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Pure Appl. Chem., 2000, Vol. 72, No. 3, pp. 333-342

The chelate effect in binding, catalysis, and chemotherapy

Ronald Breslow*, Sandro Belvedere, Leland Gershell and David Leung

Department of Chemistry, Columbia University, New York, New York 10027, USA

Abstract: Cyclodextrin (CD) dimers bind amino acid side chains, and such binding can dissociate aggregated proteins, including citrate synthase (dimer) and lactic dehydrogenase (tetramer). A CD dimer can bind a hydrophobic photosensitizer that, upon irradiation, generates singlet oxygen. This cleaves the dimer and releases the photosensitizer. CD dimers in a cytochrome P-450 mimic steer catalyzed hydroxylation to a bound steroid with geometric control. Chelate binding has also led to a group of cytodifferentiating agents whose mechanism has been recently established. They have promising anticancer properties, and are currently entering human trials as therapeutic agents.