Near-infrared mitochondria-targeted fluorescent probe with a large Stokes shift for rapid and sensitive detection of cysteine/homocysteine and its bioimaging application
In this work, tetrahydro-acridine salt hybrid coumarin dyes was designed and developed as a Near-infrared (NIR) fluorescent probe CM for the detection and fluorescent bioimaging of Cys/Hcy. The activated chlorine atom in probe facilitates more efficient nucleophilic substitution reaction, resulting...
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Veröffentlicht in: | Sensors and actuators. B, Chemical Chemical, 2023-01, Vol.374, p.132799, Article 132799 |
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container_title | Sensors and actuators. B, Chemical |
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creator | An, Shixuan Lin, Yanfei Wang, Jianbo Ye, Tianqing Mao, Yanyun Zhang, Jian Guo, Longhua Li, Lei Qian, Zhaosheng Liu, Haiying |
description | In this work, tetrahydro-acridine salt hybrid coumarin dyes was designed and developed as a Near-infrared (NIR) fluorescent probe CM for the detection and fluorescent bioimaging of Cys/Hcy. The activated chlorine atom in probe facilitates more efficient nucleophilic substitution reaction, resulting in fast responsive time (3 min toward 3 eq. Cys) and high sensitivity toward Cys with detection limit of 46 nM. More importantly, probe displays “Turn-on” near-infrared fluorescence emission (Emmax: 674 nm) with Large Strokes shift (about 200 nm) toward Cys/Hcy. Furthermore, probe could be used as efficient tool for imaging and detection of Cys/Hcy in mitochondria of living cells and in vivo. This work innovatively proposed a new design strategy for NIR fluorescent probe platform for the detection and fluorescence imaging of bio-thiols.
[Display omitted]
•A new tetrahydro-acridine salt hybrid coumarin dyes is designed as NIR fluorescent probe CM for detection of Cys/Hcy.•Probe shows remarkable “turn-on” NIR fluorescence change with Large Strokes shift, fast responsive time, high sensitivity and selectivity toward Cys/Hcy.•Probe display low cytotoxicity and mitochondria-targeting ability and can be used to visualize monitor Cys/Hcy changes in living cells and in vivo. |
doi_str_mv | 10.1016/j.snb.2022.132799 |
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[Display omitted]
•A new tetrahydro-acridine salt hybrid coumarin dyes is designed as NIR fluorescent probe CM for detection of Cys/Hcy.•Probe shows remarkable “turn-on” NIR fluorescence change with Large Strokes shift, fast responsive time, high sensitivity and selectivity toward Cys/Hcy.•Probe display low cytotoxicity and mitochondria-targeting ability and can be used to visualize monitor Cys/Hcy changes in living cells and in vivo.</description><identifier>ISSN: 0925-4005</identifier><identifier>EISSN: 1873-3077</identifier><identifier>DOI: 10.1016/j.snb.2022.132799</identifier><language>eng</language><publisher>Lausanne: Elsevier B.V</publisher><subject>Chlorine ; Coumarin ; Fluorescent indicators ; Large Stokes shift ; Medical imaging ; Mitochondria ; Mitochondria-targeted ; Near infrared radiation ; Near-infrared ; Substitution reactions ; Thiols ; Thiols florescent probe</subject><ispartof>Sensors and actuators. B, Chemical, 2023-01, Vol.374, p.132799, Article 132799</ispartof><rights>2022 Elsevier B.V.