Highly Efficient and Photostable Photosensitizer Based on BODIPY Chromophore
Photosensitizers are reagents that produce reactive oxygen species upon light illumination and are commonly used to study oxidative stress or for photodynamic therapy. There are many available photosensitizers, but most have limitations, such as low photostability, structural instability, or a limit...
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| Veröffentlicht in: | Journal of the American Chemical Society 2005-09, Vol.127 (35), p.12162-12163 |
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| container_end_page | 12163 |
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| container_issue | 35 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 127 |
| creator | Yogo, Takatoshi Urano, Yasuteru Ishitsuka, Yukiko Maniwa, Fumio Nagano, Tetsuo |
| description | Photosensitizers are reagents that produce reactive oxygen species upon light illumination and are commonly used to study oxidative stress or for photodynamic therapy. There are many available photosensitizers, but most have limitations, such as low photostability, structural instability, or a limited usable range of solvent conditions. Here, we describe a novel photosensitizer scaffold (2I-BDP) based on the unique characteristics of the BODIPY chromophore (i.e., high extinction coefficient, high photostability, and insensitivity to solvent environment). 2I-BDP shows stronger near-infrared singlet oxygen luminescence emission and higher photostability than the well-known photosensitizer, Rose Bengal. Unlike other photosensitizers, this scaffold is widely applicable under various conditions, including lipophilic and aqueous environments. HeLa cells loaded with 2I-BDP could be photosensitized by light illumination, demonstrating that 2I-BDP is potentially useful as a reagent for cell photosensitization, oxidative stress studies, or PDT. |
| doi_str_mv | 10.1021/ja0528533 |
| format | Article |
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There are many available photosensitizers, but most have limitations, such as low photostability, structural instability, or a limited usable range of solvent conditions. Here, we describe a novel photosensitizer scaffold (2I-BDP) based on the unique characteristics of the BODIPY chromophore (i.e., high extinction coefficient, high photostability, and insensitivity to solvent environment). 2I-BDP shows stronger near-infrared singlet oxygen luminescence emission and higher photostability than the well-known photosensitizer, Rose Bengal. Unlike other photosensitizers, this scaffold is widely applicable under various conditions, including lipophilic and aqueous environments. HeLa cells loaded with 2I-BDP could be photosensitized by light illumination, demonstrating that 2I-BDP is potentially useful as a reagent for cell photosensitization, oxidative stress studies, or PDT.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja0528533</identifier><identifier>PMID: 16131160</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Biological and medical sciences ; Biological effects of radiation ; Boron Compounds - chemistry ; Fluorescent Dyes - chemistry ; Fundamental and applied biological sciences. Psychology ; Molecular biophysics ; Photochemistry. Photosynthesis. Bioluminescence ; Photosensitizing Agents - chemistry ; Radiation-biomolecule interaction ; Radiosensitizing agents. Photosensitizing agents. Thermosensitizing agents ; Rose Bengal - chemistry ; Spectroscopy, Near-Infrared ; Tissues, organs and organisms biophysics</subject><ispartof>Journal of the American Chemical Society, 2005-09, Vol.127 (35), p.12162-12163</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a484t-ff1a1bf1c9fcb9166811e77988ee2b4250c46eccf3f74040279962fe1a1fa0b73</citedby><cites>FETCH-LOGICAL-a484t-ff1a1bf1c9fcb9166811e77988ee2b4250c46eccf3f74040279962fe1a1fa0b73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja0528533$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja0528533$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17098991$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16131160$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yogo, Takatoshi</creatorcontrib><creatorcontrib>Urano, Yasuteru</creatorcontrib><creatorcontrib>Ishitsuka, Yukiko</creatorcontrib><creatorcontrib>Maniwa, Fumio</creatorcontrib><creatorcontrib>Nagano, Tetsuo</creatorcontrib><title>Highly Efficient and Photostable Photosensitizer Based on BODIPY Chromophore</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Photosensitizers are reagents that produce reactive oxygen species upon light illumination and are commonly used to study oxidative stress or for photodynamic therapy. There are many available photosensitizers, but most have limitations, such as low photostability, structural instability, or a limited usable range of solvent conditions. Here, we describe a novel photosensitizer scaffold (2I-BDP) based on the unique characteristics of the BODIPY chromophore (i.e., high extinction coefficient, high photostability, and insensitivity to solvent environment). 