A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid
Hypochlorous acid (HOCl) is a reactive substance that reacts with most biomolecules and is essential in physiological and pathological processes. Abnormally elevated HOCl levels may cause inflammation and other disease responses. To further understand its key role in inflammation, HOCl must be detec...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/21/7237 |
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| author | Chunhua Zeng Zhengjun Chen Mingyan Yang Jiajia Lv Hongyu Li Jie Gao Zeli Yuan |
| author_facet | Chunhua Zeng Zhengjun Chen Mingyan Yang Jiajia Lv Hongyu Li Jie Gao Zeli Yuan |
| author_sort | Chunhua Zeng |
| collection | DOAJ |
| description | Hypochlorous acid (HOCl) is a reactive substance that reacts with most biomolecules and is essential in physiological and pathological processes. Abnormally elevated HOCl levels may cause inflammation and other disease responses. To further understand its key role in inflammation, HOCl must be detected in situ. Here, we designed a hydroxytricyanopyrrole-based small-molecule fluorescent probe (HTCP-NTC) to monitor and identify trace amounts of HOCl in biological systems. In the presence of HOCl, HTCP-NTC released hydroxyl groups that emit strong fluorescence covering a wide wavelength range from the visible to near-infrared region owing to the resumption of the intramolecular charge transfer process. Additionally, HTCP-NTC demonstrated a 202-fold fluorescence enhancement accompanied by a large Stokes shift and a low detection limit (21.7 nM). Furthermore, HTCP-NTC provided a rapid response to HOCl within 18 s, allowing real-time monitoring of intracellular HOCl. HTCP-NTC exhibited rapid kinetics and biocompatibility, allowing effective monitoring of the exogenous and endogenous HOCl fluctuations in living cells. Finally, based on fluorescence imaging, HTCP-NTC is a potential method for understanding the relationship between inflammation and HOCl. |
| first_indexed | 2024-03-09T18:48:39Z |
| format | Article |
| id | doaj.art-1de3a931e01e415cac0647f4a0714943 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T18:48:39Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-1de3a931e01e415cac0647f4a07149432023-11-24T06:00:52ZengMDPI AGMolecules1420-30492022-10-012721723710.3390/molecules27217237A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous AcidChunhua Zeng0Zhengjun Chen1Mingyan Yang2Jiajia Lv3Hongyu Li4Jie Gao5Zeli Yuan6Key Laboratory of Basic Pharmacology of the Ministry of Education and Joint International Research Laboratory of Ethnomedicine of the Ministry of Education, Zunyi Medical University, No. 6 West Xuefu Road, Xinpu District, Zunyi 563000, ChinaKey Laboratory of Basic Pharmacology of the Ministry of Education and Joint International Research Laboratory of Ethnomedicine of the Ministry of Education, Zunyi Medical University, No. 6 West Xuefu Road, Xinpu District, Zunyi 563000, ChinaKey Laboratory of Basic Pharmacology of the Ministry of Education and Joint International Research Laboratory of Ethnomedicine of the Ministry of Education, Zunyi Medical University, No. 6 West Xuefu Road, Xinpu District, Zunyi 563000, ChinaKey Laboratory of Basic Pharmacology of the Ministry of Education and Joint International Research Laboratory of Ethnomedicine of the Ministry of Education, Zunyi Medical University, No. 6 West Xuefu Road, Xinpu District, Zunyi 563000, ChinaKey Laboratory of Basic Pharmacology of the Ministry of Education and Joint International Research Laboratory of Ethnomedicine of the Ministry of Education, Zunyi Medical University, No. 6 West Xuefu Road, Xinpu District, Zunyi 563000, ChinaKey Laboratory of Basic Pharmacology of the Ministry of Education and Joint International Research Laboratory of Ethnomedicine of the Ministry of Education, Zunyi Medical University, No. 6 West Xuefu Road, Xinpu District, Zunyi 563000, ChinaKey Laboratory of Basic Pharmacology of the Ministry of Education and Joint International Research Laboratory of Ethnomedicine of the Ministry of Education, Zunyi Medical University, No. 6 West Xuefu Road, Xinpu District, Zunyi 563000, ChinaHypochlorous acid (HOCl) is a reactive substance that reacts with most biomolecules and is essential in physiological and pathological processes. Abnormally elevated HOCl levels may cause inflammation and other disease responses. To further understand its key role in inflammation, HOCl must be detected in situ. Here, we designed a hydroxytricyanopyrrole-based small-molecule fluorescent probe (HTCP-NTC) to monitor and identify trace amounts of HOCl in biological systems. In the presence of HOCl, HTCP-NTC released hydroxyl groups that emit strong fluorescence covering a wide wavelength range from the visible to near-infrared region owing to the resumption of the intramolecular charge transfer process. Additionally, HTCP-NTC demonstrated a 202-fold fluorescence enhancement accompanied by a large Stokes shift and a low detection limit (21.7 nM). Furthermore, HTCP-NTC provided a rapid response to HOCl within 18 s, allowing real-time monitoring of intracellular HOCl. HTCP-NTC exhibited rapid kinetics and biocompatibility, allowing effective monitoring of the exogenous and endogenous HOCl fluctuations in living cells. Finally, based on fluorescence imaging, HTCP-NTC is a potential method for understanding the relationship between inflammation and HOCl.https://www.mdpi.com/1420-3049/27/21/7237reactive oxygen specieshypochlorous acidfluorescencehydroxytricyanopyrroleintramolecular charge transfer |
| spellingShingle | Chunhua Zeng Zhengjun Chen Mingyan Yang Jiajia Lv Hongyu Li Jie Gao Zeli Yuan A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid Molecules reactive oxygen species hypochlorous acid fluorescence hydroxytricyanopyrrole intramolecular charge transfer |
| title | A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid |
| title_full | A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid |
| title_fullStr | A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid |
| title_full_unstemmed | A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid |
| title_short | A Hydroxytricyanopyrrole-Based Fluorescent Probe for Sensitive and Selective Detection of Hypochlorous Acid |
| title_sort | hydroxytricyanopyrrole based fluorescent probe for sensitive and selective detection of hypochlorous acid |
| topic | reactive oxygen species hypochlorous acid fluorescence hydroxytricyanopyrrole intramolecular charge transfer |
| url | https://www.mdpi.com/1420-3049/27/21/7237 |
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