</rights><rights>Copyright Elsevier Science Ltd. Jan 1, 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c325t-1d4ee4d3b35f9dbb283cbc6af6ab2b95cfaa73fa7bca3b960f0d49821e5936123</citedby><cites>FETCH-LOGICAL-c325t-1d4ee4d3b35f9dbb283cbc6af6ab2b95cfaa73fa7bca3b960f0d49821e5936123</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.snb.2022.132799$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>An, Shixuan</creatorcontrib><creatorcontrib>Lin, Yanfei</creatorcontrib><creatorcontrib>Wang, Jianbo</creatorcontrib><creatorcontrib>Ye, Tianqing</creatorcontrib><creatorcontrib>Mao, Yanyun</creatorcontrib><creatorcontrib>Zhang, Jian</creatorcontrib><creatorcontrib>Guo, Longhua</creatorcontrib><creatorcontrib>Li, Lei</creatorcontrib><creatorcontrib>Qian, Zhaosheng</creatorcontrib><creatorcontrib>Liu, Haiying</creatorcontrib><title>Near-infrared mitochondria-targeted fluorescent probe with a large Stokes shift for rapid and sensitive detection of cysteine/homocysteine and its bioimaging application</title><title>Sensors and actuators. B, Chemical</title><description>In this work, tetrahydro-acridine salt hybrid coumarin dyes was designed and developed as a Near-infrared (NIR) fluorescent probe CM for the detection and fluorescent bioimaging of Cys/Hcy. The activated chlorine atom in probe facilitates more efficient nucleophilic substitution reaction, resulting in fast responsive time (3 min toward 3 eq. Cys) and high sensitivity toward Cys with detection limit of 46 nM. More importantly, probe displays “Turn-on” near-infrared fluorescence emission (Emmax: 674 nm) with Large Strokes shift (about 200 nm) toward Cys/Hcy. Furthermore, probe could be used as efficient tool for imaging and detection of Cys/Hcy in mitochondria of living cells and in vivo. This work innovatively proposed a new design strategy for NIR fluorescent probe platform for the detection and fluorescence imaging of bio-thiols.
[Display omitted]
•A new tetrahydro-acridine salt hybrid coumarin dyes is designed as NIR fluorescent probe CM for detection of Cys/Hcy.•Probe shows remarkable “turn-on” NIR fluorescence change with Large Strokes shift, fast responsive time, high sensitivity and selectivity toward Cys/Hcy.•Probe display low cytotoxicity and mitochondria-targeting ability and can be used to visualize monitor Cys/Hcy changes in living cells and in vivo.</description><subject>Chlorine</subject><subject>Coumarin</subject><subject>Fluorescent indicators</subject><subject>Large Stokes shift</subject><subject>Medical imaging</subject><subject>Mitochondria</subject><subject>Mitochondria-targeted</subject><subject>Near infrared radiation</subject><subject>Near-infrared</subject><subject>Substitution reactions</subject><subject>Thiols</subject><subject>Thiols florescent probe</subject><issn>0925-4005</issn><issn>1873-3077</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kctuUzEQhi1UJNLSB2BnifVJfTmXWKyqiptU0UXp2vJlnExI7FPbadVH4i1xCGy7Gs3o_-b2E_KBsyVnfLzaLku0S8GEWHIpJqXekAVfTbKTbJrOyIIpMXQ9Y8M7cl7KljHWy5EtyO8fYHKHMWSTwdM91uQ2KfqMpqsmr6G2atgdUobiIFY652SBPmPdUEN3RwW9r-kXFFo2GCoNKdNsZvTURE8LxIIVn4D61slVTJGmQN1LqYARrjZpn_4nfwGshVpMuDdrjGtq5nmHzhy59-RtMLsCl__iBXn48vnnzbfu9u7r95vr285JMdSO-x6g99LKIShvrVhJZ91owmissGpwwZhJBjNZZ6RVIwvM92olOAxKjlzIC_Lx1Ldd-niAUvU2HXJsI7WYRqF6MfCpqfhJ5XIqJUPQc25L5xfNmT46ore6OaKPjuiTI435dGKgrf-EkHVxCNGBx9x-o33CV-g_ypKZVw</recordid><startdate>20230101</startdate><enddate>20230101</enddate><creator>An, Shixuan</creator><creator>Lin, Yanfei</creator><creator>Wang, Jianbo</creator><creator>Ye, Tianqing</creator><creator>Mao, Yanyun</creator><creator>Zhang, Jian</creator><creator>Guo, Longhua</creator><creator>Li, Lei</creator><creator>Qian, Zhaosheng</creator><creator>Liu, Haiying</creator><general>Elsevier B.V</general><general>Elsevier Science Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SP</scope><scope>7SR</scope><scope>7TB</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20230101</creationdate><title>Near-infrared mitochondria-targeted fluorescent probe with a large Stokes shift for rapid and sensitive detection of cysteine/homocysteine and its bioimaging application</title><author>An, Shixuan ; Lin, Yanfei ; Wang, Jianbo ; Ye, Tianqing ; Mao, Yanyun ; Zhang, Jian ; Guo, Longhua ; Li, Lei ; Qian, Zhaosheng ; Liu, Haiying</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c325t-1d4ee4d3b35f9dbb283cbc6af6ab2b95cfaa73fa7bca3b960f0d49821e5936123</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Chlorine</topic><topic>Coumarin</topic><topic>Fluorescent indicators</topic><topic>Large Stokes shift</topic><topic>Medical imaging</topic><topic>Mitochondria</topic><topic>Mitochondria-targeted</topic><topic>Near infrared radiation</topic><topic>Near-infrared</topic><topic>Substitution reactions</topic><topic>Thiols</topic><topic>Thiols florescent probe</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>An, Shixuan</creatorcontrib><creatorcontrib>Lin, Yanfei</creatorcontrib><creatorcontrib>Wang, Jianbo</creatorcontrib><creatorcontrib>Ye, Tianqing</creatorcontrib><creatorcontrib>Mao, Yanyun</creatorcontrib><creatorcontrib>Zhang, Jian</creatorcontrib><creatorcontrib>Guo, Longhua</creatorcontrib><creatorcontrib>Li, Lei</creatorcontrib><creatorcontrib>Qian, Zhaosheng</creatorcontrib><creatorcontrib>Liu, Haiying</creatorcontrib><collection>CrossRef</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Sensors and actuators. B, Chemical</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>An, Shixuan</au><au>Lin, Yanfei</au><au>Wang, Jianbo</au><au>Ye, Tianqing</au><au>Mao, Yanyun</au><au>Zhang, Jian</au><au>Guo, Longhua</au><au>Li, Lei</au><au>Qian, Zhaosheng</au><au>Liu, Haiying</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Near-infrared mitochondria-targeted fluorescent probe with a large Stokes shift for rapid and sensitive detection of cysteine/homocysteine and its bioimaging application</atitle><jtitle>Sensors and actuators. B, Chemical</jtitle><date>2023-01-01</date><risdate>2023</risdate><volume>374</volume><spage>132799</spage><pages>132799-</pages><artnum>132799</artnum><issn>0925-4005</issn><eissn>1873-3077</eissn><abstract>In this work, tetrahydro-acridine salt hybrid coumarin dyes was designed and developed as a Near-infrared (NIR) fluorescent probe CM for the detection and fluorescent bioimaging of Cys/Hcy. The activated chlorine atom in probe facilitates more efficient nucleophilic substitution reaction, resulting in fast responsive time (3 min toward 3 eq. Cys) and high sensitivity toward Cys with detection limit of 46 nM. More importantly, probe displays “Turn-on” near-infrared fluorescence emission (Emmax: 674 nm) with Large Strokes shift (about 200 nm) toward Cys/Hcy. Furthermore, probe could be used as efficient tool for imaging and detection of Cys/Hcy in mitochondria of living cells and in vivo. This work innovatively proposed a new design strategy for NIR fluorescent probe platform for the detection and fluorescence imaging of bio-thiols.
[Display omitted]
•A new tetrahydro-acridine salt hybrid coumarin dyes is designed as NIR fluorescent probe CM for detection of Cys/Hcy.•Probe shows remarkable “turn-on” NIR fluorescence change with Large Strokes shift, fast responsive time, high sensitivity and selectivity toward Cys/Hcy.•Probe display low cytotoxicity and mitochondria-targeting ability and can be used to visualize monitor Cys/Hcy changes in living cells and in vivo.</abstract><cop>Lausanne</cop><pub>Elsevier B.V</pub><doi>10.1016/j.snb.2022.132799</doi></addata></record> |
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subjects | Chlorine Coumarin Fluorescent indicators Large Stokes shift Medical imaging Mitochondria Mitochondria-targeted Near infrared radiation Near-infrared Substitution reactions Thiols Thiols florescent probe |
title | Near-infrared mitochondria-targeted fluorescent probe with a large Stokes shift for rapid and sensitive detection of cysteine/homocysteine and its bioimaging application |
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