2I-BDP shows stronger near-infrared singlet oxygen luminescence emission and higher photostability than the well-known photosensitizer, Rose Bengal. Unlike other photosensitizers, this scaffold is widely applicable under various conditions, including lipophilic and aqueous environments. HeLa cells loaded with 2I-BDP could be photosensitized by light illumination, demonstrating that 2I-BDP is potentially useful as a reagent for cell photosensitization, oxidative stress studies, or PDT.</description><subject>Biological and medical sciences</subject><subject>Biological effects of radiation</subject><subject>Boron Compounds - chemistry</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Molecular biophysics</subject><subject>Photochemistry. Photosynthesis. Bioluminescence</subject><subject>Photosensitizing Agents - chemistry</subject><subject>Radiation-biomolecule interaction</subject><subject>Radiosensitizing agents. Photosensitizing agents. Thermosensitizing agents</subject><subject>Rose Bengal - chemistry</subject><subject>Spectroscopy, Near-Infrared</subject><subject>Tissues, organs and organisms biophysics</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1P4zAQhi3ECgrLgT-AcgGJQ3Y9TmLHR1o-WqkSlbar1Z4sxx1TlzQudioBv56gRvTCaWY0z7waPYScA_0FlMHvlaYFK4ssOyADKBhNC2D8kAwopSwVJc-OyUmMq27MWQlH5Bg4ZACcDsh07J6W9VtyZ60zDps20c0imS1962Orqxr7HpvoWveOIRnqiIvEN8nw8XYy-5-MlsGv_WbpA_4kP6yuI5719ZT8vb-bj8bp9PFhMrqZpjov8za1FjRUFoy0ppLAeQmAQsiyRGRVzgpqco7G2MyKnOaUCSk5s9hdWU0rkZ2Sq13uJviXLcZWrV00WNe6Qb-NincuClnkHXi9A03wMQa0ahPcWoc3BVR9qlNf6jr2og_dVmtc7MneVQdc9oCORtc26Ma4uOcElaWU0HHpjnOxxdevvQ7PiotMFGo--6PYMLv_NxVzxfe52kS18tvQdO6-efAD7iSPrw</recordid><startdate>20050907</startdate><enddate>20050907</enddate><creator>Yogo, Takatoshi</creator><creator>Urano, Yasuteru</creator><creator>Ishitsuka, Yukiko</creator><creator>Maniwa, Fumio</creator><creator>Nagano, Tetsuo</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><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></search><sort><creationdate>20050907</creationdate><title>Highly Efficient and Photostable Photosensitizer Based on BODIPY Chromophore</title><author>Yogo, Takatoshi ; Urano, Yasuteru ; Ishitsuka, Yukiko ; Maniwa, Fumio ; Nagano, Tetsuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a484t-ff1a1bf1c9fcb9166811e77988ee2b4250c46eccf3f74040279962fe1a1fa0b73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Biological and medical sciences</topic><topic>Biological effects of radiation</topic><topic>Boron Compounds - chemistry</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Molecular biophysics</topic><topic>Photochemistry. Photosynthesis. Bioluminescence</topic><topic>Photosensitizing Agents - chemistry</topic><topic>Radiation-biomolecule interaction</topic><topic>Radiosensitizing agents. Photosensitizing agents. Thermosensitizing agents</topic><topic>Rose Bengal - chemistry</topic><topic>Spectroscopy, Near-Infrared</topic><topic>Tissues, organs and organisms biophysics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yogo, Takatoshi</creatorcontrib><creatorcontrib>Urano, Yasuteru</creatorcontrib><creatorcontrib>Ishitsuka, Yukiko</creatorcontrib><creatorcontrib>Maniwa, Fumio</creatorcontrib><creatorcontrib>Nagano, Tetsuo</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><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><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yogo, Takatoshi</au><au>Urano, Yasuteru</au><au>Ishitsuka, Yukiko</au><au>Maniwa, Fumio</au><au>Nagano, Tetsuo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly Efficient and Photostable Photosensitizer Based on BODIPY Chromophore</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2005-09-07</date><risdate>2005</risdate><volume>127</volume><issue>35</issue><spage>12162</spage><epage>12163</epage><pages>12162-12163</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>Photosensitizers are reagents that produce reactive oxygen species upon light illumination and are commonly used to study oxidative stress or for photodynamic therapy. There are many available photosensitizers, but most have limitations, such as low photostability, structural instability, or a limited usable range of solvent conditions. Here, we describe a novel photosensitizer scaffold (2I-BDP) based on the unique characteristics of the BODIPY chromophore (i.e., high extinction coefficient, high photostability, and insensitivity to solvent environment). 2I-BDP shows stronger near-infrared singlet oxygen luminescence emission and higher photostability than the well-known photosensitizer, Rose Bengal. 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| subjects | Biological and medical sciences Biological effects of radiation Boron Compounds - chemistry Fluorescent Dyes - chemistry Fundamental and applied biological sciences. Psychology Molecular biophysics Photochemistry. Photosynthesis. Bioluminescence Photosensitizing Agents - chemistry Radiation-biomolecule interaction Radiosensitizing agents. Photosensitizing agents. Thermosensitizing agents Rose Bengal - chemistry Spectroscopy, Near-Infrared Tissues, organs and organisms biophysics |
| title | Highly Efficient and Photostable Photosensitizer Based on BODIPY Chromophore |
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