Design, synthesis, and biological application of A-D-A-type boranil fluorescent dyes
For the first time, three acceptor-donor-acceptor (A-D-A)-type boranil fluorescent dyes, CSU-BF-R (R = H, CH 3 , and OCH 3 ), featuring phenothiazine as the donor, were designed and synthesized. CSU-BF-R exhibited remarkable photophysical characteristics, including large Stokes shifts (>150 nm),...
Gespeichert in:
| Veröffentlicht in: | Organic & biomolecular chemistry 2024-05, Vol.22 (18), p.3725-3731 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3731 |
|---|---|
| container_issue | 18 |
| container_start_page | 3725 |
| container_title | Organic & biomolecular chemistry |
| container_volume | 22 |
| creator | Luo, Wei Li, Yiling Wang, Liang Qin, Yanhua Cheng, Qiao Hu, Guochang Yao, Chaoyi Song, Xiangzhi |
| description | For the first time, three acceptor-donor-acceptor (A-D-A)-type boranil fluorescent dyes,
CSU-BF-R
(R = H, CH
3
, and OCH
3
), featuring phenothiazine as the donor, were designed and synthesized.
CSU-BF-R
exhibited remarkable photophysical characteristics, including large Stokes shifts (>150 nm), high fluorescence quantum yields (up to 40%), long-wavelength emissions, and strong red solid-state fluorescence. Moreover, these
CSU-BF-R
fluorescent dyes were demonstrated to function as highly selective and sensitive ratiometric fluorescent probes for detecting hypochlorous acid (HClO). The preliminary biological applications of
CSU-BF-OCH
3
for sensing intracellular HClO in living cells and zebrafish were demonstrated. Therefore,
CSU-BF-R
possess the potential to further explore the physiological and pathological functions associated with HClO and provide valuable insights into the design of high-performance A-D-A-type fluorescent dyes.
Acceptor-donor-acceptor boranil fluorescent dyes,
CSU-BF-R
(R = H, CH
3
, and OCH
3
), were developed with strong red fluorescence and large Stokes shifts.
CSU-BF-OCH
3
could selectively sense intracellular hypochlorous acid in living cells and zebrafish. |
| doi_str_mv | 10.1039/d4ob00297k |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_3051932988</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3045114174</sourcerecordid><originalsourceid>FETCH-LOGICAL-c296t-10a2c98eeaca7361cc9a909a0ad124da7477cc2704167cbe4d2c9dda039ece833</originalsourceid><addsrcrecordid>eNpd0c1PwyAYBnBiNG5OL941JF6MWRUKK-U4N7_ikl3muaHAZieDCu2h_73o5kw88ST88ublAYBzjG4xIvxOUVcilHL2cQD6mDKWoBHhh_ucoh44CWGNEOYso8egR_KMMpTnfbCY6lCt7BCGzjbvMYchFFbBsnLGrSopDBR1bWJoKmehW8JxMk3GSdPVGpbOC1sZuDSt8zpIbRuoOh1OwdFSmKDPducAvD0-LCbPyWz-9DIZzxKZ8qxJMBKp5LnWQgpGMiwlFxxxgYTCKVWCxfWlTBmiOGOy1FRFrpSIb9ZS54QMwPV2bu3dZ6tDU2yquIUxwmrXhoIgOsKYYkYjvfpH1671Nm4X1QhzkvI8j-pmq6R3IXi9LGpfbYTvCoyK766LKZ3f_3T9GvHlbmRbbrTa099yI7jYAh_k_vbvs8gXtaGCrw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3051932988</pqid></control><display><type>article</type><title>Design, synthesis, and biological application of A-D-A-type boranil fluorescent dyes</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Luo, Wei ; Li, Yiling ; Wang, Liang ; Qin, Yanhua ; Cheng, Qiao ; Hu, Guochang ; Yao, Chaoyi ; Song, Xiangzhi</creator><creatorcontrib>Luo, Wei ; Li, Yiling ; Wang, Liang ; Qin, Yanhua ; Cheng, Qiao ; Hu, Guochang ; Yao, Chaoyi ; Song, Xiangzhi</creatorcontrib><description>For the first time, three acceptor-donor-acceptor (A-D-A)-type boranil fluorescent dyes,
CSU-BF-R
(R = H, CH
3
, and OCH
3
), featuring phenothiazine as the donor, were designed and synthesized.
CSU-BF-R
exhibited remarkable photophysical characteristics, including large Stokes shifts (>150 nm), high fluorescence quantum yields (up to 40%), long-wavelength emissions, and strong red solid-state fluorescence. Moreover, these
CSU-BF-R
fluorescent dyes were demonstrated to function as highly selective and sensitive ratiometric fluorescent probes for detecting hypochlorous acid (HClO). The preliminary biological applications of
CSU-BF-OCH
3
for sensing intracellular HClO in living cells and zebrafish were demonstrated. Therefore,
CSU-BF-R
possess the potential to further explore the physiological and pathological functions associated with HClO and provide valuable insights into the design of high-performance A-D-A-type fluorescent dyes.
