Diversity-Oriented Synthesis of Highly Fluorescent Fused Isoquinolines for Specific Subcellular Localization
A multicomponent diversity-oriented synthesis of new highly emissive tetracyclic isoquinolines that target specific organelles is described. The title compounds were prepared via a three-step protocol starting with an Ugi four-component reaction, followed by either an intramolecular alkyne hydroaryl...
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| Veröffentlicht in: | Journal of organic chemistry 2020-01, Vol.85 (2), p.633-649 |
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| container_title | Journal of organic chemistry |
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| creator | Amador-Sánchez, Yoarhy A Aguilar-Granda, Andrés Flores-Cruz, Ricardo González-Calderón, Davir Orta, Cynthia Rodríguez-Molina, Braulio Jiménez-Sánchez, Arturo Miranda, Luis D |
| description | A multicomponent diversity-oriented synthesis of new highly emissive tetracyclic isoquinolines that target specific organelles is described. The title compounds were prepared via a three-step protocol starting with an Ugi four-component reaction, followed by either an intramolecular alkyne hydroarylation and subsequent alkene isomerization or through a Pomeranz–Fritsch-type cyclization with a final intramolecular Heck reaction. Subcellular localization studies of these compounds using green channel confocal microscopy revealed remarkable and distinctive distribution patterns in live cells, showing an unprecedented high selectivity and imaging contrast. The differentiated organelle visualizationincluding localizers for mitochondria, lysosomes, Golgi apparatus, endoplasmic reticulum, and plasma membranewas achieved by varying the nature of the tetracyclic system and substituent pattern, changing the original four-component set in the starting Ugi reaction. |
| doi_str_mv | 10.1021/acs.joc.9b02712 |
| format | Article |
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Org. Chem</addtitle><description>A multicomponent diversity-oriented synthesis of new highly emissive tetracyclic isoquinolines that target specific organelles is described. The title compounds were prepared via a three-step protocol starting with an Ugi four-component reaction, followed by either an intramolecular alkyne hydroarylation and subsequent alkene isomerization or through a Pomeranz–Fritsch-type cyclization with a final intramolecular Heck reaction. Subcellular localization studies of these compounds using green channel confocal microscopy revealed remarkable and distinctive distribution patterns in live cells, showing an unprecedented high selectivity and imaging contrast. The differentiated organelle visualizationincluding localizers for mitochondria, lysosomes, Golgi apparatus, endoplasmic reticulum, and plasma membranewas achieved by varying the nature of the tetracyclic system and substituent pattern, changing the original four-component set in the starting Ugi reaction.</description><subject>Fluorescent Dyes - chemistry</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Isoquinolines - chemical synthesis</subject><subject>Isoquinolines - chemistry</subject><subject>Isoquinolines - metabolism</subject><subject>Subcellular Fractions - metabolism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kD1PwzAQhi0EgvIxsyGPSCitPxI7HRFQilSJoTBHjnOmrty42AlS-PW4amHjllue99Xdg9A1JWNKGJ0oHcdrr8fTmjBJ2REa0YKRTExJfoxGhDCWcSb4GTqPcU3SFEVxis44LTmRUo6Qe7RfEKLthuw1WGg7aPByaLsVRBuxN3huP1ZuwDPX-wBRJwLP-piol-g_e9t6Z1uI2PiAl1vQ1liNl32twbneqYAXXitnv1VnfXuJToxyEa4O-wK9z57eHubZ4vX55eF-kSnOeZdNmWgKBrIgoiFUUVlDTkrOa01ZLuomLwXXpaCF1jmppTGyLFQDOgchqTE5v0C3-95tSDdC7KqNjbuLVAu-jxXj6fspF1QmdLJHdfAxBjDVNtiNCkNFSbVTXCXFVVJcHRSnxM2hvK830Pzxv04TcLcH9sk-tOnXf-t-AHuBiK8</recordid><startdate>20200117</startdate><enddate>20200117</enddate><creator>Amador-Sánchez, Yoarhy A</creator><creator>Aguilar-Granda, Andrés</creator><creator>Flores-Cruz, Ricardo</creator><creator>González-Calderón, Davir</creator><creator>Orta, Cynthia</creator><creator>Rodríguez-Molina, Braulio</creator><creator>Jiménez-Sánchez, Arturo</creator><creator>Miranda, Luis D</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><orcidid>https://orcid.org/0000-0002-8757-4589</orcidid><orcidid>https://orcid.org/0000-0002-1851-9957</orcidid><orcidid>https://orcid.org/0000-0003-0342-8160</orcidid></search><sort><creationdate>20200117</creationdate><title>Diversity-Oriented Synthesis of Highly Fluorescent Fused Isoquinolines for Specific Subcellular Localization</title><author>Amador-Sánchez, Yoarhy A ; Aguilar-Granda, Andrés ; Flores-Cruz, Ricardo ; González-Calderón, Davir ; Orta, Cynthia ; Rodríguez-Molina, Braulio ; Jiménez-Sánchez, Arturo ; Miranda, Luis D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-926d52e7506d01a17be40833bc1246bd4863c8615cc40b7ff785adec4e671ff43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Fluorescent Dyes - chemistry</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Isoquinolines - chemical synthesis</topic><topic>Isoquinolines - chemistry</topic><topic>Isoquinolines - metabolism</topic><topic>Subcellular Fractions - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Amador-Sánchez, Yoarhy A</creatorcontrib><creatorcontrib>Aguilar-Granda, Andrés</creatorcontrib><creatorcontrib>Flores-Cruz, Ricardo</creatorcontrib><creatorcontrib>González-Calderón, Davir</creatorcontrib><creatorcontrib>Orta, Cynthia</creatorcontrib><creatorcontrib>Rodríguez-Molina, Braulio</creatorcontrib><creatorcontrib>Jiménez-Sánchez, Arturo</creatorcontrib><creatorcontrib>Miranda, Luis D</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><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Amador-Sánchez, Yoarhy A</au><au>Aguilar-Granda, Andrés</au><au>Flores-Cruz, Ricardo</au><au>González-Calderón, Davir</au><au>Orta, Cynthia</au><au>Rodríguez-Molina, Braulio</au><au>Jiménez-Sánchez, Arturo</au><au>Miranda, Luis D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diversity-Oriented Synthesis of Highly Fluorescent Fused Isoquinolines for Specific Subcellular Localization</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2020-01-17</date><risdate>2020</risdate><volume>85</volume><issue>2</issue><spage>633</spage><epage>649</epage><pages>633-649</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A multicomponent diversity-oriented synthesis of new highly emissive tetracyclic isoquinolines that target specific organelles is described. The title compounds were prepared via a three-step protocol starting with an Ugi four-component reaction, followed by either an intramolecular alkyne hydroarylation and subsequent alkene isomerization or through a Pomeranz–Fritsch-type cyclization with a final intramolecular Heck reaction. Subcellular localization studies of these compounds using green channel confocal microscopy revealed remarkable and distinctive distribution patterns in live cells, showing an unprecedented high selectivity and imaging contrast. 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| subjects | Fluorescent Dyes - chemistry HeLa Cells Humans Isoquinolines - chemical synthesis Isoquinolines - chemistry Isoquinolines - metabolism Subcellular Fractions - metabolism |
| title | Diversity-Oriented Synthesis of Highly Fluorescent Fused Isoquinolines for Specific Subcellular Localization |
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