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Functionalized quinolizinium-based fluorescent reagents for modification of cysteine-containing peptides and proteins
A series of quinolizinium-based fluorescent reagents were prepared by visible light-mediated gold-catalyzed cis -difunctionalization between quinolinium diazonium salts and electron-deficient alkyne-linked phenylethynyl trimethylsilanes. The electron-deficient alkynyl group of the quinolizinium-base...
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| Published in: | RSC advances 2022-02, Vol.12 (1), p.6248-6254 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
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| cited_by | cdi_FETCH-LOGICAL-c428t-7a49eede2733f48caaf36ad1dda79952f945f8aca1d30cd5827aeae0393f4f043 |
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| cites | cdi_FETCH-LOGICAL-c428t-7a49eede2733f48caaf36ad1dda79952f945f8aca1d30cd5827aeae0393f4f043 |
| container_end_page | 6254 |
| container_issue | 1 |
| container_start_page | 6248 |
| container_title | RSC advances |
| container_volume | 12 |
| creator | Kung, Karen Ka-Yan Xu, Cai-fung O, Wa-Yi Yu, Qiong Chung, Sai-Fung Tam, Suet-Ying Leung, Yun-Chung Wong, Man-Kin |
| description | A series of quinolizinium-based fluorescent reagents were prepared by visible light-mediated gold-catalyzed
cis
-difunctionalization between quinolinium diazonium salts and electron-deficient alkyne-linked phenylethynyl trimethylsilanes. The electron-deficient alkynyl group of the quinolizinium-based fluorescent reagents underwent nucleophilic addition reaction with the sulfhydryl group on cysteine-containing peptides and proteins. The quinolizinium-based fluorescent reagents were found to function as highly selective reagents for the modification of cysteine-containing peptides and proteins with good to excellent conversions (up to 99%). Moreover, the modified BCArg mutants bearing cationic quinolizinium compounds
1b
,
1d
,
1e
and
1h
exhibit comparable activity in enzymatic and cytotoxicity assays to the unmodified one.
New quinolizinium-based fluorescent reagents were made by visible light-mediated gold-catalyzed
cis
-difunctionalization of quinolinium diazonium salts and trimethylsilyl alkyne derivatives. |
| doi_str_mv | 10.1039/d1ra08329e |
| format | article |
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cis
-difunctionalization between quinolinium diazonium salts and electron-deficient alkyne-linked phenylethynyl trimethylsilanes. The electron-deficient alkynyl group of the quinolizinium-based fluorescent reagents underwent nucleophilic addition reaction with the sulfhydryl group on cysteine-containing peptides and proteins. The quinolizinium-based fluorescent reagents were found to function as highly selective reagents for the modification of cysteine-containing peptides and proteins with good to excellent conversions (up to 99%). Moreover, the modified BCArg mutants bearing cationic quinolizinium compounds
1b
,
1d
,
1e
and
1h
exhibit comparable activity in enzymatic and cytotoxicity assays to the unmodified one.
New quinolizinium-based fluorescent reagents were made by visible light-mediated gold-catalyzed
cis
-difunctionalization of quinolinium diazonium salts and trimethylsilyl alkyne derivatives.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d1ra08329e</identifier><identifier>PMID: 35424586</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkynes ; Chemistry ; Cysteine ; Fluorescence ; Peptides ; Proteins ; Reagents ; Toxicity</subject><ispartof>RSC advances, 2022-02, Vol.12 (1), p.6248-6254</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2022</rights><rights>This journal is © The Royal Society of Chemistry 2022 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c428t-7a49eede2733f48caaf36ad1dda79952f945f8aca1d30cd5827aeae0393f4f043</citedby><cites>FETCH-LOGICAL-c428t-7a49eede2733f48caaf36ad1dda79952f945f8aca1d30cd5827aeae0393f4f043</cites><orcidid>0000-0003-1574-6860 ; 0000-0002-2732-4369</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8981741/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8981741/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35424586$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kung, Karen Ka-Yan</creatorcontrib><creatorcontrib>Xu, Cai-fung</creatorcontrib><creatorcontrib>O, Wa-Yi</creatorcontrib><creatorcontrib>Yu, Qiong</creatorcontrib><creatorcontrib>Chung, Sai-Fung</creatorcontrib><creatorcontrib>Tam, Suet-Ying</creatorcontrib><creatorcontrib>Leung, Yun-Chung</creatorcontrib><creatorcontrib>Wong, Man-Kin</creatorcontrib><title>Functionalized quinolizinium-based fluorescent reagents for modification of cysteine-containing peptides and proteins</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>A series of quinolizinium-based fluorescent reagents were prepared by visible light-mediated gold-catalyzed
cis
-difunctionalization between quinolinium diazonium salts and electron-deficient alkyne-linked phenylethynyl trimethylsilanes. The electron-deficient alkynyl group of the quinolizinium-based fluorescent reagents underwent nucleophilic addition reaction with the sulfhydryl group on cysteine-containing peptides and proteins. The quinolizinium-based fluorescent reagents were found to function as highly selective reagents for the modification of cysteine-containing peptides and proteins with good to excellent conversions (up to 99%). Moreover, the modified BCArg mutants bearing cationic quinolizinium compounds
1b
,
1d
,
1e
and
1h
exhibit comparable activity in enzymatic and cytotoxicity assays to the unmodified one.
