Sensitive and discriminative detection of cysteine by a Nile red-based NIR fluorescence probe
Cysteine (Cys) is a significant biological mercaptan that achieves key roles in several important physiological processes, such as reversible redox homeostasis in living organisms. Abnormal levels of Cys in the human body are directly related to many diseases. In this work, we constructed a sensitiv...
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| Veröffentlicht in: | Analytical and bioanalytical chemistry 2023-08, Vol.415 (20), p.4875-4883 |
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| creator | Lv, Junying Jiao, Xiaorui He, Di Demi Hussain, Ejaz Yang, Na Wang, Yongxiang Zhang, Hui Chen, Liping Jin, Xing Liu, Ning Yu, Cong |
| description | Cysteine (Cys) is a significant biological mercaptan that achieves key roles in several important physiological processes, such as reversible redox homeostasis in living organisms. Abnormal levels of Cys in the human body are directly related to many diseases. In this work, we constructed a sensitive sensor (Cys-NR) by connecting a Cys recognition group to a Nile red derivative. Due to photo-induced electron transfer (PET), the Cys-NR probe showed little fluorescence at 650 nm. With the addition of Cys to the assay solution, the chlorine unit of the probe was substituted by the thiol group of Cys. Further, the amino and sulfhydryl groups in cysteine underwent an intramolecular rearrangement, which led to the Cys-NR probe water solution turning from colorless to pink with an enhancement in fluorescence. The red fluorescence at 650 nm increased about 20 times. Based on the turn-on signal, a selective Cys detection method is developed. The probe signal is not affected by various potential interferences or other competing biothiols and the limit of detection (LOD) is determined to be 0.44 μM. In addition, the probe is further employed for imaging of Cys in live cells, revealing good biological imaging ability that could provide a new way of intracellular Cys detection.
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| doi_str_mv | 10.1007/s00216-023-04790-9 |
| format | Article |
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Graphical abstract</description><identifier>ISSN: 1618-2642</identifier><identifier>EISSN: 1618-2650</identifier><identifier>DOI: 10.1007/s00216-023-04790-9</identifier><identifier>PMID: 37318553</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Analytical Chemistry ; Aqueous solutions ; Biochemistry ; Characterization and Evaluation of Materials ; Chemistry ; Chemistry and Materials Science ; Chlorine ; Cysteine ; detection limit ; Electron transfer ; Fluorescence ; Fluorescent Dyes ; Fluorescent indicators ; Food Science ; Glutathione ; HeLa Cells ; Homeostasis ; Homocysteine ; Humans ; Laboratory Medicine ; Monitoring/Environmental Analysis ; Oxazines ; Research Paper ; Spectrometry, Fluorescence ; Sulfhydryl Compounds ; Sulfhydryl groups ; thiols</subject><ispartof>Analytical and bioanalytical chemistry, 2023-08, Vol.415 (20), p.4875-4883</ispartof><rights>Springer-Verlag GmbH Germany, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><rights>2023. Springer-Verlag GmbH Germany, part of Springer Nature.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c408t-adb6426e4ccde9644e1a036fb40d8cd01f17b15c579757cecbafc6c7862829413</citedby><cites>FETCH-LOGICAL-c408t-adb6426e4ccde9644e1a036fb40d8cd01f17b15c579757cecbafc6c7862829413</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00216-023-04790-9$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00216-023-04790-9$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,777,781,27905,27906,41469,42538,51300</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37318553$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lv, Junying</creatorcontrib><creatorcontrib>Jiao, Xiaorui</creatorcontrib><creatorcontrib>He, Di Demi</creatorcontrib><creatorcontrib>Hussain, Ejaz</creatorcontrib><creatorcontrib>Yang, Na</creatorcontrib><creatorcontrib>Wang, Yongxiang</creatorcontrib><creatorcontrib>Zhang, Hui</creatorcontrib><creatorcontrib>Chen, Liping</creatorcontrib><creatorcontrib>Jin, Xing</creatorcontrib><creatorcontrib>Liu, Ning</creatorcontrib><creatorcontrib>Yu, Cong</creatorcontrib><title>Sensitive and discriminative detection of cysteine by a Nile red-based NIR fluorescence probe</title><title>Analytical and bioanalytical chemistry</title><addtitle>Anal Bioanal Chem</addtitle><addtitle>Anal Bioanal Chem</addtitle><description>Cysteine (Cys) is a significant biological mercaptan that achieves key roles in several important physiological processes, such as reversible redox homeostasis in living organisms. Abnormal levels of Cys in the human body are directly related to many diseases. In this work, we constructed a sensitive sensor (Cys-NR) by connecting a Cys recognition group to a Nile red derivative. Due to photo-induced electron transfer (PET), the Cys-NR probe showed little fluorescence at 650 nm. With the addition of Cys to the assay solution, the chlorine unit of the probe was substituted by the thiol group of Cys. Further, the amino and sulfhydryl groups in cysteine underwent an intramolecular rearrangement, which led to the Cys-NR probe water solution turning from colorless to pink with an enhancement in fluorescence. The red fluorescence at 650 nm increased about 20 times. Based on the turn-on signal, a selective Cys detection method is developed. The probe signal is not affected by various potential interferences or other competing biothiols and the limit of detection (LOD) is determined to be 0.44 μM. In addition, the probe is further employed for imaging of Cys in live cells, revealing good biological imaging ability that could provide a new way of intracellular Cys detection.
