Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore
New firefly luciferin analogs of the 4,4′-substituted biphenyl-type were synthesized. One analog with a 4′-dimethylamino group possessed bioluminescence activity, emitting near-infrared biological window light at 675 nm suitable for deep-site bioimaging of living animals. The chemiluminescence light...
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| Veröffentlicht in: | Tetrahedron 2013-11, Vol.69 (46), p.9726-9734 |
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| container_end_page | 9734 |
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| container_issue | 46 |
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| container_title | Tetrahedron |
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| creator | Miura, Chihiro Kiyama, Masahiro Iwano, Satoshi Ito, Kazuto Obata, Rika Hirano, Takashi Maki, Shojiro Niwa, Haruki |
| description | New firefly luciferin analogs of the 4,4′-substituted biphenyl-type were synthesized. One analog with a 4′-dimethylamino group possessed bioluminescence activity, emitting near-infrared biological window light at 675 nm suitable for deep-site bioimaging of living animals. The chemiluminescence light-emission maximum of the corresponding methyl ester of the bioluminescence active analog was 500 nm, implying that biphenyl and thiazolinone rings in the light emitter might be placed in a coplanar conformation at the polar luciferase active site.
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| doi_str_mv | 10.1016/j.tet.2013.09.018 |
| format | Article |
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[Display omitted]</description><subject>Analogs</subject><subject>Biological window</subject><subject>Bioluminescence</subject><subject>Biphenyl-type</subject><subject>Chemiluminescence</subject><subject>Emittance</subject><subject>Esters</subject><subject>Fireflies</subject><subject>Firefly luciferin analog</subject><subject>Luminescence</subject><subject>Near-infrared</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kMFu1DAQhi1EJZaWB-DmIweSziTeTSJOqKK0UiUOwNlynMlmVlk72F6qvAGPjZftmYPHl_n-0f8J8R6hRMDd7aFMlMoKsC6hKwHbV2KDaqeKrcLda7EBUFAoqOCNeBvjAQAQq3oj_nxfXZoocpTGDXI-HdlRtOQsySX4hUJiitKPsudlIrfORVoXkiMHGuc1A5ZHCuwybma_j_KZ0ySNdPT8MQ8TCnZjMIFyOO-nVNCRU2K3z4H-3zm_TD7QjbgazRzp3ct_LX7ef_lx91A8ffv6ePf5qbB1DanAobGtQsKm3Y4NdKhsBV1je2v7_CqCqm0HUFWN226ooW5HoyrsewQ7tAD1tfhwyc3tfp0oJn3k3HeejSN_ihobpXYdNB3mVbys2uBjzH31EvhowqoR9Nm6PuhsXZ-ta-h0tp6ZTxeGcoffTEFHy2ebQxZmkx48_4f-CwMPjbU</recordid><startdate>20131118</startdate><enddate>20131118</enddate><creator>Miura, Chihiro</creator><creator>Kiyama, Masahiro</creator><creator>Iwano, Satoshi</creator><creator>Ito, Kazuto</creator><creator>Obata, Rika</creator><creator>Hirano, Takashi</creator><creator>Maki, Shojiro</creator><creator>Niwa, Haruki</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SP</scope><scope>7U5</scope><scope>8FD</scope><scope>FR3</scope><scope>KR7</scope><scope>L7M</scope></search><sort><creationdate>20131118</creationdate><title>Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore</title><author>Miura, Chihiro ; Kiyama, Masahiro ; Iwano, Satoshi ; Ito, Kazuto ; Obata, Rika ; Hirano, Takashi ; Maki, Shojiro ; Niwa, Haruki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c330t-1d7c841e1785f70914c2097cbccbbcc2e0288d0423159d3038fa421bb10cd8003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Analogs</topic><topic>Biological window</topic><topic>Bioluminescence</topic><topic>Biphenyl-type</topic><topic>Chemiluminescence</topic><topic>Emittance</topic><topic>Esters</topic><topic>Fireflies</topic><topic>Firefly luciferin analog</topic><topic>Luminescence</topic><topic>Near-infrared</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miura, Chihiro</creatorcontrib><creatorcontrib>Kiyama, Masahiro</creatorcontrib><creatorcontrib>Iwano, Satoshi</creatorcontrib><creatorcontrib>Ito, Kazuto</creatorcontrib><creatorcontrib>Obata, Rika</creatorcontrib><creatorcontrib>Hirano, Takashi</creatorcontrib><creatorcontrib>Maki, Shojiro</creatorcontrib><creatorcontrib>Niwa, Haruki</creatorcontrib><collection>CrossRef</collection><collection>Electronics & Communications Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Miura, Chihiro</au><au>Kiyama, Masahiro</au><au>Iwano, Satoshi</au><au>Ito, Kazuto</au><au>Obata, Rika</au><au>Hirano, Takashi</au><au>Maki, Shojiro</au><au>Niwa, Haruki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore</atitle><jtitle>Tetrahedron</jtitle><date>2013-11-18</date><risdate>2013</risdate><volume>69</volume><issue>46</issue><spage>9726</spage><epage>9734</epage><pages>9726-9734</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>New firefly luciferin analogs of the 4,4′-substituted biphenyl-type were synthesized. One analog with a 4′-dimethylamino group possessed bioluminescence activity, emitting near-infrared biological window light at 675 nm suitable for deep-site bioimaging of living animals. The chemiluminescence light-emission maximum of the corresponding methyl ester of the bioluminescence active analog was 500 nm, implying that biphenyl and thiazolinone rings in the light emitter might be placed in a coplanar conformation at the polar luciferase active site.
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| source | Elsevier ScienceDirect Journals |
| subjects | Analogs Biological window Bioluminescence Biphenyl-type Chemiluminescence Emittance Esters Fireflies Firefly luciferin analog Luminescence Near-infrared Tetrahedrons |
| title | Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore |
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