Water-Soluble BODIPY Photocages with Tunable Cellular Localization
Photoactivation of bioactive molecules allows manipulation of cellular processes with high spatiotemporal precision. The recent emergence of visible-light excitable photoprotecting groups has the potential to further expand the established utility of the photoactivation strategy in biological applic...
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| Veröffentlicht in: | Journal of the American Chemical Society 2020-03, Vol.142 (11), p.4970-4974 |
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| container_title | Journal of the American Chemical Society |
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| creator | Kand, Dnyaneshwar Liu, Pei Navarro, Marisol X Fischer, Logan J Rousso-Noori, Liat Friedmann-Morvinski, Dinorah Winter, Arthur H Miller, Evan W Weinstain, Roy |
| description | Photoactivation of bioactive molecules allows manipulation of cellular processes with high spatiotemporal precision. The recent emergence of visible-light excitable photoprotecting groups has the potential to further expand the established utility of the photoactivation strategy in biological applications by offering higher tissue penetration, diminished phototoxicity, and compatibility with other light-dependent techniques. Nevertheless, a critical barrier to such applications remains the significant hydrophobicity of most visible-light excitable photocaging groups. Here, we find that applying the conventional 2,6-sulfonation to meso-methyl BODIPY photocages is incompatible with their photoreaction due to an increase in the excited state barrier for photorelease. We present a simple, remote sulfonation solution to BODIPY photocages that imparts water solubility and provides control over cellular permeability while retaining their favorable spectroscopic and photoreaction properties. Peripherally disulfonated BODIPY photocages are cell impermeable, making them useful for modulation of cell-surface receptors, while monosulfonated BODIPY retains the ability to cross the cellular membrane and can modulate intracellular targets. This new approach is generalizable for controlling BODIPY localization and was validated by sensitization of mammalian cells and neurons by visible-light photoactivation of signaling molecules. |
| doi_str_mv | 10.1021/jacs.9b13219 |
| format | Article |
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The recent emergence of visible-light excitable photoprotecting groups has the potential to further expand the established utility of the photoactivation strategy in biological applications by offering higher tissue penetration, diminished phototoxicity, and compatibility with other light-dependent techniques. Nevertheless, a critical barrier to such applications remains the significant hydrophobicity of most visible-light excitable photocaging groups. Here, we find that applying the conventional 2,6-sulfonation to meso-methyl BODIPY photocages is incompatible with their photoreaction due to an increase in the excited state barrier for photorelease. We present a simple, remote sulfonation solution to BODIPY photocages that imparts water solubility and provides control over cellular permeability while retaining their favorable spectroscopic and photoreaction properties. Peripherally disulfonated BODIPY photocages are cell impermeable, making them useful for modulation of cell-surface receptors, while monosulfonated BODIPY retains the ability to cross the cellular membrane and can modulate intracellular targets. This new approach is generalizable for controlling BODIPY localization and was validated by sensitization of mammalian cells and neurons by visible-light photoactivation of signaling molecules.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.9b13219</identifier><identifier>PMID: 32115942</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkanesulfonates - chemical synthesis ; Alkanesulfonates - metabolism ; Alkanesulfonates - radiation effects ; Animals ; Boron Compounds - chemical synthesis ; Boron Compounds - metabolism ; Boron Compounds - radiation effects ; Cell Membrane - metabolism ; Communication ; Dopamine - chemistry ; Dopamine - pharmacology ; Drug Carriers - chemical synthesis ; Drug Carriers - metabolism ; Drug Carriers - radiation effects ; Fluorescent Dyes - chemical synthesis ; Fluorescent Dyes - metabolism ; Fluorescent Dyes - radiation effects ; HEK293 Cells ; Hippocampus - drug effects ; Histamine - chemistry ; Histamine - pharmacology ; Humans ; Light ; Microscopy, Confocal ; Microscopy, Fluorescence ; Molecular Structure ; Neurons - drug effects ; Rats ; Solubility</subject><ispartof>Journal of the American Chemical Society, 2020-03, Vol.142 (11), p.4970-4974</ispartof><rights>Copyright © 2020 American Chemical Society 2020 