A Series of Furimazine Derivatives for Sustained Live-Cell Bioluminescence Imaging and Application to the Monitoring of Myogenesis at the Single-Cell Level
Bioluminescence (BL) imaging, which utilizes light emitted through the enzymatic reaction of luciferase oxidizing its substrate luciferin, enables sensitive and noninvasive monitoring of life phenomena. Herein, we developed a series of caged furimazine (FMZ) derivatives by introducing a protective g...
Gespeichert in:
| Veröffentlicht in: | Bioconjugate chemistry 2022-03, Vol.33 (3), p.496-504 |
|---|---|
| Hauptverfasser: | , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 504 |
|---|---|
| container_issue | 3 |
| container_start_page | 496 |
| container_title | Bioconjugate chemistry |
| container_volume | 33 |
| creator | Orioka, Mariko Eguchi, Masatoshi Mizui, Yuki Ikeda, Yuma Sakama, Akihiro Li, Qiaojing Yoshimura, Hideaki Ozawa, Takeaki Citterio, Daniel Hiruta, Yuki |
| description | Bioluminescence (BL) imaging, which utilizes light emitted through the enzymatic reaction of luciferase oxidizing its substrate luciferin, enables sensitive and noninvasive monitoring of life phenomena. Herein, we developed a series of caged furimazine (FMZ) derivatives by introducing a protective group at the C-3 position and a hydroxy group at the C-6 phenyl ring to realize long-term live-cell BL imaging based on the NanoLuc (NLuc)/NanoKAZ (NKAZ)–FMZ system. The membrane permeability and cytotoxicity of the substrates were evaluated and related to their hydrophobicity. Among the series, the derivative with the bulkiest protective group (adamantanecarbonyl group) and a hydroxy substituent (named Ad-FMZ-OH) showed significantly prolonged and constant BL signal in cells expressing NLuc compared to the native FMZ substrate. This derivative enabled continuous BL imaging at the single-cell level for 24 h. Furthermore, we applied Ad-FMZ-OH to BL imaging of myocyte fusion and succeeded in the consecutive and sensitive monitoring at a single-cell level over a day. In summary, NLuc/NKAZ-caged FMZ derivatives have the potential to be applied to live-cell BL imaging of various life phenomena that require long-term observation. |
| doi_str_mv | 10.1021/acs.bioconjchem.2c00035 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2631620313</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2644436414</sourcerecordid><originalsourceid>FETCH-LOGICAL-a451t-77de6d8601e3d3324e2d3d70cccc180ca0f8d841d5ecd4c98d5b7014889e7de13</originalsourceid><addsrcrecordid>eNqFkc1uEzEUhS0EoqXwCmCJDZsJ_psZZxlSCpVSsQisR459J3XksYM9E6m8Ci_LDQkVYoM3tu79zrm2DyFvOJtxJvh7Y8ts45NNcWfvYZgJyxiT9RNyyWvBKqW5eIpnpmTFNRMX5EUpO0TmXIvn5ELWXKu61pfk54KuIXsoNPX0Zsp-MD98BHqNxYMZ_QE7fcp0PZXRYMPRFdaqJYRAP_gUpgGLxUK0QG8Hs_VxS010dLHfB2_RIEU6JjreA71L0Y8pHwmcdfeQtoBSX6gZf_fX2Aln6xUcILwkz3oTCrw671fk283Hr8vP1erLp9vlYlUZVfOxalsHjdMN4yCdlEKBcNK1zOLCx1vDeu204q4G65Sda1dvWsaV1nNAKZdX5N3Jd5_T9wnK2A0enxSCiZCm0olG8kYwySWib_9Bd2nKEW-HlFJKNoorpNoTZXMqJUPf7Y8fmx86zrpjfh3m1_2VX3fOD5Wvz_7TZgD3qPsTGALyBBwdHmf_z_YX0h-uXQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2644436414</pqid></control><display><type>article</type><title>A Series of Furimazine Derivatives for Sustained Live-Cell Bioluminescence Imaging and Application to the Monitoring of Myogenesis at the Single-Cell Level</title><source>ACS Publications</source><source>MEDLINE</source><creator>Orioka, Mariko ; Eguchi, Masatoshi ; Mizui, Yuki ; Ikeda, Yuma ; Sakama, Akihiro ; Li, Qiaojing ; Yoshimura, Hideaki ; Ozawa, Takeaki ; Citterio, Daniel ; Hiruta, Yuki</creator><creatorcontrib>Orioka, Mariko ; Eguchi, Masatoshi ; Mizui, Yuki ; Ikeda, Yuma ; Sakama, Akihiro ; Li, Qiaojing ; Yoshimura, Hideaki ; Ozawa, Takeaki ; Citterio, Daniel ; Hiruta, Yuki</creatorcontrib><description>Bioluminescence (BL) imaging, which utilizes light emitted through the enzymatic reaction of luciferase