Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile
A series of truncated analogs of α-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-γ ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2)...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2012-05, Vol.20 (9), p.2850-2859 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Toba, Tetsuya Murata, Kenji Futamura, Junko Nakanishi, Kyoko Takahashi, Bitoku Takemoto, Naohiro Tomino, Minako Nakatsuka, Takashi Imajo, Seiichi Goto, Megumi Yamamura, Takashi Miyake, Sachiko Annoura, Hirokazu |
| description | A series of truncated analogs of α-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-γ ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed. |
| doi_str_mv | 10.1016/j.bmc.2012.03.025 |
| format | Article |
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Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2012.03.025</identifier><identifier>PMID: 22480852</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Animals ; Antigens, CD1d - chemistry ; Antigens, CD1d - metabolism ; Aromatics ; Binding Sites ; Biological and medical sciences ; C-Glycoside ; Ceramide ; Computer Simulation ; galactosylceramide ; Galactosylceramides - chemical synthesis ; Galactosylceramides - chemistry ; Galactosylceramides - pharmacology ; gamma -Interferon ; Gene Expression Regulation - drug effects ; Interferon-gamma - metabolism ; Interleukin 4 ; Interleukin-4 - metabolism ; Medical sciences ; Mice ; Mice, Inbred C57BL ; OCH ; Pharmacology. 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Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed.</description><subject>Animals</subject><subject>Antigens, CD1d - chemistry</subject><subject>Antigens, CD1d - metabolism</subject><subject>Aromatics</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>C-Glycoside</subject><subject>Ceramide</subject><subject>Computer Simulation</subject><subject>galactosylceramide</subject><subject>Galactosylceramides - chemical synthesis</subject><subject>Galactosylceramides - chemistry</subject><subject>Galactosylceramides - pharmacology</subject><subject>gamma -Interferon</subject><subject>Gene Expression Regulation - drug effects</subject><subject>Interferon-gamma - metabolism</subject><subject>Interleukin 4</subject><subject>Interleukin-4 - metabolism</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Mice, Inbred C57BL</subject><subject>OCH</subject><subject>Pharmacology. Drug treatments</subject><subject>Phytosphingosine-modified analogs</subject><subject>Th2 Cells - drug effects</subject><subject>Th2 cytokine</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkcFu1DAQhi0EokvhAbggX5C4JIydxE3ECVWFIlXiAJwtZzxevGTtYicr5bF4EZ4Jl93CDXGw7MP3_x7Nx9hzAbUAoV7v6nGPtQQha2hqkN0DthGtaqumGcRDtoFB9RX0gzpjT3LeAYBsB_GYnUnZ9tB3csPWT2uYv1L2mZtg-ejjFLcezcTpYKbFzD4GHh2f0xLQzGT5zx_V1kwG55jXCSmZvbfELSV_KPSBMncRl-zDlpcornP85gNxH-yCv9tuU3R-oqfskTNTpmen-5x9eXf1-fK6uvn4_sPl25sKW6HmSrl-dAoQoOmkpBHN4IQyqkPR96CGVpVnR3YchLTOjgLbBrtOGQIrO4nNOXt17C3_fl8oz3rvM9I0mUBxybpssi2nEeo_UBhEA1LKgoojiinmnMjp2-T3Jq0FuqtUeqeLHH0nR0Oji5ySeXGqX8Y92T-JexsFeHkCTC4KXDIBff7Ldb2SF_1F4d4cOSp7O3hKOqOngGR9Ipy1jf4fY_wCuJWvZA</recordid><startdate>20120501</startdate><enddate>20120501</enddate><creator>Toba, Tetsuya</creator><creator>Murata, Kenji</creator><creator>Futamura, Junko</creator><creator>Nakanishi, Kyoko</creator><creator>Takahashi, Bitoku</creator><creator>Takemoto, Naohiro</creator><creator>Tomino, Minako</creator><creator>Nakatsuka, Takashi</creator><creator>Imajo, Seiichi</creator><creator>Goto, Megumi</creator><creator>Yamamura, Takashi</creator><creator>Miyake, Sachiko</creator><creator>Annoura, Hirokazu</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><scope>7QO</scope><scope>7T5</scope><scope>8FD</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope></search><sort><creationdate>20120501</creationdate><title>Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile</title><author>Toba, Tetsuya ; Murata, Kenji ; Futamura, Junko ; Nakanishi, Kyoko ; Takahashi, Bitoku ; Takemoto, Naohiro ; Tomino, Minako ; Nakatsuka, Takashi ; Imajo, Seiichi ; Goto, Megumi ; Yamamura, Takashi ; Miyake, Sachiko ; Annoura, Hirokazu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c416t-6f8bf60c003522ebca9f16a65c1880694665c5edb912dfdb1c43c556ae0d252c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Animals</topic><topic>Antigens, CD1d - chemistry</topic><topic>Antigens, CD1d - metabolism</topic><topic>Aromatics</topic><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>C-Glycoside</topic><topic>Ceramide</topic><topic>Computer Simulation</topic><topic>galactosylceramide</topic><topic>Galactosylceramides - chemical synthesis</topic><topic>Galactosylceramides - chemistry</topic><topic>Galactosylceramides - pharmacology</topic><topic>gamma -Interferon</topic><topic>Gene Expression Regulation - drug effects</topic><topic>Interferon-gamma - metabolism</topic><topic>Interleukin 4</topic><topic>Interleukin-4 - metabolism</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Mice, Inbred C57BL</topic><topic>OCH</topic><topic>Pharmacology. 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| ispartof | Bioorganic & medicinal chemistry, 2012-05, Vol.20 (9), p.2850-2859 |
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| language | eng |
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| subjects | Animals Antigens, CD1d - chemistry Antigens, CD1d - metabolism Aromatics Binding Sites Biological and medical sciences C-Glycoside Ceramide Computer Simulation galactosylceramide Galactosylceramides - chemical synthesis Galactosylceramides - chemistry Galactosylceramides - pharmacology gamma -Interferon Gene Expression Regulation - drug effects Interferon-gamma - metabolism Interleukin 4 Interleukin-4 - metabolism Medical sciences Mice Mice, Inbred C57BL OCH Pharmacology. Drug treatments Phytosphingosine-modified analogs Th2 Cells - drug effects Th2 cytokine |
| title | Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile |
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