A distinctive mitochondrion-targeting, in situ-activatable near-infrared fluorescent probe for visualizing sulfur dioxide derivatives and their fluctuations in vivo
Sulfur dioxide derivatives are intimately involved in some physiological processes in organisms, and high levels of these substances can cause many diseases. Herein, we rationally prepared a mitochondrion-targeting, in situ-activatable near-infrared (NIR) fluorescent probe (DCQN) by coupling 2-(3,5,...
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Veröffentlicht in: | Journal of materials chemistry. B, Materials for biology and medicine Materials for biology and medicine, 2020-03, Vol.8 (9), p.1914-1921 |
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container_title | Journal of materials chemistry. B, Materials for biology and medicine |
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creator | Zeng, Lintao Chen, Tianhong Chen, Bao-Quan Yuan, Hou-Qun Sheng, Ruilong Bao, Guang-Ming |
description | Sulfur dioxide derivatives are intimately involved in some physiological processes in organisms, and high levels of these substances can cause many diseases. Herein, we rationally prepared a mitochondrion-targeting, in situ-activatable near-infrared (NIR) fluorescent probe (DCQN) by coupling 2-(3,5,5-trimethylcyclohex-2-enylidene)malononitrile with 3-quinolinium carboxaldehyde. DCQN displayed a NIR fluorescence turn-on signal to indicate the presence of HSO3-, along with a considerable hyperchromic shift from light yellow to purple via a 1,4-nucleophilic addition reaction. We were able to use DCQN to instantaneously and quantitatively determine the concentration of HSO3- with high specificity, a low detection limit (24 nM), a large Stokes shift (∼110 nm), and a high contrast ratio. Moreover, DCQN displayed good mitochondrion-targeting abilities and was in situ-activated by HSO3- to produce NIR fluorescence for imaging HSO3- in the mitochondria of live breast cancer cells. Furthermore, DCQN was used to monitor HSO3- in zebrafish with a high contrast ratio. |
doi_str_mv | 10.1039/c9tb02593f |
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Herein, we rationally prepared a mitochondrion-targeting, in situ-activatable near-infrared (NIR) fluorescent probe (DCQN) by coupling 2-(3,5,5-trimethylcyclohex-2-enylidene)malononitrile with 3-quinolinium carboxaldehyde. DCQN displayed a NIR fluorescence turn-on signal to indicate the presence of HSO3-, along with a considerable hyperchromic shift from light yellow to purple via a 1,4-nucleophilic addition reaction. We were able to use DCQN to instantaneously and quantitatively determine the concentration of HSO3- with high specificity, a low detection limit (24 nM), a large Stokes shift (∼110 nm), and a high contrast ratio. Moreover, DCQN displayed good mitochondrion-targeting abilities and was in situ-activated by HSO3- to produce NIR fluorescence for imaging HSO3- in the mitochondria of live breast cancer cells. 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B, Materials for biology and medicine, 2020-03, Vol.8 (9), p.1914-1921</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c315t-f1e55ce2653e85ffd9547a9797c0e36a7bc677bf5b9987147f8f448e16280e363</citedby><cites>FETCH-LOGICAL-c315t-f1e55ce2653e85ffd9547a9797c0e36a7bc677bf5b9987147f8f448e16280e363</cites><orcidid>0000-0002-9224-4090 ; 0000-0002-9390-9760 ; 0000-0002-3303-3832</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32048683$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zeng, Lintao</creatorcontrib><creatorcontrib>Chen, Tianhong</creatorcontrib><creatorcontrib>Chen, Bao-Quan</creatorcontrib><creatorcontrib>Yuan, Hou-Qun</creatorcontrib><creatorcontrib>Sheng, Ruilong</creatorcontrib><creatorcontrib>Bao, Guang-Ming</creatorcontrib><title>A distinctive mitochondrion-targeting, in situ-activatable near-infrared fluorescent probe for visualizing sulfur dioxide derivatives and their fluctuations in vivo</title><title>Journal of materials chemistry. B, Materials for biology and medicine</title><addtitle>J Mater