oxidizing its substrate luciferin, enables sensitive and noninvasive monitoring of life phenomena. Herein, we developed a series of caged furimazine (FMZ) derivatives by introducing a protective group at the C-3 position and a hydroxy group at the C-6 phenyl ring to realize long-term live-cell BL imaging based on the NanoLuc (NLuc)/NanoKAZ (NKAZ)–FMZ system. The membrane permeability and cytotoxicity of the substrates were evaluated and related to their hydrophobicity. Among the series, the derivative with the bulkiest protective group (adamantanecarbonyl group) and a hydroxy substituent (named Ad-FMZ-OH) showed significantly prolonged and constant BL signal in cells expressing NLuc compared to the native FMZ substrate. This derivative enabled continuous BL imaging at the single-cell level for 24 h. Furthermore, we applied Ad-FMZ-OH to BL imaging of myocyte fusion and succeeded in the consecutive and sensitive monitoring at a single-cell level over a day. In summary, NLuc/NKAZ-caged FMZ derivatives have the potential to be applied to live-cell BL imaging of various life phenomena that require long-term observation.</description><identifier>ISSN: 1043-1802</identifier><identifier>EISSN: 1520-4812</identifier><identifier>DOI: 10.1021/acs.bioconjchem.2c00035</identifier><identifier>PMID: 35184558</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Bioluminescence ; Cytotoxicity ; Furans ; Hydrophobicity ; Imaging ; Imidazoles ; Luciferases ; Luciferin ; Luminescent Measurements - methods ; Membrane permeability ; Monitoring ; Muscle Development ; Myocytes ; Myogenesis ; Oxidation ; Pyrazines ; Rings (mathematics) ; Substrates ; Toxicity</subject><ispartof>Bioconjugate chemistry, 2022-03, Vol.33 (3), p.496-504</ispartof><rights>2022 American Chemical Society</rights><rights>Copyright American Chemical Society Mar 16, 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a451t-77de6d8601e3d3324e2d3d70cccc180ca0f8d841d5ecd4c98d5b7014889e7de13</citedby><cites>FETCH-LOGICAL-a451t-77de6d8601e3d3324e2d3d70cccc180ca0f8d841d5ecd4c98d5b7014889e7de13</cites><orcidid>0000-0002-3198-4853 ; 0000-0001-7420-045X ; 0000-0003-2937-6370 ; 0000-0001-7303-4189</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.bioconjchem.2c00035$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.bioconjchem.2c00035$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35184558$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Orioka, Mariko</creatorcontrib><creatorcontrib>Eguchi, Masatoshi</creatorcontrib><creatorcontrib>Mizui, Yuki</creatorcontrib><creatorcontrib>Ikeda, Yuma</creatorcontrib><creatorcontrib>Sakama, Akihiro</creatorcontrib><creatorcontrib>Li, Qiaojing</creatorcontrib><creatorcontrib>Yoshimura, Hideaki</creatorcontrib><creatorcontrib>Ozawa, Takeaki</creatorcontrib><creatorcontrib>Citterio, Daniel</creatorcontrib><creatorcontrib>Hiruta, Yuki</creatorcontrib><title>A Series of Furimazine Derivatives for Sustained Live-Cell Bioluminescence Imaging and Application to the Monitoring of Myogenesis at the Single-Cell Level</title><title>Bioconjugate chemistry</title><addtitle>Bioconjugate Chem</addtitle><description>Bioluminescence (BL) imaging, which utilizes light emitted through the enzymatic reaction of luciferase oxidizing its substrate luciferin, enables sensitive and noninvasive monitoring of life phenomena. Herein, we developed a series of caged furimazine (FMZ) derivatives by introducing a protective group at the C-3 position and a hydroxy group at the C-6 phenyl ring to realize long-term live-cell BL imaging based on the NanoLuc (NLuc)/NanoKAZ (NKAZ)–FMZ system. The membrane permeability and cytotoxicity of the substrates were evaluated and related to their hydrophobicity. Among the series, the derivative with the bulkiest protective group (adamantanecarbonyl group) and a hydroxy substituent (named Ad-FMZ-OH) showed significantly prolonged and constant BL signal in cells expressing NLuc compared to the native FMZ substrate. This derivative enabled continuous BL imaging at the single-cell level for 24 h. Furthermore, we applied Ad-FMZ-OH to BL imaging of myocyte fusion and succeeded in the consecutive and sensitive monitoring at a single-cell level over a day. In summary, NLuc/NKAZ-caged FMZ derivatives have the potential to be applied to live-cell BL imaging of various life phenomena that require long-term observation.