Multi-state amine sensing by electron transfers in a BODIPY probe
Amines are ubiquitous in the chemical industry and are present in a wide range of biological processes, motivating the development of amine-sensitive sensors. There are many turn-on amine sensors, however there are no examples of turn-on sensors that utilize the amine's ability to react by sing...
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creator | VanDenburgh, Katherine L Liu, Yun Sadhukhan, Tumpa Benson, Christopher R Cox, Natalie M Erbas-Cakmak, Sundus Qiao, Bo Gao, Xinfeng Pink, Maren Raghavachari, Krishnan Flood, Amar H |
description | Amines are ubiquitous in the chemical industry and are present in a wide range of biological processes, motivating the development of amine-sensitive sensors. There are many turn-on amine sensors, however there are no examples of turn-on sensors that utilize the amine's ability to react by single electron transfer (SET). We investigated a new turn-on amine probe with a 4,4-difluoro-4-bora-3a,4a-diaza-
s
-indacene (BODIPY) fluorophore. BODIPY fluorescence is first preprogrammed into an off state by internal photoinduced electron transfer (PET) to an electron-deficient quinolinium ring, resulting in fluorescence quenching. At low concentrations of aliphatic amine (0 to 10 mM), this PET pathway is shut down by external SET from the amine to the photoexcited charge-transfer state of the probe and the fluorescence is turned on. At high concentrations of amine (50 mM to 1 M), we observed collisional quenching of the BODIPY fluorescence. The probe is selective for aliphatic amines over aromatic amines, and aliphatic thiols or alcohols. The three molecular processes modulate the BODIPY fluorescence in a multi-mechanistic way with two of them producing a direct response to amine concentrations. The totality of the three molecular processes produced the first example of a multi-state and dose-responsive amine sensor.
Photoinduced electron transfer sets up the BODIPY probe for multi-state amine sensing by single-electron transfer then collisional quenching. |
doi_str_mv | 10.1039/c9ob02466b |
format | Article |
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s
-indacene (BODIPY) fluorophore. BODIPY fluorescence is first preprogrammed into an off state by internal photoinduced electron transfer (PET) to an electron-deficient quinolinium ring, resulting in fluorescence quenching. At low concentrations of aliphatic amine (0 to 10 mM), this PET pathway is shut down by external SET from the amine to the photoexcited charge-transfer state of the probe and the fluorescence is turned on. At high concentrations of amine (50 mM to 1 M), we observed collisional quenching of the BODIPY fluorescence. The probe is selective for aliphatic amines over aromatic amines, and aliphatic thiols or alcohols. The three molecular processes modulate the BODIPY fluorescence in a multi-mechanistic way with two of them producing a direct response to amine concentrations. The totality of the three molecular processes produced the first example of a multi-state and dose-responsive amine sensor.
Photoinduced electron transfer sets up the BODIPY probe for multi-state amine sensing by single-electron transfer then collisional quenching.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c9ob02466b</identifier><identifier>PMID: 31850445</identifier><language>eng</language><publisher>CAMBRIDGE: Royal Soc Chemistry</publisher><subject>Alcohols ; Aliphatic amines ; Amines ; Amines - analysis ; Biological activity ; Boron Compounds - chemical synthesis ; Boron Compounds - chemistry ; Charge transfer ; Chemical industry ; Chemistry ; Chemistry, Organic ; Crystal structure ; Crystallography ; Density Functional Theory ; Electron transfer ; Fluorescence ; Fluorescent Dyes - chemical synthesis ; Fluorescent Dyes - chemistry ; Low concentrations ; Models, Chemical ; Organic chemistry ; Physical Sciences ; Quenching ; Quinolinium Compounds - chemical synthesis ; Quinolinium Compounds - chemistry ; Science & Technology ; Sensors ; Shutdowns ; Single electrons ; Spectrometry, Fluorescence - methods ; Thiols</subject><ispartof>Organic & biomolecular chemistry, 2020-01, Vol.18 (3), p.431-44</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>20</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wos000508570400009</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-c466t-375b1b771009ac6451c1e096363f4cedadd75918cd723c18d51565a9eae948013</citedby><cites>FETCH-LOGICAL-c466t-375b1b771009ac6451c1e096363f4cedadd75918cd723c18d51565a9eae948013</cites><orcidid>0000-0001-6821-5188 ; 0000-0001-7077-363X ; 0000-0003-1995-7286 ; 0000-0001-9049-4574 ; 0000-0002-8621-9980 ; 0000-0001-6137-3239 ; 0000-0003-4168-8377 ; 0000-0003-3275-1426 ; 0000-0002-2764-9155 ; 0000000341688377 ; 000000017077363X ; 0000000161373239 ; 0000000332751426 ; 0000000168215188 ; 0000000227649155 ; 0000000319957286 ; 0000000190494574 ; 0000000286219980</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,315,782,786,887,27931,27932,28255</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31850445$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/1579762$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>VanDenburgh, Katherine L</creatorcontrib><creatorcontrib>Liu, Yun</creatorcontrib><creatorcontrib>Sadhukhan, Tumpa</creatorcontrib><creatorcontrib>Benson, Christopher R</creatorcontrib><creatorcontrib>Cox, Natalie M</creatorcontrib><creatorcontrib>Erbas-Cakmak, Sundus</creatorcontrib><creatorcontrib>Qiao, Bo</creatorcontrib><creatorcontrib>Gao, Xinfeng</creatorcontrib><creatorcontrib>Pink, Maren</creatorcontrib><creatorcontrib>Raghavachari, Krishnan</creatorcontrib><creatorcontrib>Flood, Amar H</creatorcontrib><title>Multi-state amine sensing by electron transfers in a BODIPY probe</title><title>Organic & biomolecular chemistry</title><addtitle>ORG BIOMOL CHEM</addtitle><addtitle>Org Biomol Chem</addtitle><description>Amines are ubiquitous in the chemical industry and are present in a wide range of biological processes, motivating the development of amine-sensitive sensors. There are many turn-on amine sensors, however there are no examples of turn-on sensors that utilize the amine's ability to react by single electron transfer (SET). We investigated a new turn-on amine probe with a 4,4-difluoro-4-bora-3a,4a-diaza-
s
-indacene (BODIPY) fluorophore. BODIPY fluorescence is first preprogrammed into an off state by internal photoinduced electron transfer (PET) to an electron-deficient quinolinium ring, resulting in fluorescence quenching. At low concentrations of aliphatic amine (0 to 10 mM), this PET pathway is shut down by external SET from the amine to the photoexcited charge-transfer state of the probe and the fluorescence is turned on. At high concentrations of amine (50 mM to 1 M), we observed collisional quenching of the BODIPY fluorescence. The probe is selective for aliphatic amines over aromatic amines, and aliphatic thiols or alcohols. The three molecular processes modulate the BODIPY fluorescence in a multi-mechanistic way with two of them producing a direct response to amine concentrations. The totality of the three molecular processes produced the first example of a multi-state and dose-responsive amine sensor.
Photoinduced electron transfer sets up the BODIPY probe for multi-state amine sensing by single-electron transfer then collisional quenching.</description><subject>Alcohols</subject><subject>Aliphatic amines</subject><subject>Amines</subject><subject>Amines - analysis</subject><subject>Biological activity</subject><subject>Boron Compounds - chemical synthesis</subject><subject>Boron Compounds - chemistry</subject><subject>Charge transfer</subject><subject>Chemical industry</subject><subject>Chemistry</subject><subject>Chemistry, Organic</subject><subject>Crystal structure</subject><subject>Crystallography</subject><subject>Density Functional Theory</subject><subject>Electron transfer</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Low concentrations</subject><subject>Models, Chemical</subject><subject>Organic chemistry</subject><subject>Physical Sciences</subject><subject>Quenching</subject><subject>Quinolinium Compounds - chemical synthesis</subject><subject>Quinolinium Compounds - chemistry</subject><subject>Science & Technology</subject><subject>Sensors</subject><subject>Shutdowns</subject><subject>Single electrons</subject><subject>Spectrometry, Fluorescence - methods</subject><subject>Thiols</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>AOWDO</sourceid><sourceid>EIF</sourceid><recordid>eNqN0r1v1TAQAHALUdEPWNhBFiwIFDjHdhyPfaGUSkWPAQamyHEu4CrPLrYj1P--hrQPiYnJN_zudB8m5CmDtwy4fmd1GKAWTTM8IEdMKFWB5PrhPq7hkByndAXAtGrEI3LIWStBCHlETj8tc3ZVyiYjNTvnkSb0yfnvdLihOKPNMXiao_Fpwpio89TQzfb9xedv9DqGAR-Tg8nMCZ_cvSfk64ezL93H6nJ7ftGdXla2dJYrruTABqUYgDa2EZJZhqAb3vBJWBzNOCqpWWtHVXPL2lEy2Uij0aAWLTB-Ql6sdUPKrk_WZbQ_bPC-tNgzqcpodUGvVlRa-7lgyv3OJYvzbDyGJfU1r1suGqGh0Jf_0KuwRF9GKEpwEDWTbVGvV2VjSCni1F9HtzPxpmfQ_95-3-nt5s_2NwU_vyu5DDsc9_R-3QW8WcEvHMJUZkBvcc8AQEIrFYgSgS66_X_duXJCF3wXFp9L6rM1NSa7z_j7T_gtlg-mXA</recordid><startdate>20200122</startdate><enddate>20200122</enddate><creator>VanDenburgh, Katherine L</creator><creator>Liu, Yun</creator><creator>Sadhukhan, Tumpa</creator><creator>Benson, Christopher R</creator><creator>Cox, Natalie M</creator><creator>Erbas-Cakmak, Sundus</creator><creator>Qiao, Bo</creator><creator>Gao, Xinfeng</creator><creator>Pink, Maren</creator><creator>Raghavachari, Krishnan</creator><creator>Flood, Amar H</creator><general>Royal Soc Chemistry</general><general>Royal Society of Chemistry</general><general>Royal Society of Chemistry (RSC)</general><scope>AOWDO</scope><scope>BLEPL</scope><scope>DTL</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>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><scope>OTOTI</scope><orcidid>https://orcid.org/0000-0001-6821-5188</orcidid><orcidid>https://orcid.org/0000-0001-7077-363X</orcidid><orcidid>https://orcid.org/0000-0003-1995-7286</orcidid><orcidid>https://orcid.org/0000-0001-9049-4574</orcidid><orcidid>https://orcid.org/0000-0002-8621-9980</orcidid><orcidid>https://orcid.org/0000-0001-6137-3239</orcidid><orcidid>https://orcid.org/0000-0003-4168-8377</orcidid><orcidid>https://orcid.org/0000-0003-3275-1426</orcidid><orcidid>https://orcid.org/0000-0002-2764-9155</orcidid><orcidid>https://orcid.org/0000000341688377</orcidid><orcidid>https://orcid.org/000000017077363X</orcidid><orcidid>https://orcid.org/0000000161373239</orcidid><orcidid>https://orcid.org/0000000332751426</orcidid><orcidid>https://orcid.org/0000000168215188</orcidid><orcidid>https://orcid.org/0000000227649155</orcidid><orcidid>https://orcid.org/0000000319957286</orcidid><orcidid>https://orcid.org/0000000190494574</orcidid><orcidid>https://orcid.org/0000000286219980</orcidid></search><sort><creationdate>20200122</creationdate><title>Multi-state amine sensing by electron transfers in a BODIPY probe</title><author>VanDenburgh, Katherine L ; Liu, Yun ; Sadhukhan, Tumpa ; Benson, Christopher R ; Cox, Natalie M ; Erbas-Cakmak, Sundus ; Qiao, Bo ; Gao, Xinfeng ; Pink, Maren ; Raghavachari, Krishnan ; Flood, Amar H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c466t-375b1b771009ac6451c1e096363f4cedadd75918cd723c18d51565a9eae948013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alcohols</topic><topic>Aliphatic amines</topic><topic>Amines</topic><topic>Amines - analysis</topic><topic>Biological activity</topic><topic>Boron Compounds - chemical synthesis</topic><topic>Boron Compounds - chemistry</topic><topic>Charge transfer</topic><topic>Chemical industry</topic><topic>Chemistry</topic><topic>Chemistry, Organic</topic><topic>Crystal structure</topic><topic>Crystallography</topic><topic>Density Functional Theory</topic><topic>Electron transfer</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Low concentrations</topic><topic>Models, Chemical</topic><topic>Organic chemistry</topic><topic>Physical Sciences</topic><topic>Quenching</topic><topic>Quinolinium Compounds - chemical synthesis</topic><topic>Quinolinium Compounds - chemistry</topic><topic>Science & Technology</topic><topic>Sensors</topic><topic>Shutdowns</topic><topic>Single electrons</topic><topic>Spectrometry, Fluorescence - methods</topic><topic>Thiols</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>VanDenburgh, Katherine L</creatorcontrib><creatorcontrib>Liu, Yun</creatorcontrib><creatorcontrib>Sadhukhan, Tumpa</creatorcontrib><creatorcontrib>Benson, Christopher R</creatorcontrib><creatorcontrib>Cox, Natalie M</creatorcontrib><creatorcontrib>Erbas-Cakmak, Sundus</creatorcontrib><creatorcontrib>Qiao, Bo</creatorcontrib><creatorcontrib>Gao, Xinfeng</creatorcontrib><creatorcontrib>Pink, Maren</creatorcontrib><creatorcontrib>Raghavachari, Krishnan</creatorcontrib><creatorcontrib>Flood, Amar