Isoindoline-based fluorogenic probes bearing a self-immolative linker for the sensitive and selective detection of O-GlcNAcase activity
O-GlcNAcase (OGA) is implicated in several important biological and disease-relevant processes. Here, we synthesized fluorogenic probes for OGA by grafting GlcNAc directly or using a self-immolative linker to the hydroxyl position of 4-hydroxylisoindoline (BHID), a typical excited-state intramolecul...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2024-08, Vol.6 (63), p.824-8243 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Wu, Yuan-Hao Wang, Guan-Jun Guo, Chen Wang, Pei-Pei Wang, Jun-Yi Hu, Xi-Le Zang, Yi James, Tony D Li, Jia He, Xiao-Peng |
| description | O-GlcNAcase (OGA) is implicated in several important biological and disease-relevant processes. Here, we synthesized fluorogenic probes for OGA by grafting GlcNAc directly or using a self-immolative linker to the hydroxyl position of 4-hydroxylisoindoline (BHID), a typical excited-state intramolecular proton transfer (ESIPT) probe. The probe was used for a fluorogenic assay to determine the half maximal inhibitory concentration of a known OGA inhibitor and differentiate between OGA and hexosaminidase when GlcNAc is replaced by GlcNPr, where a propionyl group is used instead of an acetyl group.
An isoindoline-based fluorogenic probe bearing a self-immolative linker was developed for the sensitive and selective detection of O-GlcNAcase. |
| doi_str_mv | 10.1039/d4cc02845g |
| format | Article |
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An isoindoline-based fluorogenic probe bearing a self-immolative linker was developed for the sensitive and selective detection of O-GlcNAcase.</description><identifier>ISSN: 1359-7345</identifier><identifier>ISSN: 1364-548X</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d4cc02845g</identifier><identifier>PMID: 39007923</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>beta-N-Acetylhexosaminidases - antagonists & inhibitors ; beta-N-Acetylhexosaminidases - metabolism ; Biological activity ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Fluorescent Dyes - chemical synthesis ; Fluorescent Dyes - chemistry ; Humans ; Isoindoles - chemical synthesis ; Isoindoles - chemistry ; Molecular Structure ; Spectrometry, Fluorescence</subject><ispartof>Chemical communications (Cambridge, England), 2024-08, Vol.6 (63), p.824-8243</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c226t-4db6b8bbcd5cb7d34aaa6ea2acf855daf3ff58df7424ff0eef997e2d714d4bc23</cites><orcidid>0000-0002-4095-2191 ; 0000-0001-7919-2727 ; 0000-0001-9835-922X ; 0000-0003-3224-001X ; 0000-0002-8893-5673 ; 0000-0002-8736-3511</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/39007923$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wu, Yuan-Hao</creatorcontrib><creatorcontrib>Wang, Guan-Jun</creatorcontrib><creatorcontrib>Guo, Chen</creatorcontrib><creatorcontrib>Wang, Pei-Pei</creatorcontrib><creatorcontrib>Wang, Jun-Yi</creatorcontrib><creatorcontrib>Hu, Xi-Le</creatorcontrib><creatorcontrib>Zang, Yi</creatorcontrib><creatorcontrib>James, Tony D</creatorcontrib><creatorcontrib>Li, Jia</creatorcontrib><creatorcontrib>He, Xiao-Peng</creatorcontrib><title>Isoindoline-based fluorogenic probes bearing a self-immolative linker for the sensitive and selective detection of O-GlcNAcase activity</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>O-GlcNAcase (OGA) is implicated in several important biological and disease-relevant processes. Here, we synthesized fluorogenic probes for OGA by grafting GlcNAc directly or using a self-immolative linker to the hydroxyl position of 4-hydroxylisoindoline (BHID), a typical excited-state intramolecular proton transfer (ESIPT) probe. The probe was used for a fluorogenic assay to determine the half maximal inhibitory concentration of a known OGA inhibitor and differentiate between OGA and hexosaminidase when GlcNAc is replaced by GlcNPr, where a propionyl group is used instead of an acetyl group.