</description><subject>Bioluminescence</subject><subject>Cytotoxicity</subject><subject>Furans</subject><subject>Hydrophobicity</subject><subject>Imaging</subject><subject>Imidazoles</subject><subject>Luciferases</subject><subject>Luciferin</subject><subject>Luminescent Measurements - methods</subject><subject>Membrane permeability</subject><subject>Monitoring</subject><subject>Muscle Development</subject><subject>Myocytes</subject><subject>Myogenesis</subject><subject>Oxidation</subject><subject>Pyrazines</subject><subject>Rings (mathematics)</subject><subject>Substrates</subject><subject>Toxicity</subject><issn>1043-1802</issn><issn>1520-4812</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1uEzEUhS0EoqXwCmCJDZsJ_psZZxlSCpVSsQisR459J3XksYM9E6m8Ci_LDQkVYoM3tu79zrm2DyFvOJtxJvh7Y8ts45NNcWfvYZgJyxiT9RNyyWvBKqW5eIpnpmTFNRMX5EUpO0TmXIvn5ELWXKu61pfk54KuIXsoNPX0Zsp-MD98BHqNxYMZ_QE7fcp0PZXRYMPRFdaqJYRAP_gUpgGLxUK0QG8Hs_VxS010dLHfB2_RIEU6JjreA71L0Y8pHwmcdfeQtoBSX6gZf_fX2Aln6xUcILwkz3oTCrw671fk283Hr8vP1erLp9vlYlUZVfOxalsHjdMN4yCdlEKBcNK1zOLCx1vDeu204q4G65Sda1dvWsaV1nNAKZdX5N3Jd5_T9wnK2A0enxSCiZCm0olG8kYwySWib_9Bd2nKEW-HlFJKNoorpNoTZXMqJUPf7Y8fmx86zrpjfh3m1_2VX3fOD5Wvz_7TZgD3qPsTGALyBBwdHmf_z_YX0h-uXQ</recordid><startdate>20220316</startdate><enddate>20220316</enddate><creator>Orioka, Mariko</creator><creator>Eguchi, Masatoshi</creator><creator>Mizui, Yuki</creator><creator>Ikeda, Yuma</creator><creator>Sakama, Akihiro</creator><creator>Li, Qiaojing</creator><creator>Yoshimura, Hideaki</creator><creator>Ozawa, Takeaki</creator><creator>Citterio, Daniel</creator><creator>Hiruta, Yuki</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>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3198-4853</orcidid><orcidid>https://orcid.org/0000-0001-7420-045X</orcidid><orcidid>https://orcid.org/0000-0003-2937-6370</orcidid><orcidid>https://orcid.org/0000-0001-7303-4189</orcidid></search><sort><creationdate>20220316</creationdate><title>A Series of Furimazine Derivatives for Sustained Live-Cell Bioluminescence Imaging and Application to the Monitoring of Myogenesis at the Single-Cell Level</title><author>Orioka, Mariko ; Eguchi, Masatoshi ; Mizui, Yuki ; Ikeda, Yuma ; Sakama, Akihiro ; Li, Qiaojing ; Yoshimura, Hideaki ; Ozawa, Takeaki ; Citterio, Daniel ; Hiruta, Yuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a451t-77de6d8601e3d3324e2d3d70cccc180ca0f8d841d5ecd4c98d5b7014889e7de13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Bioluminescence</topic><topic>Cytotoxicity</topic><topic>Furans</topic><topic>Hydrophobicity</topic><topic>Imaging</topic><topic>Imidazoles</topic><topic>Luciferases</topic><topic>Luciferin</topic><topic>Luminescent Measurements - methods</topic><topic>Membrane permeability</topic><topic>Monitoring</topic><topic>Muscle Development</topic><topic>Myocytes</topic><topic>Myogenesis</topic><topic>Oxidation</topic><topic>Pyrazines</topic><topic>Rings (mathematics)</topic><topic>Substrates</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Orioka, Mariko</creatorcontrib><creatorcontrib>Eguchi, Masatoshi</creatorcontrib><creatorcontrib>Mizui, Yuki</creatorcontrib><creatorcontrib>Ikeda, Yuma</creatorcontrib><creatorcontrib>Sakama, Akihiro</creatorcontrib><creatorcontrib>Li, Qiaojing</creatorcontrib><creatorcontrib>Yoshimura, Hideaki</creatorcontrib><creatorcontrib>Ozawa, Takeaki</creatorcontrib><creatorcontrib>Citterio, Daniel</creatorcontrib><creatorcontrib>Hiruta, Yuki</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioconjugate chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Orioka, Mariko</au><au>Eguchi, Masatoshi</au><au>Mizui, Yuki</au><au>Ikeda, Yuma</au><au>Sakama, Akihiro</au><au>Li, Qiaojing</au><au>Yoshimura, Hideaki</au><au>Ozawa, Takeaki</au><au>Citterio, Daniel</au><au>Hiruta, Yuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Series of Furimazine Derivatives for Sustained Live-Cell Bioluminescence Imaging and Application to the Monitoring of Myogenesis at the Single-Cell Level</atitle><jtitle>Bioconjugate chemistry</jtitle><addtitle>Bioconjugate Chem</addtitle><date>2022-03-16</date><risdate>2022</risdate><volume>33</volume><issue>3</issue><spage>496</spage><epage>504</epage><pages>496-504</pages><issn>1043-1802</issn><eissn>1520-4812</eissn><abstract>Bioluminescence (BL) imaging, which utilizes light emitted through the enzymatic reaction of luciferase oxidizing its substrate luciferin, enables sensitive and noninvasive monitoring of life phenomena. Herein, we developed a series of caged furimazine (FMZ) derivatives by introducing a protective group at the C-3 position and a hydroxy group at the C-6 phenyl ring to realize long-term live-cell BL imaging based on the NanoLuc (NLuc)/NanoKAZ (NKAZ)–FMZ system. The membrane permeability and cytotoxicity of the substrates were evaluated and related to their hydrophobicity. Among the series, the derivative with the bulkiest protective group (adamantanecarbonyl group) and a hydroxy substituent (named Ad-FMZ-OH) showed significantly prolonged and constant BL signal in cells expressing NLuc compared to the native FMZ substrate. This derivative enabled continuous BL imaging at the single-cell level for 24 h. Furthermore, we applied Ad-FMZ-OH to BL imaging of myocyte fusion and succeeded in the consecutive and sensitive monitoring at a single-cell level over a day. In summary, NLuc/NKAZ-caged FMZ derivatives have the potential to be applied to live-cell BL imaging of various life phenomena that require long-term observation.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>35184558</pmid><doi>10.1021/acs.bioconjchem.2c00035</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-3198-4853</orcidid><orcidid>https://orcid.org/0000-0001-7420-045X</orcidid><orcidid>https://orcid.org/0000-0003-2937-6370</orcidid><orcidid>https://orcid.org/0000-0001-7303-4189</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1043-1802 |
| ispartof | Bioconjugate chemistry, 2022-03, Vol.33 (3), p.496-504 |
| issn | 1043-1802 1520-4812 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2631620313 |
| source | ACS Publications; MEDLINE |
| subjects | Bioluminescence Cytotoxicity Furans Hydrophobicity Imaging Imidazoles Luciferases Luciferin Luminescent Measurements - methods Membrane permeability Monitoring Muscle Development Myocytes Myogenesis Oxidation Pyrazines Rings (mathematics) Substrates Toxicity |
| title | A Series of Furimazine Derivatives for Sustained Live-Cell Bioluminescence Imaging and Application to the Monitoring of Myogenesis at the Single-Cell Level |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-15T04%3A59%3A13IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Series%20of%20Furimazine%20Derivatives%20for%20Sustained%20Live-Cell%20Bioluminescence%20Imaging%20and%20Application%20to%20the%20Monitoring%20of%20Myogenesis%20at%20the%20Single-Cell%20Level&rft.jtitle=Bioconjugate%20chemistry&rft.au=Orioka,%20Mariko&rft.date=2022-03-16&rft.volume=33&rft.issue=3&rft.spage=496&rft.epage=504&rft.pages=496-504&rft.issn=1043-1802&rft.eissn=1520-4812&rft_id=info:doi/10.1021/acs.bioconjchem.2c00035&rft_dat=%3Cproquest_cross%3E2644436414%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2644436414&rft_id=info:pmid/35184558&rfr_iscdi=true |