Synthesis of One Double Bond-Inserted Retinal Analogs and Their Binding Experiments with Opsins: Preparation of Novel Red-Shifted Channelrhodopsin Variants
In optogenetics, red-shifted channelrhodopsins (ChRs) are eagerly sought. We prepared six kinds of new chromophores with one double bond inserted into the polyene side chain of retinal (A1) or 3,4-didehydroretinal (A2), and examined their binding efficiency with opsins (ReaChR and ChrimsonR). All an...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2020/03/01, Vol.68(3), pp.265-272 |
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| creator | Okitsu, Takashi Yamano, Yumiko Shen, Yi-Chung Sasaki, Toshikazu Kobayashi, Yuka Morisawa, Shoko Yamashita, Takahiro Imamoto, Yasushi Shichida, Yoshinori Wada, Akimori |
| description | In optogenetics, red-shifted channelrhodopsins (ChRs) are eagerly sought. We prepared six kinds of new chromophores with one double bond inserted into the polyene side chain of retinal (A1) or 3,4-didehydroretinal (A2), and examined their binding efficiency with opsins (ReaChR and ChrimsonR). All analogs bound with opsins to afford new ChRs. Among them, A2-10ex (an extra double bond is inserted at the C10–C11 position of A2) showed the greatest red-shift in the absorption spectrum of ChrimsonR, with a maximum absorbance at 654 nm (67 nm red-shifted from that of A1-ChrimsonR). Moreover, a long-wavelength spectral boundary of A2-10ex-ChrimsonR was extended to 756 nm, which reached into the far-red region (710–850 nm). |
| doi_str_mv | 10.1248/cpb.c19-01005 |
| format | Article |
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We prepared six kinds of new chromophores with one double bond inserted into the polyene side chain of retinal (A1) or 3,4-didehydroretinal (A2), and examined their binding efficiency with opsins (ReaChR and ChrimsonR). All analogs bound with opsins to afford new ChRs. Among them, A2-10ex (an extra double bond is inserted at the C10–C11 position of A2) showed the greatest red-shift in the absorption spectrum of ChrimsonR, with a maximum absorbance at 654 nm (67 nm red-shifted from that of A1-ChrimsonR). Moreover, a long-wavelength spectral boundary of A2-10ex-ChrimsonR was extended to 756 nm, which reached into the far-red region (710–850 nm).</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c19-01005</identifier><identifier>PMID: 32115534</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Absorption spectra ; Analogs ; Binding ; Binding Sites ; channelrhodopsin ; Channelrhodopsins - chemistry ; Channelrhodopsins - genetics ; Channelrhodopsins - metabolism ; chromophore ; Chromophores ; Doppler effect ; Genetics ; HEK293 Cells ; Humans ; Information processing ; Molecular Structure ; Opsins ; Optics ; optogenetics ; Red shift ; Retina ; retinal analog ; Retinaldehyde - analogs & derivatives ; Retinaldehyde - chemical synthesis ; Retinaldehyde - chemistry ; Structure-Activity Relationship</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2020/03/01, Vol.68(3), pp.265-272</ispartof><rights>2020 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c510t-aad38ea2ec462b2390603a01b5c7a488ef9a885613a4a3fee8cdb240491b46b43</citedby><cites>FETCH-LOGICAL-c510t-aad38ea2ec462b2390603a01b5c7a488ef9a885613a4a3fee8cdb240491b46b43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32115534$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Okitsu, Takashi</creatorcontrib><creatorcontrib>Yamano, Yumiko</creatorcontrib><creatorcontrib>Shen, Yi-Chung</creatorcontrib><creatorcontrib>Sasaki, Toshikazu</creatorcontrib><creatorcontrib>Kobayashi, Yuka</creatorcontrib><creatorcontrib>Morisawa, Shoko</creatorcontrib><creatorcontrib>Yamashita, Takahiro</creatorcontrib><creatorcontrib>Imamoto, Yasushi</creatorcontrib><creatorcontrib>Shichida, Yoshinori</creatorcontrib><creatorcontrib>Wada, Akimori</creatorcontrib><title>Synthesis