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US 2012/0238018 A1Published application
Caged Ceramide-1-Phosphate Derivatives
AssigneeResearch Foundation of the City University of New York
InventorsRobert Bittman, Antonio Gomez Munoz
Life of this patent
Estimating the term…
Abstract
The invention relates to novel caged ceramide 1-phosphate (C1P) and the method of using them for delivering C1P intracellularly in vitro and in vivo, for research and therapeutic purposes.
Claims28
A D-erythro ceramide-l-phosphate derivative having formula 1,
- wherein:
- R1 represents a benzhydryl derivative having formula 2 or a coumarinyl-4-methyl derivative having formula 3;
- R3 represents H or a benzhydryl derivative having formula 2 or a coumarinyl-4-methyl derivative having formula 3;
- n is 12 or 14
- R2 represents a fatty acyl group having formula 4
- R4 represents H or OH;
- R5 represents a saturated or unsaturated aliphatic group having 12-22 carbon atoms;
- Y and Z independently represent H, Cl, Br, OH, OCH3, or triazolyl, in which case at least one of Y or Z represents OH;
- or Y and Z join together to form a 5 or 6 member carbocyclic or heterocyclic ring that is optionally fused to a second 5 or 6 member carbocyclic or heterocyclic ring, wherein the second 5 or 6 member carbocyclic or heterocyclic ring is optionally fused to a third 5 or 6 member carbocyclic or heterocyclic ring, and wherein any of the carbocyclic or heterocyclic rings are optionally substituted with one or more functional groups selected from the group consisting of methyl, OH, OCH3, Cl, Br, NO2, NMe2, and NEt2;
- Ar1 represents phenyl, or phenyl substituted with one or more functional groups selected from the group consisting of NMe2, NEt2, OH, and OCH3;
- V, W, and X independently represent H, Cl, Br, OH, OCH3, NMe2, NEt2 or Ar2;
- and
- Ar2 represents phenyl, or phenyl substituted with one or more functional groups selected from the group consisting of OH, OCH3, NMe2, NEt2, triazolyl, and phenyltriazolyl.
10 more elements
A method for introducing a ceramide-1-phosphate molecule into a biological cell, the method comprising exposing the cell to a D-erythro ceramide-1-phosphate derivative having formula 1,
- wherein:
- R′ represents a benzhydryl derivative having formula 2 or a coumarinyl-4-methyl derivative having formula 3;
- R3 represents H or a benzhydryl derivative having formula 2 or a coumarinyl-4-methyl derivative having formula 3;
- n is 12 or 14
- R2 represents a fatty acyl group having formula 4
- R4 represents H or OH;
- R5 represents a saturated or unsaturated aliphatic group having 12-22 carbon atoms;
- Y and Z independently represent H, Cl, Br, OH, OCH3, or triazolyl, in which case at least one of Y or Z represents OH;
- or Y and Z join together to form a 5 or 6 member carbocyclic or heterocyclic ring that is optionally fused to a second 5 or 6 member carbocyclic or heterocyclic ring, wherein the second 5 or 6 member carbocyclic or heterocyclic ring is optionally fused to a third 5 or 6 member carbocyclic or heterocyclic ring, and wherein any of the carbocyclic or heterocyclic rings are optionally substituted with one or more functional groups selected from the group consisting of methyl, OH, OCH3, Cl, Br, NO2, NMe2, and NEt2;
- Ar2 represents phenyl, or phenyl substituted with one or more functional groups selected from the group consisting of NMe2, NEt2, OH, and OCH3;
- V, W, and X independently represent H, Cl, Br, OH, OCH3, NMe2, NEt2 or Ar2;
- and
- Ar2 represents phenyl, or phenyl substituted with one or more functional groups selected from the group consisting of OH, OCH3, NMe2, NEt2, triazolyl, and phenyltriazolyl.
10 more elements
Dependencies are inferred from the claim text.