Locally Excited State–Charge Transfer State Coupled Dyes as Optically Responsive Neuron Firing Probes
A selection of NIR‐optically responsive neuron probes was produced comprising of a donor julolidyl group connected to a BODIPY core and several different styryl and vinylpyridinyl derived acceptor moieties. The strength of the donor–acceptor interaction was systematically modulated by altering the e...
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| Veröffentlicht in: | Chemistry : a European journal 2017-10, Vol.23 (58), p.14639-14649 |
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| container_title | Chemistry : a European journal |
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| creator | Sirbu, Dumitru Butcher, John B. Waddell, Paul G. Andras, Peter Benniston, Andrew C. |
| description | A selection of NIR‐optically responsive neuron probes was produced comprising of a donor julolidyl group connected to a BODIPY core and several different styryl and vinylpyridinyl derived acceptor moieties. The strength of the donor–acceptor interaction was systematically modulated by altering the electron withdrawing nature of the aryl unit. The fluorescence quantum yield was observed to decrease as the electron withdrawing effect of the aryl subunit increased in line with changes of the Hammett parameter. The effectiveness of these fluorophores as optically responsive dyes for neuronal imaging was assessed by measuring the toxicity and signal‐to‐noise ratio (SNR) of each dye. A great improvement of SNR was obtained when compared to the first‐generation BODIPY‐based voltage sensitive dyes with concomitant toxicity decrease. The mechanism for the optical response is disparate from conventional cyanine‐based dyes, opening up a new way to produce effective voltage sensitive dyes that respond well into the NIR region.
Rhythm of the Light: Extended donor–acceptor BODIPY derivatives were examined as new optical neuron probes. The dyes were tested by recording the activity of neurons in the stomatogastric ganglion (STG) of the brown crab Cancer pagurus. A simple structure reactivity relationship was derived. |
| doi_str_mv | 10.1002/chem.201703366 |
| format | Article |
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Rhythm of the Light: Extended donor–acceptor BODIPY derivatives were examined as new optical neuron probes. The dyes were tested by recording the activity of neurons in the stomatogastric ganglion (STG) of the brown crab Cancer pagurus. A simple structure reactivity relationship was derived.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201703366</identifier><identifier>PMID: 28833695</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Animals ; Aromatic compounds ; BODIPY dyes ; Boron Compounds - chemistry ; Brachyura - metabolism ; Carbocyanines - chemistry ; Charge transfer ; Chemical compounds ; Chemistry ; Crystallography, X-Ray ; Dyes ; Electric potential ; Fluorescence ; Fluorescent Dyes - chemical synthesis ; Fluorescent Dyes - chemistry ; Fluorescent Dyes - metabolism ; Fluorophores ; Microscopy, Fluorescence ; Molecular Conformation ; neuron ; Neurons - metabolism ; Probes ; Quantum Theory ; Signal-To-Noise Ratio ; Spectrophotometry, Infrared ; Spectrophotometry, Ultraviolet ; structure–reactivity relationship ; Toxicity ; Voltage ; voltage response</subject><ispartof>Chemistry : a European journal, 2017-10, Vol.23 (58), p.14639-14649</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5166-831cdb2d65f9326f9062527efe8b9bbc059204e568db8b41588d6cd1a4a119d53</citedby><cites>FETCH-LOGICAL-c5166-831cdb2d65f9326f9062527efe8b9bbc059204e568db8b41588d6cd1a4a119d53</cites><orcidid>0000-0001-8878-5014</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201703366$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201703366$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28833695$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sirbu, Dumitru</creatorcontrib><creatorcontrib>Butcher, John B.</creatorcontrib><creatorcontrib>Waddell, Paul G.</creatorcontrib><creatorcontrib>Andras, Peter</creatorcontrib><creatorcontrib>Benniston, Andrew C.</creatorcontrib><title>Locally Excited State–Charge Transfer State Coupled Dyes as Optically Responsive Neuron Firing Probes</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>A selection of NIR‐optically responsive neuron probes was produced comprising of a donor julolidyl group connected to a BODIPY core and several different styryl and vinylpyridinyl derived acceptor moieties. The strength of the donor–acceptor interaction was systematically modulated by altering the electron withdrawing nature of the aryl unit. The fluorescence quantum yield was observed to decrease as the electron withdrawing effect of the aryl subunit increased in line with changes of the Hammett parameter. The effectiveness of these fluorophores as optically responsive dyes for neuronal imaging was assessed by measuring the toxicity and signal‐to‐noise ratio (SNR) of each dye. A great improvement of SNR was obtained when compared to the first‐generation BODIPY‐based voltage sensitive dyes with concomitant toxicity decrease. The mechanism for the optical response is disparate from conventional cyanine‐based dyes, opening up a new way to produce effective voltage sensitive dyes that respond well into the NIR region.
