Synthesis and biological evaluation of cationic TopFluor cholesterol analogues
[Display omitted] Cholesterol is not only a major component of the cell membrane, but also plays an important role in a wide range of biological processes and pathologies. It is therefore crucial to develop appropriate tools for visualizing intracellular cholesterol transport. Here, we describe new...
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| Veröffentlicht in: | Bioorganic chemistry 2021-12, Vol.117, p.105410-105410, Article 105410 |
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| container_title | Bioorganic chemistry |
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| creator | Jurášek, Michal Valečka, Jan Novotný, Ivan Kejík, Zdeněk Fähnrich, Jan Marešová, Anna Tauchen, Jan Bartůněk, Petr Dolenský, Bohumil Jakubek, Milan Drašar, Pavel B. Králová, Jarmila |
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Cholesterol is not only a major component of the cell membrane, but also plays an important role in a wide range of biological processes and pathologies. It is therefore crucial to develop appropriate tools for visualizing intracellular cholesterol transport. Here, we describe new cationic analogues of BODIPY-Cholesterol (TopFluor-Cholesterol, TF-Chol), which combine a positive charge on the sterol side chain and a BODIPY group connected via a C-4 linker. In contrast to TF-Chol, the new analogues TF-1 and TF-3 possessing acetyl groups on the A ring (C-3 position on steroid) internalized much faster and displayed slightly different levels of intracellular localization. Their applicability for cholesterol monitoring was indicated by the fact that they strongly label compartments with accumulated cholesterol in cells carrying a mutation of the Niemann-Pick disease-associated cholesterol transporter, NPC1. |
| doi_str_mv | 10.1016/j.bioorg.2021.105410 |
| format | Article |
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Cholesterol is not only a major component of the cell membrane, but also plays an important role in a wide range of biological processes and pathologies. It is therefore crucial to develop appropriate tools for visualizing intracellular cholesterol transport. Here, we describe new cationic analogues of BODIPY-Cholesterol (TopFluor-Cholesterol, TF-Chol), which combine a positive charge on the sterol side chain and a BODIPY group connected via a C-4 linker. In contrast to TF-Chol, the new analogues TF-1 and TF-3 possessing acetyl groups on the A ring (C-3 position on steroid) internalized much faster and displayed slightly different levels of intracellular localization. Their applicability for cholesterol monitoring was indicated by the fact that they strongly label compartments with accumulated cholesterol in cells carrying a mutation of the Niemann-Pick disease-associated cholesterol transporter, NPC1.</description><identifier>ISSN: 0045-2068</identifier><identifier>EISSN: 1090-2120</identifier><identifier>DOI: 10.1016/j.bioorg.2021.105410</identifier><identifier>PMID: 34700109</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Biological Transport ; Boron Compounds - analysis ; Boron Compounds - chemical synthesis ; Boron Compounds - chemistry ; Boron Compounds - metabolism ; Cell Line ; Cholesterol - analogs & derivatives ; Cholesterol - analysis ; Cholesterol - chemical synthesis ; Cholesterol - metabolism ; Cholesterol transport ; Fluorescence imaging ; Humans ; Optical Imaging ; Sterol ; TopFluor cholesterol analogues ; Trafficking disorders</subject><ispartof>Bioorganic chemistry, 2021-12, Vol.117, p.105410-105410, Article 105410</ispartof><rights>2021 Elsevier Inc.