Efficient visible/NIR light-driven uncaging of hydroxylated thiazole orange-based caged compounds in aqueous media
In photoactivation strategies with bioactive molecules, one-photon visible or two-photon near-infrared light-sensitive caged compounds are desirable tools for biological applications because they offer reduced phototoxicity and deep tissue penetration. However, visible-light-sensitive photoremovable...
Gespeichert in:
| Veröffentlicht in: | Chemical science (Cambridge) 2022-06, Vol.13 (25), p.7462-7467 |
|---|---|
| Hauptverfasser: | , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 7467 |
|---|---|
| container_issue | 25 |
| container_start_page | 7462 |
| container_title | Chemical science (Cambridge) |
| container_volume | 13 |
| creator | Hashimoto, Ryu Minoshima, Masafumi Sakata, Souhei Ono, Fumihito Ishii, Hirokazu Watakabe, Yuki Nemoto, Tomomi Yanaka, Saeko Kato, Koichi Kikuchi, Kazuya |
| description | In photoactivation strategies with bioactive molecules, one-photon visible or two-photon near-infrared light-sensitive caged compounds are desirable tools for biological applications because they offer reduced phototoxicity and deep tissue penetration. However, visible-light-sensitive photoremovable protecting groups (PPGs) reported so far have displayed high hydrophobicity and low uncaging cross sections (
Φ
< 50) in aqueous media, which can obstruct the control of bioactivity with high spatial and temporal precision. In this study, we developed hydroxylated thiazole orange (HTO) derivatives as visible-light-sensitive PPGs with high uncaging cross sections (
Φ
370) in aqueous solution. In addition, 2PE photolysis reactions of HTO-caged glutamate were achieved using a NIR laser (940 nm). Moreover, HTO-caged glutamate can activate
N
-methyl-
d
-aspartic acid receptors in
Xenopus
oocytes and mammalian cells with green-light illumination, thus allowing optical control of biological functions.
A hydroxylated thiazole orange (HTO)-caged glutamate efficiently releases a glutamate for temporal activation of ion channels under visible-to-NIR light in aqueous media. |
| doi_str_mv | 10.1039/d2sc02364d |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_2694414841</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2694414841</sourcerecordid><originalsourceid>FETCH-LOGICAL-c471t-5f3790822bc03297d94644f4bf84b10d11520590c9f5791e00f4b0c434e605133</originalsourceid><addsrcrecordid>eNpdkUlrHDEQhYVJsI3jS-4GgS8h0HZp6UWXQBivYBLIchZqLT0yPdJE6h4y-fXRZMyERIeSqPp4pcdD6C2BKwJMXBuaNVDWcHOETilwUjU1E68Obwon6DznZyiHMVLT9hidsLpraQfNKUq3znntbZjwxmffj_b60-MXPPphOVUm-Y0NeA5aDT4MODq83JoUf25HNVmDp6VXv-JocUwqDLbqVS7dAu9qXK3jHEzGPmD1Y7ZxznhljVdv0GunxmzPX-4z9P3u9tvioXr6fP-4-PhUad6SqaodawV0lPYaGBWtEbzh3PHedbwnYEjxArUALVzdCmIBygw0Z9w2UBPGztCHve567stiXTwmNcp18iuVtjIqL_-dBL-UQ9xIQTkRDRSBdy8CKRYDeZIrn7UdRxV2biRtBOeEd5wU9PI_9DnOKRR7hepIJ0QjdoLv95ROMedk3eEzBOQuTXlDvy7-pHlT4Is9nLI-cH_TZr8BnViajQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2681899690</pqid></control><display><type>article</type><title>Efficient visible/NIR light-driven uncaging of hydroxylated thiazole orange-based caged compounds in aqueous media</title><source>TestCollectionTL3OpenAccess</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>PubMed Central</source><source>PubMed Central Open Access</source><creator>Hashimoto, Ryu ; Minoshima, Masafumi ; Sakata, Souhei ; Ono, Fumihito ; Ishii, Hirokazu ; Watakabe, Yuki ; Nemoto, Tomomi ; Yanaka, Saeko ; Kato, Koichi ; Kikuchi, Kazuya</creator><creatorcontrib>Hashimoto, Ryu ; Minoshima, Masafumi ; Sakata, Souhei ; Ono, Fumihito ; Ishii, Hirokazu ; Watakabe, Yuki ; Nemoto, Tomomi ; Yanaka, Saeko ; Kato, Koichi ; Kikuchi, Kazuya</creatorcontrib><description>In photoactivation strategies with bioactive molecules, one-photon visible or two-photon near-infrared light-sensitive caged compounds are desirable tools for biological applications because they offer reduced phototoxicity and deep tissue penetration. However, visible-light-sensitive photoremovable protecting groups (PPGs) reported so far have displayed high hydrophobicity and low uncaging cross sections (