Rhythm of the Light: Extended donor–acceptor BODIPY derivatives were examined as new optical neuron probes. The dyes were tested by recording the activity of neurons in the stomatogastric ganglion (STG) of the brown crab Cancer pagurus. A simple structure reactivity relationship was derived.</description><subject>Animals</subject><subject>Aromatic compounds</subject><subject>BODIPY dyes</subject><subject>Boron Compounds - chemistry</subject><subject>Brachyura - metabolism</subject><subject>Carbocyanines - chemistry</subject><subject>Charge transfer</subject><subject>Chemical compounds</subject><subject>Chemistry</subject><subject>Crystallography, X-Ray</subject><subject>Dyes</subject><subject>Electric potential</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Fluorescent Dyes - metabolism</subject><subject>Fluorophores</subject><subject>Microscopy, Fluorescence</subject><subject>Molecular Conformation</subject><subject>neuron</subject><subject>Neurons - metabolism</subject><subject>Probes</subject><subject>Quantum Theory</subject><subject>Signal-To-Noise Ratio</subject><subject>Spectrophotometry, Infrared</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>structure–reactivity relationship</subject><subject>Toxicity</subject><subject>Voltage</subject><subject>voltage response</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0clOwzAUBVALgaAMW5bIEhs2KR5qN16iUAapDGJYR47zUoLSONgJ0B3_wB_yJbgKg8SGlSXrvGvrXYR2KRlSQtiheYD5kBE6JpxLuYIGVDAa8bEUq2hA1GgcScHVBtr0_pEQoiTn62iDxXHgSgzQbGqNrqoFnryasoUc37a6hY-39-RBuxngO6drX4Dr73Fiu6YK6ngBHmuPr5q27OdvwDe29uUz4EvonK3xSenKeoavnc3Ab6O1Qlcedr7OLXR_MrlLzqLp1el5cjSNjKBSRjGnJs9YLkWhOJOFIpIJNoYC4kxlmSFCMTICIeM8i7MRFXGcS5NTPdKUqlzwLXTQ5zbOPnXg23ReegNVpWuwnU9piA0PKbWk-3_oo-1cHX4XlKCCEE5kUMNeGWe9d1CkjSvn2i1SStJlBemygvSngjCw9xXbZXPIf_j3zgNQPXgpK1j8E5cmZ5OL3_BPn1iTJQ</recordid><startdate>20171017</startdate><enddate>20171017</enddate><creator>Sirbu, Dumitru</creator><creator>Butcher, John B.</creator><creator>Waddell, Paul G.</creator><creator>Andras, Peter</creator><creator>Benniston, Andrew C.</creator><general>Wiley Subscription Services, Inc</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>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8878-5014</orcidid></search><sort><creationdate>20171017</creationdate><title>Locally Excited State–Charge Transfer State Coupled Dyes as Optically Responsive Neuron Firing Probes</title><author>Sirbu, Dumitru ; Butcher, John B. ; Waddell, Paul G. ; Andras, Peter ; Benniston, Andrew C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5166-831cdb2d65f9326f9062527efe8b9bbc059204e568db8b41588d6cd1a4a119d53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Animals</topic><topic>Aromatic compounds</topic><topic>BODIPY dyes</topic><topic>Boron Compounds - chemistry</topic><topic>Brachyura - metabolism</topic><topic>Carbocyanines - chemistry</topic><topic>Charge transfer</topic><topic>Chemical compounds</topic><topic>Chemistry</topic><topic>Crystallography, X-Ray</topic><topic>Dyes</topic><topic>Electric potential</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Fluorescent Dyes - metabolism</topic><topic>Fluorophores</topic><topic>Microscopy, Fluorescence</topic><topic>Molecular Conformation</topic><topic>neuron</topic><topic>Neurons - metabolism</topic><topic>Probes</topic><topic>Quantum Theory</topic><topic>Signal-To-Noise Ratio</topic><topic>Spectrophotometry, Infrared</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>structure–reactivity relationship</topic><topic>Toxicity</topic><topic>Voltage</topic><topic>voltage response</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sirbu, Dumitru</creatorcontrib><creatorcontrib>Butcher, John B.</creatorcontrib><creatorcontrib>Waddell, Paul G.</creatorcontrib><creatorcontrib>Andras, Peter</creatorcontrib><creatorcontrib>Benniston, Andrew C.</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>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sirbu, Dumitru</au><au>Butcher, John B.</au><au>Waddell, Paul G.</au><au>Andras, Peter</au><au>Benniston, Andrew C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Locally Excited State–Charge Transfer State Coupled Dyes as Optically Responsive Neuron Firing Probes</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2017-10-17</date><risdate>2017</risdate><volume>23</volume><issue>58</issue><spage>14639</spage><epage>14649</epage><pages>14639-14649</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>A selection of NIR‐optically responsive neuron probes was produced comprising of a donor julolidyl group connected to a BODIPY core and several different styryl and vinylpyridinyl derived acceptor moieties. The strength of the donor–acceptor interaction was systematically modulated by altering the electron withdrawing nature of the aryl unit. The fluorescence quantum yield was observed to decrease as the electron withdrawing effect of the aryl subunit increased in line with changes of the Hammett parameter. The effectiveness of these fluorophores as optically responsive dyes for neuronal imaging was assessed by measuring the toxicity and signal‐to‐noise ratio (SNR) of each dye. A great improvement of SNR was obtained when compared to the first‐generation BODIPY‐based voltage sensitive dyes with concomitant toxicity decrease. The mechanism for the optical response is disparate from conventional cyanine‐based dyes, opening up a new way to produce effective voltage sensitive dyes that respond well into the NIR region.
Rhythm of the Light: Extended donor–acceptor BODIPY derivatives were examined as new optical neuron probes. The dyes were tested by recording the activity of neurons in the stomatogastric ganglion (STG) of the brown crab Cancer pagurus. A simple structure reactivity relationship was derived.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28833695</pmid><doi>10.1002/chem.201703366</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0001-8878-5014</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Animals Aromatic compounds BODIPY dyes Boron Compounds - chemistry Brachyura - metabolism Carbocyanines - chemistry Charge transfer Chemical compounds Chemistry Crystallography, X-Ray Dyes Electric potential Fluorescence Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry Fluorescent Dyes - metabolism Fluorophores Microscopy, Fluorescence Molecular Conformation neuron Neurons - metabolism Probes Quantum Theory Signal-To-Noise Ratio Spectrophotometry, Infrared Spectrophotometry, Ultraviolet structure–reactivity relationship Toxicity Voltage voltage response |
| title | Locally Excited State–Charge Transfer State Coupled Dyes as Optically Responsive Neuron Firing Probes |
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