Synthesis of fluorescent C24-ceramide: Evidence for acyl chain length dependent differences in penetration of exogenous NBD-ceramides into human skin
Topical skin lipid supplementation may provide opportunities for controlling ceramide (Cer) deficiency in skin diseases such as atopic dermatitis or psoriasis. Here we describe the synthesis of a long-chain 7-nitrobenzo[c][1,2,5]oxadiazol-4-yl (NBD)-labeled Cer and its different penetration through...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2009-12, Vol.19 (24), p.6975-6977 |
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| container_end_page | 6977 |
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| container_issue | 24 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | NOVOTNY, Jakub POSPECHOVA, Kateřina HRABALEK, Alexandr CAP, Robert VAVROVA, Kateřina |
| description | Topical skin lipid supplementation may provide opportunities for controlling ceramide (Cer) deficiency in skin diseases such as atopic dermatitis or psoriasis. Here we describe the synthesis of a long-chain 7-nitrobenzo[c][1,2,5]oxadiazol-4-yl (NBD)-labeled Cer and its different penetration through human skin compared to widely used short-chain fluorescent Cer tools. |
| doi_str_mv | 10.1016/j.bmcl.2009.10.047 |
| format | Article |
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Here we describe the synthesis of a long-chain 7-nitrobenzo[c][1,2,5]oxadiazol-4-yl (NBD)-labeled Cer and its different penetration through human skin compared to widely used short-chain fluorescent Cer tools.</description><subject>4-Chloro-7-nitrobenzofurazan - chemical synthesis</subject><subject>4-Chloro-7-nitrobenzofurazan - metabolism</subject><subject>Biological and medical sciences</subject><subject>Bisbenzimidazole - metabolism</subject><subject>Ceramide</subject><subject>Ceramides - chemical synthesis</subject><subject>Ceramides - metabolism</subject><subject>Dermatitis, Atopic - metabolism</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - metabolism</subject><subject>Fluorescent lipids</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Humans</subject><subject>Permeability</subject><subject>Psoriasis - metabolism</subject><subject>Skin</subject><subject>Skin - metabolism</subject><subject>Stratum corneum</subject><subject>Vertebrates: skin, associated glands, phaneres, light organs, various exocrine glands (salt gland, uropygial gland...), adipose tissue, connective tissue</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kcFu1DAQhi0EokvhBTggX1BPWezYcWLEhS4FKlVwACRulmOPu14Se7GTin0Q3hdHuyq3nkb6_c145v8ReknJmhIq3uzW_WiGdU2ILMKa8PYRWlEueMU4aR6jFZGCVJ3kP8_Qs5x3hFBOOH-KzqjsWkmZXKG_3w5h2kL2GUeH3TDHBNlAmPCm5pWBpEdv4S2-uislGMAuJqzNYcBmq33AA4TbaYst7CHYpc165yAtaMblvcgwJT35GJYP4E-8hRDnjL9cfrgfv5BTxNt51AHnXz48R0-cHjK8ONVz9OPj1ffN5-rm66frzfubyjBCpoo1WveN5bITlvQgLG1azRlvGgG8Yy13wHqQUjfaSmFd14Fwhe0azTvuGDtHF8e5-xR_z5AnNfpy_TDoAGVJ1TJeLBOcFLI-kibFnBM4tU9-1OmgKFFLGmqnljTUksailTRK06vT-Lkfwf5vOdlfgNcnQGejB5d0MD7fc3VNW9GIunDvjhwUM-48JJWNXzy2PoGZlI3-oT3-Abesqr4</recordid><startdate>20091215</startdate><enddate>20091215</enddate><creator>NOVOTNY, Jakub</creator><creator>POSPECHOVA, Kateřina</creator><creator>HRABALEK, Alexandr</creator><creator>CAP, Robert</creator><creator>VAVROVA, Kateřina</creator><general>Elsevier Ltd</general><general>Elsevier</general><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></search><sort><creationdate>20091215</creationdate><title>Synthesis of fluorescent C24-ceramide: Evidence for acyl chain length dependent differences in penetration of exogenous NBD-ceramides into human skin</title><author>NOVOTNY, Jakub ; POSPECHOVA, Kateřina ; HRABALEK, Alexandr ; CAP, Robert ; VAVROVA, Kateřina</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c300t-35aab5d4986d0be6d157a434556e48374fe3be99a5ad96df88e6f86d85a484f33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>4-Chloro-7-nitrobenzofurazan - chemical synthesis</topic><topic>4-Chloro-7-nitrobenzofurazan - metabolism</topic><topic>Biological and medical sciences</topic><topic>Bisbenzimidazole - metabolism</topic><topic>Ceramide</topic><topic>Ceramides - chemical synthesis</topic><topic>Ceramides - metabolism</topic><topic>Dermatitis, Atopic - metabolism</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - metabolism</topic><topic>Fluorescent lipids</topic><topic>Fundamental and applied biological sciences. 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| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2009-12, Vol.19 (24), p.6975-6977 |
| issn | 0960-894X 1464-3405 |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | 4-Chloro-7-nitrobenzofurazan - chemical synthesis 4-Chloro-7-nitrobenzofurazan - metabolism Biological and medical sciences Bisbenzimidazole - metabolism Ceramide Ceramides - chemical synthesis Ceramides - metabolism Dermatitis, Atopic - metabolism Fluorescence Fluorescent Dyes - chemical synthesis Fluorescent Dyes - metabolism Fluorescent lipids Fundamental and applied biological sciences. Psychology Humans Permeability Psoriasis - metabolism Skin Skin - metabolism Stratum corneum Vertebrates: skin, associated glands, phaneres, light organs, various exocrine glands (salt gland, uropygial gland...), adipose tissue, connective tissue |
| title | Synthesis of fluorescent C24-ceramide: Evidence for acyl chain length dependent differences in penetration of exogenous NBD-ceramides into human skin |
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