Synthesis and photophysical properties of new SNARF derivatives as dual emission pH sensors
We report the synthesis and properties of two new seminaphthorhodafluor (SNARF) derivatives, SNARF-F and SNARF-Cl. Both these derivatives exhibit typical red shifts of absorption and fluorescence, and higher cell permeability as compared to traditional SNARF, while the pH-dependent dual-emission cha...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2011-03, Vol.21 (6), p.1663-1666 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Nakata, Eiji Nazumi, Yoshijiro Yukimachi, Yoshihiro Uto, Yoshihiro Maezawa, Hiroshi Hashimoto, Toshihiro Okamoto, Yasuko Hori, Hitoshi |
| description | We report the synthesis and properties of two new seminaphthorhodafluor (SNARF) derivatives, SNARF-F and SNARF-Cl. Both these derivatives exhibit typical red shifts of absorption and fluorescence, and higher cell permeability as compared to traditional SNARF, while the pH-dependent dual-emission characteristics are well retained. In particular, the lower p
K
a (7.38) of SNARF-F makes it more suitable than traditional SNARF derivatives for intracellular applications. |
| doi_str_mv | 10.1016/j.bmcl.2011.01.105 |
| format | Article |
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K
a (7.38) of SNARF-F makes it more suitable than traditional SNARF derivatives for intracellular applications.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2011.01.105</identifier><identifier>PMID: 21324690</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>absorption ; Analytical biochemistry: general aspects, technics, instrumentation ; Analytical, structural and metabolic biochemistry ; Benzopyrans - chemical synthesis ; Benzopyrans - chemistry ; Biological and medical sciences ; Cell permeability ; fluorescence ; Fluorescent Dyes - chemical synthesis ; Fluorescent Dyes - chemistry ; Fundamental and applied biological sciences. Psychology ; Hydrogen-Ion Concentration ; Near infrared ; permeability ; pH indicator ; Photochemistry ; Ratiometry ; SNARF ; Spectrometry, Fluorescence</subject><ispartof>Bioorganic & medicinal chemistry letters, 2011-03, Vol.21 (6), p.1663-1666</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c507t-50b8206ad6bf34be3cb5e12e77f966e80c7fd9943f1b3cab26e9aed8202010733</citedby><cites>FETCH-LOGICAL-c507t-50b8206ad6bf34be3cb5e12e77f966e80c7fd9943f1b3cab26e9aed8202010733</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2011.01.105$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27922,27923,45993</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23965642$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21324690$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nakata, Eiji</creatorcontrib><creatorcontrib>Nazumi, Yoshijiro</creatorcontrib><creatorcontrib>Yukimachi, Yoshihiro</creatorcontrib><creatorcontrib>Uto, Yoshihiro</creatorcontrib><creatorcontrib>Maezawa, Hiroshi</creatorcontrib><creatorcontrib>Hashimoto, Toshihiro</creatorcontrib><creatorcontrib>Okamoto, Yasuko</creatorcontrib><creatorcontrib>Hori, Hitoshi</creatorcontrib><title>Synthesis and photophysical properties of new SNARF derivatives as dual emission pH sensors</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>We report the synthesis and properties of two new seminaphthorhodafluor (SNARF) derivatives, SNARF-F and SNARF-Cl. Both these derivatives exhibit typical red shifts of absorption and fluorescence, and higher cell permeability as compared to traditional SNARF, while the pH-dependent dual-emission characteristics are well retained. In particular, the lower p
K
a (7.38) of SNARF-F makes it more suitable than traditional SNARF derivatives for intracellular applications.</description><subject>absorption</subject><subject>Analytical biochemistry: general aspects, technics, instrumentation</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Benzopyrans - chemical synthesis</subject><subject>Benzopyrans - chemistry</subject><subject>Biological and medical sciences</subject><subject>Cell permeability</subject><subject>fluorescence</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydrogen-Ion Concentration</subject><subject>Near infrared</subject><subject>permeability</subject><subject>pH indicator</subject><subject>Photochemistry</subject><subject>Ratiometry</subject><subject>SNARF</subject><subject>Spectrometry, Fluorescence</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU-P0zAQxSMEYsvCF-AAviBOKeP4T2KJy2rFskgrkCgrIXGwHGdCXbVx8KRF_fY4aoEbnCyNf-_5zXNRPOew5MD1m82y3fntsgLOl8DzTD0oFlxqWQoJ6mGxAKOhbIz8elE8IdoAcAlSPi4uKi4qqQ0sim-r4zCtkQIxN3RsXMcpjusjBe-2bExxxDQFJBZ7NuBPtvp49fmGdZjCwU3hkC8csW6fWdwFohAHNt4ywoFioqfFo95tCZ-dz8vi_ubdl-vb8u7T-w_XV3elV1BPpYK2qUC7Tre9kC0K3yrkFdZ1b7TGBnzdd8ZI0fNWeNdWGo3DLmvy5lALcVm8PvnmvD_2SJPNWTxut27AuCfbGMNFLbn-P6mUgUbI2bM6kT5FooS9HVPYuXS0HOzcvt3YuX07t2-B55nKohdn-327w-6P5HfdGXh1BhzlgvvkBh_oLyeMVlpWmXt54noXrfueMnO_yi-p_IVCKpg3eXsiMBd7CJgs-YCDxy4k9JPtYvhX0l92L6wT</recordid><startdate>20110315</startdate><enddate>20110315</enddate><creator>Nakata, Eiji</creator><creator>Nazumi, Yoshijiro</creator><creator>Yukimachi, Yoshihiro</creator><creator>Uto, Yoshihiro</creator><creator>Maezawa, Hiroshi</creator><creator>Hashimoto, Toshihiro</creator><creator>Okamoto, Yasuko</creator><creator>Hori, Hitoshi</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20110315</creationdate><title>Synthesis and photophysical properties of new SNARF derivatives as dual emission pH sensors</title><author>Nakata, Eiji ; Nazumi, Yoshijiro ; Yukimachi, Yoshihiro ; Uto, Yoshihiro ; Maezawa, Hiroshi ; Hashimoto, Toshihiro ; Okamoto, Yasuko ; Hori, Hitoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c507t-50b8206ad6bf34be3cb5e12e77f966e80c7fd9943f1b3cab26e9aed8202010733</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>absorption</topic><topic>Analytical biochemistry: general aspects, technics, instrumentation</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Benzopyrans - chemical synthesis</topic><topic>Benzopyrans - chemistry</topic><topic>Biological and medical sciences</topic><topic>Cell permeability</topic><topic>fluorescence</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Fundamental and applied biological sciences. 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K
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| ispartof | Bioorganic & medicinal chemistry letters, 2011-03, Vol.21 (6), p.1663-1666 |
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| subjects | absorption Analytical biochemistry: general aspects, technics, instrumentation Analytical, structural and metabolic biochemistry Benzopyrans - chemical synthesis Benzopyrans - chemistry Biological and medical sciences Cell permeability fluorescence Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry Fundamental and applied biological sciences. Psychology Hydrogen-Ion Concentration Near infrared permeability pH indicator Photochemistry Ratiometry SNARF Spectrometry, Fluorescence |
| title | Synthesis and photophysical properties of new SNARF derivatives as dual emission pH sensors |
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