Acceptor-donor-acceptor boranil fluorescent dyes,
CSU-BF-R
(R = H, CH
3
, and OCH
3
), were developed with strong red fluorescence and large Stokes shifts.
CSU-BF-OCH
3
could selectively sense intracellular hypochlorous acid in living cells and zebrafish.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d4ob00297k</identifier><identifier>PMID: 38647088</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aniline Compounds - chemical synthesis ; Aniline Compounds - chemistry ; Animals ; Drug Design ; Dyes ; Fluorescence ; Fluorescent dyes ; Fluorescent Dyes - chemical synthesis ; Fluorescent Dyes - chemistry ; Fluorescent indicators ; Humans ; Hypochlorous acid ; Hypochlorous Acid - analysis ; Hypochlorous Acid - chemistry ; Molecular Structure ; Optical Imaging ; Phenothiazine ; Wavelength ; Zebrafish</subject><ispartof>Organic & biomolecular chemistry, 2024-05, Vol.22 (18), p.3725-3731</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c296t-10a2c98eeaca7361cc9a909a0ad124da7477cc2704167cbe4d2c9dda039ece833</cites><orcidid>0000-0002-4034-6386</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/38647088$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Luo, Wei</creatorcontrib><creatorcontrib>Li, Yiling</creatorcontrib><creatorcontrib>Wang, Liang</creatorcontrib><creatorcontrib>Qin, Yanhua</creatorcontrib><creatorcontrib>Cheng, Qiao</creatorcontrib><creatorcontrib>Hu, Guochang</creatorcontrib><creatorcontrib>Yao, Chaoyi</creatorcontrib><creatorcontrib>Song, Xiangzhi</creatorcontrib><title>Design, synthesis, and biological application of A-D-A-type boranil fluorescent dyes</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>For the first time, three acceptor-donor-acceptor (A-D-A)-type boranil fluorescent dyes,
CSU-BF-R
(R = H, CH
3
, and OCH
3
), featuring phenothiazine as the donor, were designed and synthesized.
CSU-BF-R
exhibited remarkable photophysical characteristics, including large Stokes shifts (>150 nm), high fluorescence quantum yields (up to 40%), long-wavelength emissions, and strong red solid-state fluorescence. Moreover, these
CSU-BF-R
fluorescent dyes were demonstrated to function as highly selective and sensitive ratiometric fluorescent probes for detecting hypochlorous acid (HClO). The preliminary biological applications of
CSU-BF-OCH
3
for sensing intracellular HClO in living cells and zebrafish were demonstrated. Therefore,
CSU-BF-R
possess the potential to further explore the physiological and pathological functions associated with HClO and provide valuable insights into the design of high-performance A-D-A-type fluorescent dyes.
Acceptor-donor-acceptor boranil fluorescent dyes,
CSU-BF-R
(R = H, CH
3
, and OCH
3
), were developed with strong red fluorescence and large Stokes shifts.
CSU-BF-OCH
3
could selectively sense intracellular hypochlorous acid in living cells and zebrafish.</description><subject>Aniline Compounds - chemical synthesis</subject><subject>Aniline Compounds - chemistry</subject><subject>Animals</subject><subject>Drug Design</subject><subject>Dyes</subject><subject>Fluorescence</subject><subject>Fluorescent dyes</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Fluorescent indicators</subject><subject>Humans</subject><subject>Hypochlorous acid</subject><subject>Hypochlorous Acid - analysis</subject><subject>Hypochlorous Acid - chemistry</subject><subject>Molecular Structure</subject><subject>Optical Imaging</subject><subject>Phenothiazine</subject><subject>Wavelength</subject><subject>Zebrafish</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0c1PwyAYBnBiNG5OL941JF6MWRUKK-U4N7_ikl3muaHAZieDCu2h_73o5kw88ST88ublAYBzjG4xIvxOUVcilHL2cQD6mDKWoBHhh_ucoh44CWGNEOYso8egR_KMMpTnfbCY6lCt7BCGzjbvMYchFFbBsnLGrSopDBR1bWJoKmehW8JxMk3GSdPVGpbOC1sZuDSt8zpIbRuoOh1OwdFSmKDPducAvD0-LCbPyWz-9DIZzxKZ8qxJMBKp5LnWQgpGMiwlFxxxgYTCKVWCxfWlTBmiOGOy1FRFrpSIb9ZS54QMwPV2bu3dZ6tDU2yquIUxwmrXhoIgOsKYYkYjvfpH1671Nm4X1QhzkvI8j-pmq6R3IXi9LGpfbYTvCoyK766LKZ3f_3T9GvHlbmRbbrTa099yI7jYAh_k_vbvs8gXtaGCrw</recordid><startdate>20240508</startdate><enddate>20240508</enddate><creator>Luo, Wei</creator><creator>Li, Yiling</creator><creator>Wang, Liang</creator><creator>Qin, Yanhua</creator><creator>Cheng, Qiao</creator><creator>Hu, Guochang</creator><creator>Yao, Chaoyi</creator><creator>Song, Xiangzhi</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>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-4034-6386</orcidid></search><sort><creationdate>20240508</creationdate><title>Design, synthesis, and