creatorcontrib>Eichhorn, Antonius</creatorcontrib><creatorcontrib>Blanchard-Desce, Mireille</creatorcontrib><creatorcontrib>Meinel, Lorenz</creatorcontrib><creatorcontrib>Marder, Todd B.</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Griesbeck, Stefanie</au><au>Zhang, Zuolun</au><au>Gutmann, Marcus</au><au>Lühmann, Tessa</au><au>Edkins, Robert M.</au><au>Clermont, Guillaume</au><au>Lazar, Adina N.</au><au>Haehnel, Martin</au><au>Edkins, Katharina</au><au>Eichhorn, Antonius</au><au>Blanchard-Desce, Mireille</au><au>Meinel, Lorenz</au><au>Marder, Todd B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Water-Soluble Triarylborane Chromophores for One- and Two-Photon Excited Fluorescence Imaging of Mitochondria in Cells</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2016-10-04</date><risdate>2016</risdate><volume>22</volume><issue>41</issue><spage>14701</spage><epage>14706</epage><pages>14701-14706</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Three water‐soluble tetracationic quadrupolar chromophores comprising two three‐coordinate boron π‐acceptor groups bridged by thiophene‐containing moieties were synthesised for biological imaging applications. Compound 3 containing the bulkier 5‐(3,5‐Me2C6H2)‐2,2′‐(C4H2S)2‐5′‐(3,5‐Me2C6H2) bridge is stable over a long period of time, exhibits a high fluorescence quantum yield and strong one‐ and two‐photon absorption (TPA), and has a TPA cross section of 268 GM at 800 nm in water. Confocal laser scanning fluorescence microscopy studies in live cells indicated localisation of the chromophore at the mitochondria; moreover, cytotoxicity measurements proved biocompatibility. Thus, chromophore 3 has excellent potential for one‐ and two‐photon‐excited fluorescence imaging of mitochondrial function in cells.
Very positive image of boron: A new tetracationic, quadrupolar, three‐coordinate boron compound is water‐soluble and stable, and has a large two‐photon absorption cross section σ2 and fluorescence quantum yield, even in water. It localises at mitochondria and is non‐toxic to cells at concentrations required for one‐ and two‐photon excited fluorescence imaging of mitochondrial function (see figure).</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27627995</pmid><doi>10.1002/chem.201602639</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-9990-0169</orcidid><orcidid>https://orcid.org/0000-0002-6885-5457</orcidid><orcidid>https://orcid.org/0000-0002-1572-9545</orcidid><orcidid>https://orcid.org/0000-0001-6117-5275</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Absorption Bioengineering Boranes - chemical synthesis boron Boron compounds Chemical Sciences Chemistry Chromophores Confocal Cross sections Fluorescence Fluorescent Dyes - chemistry fluorescent probes HEK293 Cells Hep G2 Cells Humans Imaging imaging agents Life Sciences Microscopy, Fluorescence Mitochondria Mitochondria - metabolism Molecular Imaging - methods Molecular Structure nonlinear optics Optical Imaging or physical chemistry Organic chemistry Solubility Structure-Activity Relationship Theoretical and Thiophenes - chemistry Water |
| title | Water-Soluble Triarylborane Chromophores for One- and Two-Photon Excited Fluorescence Imaging of Mitochondria in Cells |
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