</rights><rights>Copyright © 2021 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-9e1418e618af6c105cfb2df128a446d8a8b14b48aa26dd75472c716038c7718a3</citedby><cites>FETCH-LOGICAL-c362t-9e1418e618af6c105cfb2df128a446d8a8b14b48aa26dd75472c716038c7718a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0045206821007872$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34700109$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jurášek, Michal</creatorcontrib><creatorcontrib>Valečka, Jan</creatorcontrib><creatorcontrib>Novotný, Ivan</creatorcontrib><creatorcontrib>Kejík, Zdeněk</creatorcontrib><creatorcontrib>Fähnrich, Jan</creatorcontrib><creatorcontrib>Marešová, Anna</creatorcontrib><creatorcontrib>Tauchen, Jan</creatorcontrib><creatorcontrib>Bartůněk, Petr</creatorcontrib><creatorcontrib>Dolenský, Bohumil</creatorcontrib><creatorcontrib>Jakubek, Milan</creatorcontrib><creatorcontrib>Drašar, Pavel B.</creatorcontrib><creatorcontrib>Králová, Jarmila</creatorcontrib><title>Synthesis and biological evaluation of cationic TopFluor cholesterol analogues</title><title>Bioorganic chemistry</title><addtitle>Bioorg Chem</addtitle><description>[Display omitted]
Cholesterol is not only a major component of the cell membrane, but also plays an important role in a wide range of biological processes and pathologies. It is therefore crucial to develop appropriate tools for visualizing intracellular cholesterol transport. Here, we describe new cationic analogues of BODIPY-Cholesterol (TopFluor-Cholesterol, TF-Chol), which combine a positive charge on the sterol side chain and a BODIPY group connected via a C-4 linker. In contrast to TF-Chol, the new analogues TF-1 and TF-3 possessing acetyl groups on the A ring (C-3 position on steroid) internalized much faster and displayed slightly different levels of intracellular localization. Their applicability for cholesterol monitoring was indicated by the fact that they strongly label compartments with accumulated cholesterol in cells carrying a mutation of the Niemann-Pick disease-associated cholesterol transporter, NPC1.</description><subject>Biological Transport</subject><subject>Boron Compounds - analysis</subject><subject>Boron Compounds - chemical synthesis</subject><subject>Boron Compounds - chemistry</subject><subject>Boron Compounds - metabolism</subject><subject>Cell Line</subject><subject>Cholesterol - analogs & derivatives</subject><subject>Cholesterol - analysis</subject><subject>Cholesterol - chemical synthesis</subject><subject>Cholesterol - metabolism</subject><subject>Cholesterol transport</subject><subject>Fluorescence imaging</subject><subject>Humans</subject><subject>Optical Imaging</subject><subject>Sterol</subject><subject>TopFluor cholesterol analogues</subject><subject>Trafficking disorders</subject><issn>0045-2068</issn><issn>1090-2120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEFPAyEQhYnR2Fr9B8bs0ctWYClLLybGWDVp9GA9ExZmWxq6VNht0n8vdatHT8OQ9-bNfAhdEzwmmPC79biy3oflmGJK0teEEXyChgRPcU4JxadoiDGb5BRzMUAXMa4xJoSV_BwNClamBk-H6O1j37QriDZmqjFZGun80mrlMtgp16nW-ibzdaZ_XlZnC7-duc6HTK-8g9hC8C5ZVbJ1EC_RWa1chKtjHaHP2dPi8SWfvz-_Pj7Mc11w2uZTIIwI4ESomuu0u64rampChWKMG6FERVjFhFKUG1NOWEl1STguhC7LZCpG6Lafuw3-K-W2cmOjBudUA76Lkk5EuhAzwZKU9VIdfIwBarkNdqPCXhIsDyTlWvYk5YGk7Ekm280xoas2YP5Mv-iS4L4XQLpzZyHIqC00GowNoFtpvP0_4RtqSIZO</recordid><startdate>202112</startdate><enddate>202112</enddate><creator>Jurášek, Michal</creator><creator>Valečka, Jan</creator><creator>Novotný, Ivan</creator><creator>Kejík, Zdeněk</creator><creator>Fähnrich, Jan</creator><creator>Marešová, Anna</creator><creator>Tauchen, Jan</creator><creator>Bartůněk, Petr</creator><creator>Dolenský, Bohumil</creator><creator>Jakubek, Milan</creator><creator>Drašar, Pavel B.