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We have used isothermal titration calorimetry (ITC) to study the thermodynamics of binding of 12 bisphosphonates to human bone. The ITC results show that there are two binding sites. Site A is the weak, highly populated site seen by NMR and is characterized by an average DeltaG of binding of -5.2 kcal. Site B is a strong binding site characterized by a DeltaG of binding of -8.5 kcal. Binding to both sites is overwhelmingly entropy driven. Using a thermodynamic group approach and a linear regression method, we predict the DeltaG of binding of all 12 compounds with an R(2) = 0.95 (a 0.19 kcal error variance estimate, approximately 3% of the total DeltaG range), opening up the way to designing novel chemotherapy, immunotherapy, and anti-infectious disease drugs having weak bone binding affinity.

Thermodynamics of Bisphosphonates Binding to Human Bone: A Two-Site Model