An isoindoline-based fluorogenic probe bearing a self-immolative linker was developed for the sensitive and selective detection of O-GlcNAcase.</description><subject>beta-N-Acetylhexosaminidases - antagonists & inhibitors</subject><subject>beta-N-Acetylhexosaminidases - metabolism</subject><subject>Biological activity</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Humans</subject><subject>Isoindoles - chemical synthesis</subject><subject>Isoindoles - chemistry</subject><subject>Molecular Structure</subject><subject>Spectrometry, Fluorescence</subject><issn>1359-7345</issn><issn>1364-548X</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkU9LHTEUxUNpUatuum8JdCOFqZlJMpMs5dW-CqKbCu6G_Ll5jZ1JbDJT8BP4tZt5zyqYzb3h_HJuLgehDzX5WhMqTy0zhjSC8c0bdFDTllWcidu3S89l1VHG99H7nO9IOTUXe2ifSkI62dAD9HiRow82Dj5ApVUGi90wxxQ3ELzB9ylqyFiDSj5ssMIZBlf5cYyDmvxfwOXdb0jYxYSnX1DkkP1WUMEuMJjtzcK0dDHg6PB1tR7M1Zkp07BadD89HKF3Tg0Zjp_qIbr5fv5z9aO6vF5frM4uK9M07VQxq1sttDaWG91ZypRSLahGGSc4t8pR57iwrmMNc44AOCk7aGxXM8u0aeghOtn5ls3-zJCnfvTZwDCoAHHOPSWCtFTQWhT08yv0Ls4plN8tVNtJIWVbqC87yqSYcwLX3yc_qvTQ16Rf4um_sdVqG8-6wJ-eLGc9gn1G_-dRgI87IGXzrL7kS_8BWiGYEQ</recordid><startdate>20240801</startdate><enddate>20240801</enddate><creator>Wu, Yuan-Hao</creator><creator>Wang, Guan-Jun</creator><creator>Guo, Chen</creator><creator>Wang, Pei-Pei</creator><creator>Wang, Jun-Yi</creator><creator>Hu, Xi-Le</creator><creator>Zang, Yi</creator><creator>James, Tony D</creator><creator>Li, Jia</creator><creator>He, Xiao-Peng</creator><general>Royal Society of Chemistry</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>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-4095-2191</orcidid><orcidid>https://orcid.org/0000-0001-7919-2727</orcidid><orcidid>https://orcid.org/0000-0001-9835-922X</orcidid><orcidid>https://orcid.org/0000-0003-3224-001X</orcidid><orcidid>https://orcid.org/0000-0002-8893-5673</orcidid><orcidid>https://orcid.org/0000-0002-8736-3511</orcidid></search><sort><creationdate>20240801</creationdate><title>Isoindoline-based fluorogenic probes bearing a self-immolative linker for the sensitive and selective detection of O-GlcNAcase activity</title><author>Wu, Yuan-Hao ; Wang, Guan-Jun ; Guo, Chen ; Wang, Pei-Pei ; Wang, Jun-Yi ; Hu, Xi-Le ; Zang, Yi ; James, Tony D ; Li, Jia ; He, Xiao-Peng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c226t-4db6b8bbcd5cb7d34aaa6ea2acf855daf3ff58df7424ff0eef997e2d714d4bc23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>beta-N-Acetylhexosaminidases - antagonists & inhibitors</topic><topic>beta-N-Acetylhexosaminidases - metabolism</topic><topic>Biological activity</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Humans</topic><topic>Isoindoles - chemical synthesis</topic><topic>Isoindoles - chemistry</topic><topic>Molecular Structure</topic><topic>Spectrometry, Fluorescence</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Yuan-Hao</creatorcontrib><creatorcontrib>Wang, Guan-Jun</creatorcontrib><creatorcontrib>Guo, Chen</creatorcontrib><creatorcontrib>Wang, Pei-Pei</creatorcontrib><creatorcontrib>Wang, Jun-Yi</creatorcontrib><creatorcontrib>Hu, Xi-Le</creatorcontrib><creatorcontrib>Zang, Yi</creatorcontrib><creatorcontrib>James, Tony D</creatorcontrib><creatorcontrib>Li, Jia</creatorcontrib><creatorcontrib>He, Xiao-Peng</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, Yuan-Hao</au><au>Wang, Guan-Jun</au><au>Guo, Chen</au><au>Wang, Pei-Pei</au><au>Wang, Jun-Yi</au><au>Hu, Xi-Le</au><au>Zang, Yi</au><au>James, Tony D</au><au>Li, Jia</au><au>He, Xiao-Peng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isoindoline-based fluorogenic probes bearing a self-immolative linker for the sensitive and selective detection of O-GlcNAcase activity</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2024-08-01</date><risdate>2024</risdate><volume>6</volume><issue>63</issue><spage>824</spage><epage>8243</epage><pages>824-8243</pages><issn>1359-7345</issn><issn>1364-548X</issn><eissn>1364-548X</eissn><abstract>O-GlcNAcase (OGA) is implicated in several important biological and disease-relevant processes. Here, we synthesized fluorogenic probes for OGA by grafting GlcNAc directly or using a self-immolative linker to the hydroxyl position of 4-hydroxylisoindoline (BHID), a typical excited-state intramolecular proton transfer (ESIPT) probe. The probe was used for a fluorogenic assay to determine the half maximal inhibitory concentration of a known OGA inhibitor and differentiate between OGA and hexosaminidase when GlcNAc is replaced by GlcNPr, where a propionyl group is used instead of an acetyl group.
An isoindoline-based fluorogenic probe bearing a self-immolative linker was developed for the sensitive and selective detection of O-GlcNAcase.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>39007923</pmid><doi>10.1039/d4cc02845g</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-4095-2191</orcidid><orcidid>https://orcid.org/0000-0001-7919-2727</orcidid><orcidid>https://orcid.org/0000-0001-9835-922X</orcidid><orcidid>https://orcid.org/0000-0003-3224-001X</orcidid><orcidid>https://orcid.org/0000-0002-8893-5673</orcidid><orcidid>https://orcid.org/0000-0002-8736-3511</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical communications (Cambridge, England), 2024-08, Vol.6 (63), p.824-8243 |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | beta-N-Acetylhexosaminidases - antagonists & inhibitors beta-N-Acetylhexosaminidases - metabolism Biological activity Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry Humans Isoindoles - chemical synthesis Isoindoles - chemistry Molecular Structure Spectrometry, Fluorescence |
| title | Isoindoline-based fluorogenic probes bearing a self-immolative linker for the sensitive and selective detection of O-GlcNAcase activity |
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