Near-Infrared Fluorescent Probes for Hypoxia Detection via Joint Regulated Enzymes: Design, Synthesis, and Application in Living Cells and Mice
Hypoxia detection is emphasized with attention due to tumor and related diseases diagnosis, which could provide useful methods for exploring the mechanism of hypoxic tumor. Herein, we report two unprecedented hypoxia-sensitive probes that specifically switch-on their near-infrared fluorescence signa...
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| Veröffentlicht in: | Analytical chemistry (Washington) 2018-11, Vol.90 (22), p.13759-13766 |
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| creator | Tian, Xinwei Li, Zhao Sun, Yue Wang, Pan Ma, Huimin |
| description | Hypoxia detection is emphasized with attention due to tumor and related diseases diagnosis, which could provide useful methods for exploring the mechanism of hypoxic tumor. Herein, we report two unprecedented hypoxia-sensitive probes that specifically switch-on their near-infrared fluorescence signals in the presence of hypoxia up-regulated enzymes (nitroreductase and cytochrome P450 reductase). The probes were designed by featuring the decomposition of IR-780 coupled to hypoxia activatable p-nitrobenzyl or azo moiety, which exhibit near-infrared fluorescence emission, high sensitivity, selectivity, stable photostability, and low cytotoxicity. Besides, the joint use of two probes could differentiate the 4T1 and HepG2 cells lines through fluorescence signals successfully. More importantly, applied to monitor hypoxia in 4T1 tumor-bearing BALB/c mice, the two probes have ideal biodistribution with passive accumulation and fast clearance, and there is negligible organ damage by hematoxylin and eosin staining analysis. To the best of our knowledge, there is no fluorescent probe for hypoxia detection via joint hypoxia regulated enzymes reported so far. This method may be of great potential use in cancer and other relevant diseases diagnosis. |
| doi_str_mv | 10.1021/acs.analchem.8b04249 |
| format | Article |
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Herein, we report two unprecedented hypoxia-sensitive probes that specifically switch-on their near-infrared fluorescence signals in the presence of hypoxia up-regulated enzymes (nitroreductase and cytochrome P450 reductase). The probes were designed by featuring the decomposition of IR-780 coupled to hypoxia activatable p-nitrobenzyl or azo moiety, which exhibit near-infrared fluorescence emission, high sensitivity, selectivity, stable photostability, and low cytotoxicity. Besides, the joint use of two probes could differentiate the 4T1 and HepG2 cells lines through fluorescence signals successfully. More importantly, applied to monitor hypoxia in 4T1 tumor-bearing BALB/c mice, the two probes have ideal biodistribution with passive accumulation and fast clearance, and there is negligible organ damage by hematoxylin and eosin staining analysis. To the best of our knowledge, there is no fluorescent probe for hypoxia detection via joint hypoxia regulated enzymes reported so far. This method may be of great potential use in cancer and other relevant diseases diagnosis.</description><identifier>ISSN: 0003-2700</identifier><identifier>EISSN: 1520-6882</identifier><identifier>DOI: 10.1021/acs.analchem.8b04249</identifier><identifier>PMID: 30373362</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Cancer ; Cell Line, Tumor ; Chemistry ; Cytochrome ; Cytochrome P450 ; Cytochromes P450 ; Cytotoxicity ; Damage accumulation ; Diagnosis ; Enzymes ; Enzymes - metabolism ; Female ; Fluorescence ; Fluorescent Dyes - chemistry ; Fluorescent indicators ; Hypoxia ; Hypoxia - diagnosis ; I.R. radiation ; Infrared imaging systems ; Joints - metabolism ; Medical diagnosis ; Mice ; Mice, Inbred BALB C ; NADPH-ferrihemoprotein reductase ; Near infrared radiation ; Nitroreductase ; Probes ; Selectivity ; Sensors ; Spectrum Analysis - methods ; Toxicity ; Tumors</subject><ispartof>Analytical chemistry (Washington), 2018-11, Vol.90 (22), p.13759-13766</ispartof><rights>Copyright American Chemical Society Nov 20, 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a442t-5d98ac526b7a612645b74cc236561fe4e97f54547a8b146e9a86a2bbf204ac413</citedby><cites>FETCH-LOGICAL-a442t-5d98ac526b7a612645b74cc236561fe4e97f54547a8b146e9a86a2bbf204ac413</cites><orcidid>0000-0001-5868-8037 ; 0000-0001-7702-3348 ; 