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a417t-79e703a80924db819ae8f3d08b36373da018727bb60330276ed79c9a6dc8764a3</citedby><cites>FETCH-LOGICAL-a417t-79e703a80924db819ae8f3d08b36373da018727bb60330276ed79c9a6dc8764a3</cites><orcidid>0000-0002-6556-7679 ; 0000-0003-2421-5578 ; 0000-0002-1300-6802 ; 0000-0003-1166-2379</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/jacs.9b13219$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jacs.9b13219$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32115942$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kand, Dnyaneshwar</creatorcontrib><creatorcontrib>Liu, Pei</creatorcontrib><creatorcontrib>Navarro, Marisol X</creatorcontrib><creatorcontrib>Fischer, Logan J</creatorcontrib><creatorcontrib>Rousso-Noori, Liat</creatorcontrib><creatorcontrib>Friedmann-Morvinski, Dinorah</creatorcontrib><creatorcontrib>Winter, Arthur H</creatorcontrib><creatorcontrib>Miller, Evan W</creatorcontrib><creatorcontrib>Weinstain, Roy</creatorcontrib><title>Water-Soluble BODIPY Photocages with Tunable Cellular Localization</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Photoactivation of bioactive molecules allows manipulation of cellular processes with high spatiotemporal precision. The recent emergence of visible-light excitable photoprotecting groups has the potential to further expand the established utility of the photoactivation strategy in biological applications by offering higher tissue penetration, diminished phototoxicity, and compatibility with other light-dependent techniques. Nevertheless, a critical barrier to such applications remains the significant hydrophobicity of most visible-light excitable photocaging groups. Here, we find that applying the conventional 2,6-sulfonation to meso-methyl BODIPY photocages is incompatible with their photoreaction due to an increase in the excited state barrier for photorelease. We present a simple, remote sulfonation solution to BODIPY photocages that imparts water solubility and provides control over cellular permeability while retaining their favorable spectroscopic and photoreaction properties. Peripherally disulfonated BODIPY photocages are cell impermeable, making them useful for modulation of cell-surface receptors, while monosulfonated BODIPY retains the ability to cross the cellular membrane and can modulate intracellular targets. This new approach is generalizable for controlling BODIPY localization and was validated by sensitization of mammalian cells and neurons by visible-light photoactivation of signaling molecules.</description><subject>Alkanesulfonates - chemical synthesis</subject><subject>Alkanesulfonates - metabolism</subject><subject>Alkanesulfonates - radiation effects</subject><subject>Animals</subject><subject>Boron Compounds - chemical synthesis</subject><subject>Boron Compounds - metabolism</subject><subject>Boron Compounds - radiation effects</subject><subject>Cell Membrane - metabolism</subject><subject>Communication</subject><subject>Dopamine - chemistry</subject><subject>Dopamine - pharmacology</subject><subject>Drug Carriers - chemical synthesis</subject><subject>Drug Carriers - metabolism</subject><subject>Drug Carriers - radiation effects</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - metabolism</subject><subject>Fluorescent Dyes - radiation effects</subject><subject>HEK293 Cells</subject><subject>Hippocampus - drug effects</subject><subject>Histamine - chemistry</subject><subject>Histamine - pharmacology</subject><subject>Humans</subject><subject>Light</subject><subject>Microscopy, Confocal</subject><subject>Microscopy, Fluorescence</subject><subject>Molecular Structure</subject><subject>Neurons - drug effects</subject><subject>Rats</subject><subject>Solubility</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkN1LwzAUxYMobk7ffJY--mBnPtomeRHc_BoMNnAiPoXbNts6umYmraJ_vRmbU8Gny-WcnHPzQ-iU4C7BlFwuIHNdmRJGidxDbRJTHMaEJvuojTGmIRcJa6Ej5xZ-jaggh6jlvSSWEW2j3jPU2oaPpmzSUge90c1g_BKM56Y2Gcy0C96Leh5MmgrWcl-XZVOCDYZeLYtPqAtTHaODKZROn2xnBz3d3U76D-FwdD_oXw9DiAivQy41xwwEljTKU0EkaDFlORYpSxhnOWAiOOVpmmDGMOWJzrnMJCR5JngSAeugq03uqkmXOs90VVso1coWS7AfykCh_ipVMVcz86a4j4sx9wHn2wBrXhvtarUsXOa_BJU2jVOUJVJwHvv-DrrYWDNrnLN6uqshWK2xqzV2tcXu7We_T9uZvzn_VK9fLUxjK0_q_6wvmgiK9A</recordid><startdate>20200318</startdate><enddate>20200318</enddate><creator>Kand, Dnyaneshwar</creator><creator>Liu, Pei</creator><creator>Navarro, Marisol X</creator><creator>Fischer, Logan J</creator><creator>Rousso-Noori, Liat</creator><creator>Friedmann-Morvinski, Dinorah</creator><creator>Winter, Arthur H</creator><creator>Miller, Evan W</creator><creator>Weinstain, Roy</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>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-6556-7679</orcidid><orcidid>https://orcid.org/0000-0003-2421-5578</orcidid><orcidid>https://orcid.org/0000-0002-1300-6802</orcidid><orcidid>https://orcid.org/0000-0003-1166-2379</orcidid></search><sort><creationdate>20200318</creationdate><title>Water-Soluble