Water-Soluble NIR Absorbing and Emitting Indolizine Cyanine and Indolizine Squaraine Dyes for Biological Imaging
Organic dyes that absorb and emit in the near-infrared (NIR) region are potentially noninvasive, high-resolution, and rapid biological imaging materials. Indolizine donor-based cyanine and squaraine dyes with water-solubilizing sulfonate groups were targeted in this study due to strong absorptions a...
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| Veröffentlicht in: | Journal of organic chemistry 2020-03, Vol.85 (6), p.4089-4095 |
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| container_title | Journal of organic chemistry |
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| creator | Meador, William E Autry, Shane A Bessetti, Riley N Gayton, Jacqueline N Flynt, Alex S Hammer, Nathan I Delcamp, Jared H |
| description | Organic dyes that absorb and emit in the near-infrared (NIR) region are potentially noninvasive, high-resolution, and rapid biological imaging materials. Indolizine donor-based cyanine and squaraine dyes with water-solubilizing sulfonate groups were targeted in this study due to strong absorptions and emissions in the NIR region. As previously observed for nonwater-soluble derivatives, the indolizine group with water-solubilizing groups retains a substantial shift toward longer wavelengths for both absorption and emission with squaraines and cyanines relative to classically researched indoline donor analogues. Very high quantum yields (as much as 58%) have been observed with absorption and emission >700 nm in fetal bovine serum. Photostability studies, cell culture cytotoxicity, and cell uptake specificity profiles were all studied for these dyes, demonstrating exceptional biological imaging suitability. |
| doi_str_mv | 10.1021/acs.joc.9b03108 |
| format | Article |
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Indolizine donor-based cyanine and squaraine dyes with water-solubilizing sulfonate groups were targeted in this study due to strong absorptions and emissions in the NIR region. As previously observed for nonwater-soluble derivatives, the indolizine group with water-solubilizing groups retains a substantial shift toward longer wavelengths for both absorption and emission with squaraines and cyanines relative to classically researched indoline donor analogues. Very high quantum yields (as much as 58%) have been observed with absorption and emission >700 nm in fetal bovine serum. 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Org. Chem</addtitle><description>Organic dyes that absorb and emit in the near-infrared (NIR) region are potentially noninvasive, high-resolution, and rapid biological imaging materials. Indolizine donor-based cyanine and squaraine dyes with water-solubilizing sulfonate groups were targeted in this study due to strong absorptions and emissions in the NIR region. As previously observed for nonwater-soluble derivatives, the indolizine group with water-solubilizing groups retains a substantial shift toward longer wavelengths for both absorption and emission with squaraines and cyanines relative to classically researched indoline donor analogues. Very high quantum yields (as much as 58%) have been observed with absorption and emission >700 nm in fetal bovine serum. Photostability studies, cell culture cytotoxicity, and cell uptake specificity profiles were all studied for these dyes, demonstrating exceptional biological imaging suitability.