biological application of A-D-A-type boranil fluorescent dyes</title><author>Luo, Wei ; Li, Yiling ; Wang, Liang ; Qin, Yanhua ; Cheng, Qiao ; Hu, Guochang ; Yao, Chaoyi ; Song, Xiangzhi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-10a2c98eeaca7361cc9a909a0ad124da7477cc2704167cbe4d2c9dda039ece833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Aniline Compounds - chemical synthesis</topic><topic>Aniline Compounds - chemistry</topic><topic>Animals</topic><topic>Drug Design</topic><topic>Dyes</topic><topic>Fluorescence</topic><topic>Fluorescent dyes</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Fluorescent indicators</topic><topic>Humans</topic><topic>Hypochlorous acid</topic><topic>Hypochlorous Acid - analysis</topic><topic>Hypochlorous Acid - chemistry</topic><topic>Molecular Structure</topic><topic>Optical Imaging</topic><topic>Phenothiazine</topic><topic>Wavelength</topic><topic>Zebrafish</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Luo, Wei</creatorcontrib><creatorcontrib>Li, Yiling</creatorcontrib><creatorcontrib>Wang, Liang</creatorcontrib><creatorcontrib>Qin, Yanhua</creatorcontrib><creatorcontrib>Cheng, Qiao</creatorcontrib><creatorcontrib>Hu, Guochang</creatorcontrib><creatorcontrib>Yao, Chaoyi</creatorcontrib><creatorcontrib>Song, Xiangzhi</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Luo, Wei</au><au>Li, Yiling</au><au>Wang, Liang</au><au>Qin, Yanhua</au><au>Cheng, Qiao</au><au>Hu, Guochang</au><au>Yao, Chaoyi</au><au>Song, Xiangzhi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis, and biological application of A-D-A-type boranil fluorescent dyes</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2024-05-08</date><risdate>2024</risdate><volume>22</volume><issue>18</issue><spage>3725</spage><epage>3731</epage><pages>3725-3731</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>For the first time, three acceptor-donor-acceptor (A-D-A)-type boranil fluorescent dyes,
CSU-BF-R
(R = H, CH
3
, and OCH
3
), featuring phenothiazine as the donor, were designed and synthesized.
CSU-BF-R
exhibited remarkable photophysical characteristics, including large Stokes shifts (>150 nm), high fluorescence quantum yields (up to 40%), long-wavelength emissions, and strong red solid-state fluorescence. Moreover, these
CSU-BF-R
fluorescent dyes were demonstrated to function as highly selective and sensitive ratiometric fluorescent probes for detecting hypochlorous acid (HClO). The preliminary biological applications of
CSU-BF-OCH
3
for sensing intracellular HClO in living cells and zebrafish were demonstrated. Therefore,
CSU-BF-R
possess the potential to further explore the physiological and pathological functions associated with HClO and provide valuable insights into the design of high-performance A-D-A-type fluorescent dyes.
Acceptor-donor-acceptor boranil fluorescent dyes,
CSU-BF-R
(R = H, CH
3
, and OCH
3
), were developed with strong red fluorescence and large Stokes shifts.
CSU-BF-OCH
3
could selectively sense intracellular hypochlorous acid in living cells and zebrafish.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38647088</pmid><doi>10.1039/d4ob00297k</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-4034-6386</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2024-05, Vol.22 (18), p.3725-3731 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_journals_3051932988 |
| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aniline Compounds - chemical synthesis Aniline Compounds - chemistry Animals Drug Design Dyes Fluorescence Fluorescent dyes Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry Fluorescent indicators Humans Hypochlorous acid Hypochlorous Acid - analysis Hypochlorous Acid - chemistry Molecular Structure Optical Imaging Phenothiazine Wavelength Zebrafish |
| title | Design, synthesis, and biological application of A-D-A-type boranil fluorescent dyes |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T11%3A03%3A51IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Design,%20synthesis,%20and%20biological%20application%20of%20A-D-A-type%20boranil%20fluorescent%20dyes&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Luo,%20Wei&rft.date=2024-05-08&rft.volume=22&rft.issue=18&rft.spage=3725&rft.epage=3731&rft.pages=3725-3731&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/d4ob00297k&rft_dat=%3Cproquest_cross%3E3045114174%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=3051932988&rft_id=info:pmid/38647088&rfr_iscdi=true |