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Diketopyrrolopyrrole-based fluorescence probes for the imaging of lysosomal Zn2+ and identification of prostate cancer in human tissue
A series of diketopyrrolopyrrole-based fluorescent probes (DPP-C2, LysoDPP-C2, LysoDPP-C3, and LysoDPP-C4) have been developed for the detection of low pH and Zn2+ in an AND logic fashion. The chelation of Zn2+ or the protonation of a morpholine moiety within these probes results in a partial increa...
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Published in: | Chemical science (Cambridge) 2019-06, Vol.10 (22), p.5699-5704 |
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creator | Du, Chenchen Fu, Shibo Wang, Xiaohua Sedgwick, Adam C Wei, Zhen Li, Minjie Li, Xinqiang Zhou, Juan Wang, Zhong Wang, Hongyu Sessler, Jonathan L |
description | A series of diketopyrrolopyrrole-based fluorescent probes (DPP-C2, LysoDPP-C2, LysoDPP-C3, and LysoDPP-C4) have been developed for the detection of low pH and Zn2+ in an AND logic fashion. The chelation of Zn2+ or the protonation of a morpholine moiety within these probes results in a partial increase in the fluorescence intensity, an effect ascribed to suppression of one possible photo-induced electron transfer (PET) pathway. In contrast, a large increase in the observed fluorescence intensity is observed at low pH and in the presence of Zn2+; this is rationalized in terms of both possible PET pathways within the probes being blocked. Job plots, fluorescence titration curves, and isothermal titration calorimetry proved consistent with a 1 : 1 Zn2+ complexation stoichiometry. Each probe demonstrated an excellent selectivity towards Zn2+ and the resulting Zn2+ complexes demonstrated pH sensitivity over the 3.5–9 pH range. Fluorescence imaging experiments confirmed that LysoDPP-C4 was capable of imaging lysosomal Zn2+ in live cells. Little evidence of cytotoxicity was seen. LysoDPP-C4 was successfully applied to the bioimaging of nude mice, wherein it was shown capable of imaging the prostate. Histological studies using a human sample revealed that LysoDPP-C4 can discriminate cancerous prostate tissue from healthy prostate tissue. |
doi_str_mv | 10.1039/c9sc01153f |
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The chelation of Zn2+ or the protonation of a morpholine moiety within these probes results in a partial increase in the fluorescence intensity, an effect ascribed to suppression of one possible photo-induced electron transfer (PET) pathway. In contrast, a large increase in the observed fluorescence intensity is observed at low pH and in the presence of Zn2+; this is rationalized in terms of both possible PET pathways within the probes being blocked. Job plots, fluorescence titration curves, and isothermal titration calorimetry proved consistent with a 1 : 1 Zn2+ complexation stoichiometry. Each probe demonstrated an excellent selectivity towards Zn2+ and the resulting Zn2+ complexes demonstrated pH sensitivity over the 3.5–9 pH range. Fluorescence imaging experiments confirmed that LysoDPP-C4 was capable of imaging lysosomal Zn2+ in live cells. Little evidence of cytotoxicity was seen. LysoDPP-C4 was successfully applied to the bioimaging of nude mice, wherein it was shown capable of imaging the prostate. Histological studies using a human sample revealed that LysoDPP-C4 can discriminate cancerous prostate tissue from healthy prostate tissue.