Peptide-phospholipid conjugates

A method of manufacturing a peptide-phospholipid conjugate of Formula 2:

• the method comprising forming a mixture comprising an acid of Formula 3 and lyso-PC:
• wherein:
• R3 is selected from the group consisting of alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, aminoalkyl, amino, ether, cycloamino, cycloether, aryl, heteroaryl, arylalkyl, heteroarylalkyl, hydroxyaryl, arylether, cycloalkyl, heterocycloalkyl, hydroxycycloalkyl, halocycloalkyl, and aminocycloalkyl;
• and
• Z is a peptide comprising 1 to 50 amino acids.

A pharmaceutical formulation for treating atherosclerosis, the formulation comprising:

• a peptide-phospholipid conjugate of Formula 1 or a pharmaceutically acceptable salt, prodrug, salt of a prodrug, or a combination thereof, and a pharmaceutically acceptable excipient:
• wherein:
• X is selected from the group consisting of —CR1R2—, —NR3—, —O—, —S—, and —S+(R3)—;
• Y is selected from the group consisting of a bond, alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, amino, ether, cycloamino, cycloether, aryl, heteroaryl, arylalkyl, heteroarylalkyl, hydroxyaryl, arylether, cycloalkyl, heterocycloalkyl, hydroxycycloalkyl, halocycloalkyl, and aminocycloalkyl;
• Z is a peptide comprising 1 to 50 amino acids;
• R1 and R2 are each independently selected from the group consisting of alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, amino, ether, cycloamino, cycloether, aryl, heteroaryl, arylalkyl, heteroarylalkyl, hydroxyaryl, arylether, cycloalkyl, heterocycloalkyl, hydroxycycloalkyl, halocycloalkyl, and aminocycloalkyl;
• and
• R3 is selected from the group consisting of alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, hydroxyalkyl, aminoalkyl, amino, ether, cycloamino, cycloether, aryl, heteroaryl, arylalkyl, heteroarylalkyl, hydroxyaryl, arylether, cycloalkyl, heterocycloalkyl, hydroxycycloalkyl, halocycloalkyl, and aminocycloalkyl.