Method of stimulating NKT with 6″-amino-6″-deoxygalactosylceramides
View Patent ↗This invention relates to galactosylceramide compounds.
1. A method of stimulating NKT cells comprising contacting an NKT cell with a compound of Formula (I) and a CD1 protein, wherein the compound of Formula (I) comprises:
wherein,
R 1 is —C(O)R 10 , wherein R 10 is C 1 -C 12 alkyl optionally substituted with carboxyl;
R 2 is hydrogen;
R 3 , R 4 , R 5 , R 6 and R 7 are each hydrogen;
R 8 is —(CH 2 ) x CH 3 ;
R 9 is a linear or branched C 3 -C 100 alkyl; and
x is 1-100.
2. An isolated antigen presenting cell for presenting a lipid antigen to NKT cells, the antigen presenting cell comprising CD1d molecules loaded with a compound of Formula (I), the compound of Formula (I) comprising:
wherein,
R 1 is —C(O)R 10 , wherein R 10 is C 1 -C 12 alkyl optionally substituted with carboxyl;
R 2 is hydrogen;
R 3 , R 4 , R 5 , R 6 and R 7 are each hydrogen;
R 8 is —(CH 2 ) x CH 3 ;
R 9 is a linear or branched C 3 -C 100 alkyl; and
x is 1-100.
3. The isolated antigen presenting cell of claim 2 , wherein x is 24 and R 9 is n-tetradecyl.
4. The isolated antigen presenting cell of claim 2 , wherein R 10 is CH 3 .
5. The isolated antigen presenting cell of claim 4 , wherein R 9 is C 14 alkyl.
6. The isolated antigen presenting cell of claim 5 , wherein R 8 is —(CH 2 ) 24 CH 3 .
7. The isolated antigen presenting cell of claim 5 , wherein R 8 is —(CH 2 ) 22 CH 3 .
8. The isolated antigen presenting cell of claim 2 , wherein R 10 is selected from —(CH 2 ) 2 COOH, —(CH 2 ) 3 COOH, and —(CH 2 ) 4 COOH.
9. A method of stimulating an NKT cell, comprising contacting the NKT cell with an antigen presenting cell according to claim 2 .
10. The method of claim 1 , wherein contacting comprises contacting the NKT cell with an antigen presenting cell comprising CD1d molecules loaded with the compound of Formula (I).
11. The method of claim 1 , wherein x is 24 and R 9 is n-tetradecyl.
12. The method of claim 1 , wherein R 10 is CH 3 .
13. The method of claim 12 , wherein R 9 is C 14 alkyl.
14. The method of claim 13 , wherein R 8 is —(CH 2 ) 24 CH 3 .
15. The method of claim 13 , wherein R 8 is —(CH 2 ) 22 CH 3 .
16. The method of claim 1 , wherein R 10 is selected from —(CH 2 ) 2 COOH, —(CH 2 ) 3 COOH, and —(CH 2 ) 4 COOH.