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/c9sc01153f</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Chelation ; Electron transfer ; Fluorescent indicators ; Human tissues ; Mass spectra ; Medical imaging ; Morpholine ; NMR ; Nuclear magnetic resonance ; Prostate ; Protonation ; Selectivity ; Stoichiometry ; Titration calorimetry ; Toxicity</subject><ispartof>Chemical science (Cambridge), 2019-06, Vol.10 (22), p.5699-5704</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Du, Chenchen</creatorcontrib><creatorcontrib>Fu, Shibo</creatorcontrib><creatorcontrib>Wang, Xiaohua</creatorcontrib><creatorcontrib>Sedgwick, Adam C</creatorcontrib><creatorcontrib>Wei, Zhen</creatorcontrib><creatorcontrib>Li, Minjie</creatorcontrib><creatorcontrib>Li, Xinqiang</creatorcontrib><creatorcontrib>Zhou, Juan</creatorcontrib><creatorcontrib>Wang, Zhong</creatorcontrib><creatorcontrib>Wang, Hongyu</creatorcontrib><creatorcontrib>Sessler, Jonathan L</creatorcontrib><title>Diketopyrrolopyrrole-based fluorescence probes for the imaging of lysosomal Zn2+ and identification of prostate cancer in human tissue</title><title>Chemical science (Cambridge)</title><description>A series of diketopyrrolopyrrole-based fluorescent probes (DPP-C2, LysoDPP-C2, LysoDPP-C3, and LysoDPP-C4) have been developed for the detection of low pH and Zn2+ in an AND logic fashion. The chelation of Zn2+ or the protonation of a morpholine moiety within these probes results in a partial increase in the fluorescence intensity, an effect ascribed to suppression of one possible photo-induced electron transfer (PET) pathway. In contrast, a large increase in the observed fluorescence intensity is observed at low pH and in the presence of Zn2+; this is rationalized in terms of both possible PET pathways within the probes being blocked. Job plots, fluorescence titration curves, and isothermal titration calorimetry proved consistent with a 1 : 1 Zn2+ complexation stoichiometry. Each probe demonstrated an excellent selectivity towards Zn2+ and the resulting Zn2+ complexes demonstrated pH sensitivity over the 3.5–9 pH range. Fluorescence imaging experiments confirmed that LysoDPP-C4 was capable of imaging lysosomal Zn2+ in live cells. Little evidence of cytotoxicity was seen. LysoDPP-C4 was successfully applied to the bioimaging of nude mice, wherein it was shown capable of imaging the prostate. Histological studies using a human sample revealed that LysoDPP-C4 can discriminate cancerous prostate tissue from healthy prostate tissue.</description><subject>Chelation</subject><subject>Electron transfer</subject><subject>Fluorescent indicators</subject><subject>Human tissues</subject><subject>Mass spectra</subject><subject>Medical imaging</subject><subject>Morpholine</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Prostate</subject><subject>Protonation</subject><subject>Selectivity</subject><subject>Stoichiometry</subject><subject>Titration calorimetry</subject><subject>Toxicity</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpdkL1OwzAUhS0EElXpwhNYYkFCAf8m8YgKBaRKLLCwVI5z3bokdomdoS_Ac-OKioG7nDt85-jci9AlJbeUcHVnVDSEUsntCZowImhRSq5O_3ZGztEsxi3JwzmVrJqg7wf3CSns9sMQuqNA0egILbbdGAaIBrwBvBtCAxHbMOC0Aex6vXZ-jYPF3T6GGHrd4Q_PbrD2LXYt-OSsMzq54A9QtsekE2Cjc9qAncebsdceJxfjCBfozOouwuyoU_S-eHybPxfL16eX-f2y2DJRp6I1pZTU1kwpK4RtVQPCGMWEILoSlNRU81YJJhpb6bKhpSKVag-OTLLa8Cm6_s3Nfb5GiGnVu3xg12kPYYwrxmRJDy9UGb36h27DOPjcLlNciooTyfkPBb9zgw</recordid><startdate>20190614</startdate><enddate>20190614</enddate><creator>Du, Chenchen</creator><creator>Fu, Shibo</creator><creator>Wang, Xiaohua</creator><creator>Sedgwick, Adam C</creator><creator>Wei, Zhen</creator><creator>Li, Minjie</creator><creator>Li, Xinqiang</creator><creator>Zhou, Juan</creator><creator>Wang, Zhong</creator><creator>Wang, Hongyu</creator><creator>Sessler, Jonathan L</creator><general>Royal Society of Chemistry</general><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope></search><sort><creationdate>20190614</creationdate><title>Diketopyrrolopyrrole-based fluorescence probes for the imaging of lysosomal Zn2+ and identification of prostate cancer in human tissue</title><author>Du, Chenchen ; Fu, Shibo ; Wang, Xiaohua ; Sedgwick, Adam C ; Wei, Zhen ; Li, Minjie ; Li, Xinqiang ; Zhou, Juan ; Wang, Zhong ; Wang, Hongyu ; Sessler, Jonathan L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-j248t-dc6551f8299f44fd9be4cc92440a741081a3d9424bf7a6b169079d51f89be28c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Chelation</topic><topic>Electron transfer</topic><topic>Fluorescent indicators</topic><topic>Human tissues</topic><topic>Mass spectra</topic><topic>Medical imaging</topic><topic>Morpholine</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Prostate</topic><topic>Protonation</topic><topic>Selectivity</topic><topic>Stoichiometry</topic><topic>Titration calorimetry</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Du, Chenchen</creatorcontrib><creatorcontrib>Fu, Shibo</creatorcontrib><creatorcontrib>Wang, Xiaohua</creatorcontrib><creatorcontrib>Sedgwick, Adam C</creatorcontrib><creatorcontrib>Wei, Zhen</creatorcontrib><creatorcontrib>Li, Minjie</creatorcontrib><creatorcontrib>Li, Xinqiang</creatorcontrib><creatorcontrib>Zhou, Juan</creatorcontrib><creatorcontrib>Wang, Zhong</creatorcontrib><creatorcontrib>Wang, Hongyu</creatorcontrib><creatorcontrib>Sessler, Jonathan L</creatorcontrib><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Du, Chenchen</au><au>Fu, Shibo</au><au>Wang, Xiaohua</au><au>Sedgwick, Adam C</au><au>Wei, Zhen</au><au>Li, Minjie</au><au>Li, Xinqiang</au><au>Zhou, Juan</au><au>Wang, Zhong</au><au>Wang, Hongyu</au><au>Sessler, Jonathan L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diketopyrrolopyrrole-based fluorescence probes for the imaging of lysosomal Zn2+ and identification of prostate cancer in human tissue</atitle><jtitle>Chemical science (Cambridge)</jtitle><date>2019-06-14</date><risdate>2019</risdate><volume>10</volume><issue>22</issue><spage>5699</spage><epage>5704</epage><pages>5699-5704</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>A series of diketopyrrolopyrrole-based fluorescent probes (DPP-C2, LysoDPP-C2, LysoDPP-C3, and LysoDPP-C4) have been developed for the detection of low pH and Zn2+ in an AND logic fashion. The chelation of Zn2+ or the protonation of a morpholine moiety within these probes results in a partial increase in the fluorescence intensity, an effect ascribed to suppression of one possible photo-induced electron transfer (PET) pathway. In contrast, a large increase in the observed fluorescence intensity is observed at low pH and in the presence of Zn2+; this is rationalized in terms of both possible PET pathways within the probes being blocked. Job plots, fluorescence titration curves, and isothermal titration calorimetry proved consistent with a 1 : 1 Zn2+ complexation stoichiometry. Each probe demonstrated an excellent selectivity towards Zn2+ and the resulting Zn2+ complexes demonstrated pH sensitivity over the 3.5–9 pH range. Fluorescence imaging experiments confirmed that LysoDPP-C4 was capable of imaging lysosomal Zn2+ in live cells. Little evidence of cytotoxicity was seen. LysoDPP-C4 was successfully applied to the bioimaging of nude mice, wherein it was shown capable of imaging the prostate. Histological studies using a human sample revealed that LysoDPP-C4 can discriminate cancerous prostate tissue from healthy prostate tissue.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/c9sc01153f</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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subjects | Chelation Electron transfer Fluorescent indicators Human tissues Mass spectra Medical imaging Morpholine NMR Nuclear magnetic resonance Prostate Protonation Selectivity Stoichiometry Titration calorimetry Toxicity |
title | Diketopyrrolopyrrole-based fluorescence probes for the imaging of lysosomal Zn2+ and identification of prostate cancer in human tissue |
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