A ratiometric ESIPT probe based on 2-aza-Cope rearrangement for rapid and selective detection of formaldehyde in living cells
Formaldehyde (FA) is a crucial reactive signaling molecule participating in epigenetic and metabolic pathways. However, abnormally elevated levels of FA are implicated in various diseases spanning from tumors to neurodegenerative disorders. Despite being highly selective for FA, current 2-aza-Cope-b...
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| Veröffentlicht in: | Analyst (London) 2022-01, Vol.147 (2), p.252-261 |
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| creator | Quan, Tingting Liang, Zhenhao Pang, Huaiting Zeng, Guanling Chen, Tongsheng |
| description | Formaldehyde (FA) is a crucial reactive signaling molecule participating in epigenetic and metabolic pathways. However, abnormally elevated levels of FA are implicated in various diseases spanning from tumors to neurodegenerative disorders. Despite being highly selective for FA, current 2-aza-Cope-based fluorescent probes leave room for improvement because their relatively slow reaction kinetics (1-9 hours response time) hinder their capability to track transient biological FA. Herein, we present a ratiometric fluorescent probe,
FormAFP
, based on excited state intramolecular photon transfer (ESIPT) for rapid (within 10 min), selective (above 70-fold over other RCS) and sensitive (240-times fluorescence enhancement with 66 nM detection limit) detection of FA
via
2-aza-Cope rearrangement. The probe also displayed a fast response ( |
| doi_str_mv | 10.1039/d1an01722e |
| format | Article |
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FormAFP
, based on excited state intramolecular photon transfer (ESIPT) for rapid (within 10 min), selective (above 70-fold over other RCS) and sensitive (240-times fluorescence enhancement with 66 nM detection limit) detection of FA
via
2-aza-Cope rearrangement. The probe also displayed a fast response (<20 min) to both exogenous and endogenous FA in living cells. Besides,
FormAFP
was capable of monitoring FA released by folate degradation in living MCF7 cells. More importantly,
FormAFP
successfully detected fluctuations of endogenous FA levels in oxidative stress stimulation, demonstrating its potential as an ideal tool to explore FA biology.
A ratiometric ESIPT probe,
FormAFP
, has been developed for rapid, selective and sensitive detection of FA
via
2-aza-Cope rearrangement. The probe also showed a fast response (<20 min) to both exogenous and endogenous FA in living cells.</description><identifier>ISSN: 0003-2654</identifier><identifier>EISSN: 1364-5528</identifier><identifier>DOI: 10.1039/d1an01722e</identifier><identifier>PMID: 34931639</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Cells (biology) ; Fluorescence ; Fluorescent Dyes ; Fluorescent indicators ; Formaldehyde ; HeLa Cells ; Humans ; MCF-7 Cells ; Photons ; Reaction kinetics ; Response time</subject><ispartof>Analyst (London), 2022-01, Vol.147 (2), p.252-261</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c403t-79bc7f30184e855d0ddd75937cbfff0623ebb7e4392e576cbc73e726911054323</citedby><cites>FETCH-LOGICAL-c403t-79bc7f30184e855d0ddd75937cbfff0623ebb7e4392e576cbc73e726911054323</cites><orcidid>0000-0002-0305-2629 ; 0000-0002-4647-4645</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,2831,2832,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34931639$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Quan, Tingting</creatorcontrib><creatorcontrib>Liang, Zhenhao</creatorcontrib><creatorcontrib>Pang, Huaiting</creatorcontrib><creatorcontrib>Zeng, Guanling</creatorcontrib><creatorcontrib>Chen, Tongsheng</creatorcontrib><title>A ratiometric ESIPT probe based on 2-aza-Cope rearrangement for rapid and selective detection of formaldehyde in living cells</title><title>Analyst (London)</title><addtitle>Analyst</addtitle><description>Formaldehyde (FA) is a crucial reactive signaling molecule participating in epigenetic and metabolic pathways. However, abnormally elevated levels of FA are implicated in various diseases spanning from tumors to neurodegenerative disorders. Despite being highly selective for FA, current 2-aza-Cope-based fluorescent probes leave room for improvement because their relatively slow reaction kinetics (1-9 hours response time) hinder their capability to track transient biological FA. Herein, we present a ratiometric fluorescent probe,
FormAFP
, based on excited state intramolecular photon transfer (ESIPT) for rapid (within 10 min), selective (above 70-fold over other RCS) and sensitive (240-times fluorescence enhancement with 66 nM detection limit) detection of FA
via
2-aza-Cope rearrangement. The probe also displayed a fast response (<20 min) to both exogenous and endogenous FA in living cells. Besides,
FormAFP
was capable of monitoring FA released by folate degradation in living MCF7 cells. More importantly,
FormAFP
successfully detected fluctuations of endogenous FA levels in oxidative stress stimulation, demonstrating its potential as an ideal tool to explore FA biology.