of One Double Bond-Inserted Retinal Analogs and Their Binding Experiments with Opsins: Preparation of Novel Red-Shifted Channelrhodopsin Variants</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>In optogenetics, red-shifted channelrhodopsins (ChRs) are eagerly sought. We prepared six kinds of new chromophores with one double bond inserted into the polyene side chain of retinal (A1) or 3,4-didehydroretinal (A2), and examined their binding efficiency with opsins (ReaChR and ChrimsonR). All analogs bound with opsins to afford new ChRs. Among them, A2-10ex (an extra double bond is inserted at the C10–C11 position of A2) showed the greatest red-shift in the absorption spectrum of ChrimsonR, with a maximum absorbance at 654 nm (67 nm red-shifted from that of A1-ChrimsonR). Moreover, a long-wavelength spectral boundary of A2-10ex-ChrimsonR was extended to 756 nm, which reached into the far-red region (710–850 nm).</description><subject>Absorption spectra</subject><subject>Analogs</subject><subject>Binding</subject><subject>Binding Sites</subject><subject>channelrhodopsin</subject><subject>Channelrhodopsins - chemistry</subject><subject>Channelrhodopsins - genetics</subject><subject>Channelrhodopsins - metabolism</subject><subject>chromophore</subject><subject>Chromophores</subject><subject>Doppler effect</subject><subject>Genetics</subject><subject>HEK293 Cells</subject><subject>Humans</subject><subject>Information processing</subject><subject>Molecular Structure</subject><subject>Opsins</subject><subject>Optics</subject><subject>optogenetics</subject><subject>Red shift</subject><subject>Retina</subject><subject>retinal analog</subject><subject>Retinaldehyde - analogs & derivatives</subject><subject>Retinaldehyde - chemical synthesis</subject><subject>Retinaldehyde - chemistry</subject><subject>Structure-Activity Relationship</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkU1v1DAQhiMEokvhyBVZ4sIlrb-Sdbi1S6GVKhbRwtWaJJONV1k7tR2gv4U_i9Mti8RlfJjHz0jvm2WvGT1hXKrTZqxPGlbllFFaPMkWTMhlXnAunmYLSmmVc1GKo-xFCFtKeUGX4nl2JDhjRSHkIvt9c29jj8EE4jqytkg-uKkekJw72-ZXNqCP2JKvGI2FgZyl4TaBgG3JbY_Gk3NjW2M35OLXiN7s0MZAfprYk_UYjA3vyRePI3iIxtn5xGf3A4fka_Ob3nSze9WDtTj43rVu_kO-gzeQPC-zZx0MAV89vsfZt48Xt6vL_Hr96Wp1dp03BaMxB2iFQuDYyJLXXFS0pAIoq4tmCVIp7CpQqiiZAAmiQ1RNW3NJZcVqWdZSHGfv9t7Ru7sJQ9Q7ExocBrDopqBTgpVaKkFpQt_-h27d5FMoe6rglEmVqHxPNd6F4LHTY4oG_L1mVM-t6dSaTq3ph9YS_-bROtU7bA_035oSsNoD2xBhgwcAfDTNgA-6Umkxj4P237YHr9GKPz6vrHg</recordid><startdate>20200301</startdate><enddate>20200301</enddate><creator>Okitsu, Takashi</creator><creator>Yamano, Yumiko</creator><creator>Shen, Yi-Chung</creator><creator>Sasaki, Toshikazu</creator><creator>Kobayashi, Yuka</creator><creator>Morisawa, Shoko</creator><creator>Yamashita, Takahiro</creator><creator>Imamoto, Yasushi</creator><creator>Shichida, Yoshinori</creator><creator>Wada, Akimori</creator><general>The Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>20200301</creationdate><title>Synthesis of One Double Bond-Inserted Retinal Analogs and Their Binding Experiments with Opsins: Preparation of Novel Red-Shifted Channelrhodopsin Variants</title><author>Okitsu, Takashi ; Yamano, Yumiko ; Shen, Yi-Chung ; Sasaki, Toshikazu ; Kobayashi, Yuka ; Morisawa, Shoko ; Yamashita, Takahiro ; Imamoto, Yasushi ; Shichida, Yoshinori ; Wada, Akimori</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c510t-aad38ea2ec462b2390603a01b5c7a488ef9a885613a4a3fee8cdb240491b46b43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Absorption