H</creatorcontrib><collection>Web of Science - Science Citation Index Expanded - 2020</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><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><collection>OSTI.GOV</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>VanDenburgh, Katherine L</au><au>Liu, Yun</au><au>Sadhukhan, Tumpa</au><au>Benson, Christopher R</au><au>Cox, Natalie M</au><au>Erbas-Cakmak, Sundus</au><au>Qiao, Bo</au><au>Gao, Xinfeng</au><au>Pink, Maren</au><au>Raghavachari, Krishnan</au><au>Flood, Amar H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Multi-state amine sensing by electron transfers in a BODIPY probe</atitle><jtitle>Organic & biomolecular chemistry</jtitle><stitle>ORG BIOMOL CHEM</stitle><addtitle>Org Biomol Chem</addtitle><date>2020-01-22</date><risdate>2020</risdate><volume>18</volume><issue>3</issue><spage>431</spage><epage>44</epage><pages>431-44</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Amines are ubiquitous in the chemical industry and are present in a wide range of biological processes, motivating the development of amine-sensitive sensors. There are many turn-on amine sensors, however there are no examples of turn-on sensors that utilize the amine's ability to react by single electron transfer (SET). We investigated a new turn-on amine probe with a 4,4-difluoro-4-bora-3a,4a-diaza-
s
-indacene (BODIPY) fluorophore. BODIPY fluorescence is first preprogrammed into an off state by internal photoinduced electron transfer (PET) to an electron-deficient quinolinium ring, resulting in fluorescence quenching. At low concentrations of aliphatic amine (0 to 10 mM), this PET pathway is shut down by external SET from the amine to the photoexcited charge-transfer state of the probe and the fluorescence is turned on. At high concentrations of amine (50 mM to 1 M), we observed collisional quenching of the BODIPY fluorescence. The probe is selective for aliphatic amines over aromatic amines, and aliphatic thiols or alcohols. The three molecular processes modulate the BODIPY fluorescence in a multi-mechanistic way with two of them producing a direct response to amine concentrations. The totality of the three molecular processes produced the first example of a multi-state and dose-responsive amine sensor.
Photoinduced electron transfer sets up the BODIPY probe for multi-state amine sensing by single-electron transfer then collisional quenching.</abstract><cop>CAMBRIDGE</cop><pub>Royal Soc Chemistry</pub><pmid>31850445</pmid><doi>10.1039/c9ob02466b</doi><orcidid>https://orcid.org/0000-0001-6821-5188</orcidid><orcidid>https://orcid.org/0000-0001-7077-363X</orcidid><orcidid>https://orcid.org/0000-0003-1995-7286</orcidid><orcidid>https://orcid.org/0000-0001-9049-4574</orcidid><orcidid>https://orcid.org/0000-0002-8621-9980</orcidid><orcidid>https://orcid.org/0000-0001-6137-3239</orcidid><orcidid>https://orcid.org/0000-0003-4168-8377</orcidid><orcidid>https://orcid.org/0000-0003-3275-1426</orcidid><orcidid>https://orcid.org/0000-0002-2764-9155</orcidid><orcidid>https://orcid.org/0000000341688377</orcidid><orcidid>https://orcid.org/000000017077363X</orcidid><orcidid>https://orcid.org/0000000161373239</orcidid><orcidid>https://orcid.org/0000000332751426</orcidid><orcidid>https://orcid.org/0000000168215188</orcidid><orcidid>https://orcid.org/0000000227649155</orcidid><orcidid>https://orcid.org/0000000319957286</orcidid><orcidid>https://orcid.org/0000000190494574</orcidid><orcidid>https://orcid.org/0000000286219980</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Alcohols Aliphatic amines Amines Amines - analysis Biological activity Boron Compounds - chemical synthesis Boron Compounds - chemistry Charge transfer Chemical industry Chemistry Chemistry, Organic Crystal structure Crystallography Density Functional Theory Electron transfer Fluorescence Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry Low concentrations Models, Chemical Organic chemistry Physical Sciences Quenching Quinolinium Compounds - chemical synthesis Quinolinium Compounds - chemistry Science & Technology Sensors Shutdowns Single electrons Spectrometry, Fluorescence - methods Thiols |
title | Multi-state amine sensing by electron transfers in a BODIPY probe |
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