New quinolizinium-based fluorescent reagents were made by visible light-mediated gold-catalyzed
cis
-difunctionalization of quinolinium diazonium salts and trimethylsilyl alkyne derivatives.</description><subject>Alkynes</subject><subject>Chemistry</subject><subject>Cysteine</subject><subject>Fluorescence</subject><subject>Peptides</subject><subject>Proteins</subject><subject>Reagents</subject><subject>Toxicity</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpdkttrFTEQxhex2FL74ruy4IsIa3PZS_IilF5UKBREn8M0mRxTdpNtsinUv75ZTz3W5mWGzC9fJt-kqt5Q8okSLo8NjUAEZxJfVAeMtH3DSC9fPsn3q6OUbkhZfUdZT19V-7xrWduJ_qDKF9nrxQUPo_uNpr7NzoeSOu_y1FxDKnt2zCFi0uiXOiJsSky1DbGegnHWaVjP18HW-j4t6Dw2OvgFioTf1DPOizOYavCmnmNYgfS62rMwJjx6jIfVz4vzH6dfm8urL99OTy4b3TKxNAO0EtEgGzi3rdAAlvdgqDEwSNkxK9vOCtBADSfadIINgIDFloJb0vLD6vNWd87XE5r1BRFGNUc3QbxXAZz6v-LdL7UJd0pIQYeWFoEPjwIx3GZMi5pcMWIcwWPISbFiaS8E4-td75-hNyHH4utKFcMllbIv1MctpWNIKaLdNUOJWgeqzuj3kz8DPS_wu6ft79C_4yvA2y0Qk95V__0I_gBB66nO</recordid><startdate>20220216</startdate><enddate>20220216</enddate><creator>Kung, Karen Ka-Yan</creator><creator>Xu, Cai-fung</creator><creator>O, Wa-Yi</creator><creator>Yu, Qiong</creator><creator>Chung, Sai-Fung</creator><creator>Tam, Suet-Ying</creator><creator>Leung, Yun-Chung</creator><creator>Wong, Man-Kin</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-1574-6860</orcidid><orcidid>https://orcid.org/0000-0002-2732-4369</orcidid></search><sort><creationdate>20220216</creationdate><title>Functionalized quinolizinium-based fluorescent reagents for modification of cysteine-containing peptides and proteins</title><author>Kung, Karen Ka-Yan ; Xu, Cai-fung ; O, Wa-Yi ; Yu, Qiong ; Chung, Sai-Fung ; Tam, Suet-Ying ; Leung, Yun-Chung ; Wong, Man-Kin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c428t-7a49eede2733f48caaf36ad1dda79952f945f8aca1d30cd5827aeae0393f4f043</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkynes</topic><topic>Chemistry</topic><topic>Cysteine</topic><topic>Fluorescence</topic><topic>Peptides</topic><topic>Proteins</topic><topic>Reagents</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kung, Karen Ka-Yan</creatorcontrib><creatorcontrib>Xu, Cai-fung</creatorcontrib><creatorcontrib>O, Wa-Yi</creatorcontrib><creatorcontrib>Yu, Qiong</creatorcontrib><creatorcontrib>Chung, Sai-Fung</creatorcontrib><creatorcontrib>Tam, Suet-Ying</creatorcontrib><creatorcontrib>Leung, Yun-Chung</creatorcontrib><creatorcontrib>Wong, Man-Kin</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kung, Karen Ka-Yan</au><au>Xu, Cai-fung</au><au>O, Wa-Yi</au><au>Yu, Qiong</au><au>Chung, Sai-Fung</au><au>Tam, Suet-Ying</au><au>Leung, Yun-Chung</au><au>Wong, Man-Kin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Functionalized quinolizinium-based fluorescent reagents for modification of cysteine-containing peptides and proteins</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2022-02-16</date><risdate>2022</risdate><volume>12</volume><issue>1</issue><spage>6248</spage><epage>6254</epage><pages>6248-6254</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>A series of quinolizinium-based fluorescent reagents were prepared by visible light-mediated gold-catalyzed
cis
-difunctionalization between quinolinium diazonium salts and electron-deficient alkyne-linked phenylethynyl trimethylsilanes. The electron-deficient alkynyl group of the quinolizinium-based fluorescent reagents underwent nucleophilic addition reaction with the sulfhydryl group on cysteine-containing peptides and proteins. The quinolizinium-based fluorescent reagents were found to function as highly selective reagents for the modification of cysteine-containing peptides and proteins with good to excellent conversions (up to 99%). Moreover, the modified BCArg mutants bearing cationic quinolizinium compounds
1b
,
1d
,
1e
and
1h
exhibit comparable activity in enzymatic and cytotoxicity assays to the unmodified one.
New quinolizinium-based fluorescent reagents were made by visible light-mediated gold-catalyzed
cis
-difunctionalization of quinolinium diazonium salts and trimethylsilyl alkyne derivatives.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35424586</pmid><doi>10.1039/d1ra08329e</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-1574-6860</orcidid><orcidid>https://orcid.org/0000-0002-2732-4369</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
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| ispartof | RSC advances, 2022-02, Vol.12 (1), p.6248-6254 |
| issn | 2046-2069 2046-2069 |
| language | eng |
| recordid | cdi_proquest_journals_2635491996 |
| source | PubMed (Medline) |
| subjects | Alkynes Chemistry Cysteine Fluorescence Peptides Proteins Reagents Toxicity |
| title | Functionalized quinolizinium-based fluorescent reagents for modification of cysteine-containing peptides and proteins |
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