Ladderane lipid compounds and liposomes and methods of preparing and using the same

A method of preparing a ladderane compound of formula (IX) from a compound selected from one of formulae (V) and (VIII):

• wherein:
• A is selected from a compound of formulae (V) and (VIII):
• L1 is a linker;
• Z1 is a chemoselective group or a tag;
• X3 is selected from the group consisting of:
• L2 is an optional linker;
• n is an integer from 1 to 6;
• m is 0 or an integer from 1 to 6;
• p is 1 or 2;
• and
• Y1 is a hydrophilic head group.

A ladderane compound, having one of the following formula:

• wherein:
• n is an integer from 1 to 6;
• m is 0 or an integer from 1 to 6;
• each R1 is independently an alkyl or a substituted alkyl and are optionally cyclically linked;
• X2 is a halogen;
• L1 is a linker;
• and
• Z1 is selected from the group consisting of, ester, ether, amine, amide, and thiol.

A composition comprising:

• a liposome carrier comprising a ladderane lipid of formula (IX):
• Y1-L2L1-X3]p (IX)
• wherein:
• X3 is selected from the group consisting of:
• L1 is a linker;
• and
• L2 is an optional linker;
• n is an integer from 1 to 6;
• m is 0 or an integer from 1 to 6;
• p is 1 or 2;
• and
• Y1 is a hydrophilic head group;
• and
• one or more cargo moieties encapsulated in the liposome carrier.