Synthetic glycolipids and glycoliposome compositions : suitable for cargo delivery to the central nervous system

A method for delivering a therapeutic or diagnostic agent to the central nervous system of a patient in need of the therapeutic or diagnostic agent, the method comprising:

• entrapping the therapeutic or diagnostic agent into a glycoliposome comprising a plurality of synthetic glycolipids;
• and
• administering the glycoliposome with the entrapped therapeutic or diagnostic agent to the patient;
• wherein each synthetic glycolipid has the following formula (I)
• wherein
• A represents (CH2) n with n being an integer from 2 to 10 or CH2—CH2—[O—CH2—CH2]m with m being an integer from 1 to 5;
• B represents NR3, with R3 representing H, Me, Et or n-Pr;
• represents
• where R1 represents OH and R2 represents H, or where R1 represents H and R2 represents OH;
• Y represents H when X and Z which are identical represent O—(CH2)p—CH3, or X represents H when Y and Z which are identical represent O—(CH2)p—CH3, with p being an integer from 5 to 18.

A process for preparing a synthetic glycolipid having the following formula (I)

• wherein
• A represents (CH2) n with n being an integer from 2 to 10 or CH2—CH2—[O—CH2—CH2]m with m being an integer from 1 to 5;
• B represents NH;
• represents
• where R1 represents OH and R2 represents H, or where R1 represents H and R2 represents OH;
• Y represents H when X and Z which are identical represent O—(CH2)p—CH3, or X represents H when Y and Z which are identical represent O—(CH2) p-CH3, with p being an integer from 5 to 18;
• the process comprising:
• reducing a compound of formula (V)
• where represents
• R′1 represents OAc and R′2 represents H, or where R′1 represents H and R′2 represents OAc;
• into the corresponding amine;
• and
• coupling the amine with a compound of formula (VI)
• thereby forming the compound of formula (IAc)
• and
• converting the compound of formula (IAc) into the synthetic glycolipid of formula (I).