Cyclodextrins with one or more poly(ethylene glycol) units, inclusion compounds and drug delivery vehicles including the same, and methods of making and using the same

Abstract

A compound comprising a cyclodextrin and a monoalkoxy polyethylene glycol linked thereto through an ether bond (a 'pegylated cyclodextrin') is disclosed, as are drug delivery vehicles and pharmaceutical formulations including the same, and methods for making the compound and the drug delivery vehicle and for delivering the drug to a patient in need thereof. The method of making includes the steps of creating either a tosylated monoalkoxy polyethylene glycol or a tosylated cyclodextrin, and either reacting the tosylated monoalkoxy polyethylene glycol with a deprotonated cyclodextrin, or reacting the tosylated cyclodextrin with a deprotonated monoalkoxy polyethylene glycol. The present pegylated cyclodextrin readily forms an inclusion compound with certain drugs to protect the drug against adverse interactions with mucin (e.g., in a mucus membrane).