0000-0001-6155-9076</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.analchem.8b04249$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.analchem.8b04249$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30373362$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tian, Xinwei</creatorcontrib><creatorcontrib>Li, Zhao</creatorcontrib><creatorcontrib>Sun, Yue</creatorcontrib><creatorcontrib>Wang, Pan</creatorcontrib><creatorcontrib>Ma, Huimin</creatorcontrib><title>Near-Infrared Fluorescent Probes for Hypoxia Detection via Joint Regulated Enzymes: Design, Synthesis, and Application in Living Cells and Mice</title><title>Analytical chemistry (Washington)</title><addtitle>Anal. Chem</addtitle><description>Hypoxia detection is emphasized with attention due to tumor and related diseases diagnosis, which could provide useful methods for exploring the mechanism of hypoxic tumor. Herein, we report two unprecedented hypoxia-sensitive probes that specifically switch-on their near-infrared fluorescence signals in the presence of hypoxia up-regulated enzymes (nitroreductase and cytochrome P450 reductase). The probes were designed by featuring the decomposition of IR-780 coupled to hypoxia activatable p-nitrobenzyl or azo moiety, which exhibit near-infrared fluorescence emission, high sensitivity, selectivity, stable photostability, and low cytotoxicity. Besides, the joint use of two probes could differentiate the 4T1 and HepG2 cells lines through fluorescence signals successfully. More importantly, applied to monitor hypoxia in 4T1 tumor-bearing BALB/c mice, the two probes have ideal biodistribution with passive accumulation and fast clearance, and there is negligible organ damage by hematoxylin and eosin staining analysis. To the best of our knowledge, there is no fluorescent probe for hypoxia detection via joint hypoxia regulated enzymes reported so far. This method may be of great potential use in cancer and other relevant diseases diagnosis.</description><subject>Animals</subject><subject>Cancer</subject><subject>Cell Line, Tumor</subject><subject>Chemistry</subject><subject>Cytochrome</subject><subject>Cytochrome P450</subject><subject>Cytochromes P450</subject><subject>Cytotoxicity</subject><subject>Damage accumulation</subject><subject>Diagnosis</subject><subject>Enzymes</subject><subject>Enzymes - metabolism</subject><subject>Female</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Fluorescent indicators</subject><subject>Hypoxia</subject><subject>Hypoxia - diagnosis</subject><subject>I.R. radiation</subject><subject>Infrared imaging systems</subject><subject>Joints - metabolism</subject><subject>Medical diagnosis</subject><subject>Mice</subject><subject>Mice, Inbred BALB C</subject><subject>NADPH-ferrihemoprotein reductase</subject><subject>Near infrared radiation</subject><subject>Nitroreductase</subject><subject>Probes</subject><subject>Selectivity</subject><subject>Sensors</subject><subject>Spectrum Analysis - methods</subject><subject>Toxicity</subject><subject>Tumors</subject><issn>0003-2700</issn><issn>1520-6882</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kctu1DAUhi0EokPhDRCyxIZFM9iOYyfsqqE3NNCKyzo68ZxMXSV2aicVw0vwyvV0pl2wYGVb_v7f8vkIecvZnDPBP4KJc3DQmWvs52XDpJDVMzLjhWCZKkvxnMwYY3kmNGMH5FWMN4xxzrh6SQ5ylus8V2JG_n5DCNmFawMEXNHTbvIBo0E30qvgG4y09YGebwb_2wL9jCOa0XpH79Lpi7cJ-47rqYMxhU_cn02P8VPCol27I_pj48brtI9HFNyKHg9DZw085K2jS3tn3ZousOviw_1Xa_A1edFCF_HNfj0kv05Pfi7Os-Xl2cXieJmBlGLMilVVgimEajQoLpQsGi2NEbkqFG9RYqXbQhZSQ9lwqbCCUoFomlYwCUby_JB82PUOwd9OGMe6t-nbXQcO_RRrwYXmlZYVS-j7f9AbP4U0-S1VpCmWWuSJkjvKBB9jwLYegu0hbGrO6q2wOgmrH4XVe2Ep9m5fPjU9rp5Cj4YSwHbANv708H877wGd5KUI</recordid><startdate>20181120</startdate><enddate>20181120</enddate><creator>Tian, Xinwei</creator><creator>Li, Zhao</creator><creator>Sun, Yue</creator><creator>Wang, Pan</creator><creator>Ma, Huimin</creator><general>American Chemical Society</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>7QF</scope><scope>7QO</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7TM</scope><scope>7U5</scope><scope>7U7</scope><scope>7U9</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>H94</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-5868-8037</orcidid><orcidid>https://orcid.org/0000-0001-7702-3348</orcidid><orcidid>https://orcid.org/0000-0001-6155-9076</orcidid></search><sort><creationdate>20181120</creationdate><title>Near-Infrared Fluorescent Probes for Hypoxia Detection via Joint Regulated Enzymes: Design, Synthesis, and Application in Living Cells and Mice</title><author>Tian, Xinwei ; Li, Zhao ; Sun, Yue ; Wang, Pan ; Ma, Huimin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a442t-5d98ac526b7a612645b74cc236561fe4e97f54547a8b146e9a86a2bbf204ac413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Animals</topic><topic>Cancer</topic><topic>Cell Line, Tumor</topic><topic>Chemistry</topic><topic>Cytochrome</topic><topic>Cytochrome P450</topic><topic>Cytochromes P450</topic><topic>Cytotoxicity</topic><topic>Damage accumulation</topic><topic>Diagnosis</topic><topic>Enzymes</topic><topic>Enzymes - metabolism</topic><topic>Female</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Fluorescent indicators</topic><topic>Hypoxia</topic><topic>Hypoxia - diagnosis</topic><topic>I.R. radiation</topic><topic>Infrared imaging systems</topic><topic>Joints - metabolism</topic><topic>Medical diagnosis</topic><topic>Mice</topic><topic>Mice, Inbred BALB C</topic><topic>NADPH-ferrihemoprotein reductase</topic><topic>Near infrared radiation</topic><topic>Nitroreductase</topic><topic>Probes</topic><topic>Selectivity</topic><topic>Sensors</topic><topic>Spectrum Analysis - methods</topic><topic>Toxicity</topic><topic>Tumors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tian, Xinwei</creatorcontrib><creatorcontrib>Li, Zhao</creatorcontrib><creatorcontrib>Sun, Yue</creatorcontrib><creatorcontrib>Wang, Pan</creatorcontrib><creatorcontrib>Ma, Huimin</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>Nucleic Acids Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</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>AIDS and Cancer Research Abstracts</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><collection>MEDLINE - Academic</collection><jtitle>Analytical chemistry (Washington)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tian, Xinwei</au><au>Li, Zhao</au><au>Sun, Yue</au><au>Wang, Pan</au><au>Ma, Huimin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Near-Infrared Fluorescent Probes for Hypoxia Detection via Joint Regulated Enzymes: Design, Synthesis, and Application in Living Cells and Mice</atitle><jtitle>Analytical chemistry (Washington)</jtitle><addtitle>Anal. Chem</addtitle><date>2018-11-20</date><risdate>2018</risdate><volume>90</volume><issue>22</issue><spage>13759</spage><epage>13766</epage><pages>13759-13766</pages><issn>0003-2700</issn><eissn>1520-6882</eissn><abstract>Hypoxia detection is emphasized with attention due to tumor and related diseases diagnosis, which could provide useful methods for exploring the mechanism of hypoxic tumor. Herein, we report two unprecedented hypoxia-sensitive probes that specifically switch-on their near-infrared fluorescence signals in the presence of hypoxia up-regulated enzymes (nitroreductase and cytochrome P450 reductase). The probes were designed by featuring the decomposition of IR-780 coupled to hypoxia activatable p-nitrobenzyl or azo moiety, which exhibit near-infrared fluorescence emission, high sensitivity, selectivity, stable photostability, and low cytotoxicity. Besides, the joint use of two probes could differentiate the 4T1 and HepG2 cells lines through fluorescence signals successfully. More importantly, applied to monitor hypoxia in 4T1 tumor-bearing BALB/c mice, the two probes have ideal biodistribution with passive accumulation and fast clearance, and there is negligible organ damage by hematoxylin and eosin staining analysis. To the best of our knowledge, there is no fluorescent probe for hypoxia detection via joint hypoxia regulated enzymes reported so far. This method may be of great potential use in cancer and other relevant diseases diagnosis.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>30373362</pmid><doi>10.1021/acs.analchem.8b04249</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-5868-8037</orcidid><orcidid>https://orcid.org/0000-0001-7702-3348</orcidid><orcidid>https://orcid.org/0000-0001-6155-9076</orcidid></addata></record> |
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| subjects | Animals Cancer Cell Line, Tumor Chemistry Cytochrome Cytochrome P450 Cytochromes P450 Cytotoxicity Damage accumulation Diagnosis Enzymes Enzymes - metabolism Female Fluorescence Fluorescent Dyes - chemistry Fluorescent indicators Hypoxia Hypoxia - diagnosis I.R. radiation Infrared imaging systems Joints - metabolism Medical diagnosis Mice Mice, Inbred BALB C NADPH-ferrihemoprotein reductase Near infrared radiation Nitroreductase Probes Selectivity Sensors Spectrum Analysis - methods Toxicity Tumors |
| title | Near-Infrared Fluorescent Probes for Hypoxia Detection via Joint Regulated Enzymes: Design, Synthesis, and Application in Living Cells and Mice |
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