Φ
< 50) in aqueous media, which can obstruct the control of bioactivity with high spatial and temporal precision. In this study, we developed hydroxylated thiazole orange (HTO) derivatives as visible-light-sensitive PPGs with high uncaging cross sections (
Φ
370) in aqueous solution. In addition, 2PE photolysis reactions of HTO-caged glutamate were achieved using a NIR laser (940 nm). Moreover, HTO-caged glutamate can activate
N
-methyl-
d
-aspartic acid receptors in
Xenopus
oocytes and mammalian cells with green-light illumination, thus allowing optical control of biological functions.
A hydroxylated thiazole orange (HTO)-caged glutamate efficiently releases a glutamate for temporal activation of ion channels under visible-to-NIR light in aqueous media.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/d2sc02364d</identifier><identifier>PMID: 35872806</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Aqueous solutions ; Aspartic acid ; Biological activity ; Cage compounds ; Chemistry ; Cross-sections ; Gametocytes ; Hydrophobicity ; Near infrared radiation ; Optical control ; Photolysis ; Photons</subject><ispartof>Chemical science (Cambridge), 2022-06, Vol.13 (25), p.7462-7467</ispartof><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-c471t-5f3790822bc03297d94644f4bf84b10d11520590c9f5791e00f4b0c434e605133</citedby><cites>FETCH-LOGICAL-c471t-5f3790822bc03297d94644f4bf84b10d11520590c9f5791e00f4b0c434e605133</cites><orcidid>0000-0001-8391-194X ; 0000-0002-3513-5701 ; 0000-0001-6102-1495 ; 0000-0001-7103-1275 ; 0000-0002-6580-1007 ; 0000-0001-7187-9612 ; 0000-0002-9352-3454</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/PMC9241960/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9241960/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids></links><search><creatorcontrib>Hashimoto, Ryu</creatorcontrib><creatorcontrib>Minoshima, Masafumi</creatorcontrib><creatorcontrib>Sakata, Souhei</creatorcontrib><creatorcontrib>Ono, Fumihito</creatorcontrib><creatorcontrib>Ishii, Hirokazu</creatorcontrib><creatorcontrib>Watakabe, Yuki</creatorcontrib><creatorcontrib>Nemoto, Tomomi</creatorcontrib><creatorcontrib>Yanaka, Saeko</creatorcontrib><creatorcontrib>Kato, Koichi</creatorcontrib><creatorcontrib>Kikuchi, Kazuya</creatorcontrib><title>Efficient visible/NIR light-driven uncaging of hydroxylated thiazole orange-based caged compounds in aqueous media</title><title>Chemical science (Cambridge)</title><description>In photoactivation strategies with bioactive molecules, one-photon visible or two-photon near-infrared light-sensitive caged compounds are desirable tools for biological applications because they offer reduced phototoxicity and deep tissue penetration. However, visible-light-sensitive photoremovable protecting groups (PPGs) reported so far have displayed high hydrophobicity and low uncaging cross sections (
Φ
< 50) in aqueous media, which can obstruct the control of bioactivity with high spatial and temporal precision. In this study, we developed hydroxylated thiazole orange (HTO) derivatives as visible-light-sensitive PPGs with high uncaging cross sections (
Φ
370) in aqueous solution. In addition, 2PE photolysis reactions of HTO-caged glutamate were achieved using a NIR laser (940 nm). Moreover, HTO-caged glutamate can activate
N
-methyl-
d
-aspartic acid receptors in
Xenopus
oocytes and mammalian cells with green-light illumination, thus allowing optical control of biological functions.
