Vesicle Compositions

A vesicle composition, comprising:

• a first liposome, comprising:
• a first phospholipid;
• cholesterol;
• and a phospholipid-polyethylene glycol-boronic acid derivative conjugate;
• a second liposome, comprising:
• a second phospholipid;
• cholesterol;
• and a phospholipid-polyethylene glycol-glycosyl conjugate, at least one of the first liposome or the second liposome respectively encapsulating a first therapeutic compound or a second therapeutic compound;
• and
• the phospholipid-polyethylene glycol-boronic acid derivative conjugate of the first liposome and the phospholipid-polyethylene glycol-glycosyl conjugate of the second liposome together being configured to form at least one reversible boronic-glycosyl crosslink between the first liposome and the second liposome,
• provided that when:
• a glycosyl moiety of the phospholipid-polyethylene glycol-glycosyl conjugate comprises a glucosyl moiety, a galactosyl moiety, or a mannopyranosidyl moiety;
• the first liposome encapsulates the first therapeutic compound;
• the second liposome encapsulates the second therapeutic compound;
• and
• the first liposome is coupled to the second liposome by the at least one reversible boronic-glycosyl crosslink,
• the phospholipid-polyethylene glycol-boronic acid derivative conjugate is not represented by
• wherein n=30-60.