</creator><creator>Králová, Jarmila</creator><general>Elsevier Inc</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></search><sort><creationdate>202112</creationdate><title>Synthesis and biological evaluation of cationic TopFluor cholesterol analogues</title><author>Jurášek, Michal ; Valečka, Jan ; Novotný, Ivan ; Kejík, Zdeněk ; Fähnrich, Jan ; Marešová, Anna ; Tauchen, Jan ; Bartůněk, Petr ; Dolenský, Bohumil ; Jakubek, Milan ; Drašar, Pavel B. ; Králová, Jarmila</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-9e1418e618af6c105cfb2df128a446d8a8b14b48aa26dd75472c716038c7718a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Biological Transport</topic><topic>Boron Compounds - analysis</topic><topic>Boron Compounds - chemical synthesis</topic><topic>Boron Compounds - chemistry</topic><topic>Boron Compounds - metabolism</topic><topic>Cell Line</topic><topic>Cholesterol - analogs & derivatives</topic><topic>Cholesterol - analysis</topic><topic>Cholesterol - chemical synthesis</topic><topic>Cholesterol - metabolism</topic><topic>Cholesterol transport</topic><topic>Fluorescence imaging</topic><topic>Humans</topic><topic>Optical Imaging</topic><topic>Sterol</topic><topic>TopFluor cholesterol analogues</topic><topic>Trafficking disorders</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jurášek, Michal</creatorcontrib><creatorcontrib>Valečka, Jan</creatorcontrib><creatorcontrib>Novotný, Ivan</creatorcontrib><creatorcontrib>Kejík, Zdeněk</creatorcontrib><creatorcontrib>Fähnrich, Jan</creatorcontrib><creatorcontrib>Marešová, Anna</creatorcontrib><creatorcontrib>Tauchen, Jan</creatorcontrib><creatorcontrib>Bartůněk, Petr</creatorcontrib><creatorcontrib>Dolenský, Bohumil</creatorcontrib><creatorcontrib>Jakubek, Milan</creatorcontrib><creatorcontrib>Drašar, Pavel B.</creatorcontrib><creatorcontrib>Králová, Jarmila</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>Bioorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jurášek, Michal</au><au>Valečka, Jan</au><au>Novotný, Ivan</au><au>Kejík, Zdeněk</au><au>Fähnrich, Jan</au><au>Marešová, Anna</au><au>Tauchen, Jan</au><au>Bartůněk, Petr</au><au>Dolenský, Bohumil</au><au>Jakubek, Milan</au><au>Drašar, Pavel B.</au><au>Králová, Jarmila</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological evaluation of cationic TopFluor cholesterol analogues</atitle><jtitle>Bioorganic chemistry</jtitle><addtitle>Bioorg Chem</addtitle><date>2021-12</date><risdate>2021</risdate><volume>117</volume><spage>105410</spage><epage>105410</epage><pages>105410-105410</pages><artnum>105410</artnum><issn>0045-2068</issn><eissn>1090-2120</eissn><abstract>[Display omitted]
Cholesterol is not only a major component of the cell membrane, but also plays an important role in a wide range of biological processes and pathologies. It is therefore crucial to develop appropriate tools for visualizing intracellular cholesterol transport. Here, we describe new cationic analogues of BODIPY-Cholesterol (TopFluor-Cholesterol, TF-Chol), which combine a positive charge on the sterol side chain and a BODIPY group connected via a C-4 linker. In contrast to TF-Chol, the new analogues TF-1 and TF-3 possessing acetyl groups on the A ring (C-3 position on steroid) internalized much faster and displayed slightly different levels of intracellular localization. Their applicability for cholesterol monitoring was indicated by the fact that they strongly label compartments with accumulated cholesterol in cells carrying a mutation of the Niemann-Pick disease-associated cholesterol transporter, NPC1.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>34700109</pmid><doi>10.1016/j.bioorg.2021.105410</doi><tpages>1</tpages></addata></record> |
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| subjects | Biological Transport Boron Compounds - analysis Boron Compounds - chemical synthesis Boron Compounds - chemistry Boron Compounds - metabolism Cell Line Cholesterol - analogs & derivatives Cholesterol - analysis Cholesterol - chemical synthesis Cholesterol - metabolism Cholesterol transport Fluorescence imaging Humans Optical Imaging Sterol TopFluor cholesterol analogues Trafficking disorders |
| title | Synthesis and biological evaluation of cationic TopFluor cholesterol analogues |
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