</description><subject>bioimaging</subject><subject>cell culture</subject><subject>chemical reactions</subject><subject>chemical structure</subject><subject>Cyclobutanes</subject><subject>cytotoxicity</subject><subject>dyes</subject><subject>emissions</subject><subject>fetal bovine serum</subject><subject>Fluorescent Dyes</subject><subject>Indolizines</subject><subject>near-infrared spectroscopy</subject><subject>Phenols</subject><subject>photostability</subject><subject>sulfonates</subject><subject>Water</subject><subject>water solubility</subject><subject>wavelengths</subject><issn>0022-3263</issn><issn>1520-6904</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc9rFDEUx4Modls9e5M5CjLb_JjMJBehXasuFAVb8BjeJNk1JZNskxlh_eubYddSD2Iu3-S9z_uS5IvQG4KXBFNyDjov76Jeyh4zgsUztCCc4rqVuHmOFhhTWjPashN0mvMdLotz_hKdMIpZJyhfoN0PGG2qb6Kfem-rr-vv1UWfY-pd2FYQTHU1uHGcD-tgone_XbDVag9h1rn_pHxzP0GCefdxb3O1iam6dNHHrdPgq_UA2-LzCr3YgM_29VHP0O2nq9vVl_r62-f16uK6Bk7FWBvbtFyClBwaK43UlFPd9NByoUmRttS5IbpjnZFMYCIl06brMDTEbDA7Qx8OtrupH6zRNowJvNolN0DaqwhO_d0J7qfaxl-qIy0jLS0G744GKd5PNo9qcFlb7yHYOGVFG0ZEI6To_o8yzjAhreAFPT-gOsWck9083ohgNSeqSqKqJKqOiZaJt08f8sj_ibAA7w_AYXJKoXzrP-0eABprrSI</recordid><startdate>20200320</startdate><enddate>20200320</enddate><creator>Meador, William E</creator><creator>Autry, Shane A</creator><creator>Bessetti, Riley N</creator><creator>Gayton, Jacqueline N</creator><creator>Flynt, Alex S</creator><creator>Hammer, Nathan I</creator><creator>Delcamp, Jared H</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>7S9</scope><scope>L.6</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-0601-1603</orcidid><orcidid>https://orcid.org/0000-0002-6221-2709</orcidid><orcidid>https://orcid.org/0000-0001-5313-4078</orcidid><orcidid>https://orcid.org/0000-0002-6872-7885</orcidid><orcidid>https://orcid.org/0000-0002-3564-1663</orcidid><orcidid>https://orcid.org/0000-0002-9869-026X</orcidid></search><sort><creationdate>20200320</creationdate><title>Water-Soluble NIR Absorbing and Emitting Indolizine Cyanine and Indolizine Squaraine Dyes for Biological Imaging</title><author>Meador, William E ; Autry, Shane A ; Bessetti, Riley N ; Gayton, Jacqueline N ; Flynt, Alex S ; Hammer, Nathan I ; Delcamp, Jared H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a528t-de4659a995a4e9d9c252c4ba658c1ba665a45d1c737d93801993cd770a41df03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>bioimaging</topic><topic>cell culture</topic><topic>chemical reactions</topic><topic>chemical structure</topic><topic>Cyclobutanes</topic><topic>cytotoxicity</topic><topic>dyes</topic><topic>emissions</topic><topic>fetal bovine serum</topic><topic>Fluorescent Dyes</topic><topic>Indolizines</topic><topic>near-infrared spectroscopy</topic><topic>Phenols</topic><topic>photostability</topic><topic>sulfonates</topic><topic>Water</topic><topic>water solubility</topic><topic>wavelengths</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Meador, William E</creatorcontrib><creatorcontrib>Autry, Shane A</creatorcontrib><creatorcontrib>Bessetti, Riley N</creatorcontrib><creatorcontrib>Gayton, Jacqueline N</creatorcontrib><creatorcontrib>Flynt, Alex S</creatorcontrib><creatorcontrib>Hammer, Nathan I</creatorcontrib><creatorcontrib>Delcamp, Jared H</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>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Meador, William E</au><au>Autry, Shane A</au><au>Bessetti, Riley N</au><au>Gayton, Jacqueline N</au><au>Flynt, Alex S</au><au>Hammer, Nathan I</au><au>Delcamp, Jared H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Water-Soluble NIR Absorbing and Emitting Indolizine Cyanine and Indolizine Squaraine Dyes for Biological Imaging</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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| subjects | bioimaging cell culture chemical reactions chemical structure Cyclobutanes cytotoxicity dyes emissions fetal bovine serum Fluorescent Dyes Indolizines near-infrared spectroscopy Phenols photostability sulfonates Water water solubility wavelengths |
| title | Water-Soluble NIR Absorbing and Emitting Indolizine Cyanine and Indolizine Squaraine Dyes for Biological Imaging |
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