Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom
An efficient synthesis of boron-functionalized cyclic BODIPY–Gly conjugates, using commercially available N-protected glycine amino acids and a BF2–BODIPY moiety as starting materials, is reported. The existence of two conformers (up and down) is revealed through comprehensive DFT calculations and 1...
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| Veröffentlicht in: | Inorganic chemistry 2019-09, Vol.58 (17), p.11614-11621 |
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| container_end_page | 11621 |
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| container_issue | 17 |
| container_start_page | 11614 |
| container_title | Inorganic chemistry |
| container_volume | 58 |
| creator | Wang, Maodie Zhang, Guanyu Bobadova-Parvanova, Petia Merriweather, Ashley N Odom, Lilian Barbosa, David Fronczek, Frank R Smith, Kevin M Vicente, M. Graça H |
| description | An efficient synthesis of boron-functionalized cyclic BODIPY–Gly conjugates, using commercially available N-protected glycine amino acids and a BF2–BODIPY moiety as starting materials, is reported. The existence of two conformers (up and down) is revealed through comprehensive DFT calculations and 1H and 11B NMR analyses. The experimental and computational results indicate that all BODIPYs are stable in aqueous solutions at neutral pH and that Fmoc-BODIPY (4) is more stable than Ac-BODIPY (6) in the presence of trifluoroacetic acid (TFA). In part due to their enhanced rigidity, all BODIPY–Gly conjugates display increased fluorescence quantum yields (0.6 < Φ < 0.9) relative to the corresponding BF2–BODIPY, making them excellent candidates for fluorescence imaging applications. |
| doi_str_mv | 10.1021/acs.inorgchem.9b01474 |
| format | Article |
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Graça H</creator><creatorcontrib>Wang, Maodie ; Zhang, Guanyu ; Bobadova-Parvanova, Petia ; Merriweather, Ashley N ; Odom, Lilian ; Barbosa, David ; Fronczek, Frank R ; Smith, Kevin M ; Vicente, M. Graça H</creatorcontrib><description>An efficient synthesis of boron-functionalized cyclic BODIPY–Gly conjugates, using commercially available N-protected glycine amino acids and a BF2–BODIPY moiety as starting materials, is reported. The existence of two conformers (up and down) is revealed through comprehensive DFT calculations and 1H and 11B NMR analyses. The experimental and computational results indicate that all BODIPYs are stable in aqueous solutions at neutral pH and that Fmoc-BODIPY (4) is more stable than Ac-BODIPY (6) in the presence of trifluoroacetic acid (TFA). In part due to their enhanced rigidity, all BODIPY–Gly conjugates display increased fluorescence quantum yields (0.6 < Φ < 0.9) relative to the corresponding BF2–BODIPY, making them excellent candidates for fluorescence imaging applications.</description><identifier>ISSN: 0020-1669</identifier><identifier>EISSN: 1520-510X</identifier><identifier>DOI: 10.1021/acs.inorgchem.9b01474</identifier><identifier>PMID: 31430148</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Inorganic chemistry, 2019-09, Vol.58 (17), p.11614-11621</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a351t-6df48796fd8ed1bf6e8ffd366f75de41ea51ada99931a244b83b608755e14c643</citedby><cites>FETCH-LOGICAL-a351t-6df48796fd8ed1bf6e8ffd366f75de41ea51ada99931a244b83b608755e14c643</cites><orcidid>0000-0001-5544-2779 ; 0000-0002-4429-7868 ; 0000-0002-1965-419X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.inorgchem.9b01474$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.inorgchem.9b01474$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31430148$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Maodie</creatorcontrib><creatorcontrib>Zhang, Guanyu</creatorcontrib><creatorcontrib>Bobadova-Parvanova, Petia</creatorcontrib><creatorcontrib>Merriweather, Ashley N</creatorcontrib><creatorcontrib>Odom, Lilian</creatorcontrib><creatorcontrib>Barbosa, David</creatorcontrib><creatorcontrib>Fronczek, Frank R</creatorcontrib><creatorcontrib>Smith, Kevin M</creatorcontrib><creatorcontrib>Vicente, M. Graça H</creatorcontrib><title>Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom</title><title>Inorganic chemistry</title><addtitle>Inorg. Chem</addtitle><description>An efficient synthesis of boron-functionalized cyclic BODIPY–Gly conjugates, using commercially available N-protected glycine amino acids and a BF2–BODIPY moiety as starting materials, is reported. The existence of two conformers (up and down) is revealed through comprehensive DFT calculations and 1H and 11B NMR analyses. The experimental and computational results indicate that all BODIPYs are stable in aqueous solutions at neutral pH and that Fmoc-BODIPY (4) is more stable than Ac-BODIPY (6) in the presence of trifluoroacetic acid (TFA). 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Graça H</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Maodie</au><au>Zhang, Guanyu</au><au>Bobadova-Parvanova, Petia</au><au>Merriweather, Ashley N</au><au>Odom, Lilian</au><au>Barbosa, David</au><au>Fronczek, Frank R</au><au>Smith, Kevin M</au><au>Vicente, M. Graça H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom</atitle><jtitle>Inorganic chemistry</jtitle><addtitle>Inorg. Chem</addtitle><date>2019-09-03</date><risdate>2019</risdate><volume>58</volume><issue>17</issue><spage>11614</spage><epage>11621</epage><pages>11614-11621</pages><issn>0020-1669</issn><eissn>1520-510X</eissn><abstract>An efficient synthesis of boron-functionalized cyclic BODIPY–Gly conjugates, using commercially available N-protected glycine amino acids and a BF2–BODIPY moiety as starting materials, is reported. The existence of two conformers (up and down) is revealed through comprehensive DFT calculations and 1H and 11B NMR analyses. The experimental and computational results indicate that all BODIPYs are stable in aqueous solutions at neutral pH and that Fmoc-BODIPY (4) is more stable than Ac-BODIPY (6) in the presence of trifluoroacetic acid (TFA). In part due to their enhanced rigidity, all BODIPY–Gly conjugates display increased fluorescence quantum yields (0.6 < Φ < 0.9) relative to the corresponding BF2–BODIPY, making them excellent candidates for fluorescence imaging applications.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>31430148</pmid><doi>10.1021/acs.inorgchem.9b01474</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-5544-2779</orcidid><orcidid>https://orcid.org/0000-0002-4429-7868</orcidid><orcidid>https://orcid.org/0000-0002-1965-419X</orcidid></addata></record> |
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| title | Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom |
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