spectra</topic><topic>Analogs</topic><topic>Binding</topic><topic>Binding Sites</topic><topic>channelrhodopsin</topic><topic>Channelrhodopsins - chemistry</topic><topic>Channelrhodopsins - genetics</topic><topic>Channelrhodopsins - metabolism</topic><topic>chromophore</topic><topic>Chromophores</topic><topic>Doppler effect</topic><topic>Genetics</topic><topic>HEK293 Cells</topic><topic>Humans</topic><topic>Information processing</topic><topic>Molecular Structure</topic><topic>Opsins</topic><topic>Optics</topic><topic>optogenetics</topic><topic>Red shift</topic><topic>Retina</topic><topic>retinal analog</topic><topic>Retinaldehyde - analogs & derivatives</topic><topic>Retinaldehyde - chemical synthesis</topic><topic>Retinaldehyde - chemistry</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Okitsu, Takashi</creatorcontrib><creatorcontrib>Yamano, Yumiko</creatorcontrib><creatorcontrib>Shen, Yi-Chung</creatorcontrib><creatorcontrib>Sasaki, Toshikazu</creatorcontrib><creatorcontrib>Kobayashi, Yuka</creatorcontrib><creatorcontrib>Morisawa, Shoko</creatorcontrib><creatorcontrib>Yamashita, Takahiro</creatorcontrib><creatorcontrib>Imamoto, Yasushi</creatorcontrib><creatorcontrib>Shichida, Yoshinori</creatorcontrib><creatorcontrib>Wada, Akimori</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Okitsu, Takashi</au><au>Yamano, Yumiko</au><au>Shen, Yi-Chung</au><au>Sasaki, Toshikazu</au><au>Kobayashi, Yuka</au><au>Morisawa, Shoko</au><au>Yamashita, Takahiro</au><au>Imamoto, Yasushi</au><au>Shichida, Yoshinori</au><au>Wada, Akimori</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of One Double Bond-Inserted Retinal Analogs and Their Binding Experiments with Opsins: Preparation of Novel Red-Shifted Channelrhodopsin Variants</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2020-03-01</date><risdate>2020</risdate><volume>68</volume><issue>3</issue><spage>265</spage><epage>272</epage><pages>265-272</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>In optogenetics, red-shifted channelrhodopsins (ChRs) are eagerly sought. We prepared six kinds of new chromophores with one double bond inserted into the polyene side chain of retinal (A1) or 3,4-didehydroretinal (A2), and examined their binding efficiency with opsins (ReaChR and ChrimsonR). All analogs bound with opsins to afford new ChRs. Among them, A2-10ex (an extra double bond is inserted at the C10–C11 position of A2) showed the greatest red-shift in the absorption spectrum of ChrimsonR, with a maximum absorbance at 654 nm (67 nm red-shifted from that of A1-ChrimsonR). Moreover, a long-wavelength spectral boundary of A2-10ex-ChrimsonR was extended to 756 nm, which reached into the far-red region (710–850 nm).</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>32115534</pmid><doi>10.1248/cpb.c19-01005</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Absorption spectra Analogs Binding Binding Sites channelrhodopsin Channelrhodopsins - chemistry Channelrhodopsins - genetics Channelrhodopsins - metabolism chromophore Chromophores Doppler effect Genetics HEK293 Cells Humans Information processing Molecular Structure Opsins Optics optogenetics Red shift Retina retinal analog Retinaldehyde - analogs & derivatives Retinaldehyde - chemical synthesis Retinaldehyde - chemistry Structure-Activity Relationship |
| title | Synthesis of One Double Bond-Inserted Retinal Analogs and Their Binding Experiments with Opsins: Preparation of Novel Red-Shifted Channelrhodopsin Variants |
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