A ratiometric ESIPT probe,
FormAFP
, has been developed for rapid, selective and sensitive detection of FA
via
2-aza-Cope rearrangement. The probe also showed a fast response (<20 min) to both exogenous and endogenous FA in living cells.</description><subject>Cells (biology)</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes</subject><subject>Fluorescent indicators</subject><subject>Formaldehyde</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>MCF-7 Cells</subject><subject>Photons</subject><subject>Reaction kinetics</subject><subject>Response time</subject><issn>0003-2654</issn><issn>1364-5528</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0c9r2zAUB3BROpYs26X3FkEvY-BOPyzLPoY02wqlHaw7G1l6bhVsKZWcQAr93ysvbQo7SUKfJ73HF6ETSi4o4dV3Q5UjVDIGR2hKeZFnQrDyGE0JITxjhcgn6FOMq3SkRJCPaMLzitOCV1P0PMdBDdb3MASr8fLP1e87vA6-AdyoCAZ7h1mmnlS28GvAAVQIyt1DD27ArQ-pem0NVs7gCB3owW4BGxjGXSr17Yh61Rl42BnA1uHObq27xxq6Ln5GH1rVRfjyus7Q3x_Lu8Wv7Pr259Vifp3pnPAhk1WjZcsJLXMohTDEGCNFxaVu2rYlBePQNBJyXjEQstBJc5CsqGiaN-eMz9DX_btpsscNxKHubRw7UA78JtasoIyXkoqRnv9HV34TXOouKUbSZ2VZJPVtr3TwMQZo63WwvQq7mpJ6DKW-pPObf6EsEz57fXLT9GAO9C2FBE73IER9uH1Plb8AwcaQMw</recordid><startdate>20220117</startdate><enddate>20220117</enddate><creator>Quan, Tingting</creator><creator>Liang, Zhenhao</creator><creator>Pang, Huaiting</creator><creator>Zeng, Guanling</creator><creator>Chen, Tongsheng</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>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-0305-2629</orcidid><orcidid>https://orcid.org/0000-0002-4647-4645</orcidid></search><sort><creationdate>20220117</creationdate><title>A ratiometric ESIPT probe based on 2-aza-Cope rearrangement for rapid and selective detection of formaldehyde in living cells</title><author>Quan, Tingting ; Liang, Zhenhao ; Pang, Huaiting ; Zeng, Guanling ; Chen, Tongsheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c403t-79bc7f30184e855d0ddd75937cbfff0623ebb7e4392e576cbc73e726911054323</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Cells (biology)</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes</topic><topic>Fluorescent indicators</topic><topic>Formaldehyde</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>MCF-7 Cells</topic><topic>Photons</topic><topic>Reaction kinetics</topic><topic>Response time</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Quan, Tingting</creatorcontrib><creatorcontrib>Liang, Zhenhao</creatorcontrib><creatorcontrib>Pang, Huaiting</creatorcontrib><creatorcontrib>Zeng, Guanling</creatorcontrib><creatorcontrib>Chen, Tongsheng</creatorcontrib><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>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Analyst (London)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Quan, Tingting</au><au>Liang, Zhenhao</au><au>Pang, Huaiting</au><au>Zeng, Guanling</au><au>Chen, Tongsheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A ratiometric ESIPT probe based on 2-aza-Cope rearrangement for rapid and selective detection of formaldehyde in living cells</atitle><jtitle>Analyst (London)</jtitle><addtitle>Analyst</addtitle><date>2022-01-17</date><risdate>2022</risdate><volume>147</volume><issue>2</issue><spage>252</spage><epage>261</epage><pages>252-261</pages><issn>0003-2654</issn><eissn>1364-5528</eissn><abstract>Formaldehyde (FA) is a crucial reactive signaling molecule participating in epigenetic and metabolic pathways. However, abnormally elevated levels of FA are implicated in various diseases spanning from tumors to neurodegenerative disorders. Despite being highly selective for FA, current 2-aza-Cope-based fluorescent probes leave room for improvement because their relatively slow reaction kinetics (1-9 hours response time) hinder their capability to track transient biological FA. Herein, we present a ratiometric fluorescent probe,
FormAFP
, based on excited state intramolecular photon transfer (ESIPT) for rapid (within 10 min), selective (above 70-fold over other RCS) and sensitive (240-times fluorescence enhancement with 66 nM detection limit) detection of FA
via
2-aza-Cope rearrangement. The probe also displayed a fast response (<20 min) to both exogenous and endogenous FA in living cells. Besides,
FormAFP
was capable of monitoring FA released by folate degradation in living MCF7 cells. More importantly,
FormAFP
successfully detected fluctuations of endogenous FA levels in oxidative stress stimulation, demonstrating its potential as an ideal tool to explore FA biology.
A ratiometric ESIPT probe,
FormAFP
, has been developed for rapid, selective and sensitive detection of FA
via
2-aza-Cope rearrangement. The probe also showed a fast response (<20 min) to both exogenous and endogenous FA in living cells.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>34931639</pmid><doi>10.1039/d1an01722e</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0002-0305-2629</orcidid><orcidid>https://orcid.org/0000-0002-4647-4645</orcidid></addata></record> |
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| ispartof | Analyst (London), 2022-01, Vol.147 (2), p.252-261 |
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| source | MEDLINE; Royal Society of Chemistry Journals Archive (1841-2007); Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Cells (biology) Fluorescence Fluorescent Dyes Fluorescent indicators Formaldehyde HeLa Cells Humans MCF-7 Cells Photons Reaction kinetics Response time |
| title | A ratiometric ESIPT probe based on 2-aza-Cope rearrangement for rapid and selective detection of formaldehyde in living cells |
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