Water-solubilisation and bio-conjugation of a red-emitting BODIPY marker
The synthesis and preliminary bio-conjugation studies of a novel water-soluble red-emitting di-styryl BODIPY dye are disclosed. Aggregation behaviour of this compound under physiological conditions was suppressed by specific introduction of a di-sulfonated peptide-based linker at the meso phenyl sub...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2011-01, Vol.9 (1), p.66-69 |
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| container_end_page | 69 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Niu, Song Lin Massif, Cédrik Ulrich, Gilles Ziessel, Raymond Renard, Pierre-Yves Romieu, Anthony |
| description | The synthesis and preliminary bio-conjugation studies of a novel water-soluble red-emitting di-styryl BODIPY dye are disclosed. Aggregation behaviour of this compound under physiological conditions was suppressed by specific introduction of a di-sulfonated peptide-based linker at the meso phenyl substituent, sultonated styryl arms and short polyethyleneglycol chains at the boron center. Thus, a good quantum yield of 22% in PBS for this red-emitting BODIPY was obtained. Introduction of an activated ester function enabled successful bio-conjugation to monoclonal antibodies and proteins. |
| doi_str_mv | 10.1039/c0ob00693a |
| format | Article |
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Aggregation behaviour of this compound under physiological conditions was suppressed by specific introduction of a di-sulfonated peptide-based linker at the meso phenyl substituent, sultonated styryl arms and short polyethyleneglycol chains at the boron center. Thus, a good quantum yield of 22% in PBS for this red-emitting BODIPY was obtained. 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Introduction of an activated ester function enabled successful bio-conjugation to monoclonal antibodies and proteins.</description><subject>Alkylation</subject><subject>Boron Compounds - chemistry</subject><subject>Chemical Sciences</subject><subject>Color</subject><subject>Dipeptides - chemistry</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Organic chemistry</subject><subject>Solubility</subject><subject>Water - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kEtPwzAQhC0EoqVw4Qeg3BBIgfUjjn1sy6OVKpUDCHGKnNgpLmlc7ASJf09KoKcdzX6aXQ1C5xhuMFB5W4DLAbik6gANMUvTGBIqD_eawACdhLAGwDLl7BgNCAYhOjlEs1fVGB8HV7W5rWxQjXV1pGod5dbFhavX7ar3XBmpyBsdm41tGluvosnybv70Fm2U_zD-FB2Vqgrm7G-O0MvD_fN0Fi-Wj_PpeBEXVPAmJlrLnDNNlJJE6pKT7iVtQDNGqcEFEd02FSxPtWBQmsKUCS0SmkrOjUiAjtBVn_uuqmzrbXf9O3PKZrPxItt5AFJiidkX7tjLnt1699ma0GQbGwpTVao2rg2ZIJgJJinvyOueLLwLwZtyH40h25WcTWE5-S153MEXf7FtvjF6j_63Sn8Aa291aQ</recordid><startdate>20110101</startdate><enddate>20110101</enddate><creator>Niu, Song Lin</creator><creator>Massif, Cédrik</creator><creator>Ulrich, Gilles</creator><creator>Ziessel, Raymond</creator><creator>Renard, Pierre-Yves</creator><creator>Romieu, Anthony</creator><general>Royal Society of Chemistry</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>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-6980-6091</orcidid><orcidid>https://orcid.org/0000-0001-9094-9778</orcidid><orcidid>https://orcid.org/0000-0002-2300-4499</orcidid></search><sort><creationdate>20110101</creationdate><title>Water-solubilisation and bio-conjugation of a red-emitting BODIPY marker</title><author>Niu, Song Lin ; Massif, Cédrik ; Ulrich, Gilles ; Ziessel, Raymond ; Renard, Pierre-Yves ; Romieu, Anthony</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c386t-2dd9b64d2aa929df62976de0d4433e1c28b64784b7d840fecef53c537966e8503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Alkylation</topic><topic>Boron Compounds - chemistry</topic><topic>Chemical Sciences</topic><topic>Color</topic><topic>Dipeptides - chemistry</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Organic chemistry</topic><topic>Solubility</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Niu, Song Lin</creatorcontrib><creatorcontrib>Massif, Cédrik</creatorcontrib><creatorcontrib>Ulrich, Gilles</creatorcontrib><creatorcontrib>Ziessel, Raymond</creatorcontrib><creatorcontrib>Renard, Pierre-Yves</creatorcontrib><creatorcontrib>Romieu, Anthony</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Niu, Song Lin</au><au>Massif, Cédrik</au><au>Ulrich, Gilles</au><au>Ziessel, Raymond</au><au>Renard, Pierre-Yves</au><au>Romieu, Anthony</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Water-solubilisation and bio-conjugation of a red-emitting BODIPY marker</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2011-01-01</date><risdate>2011</risdate><volume>9</volume><issue>1</issue><spage>66</spage><epage>69</epage><pages>66-69</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>The synthesis and preliminary bio-conjugation studies of a novel water-soluble red-emitting di-styryl BODIPY dye are disclosed. 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| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2011-01, Vol.9 (1), p.66-69 |
| issn | 1477-0520 1477-0539 |
| language | eng |
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| source | MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Alkylation Boron Compounds - chemistry Chemical Sciences Color Dipeptides - chemistry Fluorescent Dyes - chemistry Organic chemistry Solubility Water - chemistry |
| title | Water-solubilisation and bio-conjugation of a red-emitting BODIPY marker |
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