Graphical abstract</description><subject>Analytical Chemistry</subject><subject>Aqueous solutions</subject><subject>Biochemistry</subject><subject>Characterization and Evaluation of Materials</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chlorine</subject><subject>Cysteine</subject><subject>detection limit</subject><subject>Electron transfer</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes</subject><subject>Fluorescent indicators</subject><subject>Food Science</subject><subject>Glutathione</subject><subject>HeLa Cells</subject><subject>Homeostasis</subject><subject>Homocysteine</subject><subject>Humans</subject><subject>Laboratory Medicine</subject><subject>Monitoring/Environmental Analysis</subject><subject>Oxazines</subject><subject>Research Paper</subject><subject>Spectrometry, Fluorescence</subject><subject>Sulfhydryl Compounds</subject><subject>Sulfhydryl 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and discriminative detection of cysteine by a Nile red-based NIR fluorescence probe</title><author>Lv, Junying ; Jiao, Xiaorui ; He, Di Demi ; Hussain, Ejaz ; Yang, Na ; Wang, Yongxiang ; Zhang, Hui ; Chen, Liping ; Jin, Xing ; Liu, Ning ; Yu, Cong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c408t-adb6426e4ccde9644e1a036fb40d8cd01f17b15c579757cecbafc6c7862829413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Analytical Chemistry</topic><topic>Aqueous solutions</topic><topic>Biochemistry</topic><topic>Characterization and Evaluation of Materials</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chlorine</topic><topic>Cysteine</topic><topic>detection limit</topic><topic>Electron transfer</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes</topic><topic>Fluorescent indicators</topic><topic>Food 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Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lv, Junying</au><au>Jiao, Xiaorui</au><au>He, Di Demi</au><au>Hussain, Ejaz</au><au>Yang, Na</au><au>Wang, Yongxiang</au><au>Zhang, Hui</au><au>Chen, Liping</au><au>Jin, Xing</au><au>Liu, Ning</au><au>Yu, Cong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sensitive and discriminative detection of cysteine by a Nile red-based NIR fluorescence probe</atitle><jtitle>Analytical and bioanalytical chemistry</jtitle><stitle>Anal Bioanal Chem</stitle><addtitle>Anal Bioanal Chem</addtitle><date>2023-08-01</date><risdate>2023</risdate><volume>415</volume><issue>20</issue><spage>4875</spage><epage>4883</epage><pages>4875-4883</pages><issn>1618-2642</issn><eissn>1618-2650</eissn><abstract>Cysteine (Cys) is a significant biological mercaptan that achieves key roles in several important physiological processes, such as reversible redox homeostasis in living organisms. Abnormal levels of Cys in the human body are directly related to many diseases. In this work, we constructed a sensitive sensor (Cys-NR) by connecting a Cys recognition group to a Nile red derivative. Due to photo-induced electron transfer (PET), the Cys-NR probe showed little fluorescence at 650 nm. With the addition of Cys to the assay solution, the chlorine unit of the probe was substituted by the thiol group of Cys. Further, the amino and sulfhydryl groups in cysteine underwent an intramolecular rearrangement, which led to the Cys-NR probe water solution turning from colorless to pink with an enhancement in fluorescence. The red fluorescence at 650 nm increased about 20 times. Based on the turn-on signal, a selective Cys detection method is developed. The probe signal is not affected by various potential interferences or other competing biothiols and the limit of detection (LOD) is determined to be 0.44 μM. In addition, the probe is further employed for imaging of Cys in live cells, revealing good biological imaging ability that could provide a new way of intracellular Cys detection.
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| subjects | Analytical Chemistry Aqueous solutions Biochemistry Characterization and Evaluation of Materials Chemistry Chemistry and Materials Science Chlorine Cysteine detection limit Electron transfer Fluorescence Fluorescent Dyes Fluorescent indicators Food Science Glutathione HeLa Cells Homeostasis Homocysteine Humans Laboratory Medicine Monitoring/Environmental Analysis Oxazines Research Paper Spectrometry, Fluorescence Sulfhydryl Compounds Sulfhydryl groups thiols |
| title | Sensitive and discriminative detection of cysteine by a Nile red-based NIR fluorescence probe |
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