Phosphatase-triggered guest release from a cyclodextrin complex.
[reaction: see text] A synthetic supramolecular system is described that models the effect of phosphoryl transfer in molecular recognition. beta-Cyclodextrin-6A-phosphate (pCD), which is shown to be a substrate of alkaline phosphatase, binds cationic aromatic guests, including anticancer agents, up to 100-fold better than native beta-CD. The above observations demonstrate that pCD is capable of releasing the guests from its cavity upon hydrolysis with the phosphatase, as also confirmed by monitoring the hydrolysis in the presence of a guest.
Cho
A
A
Department of Medicinal Chemistry, State University of New York at Buffalo, 14260, USA.
Ochoa Lara
K L
KL
Yatsimirsky
A K
AK
Eliseev
A V
AV
D000469:Alkaline Phosphatase / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000378:metabolism; D001665:Binding Sites; D003505:Cyclodextrins / Q000138:chemical synthesis / Q000378:metabolism*; D004133:Diminazene / Q000031:analogs & derivatives / Q000378:metabolism; D006207:Half-Life; D006868:Hydrolysis; D007211:Indoles / Q000378:metabolism; D007364:Intercalating Agents / Q000378:metabolism; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D018716:Molecular Mimicry; D017553:Phosphorus Compounds / Q000138:chemical synthesis; D010766:Phosphorylation; D017186:Titrimetry
D000970:Antineoplastic Agents; D003505:Cyclodextrins; D007211:Indoles; D007364:Intercalating Agents; D008024:Ligands; D017553:Phosphorus Compounds; C007293:DAPI; C013196:phosphoryl chloride; D000469:Alkaline Phosphatase; C003915:diminazene aceturate; D004133:Diminazene