Modified glycolipids and methods of making and using the same
AssigneesVaccinex, Inc., Albert Einstein College of Medicine
InventorsSteven A. Porcelli, Maurice Zauderer
Life of this patent
Estimating the term…
Abstract
The invention is directed to compositions and methods related to proteins that are physically associated with ceramide-like glycolipids for use as activators of NKT cells. The compositions and methods of the present invention are useful for the prevention and treatment of diseases.
Claims43
A modified ceramide-like glycolipid comprising a photoreactive group, wherein said photoreactive group has been covalently bound to the N-acyl lipophilic moiety of a ceramide-like glycolipid.
A method for synthesizing a modified glycolipid of Formula (VI) comprising a benzophenone group, said method comprising the steps of:
- activating a carboxylic acid derivative of Formula (IV) to form an activated acyl derivative
- and
- coupling the activated acyl derivative with a glycolipid of Formula (V)
- thereby forming the modified glycolipid comprising a benzophenone group of Formula (VI)
- wherein
- G is a linear or branched C1-C27 alkane or C2-C27 alkene;
- or G is —C(OH)—R3 wherein R3 is a linear or branched C1-C26 alkane or C2-C26 alkene;
- or R1 is a C6-C27 alkane or alkene wherein (i) the C6-C27 alkane or alkene is substituted with a C5-C15 cycloalkane, C5-C15 cycloalkene, heterocycle, or aromatic ring or (ii) the C6-C27 alkane or alkene includes, within the C6-C27 alkyl or alkenyl chain, a C5-C15 cycloalkane, C5-C15 cycloalkene, heterocycle, or aromatic ring;
- or R1 is an optionally substituted aromatic ring, or an aralkyl;
- R4 is a substituted or unsubstituted sugar or analogs thereof;
- A if present is —O—, —CH2—;
- or is a single bond,
- Y is —O—, —CH2— or —S—, and
- R2 is a substituted or an unsubstituted C3-C40 alkyl, alkenyl or alkynyl chain.
Dependencies are inferred from the claim text.