Chem B</addtitle><description>Sulfur dioxide derivatives are intimately involved in some physiological processes in organisms, and high levels of these substances can cause many diseases. Herein, we rationally prepared a mitochondrion-targeting, in situ-activatable near-infrared (NIR) fluorescent probe (DCQN) by coupling 2-(3,5,5-trimethylcyclohex-2-enylidene)malononitrile with 3-quinolinium carboxaldehyde. DCQN displayed a NIR fluorescence turn-on signal to indicate the presence of HSO3-, along with a considerable hyperchromic shift from light yellow to purple via a 1,4-nucleophilic addition reaction. We were able to use DCQN to instantaneously and quantitatively determine the concentration of HSO3- with high specificity, a low detection limit (24 nM), a large Stokes shift (∼110 nm), and a high contrast ratio. 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Chen, Tianhong ; Chen, Bao-Quan ; Yuan, Hou-Qun ; Sheng, Ruilong ; Bao, Guang-Ming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c315t-f1e55ce2653e85ffd9547a9797c0e36a7bc677bf5b9987147f8f448e16280e363</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Animals</topic><topic>Breast cancer</topic><topic>Derivatives</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Fluorescent indicators</topic><topic>Humans</topic><topic>I.R. radiation</topic><topic>Infrared Rays</topic><topic>Malononitrile</topic><topic>MCF-7 Cells</topic><topic>Mitochondria</topic><topic>Mitochondria - chemistry</topic><topic>Molecular Structure</topic><topic>Optical Imaging</topic><topic>Sulfur</topic><topic>Sulfur dioxide</topic><topic>Sulfur Dioxide - analysis</topic><topic>Tumor Cells, Cultured</topic><topic>Variation</topic><topic>Zebrafish</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zeng, Lintao</creatorcontrib><creatorcontrib>Chen, Tianhong</creatorcontrib><creatorcontrib>Chen, Bao-Quan</creatorcontrib><creatorcontrib>Yuan, Hou-Qun</creatorcontrib><creatorcontrib>Sheng, Ruilong</creatorcontrib><creatorcontrib>Bao, Guang-Ming</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of materials chemistry. B, Materials for biology and medicine</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zeng, Lintao</au><au>Chen, Tianhong</au><au>Chen, Bao-Quan</au><au>Yuan, Hou-Qun</au><au>Sheng, Ruilong</au><au>Bao, Guang-Ming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A distinctive mitochondrion-targeting, in situ-activatable near-infrared fluorescent probe for visualizing sulfur dioxide derivatives and their fluctuations in vivo</atitle><jtitle>Journal of materials chemistry. B, Materials for biology and medicine</jtitle><addtitle>J Mater Chem B</addtitle><date>2020-03-04</date><risdate>2020</risdate><volume>8</volume><issue>9</issue><spage>1914</spage><epage>1921</epage><pages>1914-1921</pages><issn>2050-750X</issn><eissn>2050-7518</eissn><abstract>Sulfur dioxide derivatives are intimately involved in some physiological processes in organisms, and high levels of these substances can cause many diseases. Herein, we rationally prepared a mitochondrion-targeting, in situ-activatable near-infrared (NIR) fluorescent probe (DCQN) by coupling 2-(3,5,5-trimethylcyclohex-2-enylidene)malononitrile with 3-quinolinium carboxaldehyde. DCQN displayed a NIR fluorescence turn-on signal to indicate the presence of HSO3-, along with a considerable hyperchromic shift from light yellow to purple via a 1,4-nucleophilic addition reaction. 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subjects | Animals Breast cancer Derivatives Fluorescence Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry Fluorescent indicators Humans I.R. radiation Infrared Rays Malononitrile MCF-7 Cells Mitochondria Mitochondria - chemistry Molecular Structure Optical Imaging Sulfur Sulfur dioxide Sulfur Dioxide - analysis Tumor Cells, Cultured Variation Zebrafish |
title | A distinctive mitochondrion-targeting, in situ-activatable near-infrared fluorescent probe for visualizing sulfur dioxide derivatives and their fluctuations in vivo |
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