A hydroxylated thiazole orange (HTO)-caged glutamate efficiently releases a glutamate for temporal activation of ion channels under visible-to-NIR light in aqueous media.</description><subject>Aqueous solutions</subject><subject>Aspartic acid</subject><subject>Biological activity</subject><subject>Cage compounds</subject><subject>Chemistry</subject><subject>Cross-sections</subject><subject>Gametocytes</subject><subject>Hydrophobicity</subject><subject>Near infrared radiation</subject><subject>Optical control</subject><subject>Photolysis</subject><subject>Photons</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpdkUlrHDEQhYVJsI3jS-4GgS8h0HZp6UWXQBivYBLIchZqLT0yPdJE6h4y-fXRZMyERIeSqPp4pcdD6C2BKwJMXBuaNVDWcHOETilwUjU1E68Obwon6DznZyiHMVLT9hidsLpraQfNKUq3znntbZjwxmffj_b60-MXPPphOVUm-Y0NeA5aDT4MODq83JoUf25HNVmDp6VXv-JocUwqDLbqVS7dAu9qXK3jHEzGPmD1Y7ZxznhljVdv0GunxmzPX-4z9P3u9tvioXr6fP-4-PhUad6SqaodawV0lPYaGBWtEbzh3PHedbwnYEjxArUALVzdCmIBygw0Z9w2UBPGztCHve567stiXTwmNcp18iuVtjIqL_-dBL-UQ9xIQTkRDRSBdy8CKRYDeZIrn7UdRxV2biRtBOeEd5wU9PI_9DnOKRR7hepIJ0QjdoLv95ROMedk3eEzBOQuTXlDvy7-pHlT4Is9nLI-cH_TZr8BnViajQ</recordid><startdate>20220629</startdate><enddate>20220629</enddate><creator>Hashimoto, Ryu</creator><creator>Minoshima, Masafumi</creator><creator>Sakata, Souhei</creator><creator>Ono, Fumihito</creator><creator>Ishii, Hirokazu</creator><creator>Watakabe, Yuki</creator><creator>Nemoto, Tomomi</creator><creator>Yanaka, Saeko</creator><creator>Kato, Koichi</creator><creator>Kikuchi, Kazuya</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><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/0000-0001-8391-194X</orcidid><orcidid>https://orcid.org/0000-0002-3513-5701</orcidid><orcidid>https://orcid.org/0000-0001-6102-1495</orcidid><orcidid>https://orcid.org/0000-0001-7103-1275</orcidid><orcidid>https://orcid.org/0000-0002-6580-1007</orcidid><orcidid>https://orcid.org/0000-0001-7187-9612</orcidid><orcidid>https://orcid.org/0000-0002-9352-3454</orcidid></search><sort><creationdate>20220629</creationdate><title>Efficient visible/NIR light-driven uncaging of hydroxylated thiazole orange-based caged compounds in aqueous media</title><author>Hashimoto, Ryu ; Minoshima, Masafumi ; Sakata, Souhei ; Ono, Fumihito ; Ishii, Hirokazu ; Watakabe, Yuki ; Nemoto, Tomomi ; Yanaka, Saeko ; Kato, Koichi ; Kikuchi, Kazuya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c471t-5f3790822bc03297d94644f4bf84b10d11520590c9f5791e00f4b0c434e605133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Aqueous solutions</topic><topic>Aspartic acid</topic><topic>Biological activity</topic><topic>Cage compounds</topic><topic>Chemistry</topic><topic>Cross-sections</topic><topic>Gametocytes</topic><topic>Hydrophobicity</topic><topic>Near infrared radiation</topic><topic>Optical control</topic><topic>Photolysis</topic><topic>Photons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hashimoto, Ryu</creatorcontrib><creatorcontrib>Minoshima, Masafumi</creatorcontrib><creatorcontrib>Sakata, Souhei</creatorcontrib><creatorcontrib>Ono, Fumihito</creatorcontrib><creatorcontrib>Ishii, Hirokazu</creatorcontrib><creatorcontrib>Watakabe, Yuki</creatorcontrib><creatorcontrib>Nemoto, Tomomi</creatorcontrib><creatorcontrib>Yanaka, Saeko</creatorcontrib><creatorcontrib>Kato, Koichi</creatorcontrib><creatorcontrib>Kikuchi, Kazuya</creatorcontrib><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>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hashimoto, Ryu</au><au>Minoshima, Masafumi</au><au>Sakata, Souhei</au><au>Ono, Fumihito</au><au>Ishii, Hirokazu</au><au>Watakabe, Yuki</au><au>Nemoto, Tomomi</au><au>Yanaka, Saeko</au><au>Kato, Koichi</au><au>Kikuchi, Kazuya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient visible/NIR light-driven uncaging of hydroxylated thiazole orange-based caged compounds in aqueous media</atitle><jtitle>Chemical science (Cambridge)</jtitle><date>2022-06-29</date><risdate>2022</risdate><volume>13</volume><issue>25</issue><spage>7462</spage><epage>7467</epage><pages>7462-7467</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>In photoactivation strategies with bioactive molecules, one-photon visible or two-photon near-infrared light-sensitive caged compounds are desirable tools for biological applications because they offer reduced phototoxicity and deep tissue penetration. However, visible-light-sensitive photoremovable protecting groups (PPGs) reported so far have displayed high hydrophobicity and low uncaging cross sections (
Φ
< 50) in aqueous media, which can obstruct the control of bioactivity with high spatial and temporal precision. In this study, we developed hydroxylated thiazole orange (HTO) derivatives as visible-light-sensitive PPGs with high uncaging cross sections (
Φ
370) in aqueous solution. In addition, 2PE photolysis reactions of HTO-caged glutamate were achieved using a NIR laser (940 nm). Moreover, HTO-caged glutamate can activate
N
-methyl-
d
-aspartic acid receptors in
Xenopus
oocytes and mammalian cells with green-light illumination, thus allowing optical control of biological functions.
A hydroxylated thiazole orange (HTO)-caged glutamate efficiently releases a glutamate for temporal activation of ion channels under visible-to-NIR light in aqueous media.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><pmid>35872806</pmid><doi>10.1039/d2sc02364d</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-8391-194X</orcidid><orcidid>https://orcid.org/0000-0002-3513-5701</orcidid><orcidid>https://orcid.org/0000-0001-6102-1495</orcidid><orcidid>https://orcid.org/0000-0001-7103-1275</orcidid><orcidid>https://orcid.org/0000-0002-6580-1007</orcidid><orcidid>https://orcid.org/0000-0001-7187-9612</orcidid><orcidid>https://orcid.org/0000-0002-9352-3454</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2022-06, Vol.13 (25), p.7462-7467 |
| issn | 2041-6520 2041-6539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2694414841 |
| source | TestCollectionTL3OpenAccess; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; PubMed Central Open Access |
| subjects | Aqueous solutions Aspartic acid Biological activity Cage compounds Chemistry Cross-sections Gametocytes Hydrophobicity Near infrared radiation Optical control Photolysis Photons |
| title | Efficient visible/NIR light-driven uncaging of hydroxylated thiazole orange-based caged compounds in aqueous media |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-13T08%3A57%3A17IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Efficient%20visible/NIR%20light-driven%20uncaging%20of%20hydroxylated%20thiazole%20orange-based%20caged%20compounds%20in%20aqueous%20media&rft.jtitle=Chemical%20science%20(Cambridge)&rft.au=Hashimoto,%20Ryu&rft.date=2022-06-29&rft.volume=13&rft.issue=25&rft.spage=7462&rft.epage=7467&rft.pages=7462-7467&rft.issn=2041-6520&rft.eissn=2041-6539&rft_id=info:doi/10.1039/d2sc02364d&rft_dat=%3Cproquest_pubme%3E2694414841%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2681899690&rft_id=info:pmid/35872806&rfr_iscdi=true |