Cyclodextrins (CDs) are water-soluble cyclic oligosaccharides, composed of a-D-glucopyranoside units linked 1-4. The annulus interior of CD is hydrophobic, which enables the formation of inclusion complexes with many lipophilic compounds. Being biologically inert, CDs have been approved by US FDA as pharmaceutical excipients for numerous drug formulations. Using Cu-catalyzed Huisgen 1,3-dipolar cycloaddition, we have recently synthesized an alendronate-�-cyclodextrin (ALN-�-CD) conjugate for local drug delivery to the bone and teeth . ALN-�-CD demonstrated strong biomineral-binding capacity and was found to be bone anabolic, probably due to an endogenous anabolic agent sequestration mechanism.  Using similar approach, ALN-a-CD was also synthesized and used to assemble a polyrotaxane conjugate, which has precisely controlled osteotropicity. When tested in a breast cancer bone metastasis mouse model, the conjugate shows great promise in early detection of the micro-metastasis lesion. Due to its drug loading potential, the polyrotaxane also hold great promise for targeted bone cancer chemotherapy.

Click-modified cyclodextrins for pharmaceutical applications

241st National Meeting (2011)

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