BODIPY Photocages with Tunable Cellular Localization</title><author>Kand, Dnyaneshwar ; Liu, Pei ; Navarro, Marisol X ; Fischer, Logan J ; Rousso-Noori, Liat ; Friedmann-Morvinski, Dinorah ; Winter, Arthur H ; Miller, Evan W ; Weinstain, Roy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a417t-79e703a80924db819ae8f3d08b36373da018727bb60330276ed79c9a6dc8764a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkanesulfonates - chemical synthesis</topic><topic>Alkanesulfonates - metabolism</topic><topic>Alkanesulfonates - radiation effects</topic><topic>Animals</topic><topic>Boron Compounds - chemical synthesis</topic><topic>Boron Compounds - metabolism</topic><topic>Boron Compounds - radiation effects</topic><topic>Cell Membrane - metabolism</topic><topic>Communication</topic><topic>Dopamine - chemistry</topic><topic>Dopamine - pharmacology</topic><topic>Drug Carriers - chemical synthesis</topic><topic>Drug Carriers - metabolism</topic><topic>Drug Carriers - radiation effects</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - metabolism</topic><topic>Fluorescent Dyes - radiation effects</topic><topic>HEK293 Cells</topic><topic>Hippocampus - drug effects</topic><topic>Histamine - chemistry</topic><topic>Histamine - pharmacology</topic><topic>Humans</topic><topic>Light</topic><topic>Microscopy, Confocal</topic><topic>Microscopy, Fluorescence</topic><topic>Molecular Structure</topic><topic>Neurons - drug effects</topic><topic>Rats</topic><topic>Solubility</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kand, Dnyaneshwar</creatorcontrib><creatorcontrib>Liu, Pei</creatorcontrib><creatorcontrib>Navarro, Marisol X</creatorcontrib><creatorcontrib>Fischer, Logan J</creatorcontrib><creatorcontrib>Rousso-Noori, Liat</creatorcontrib><creatorcontrib>Friedmann-Morvinski, Dinorah</creatorcontrib><creatorcontrib>Winter, Arthur H</creatorcontrib><creatorcontrib>Miller, Evan W</creatorcontrib><creatorcontrib>Weinstain, Roy</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kand, Dnyaneshwar</au><au>Liu, Pei</au><au>Navarro, Marisol X</au><au>Fischer, Logan J</au><au>Rousso-Noori, Liat</au><au>Friedmann-Morvinski, Dinorah</au><au>Winter, Arthur H</au><au>Miller, Evan W</au><au>Weinstain, Roy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Water-Soluble BODIPY Photocages with Tunable Cellular Localization</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2020-03-18</date><risdate>2020</risdate><volume>142</volume><issue>11</issue><spage>4970</spage><epage>4974</epage><pages>4970-4974</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Photoactivation of bioactive molecules allows manipulation of cellular processes with high spatiotemporal precision. The recent emergence of visible-light excitable photoprotecting groups has the potential to further expand the established utility of the photoactivation strategy in biological applications by offering higher tissue penetration, diminished phototoxicity, and compatibility with other light-dependent techniques. Nevertheless, a critical barrier to such applications remains the significant hydrophobicity of most visible-light excitable photocaging groups. Here, we find that applying the conventional 2,6-sulfonation to meso-methyl BODIPY photocages is incompatible with their photoreaction due to an increase in the excited state barrier for photorelease. We present a simple, remote sulfonation solution to BODIPY photocages that imparts water solubility and provides control over cellular permeability while retaining their favorable spectroscopic and photoreaction properties. Peripherally disulfonated BODIPY photocages are cell impermeable, making them useful for modulation of cell-surface receptors, while monosulfonated BODIPY retains the ability to cross the cellular membrane and can modulate intracellular targets. 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| source | MEDLINE; ACS Publications |
| subjects | Alkanesulfonates - chemical synthesis Alkanesulfonates - metabolism Alkanesulfonates - radiation effects Animals Boron Compounds - chemical synthesis Boron Compounds - metabolism Boron Compounds - radiation effects Cell Membrane - metabolism Communication Dopamine - chemistry Dopamine - pharmacology Drug Carriers - chemical synthesis Drug Carriers - metabolism Drug Carriers - radiation effects Fluorescent Dyes - chemical synthesis Fluorescent Dyes - metabolism Fluorescent Dyes - radiation effects HEK293 Cells Hippocampus - drug effects Histamine - chemistry Histamine - pharmacology Humans Light Microscopy, Confocal Microscopy, Fluorescence Molecular Structure Neurons - drug effects Rats Solubility |
| title | Water-Soluble BODIPY Photocages with Tunable Cellular Localization |
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