Phosphatase-Triggered Guest Release from a Cyclodextrin Complex

A synthetic supramolecular system is described that models the effect of phosphoryl transfer in molecular recognition. β-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...

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Bibliographic Details
Published in:Organic letters 2000-06, Vol.2 (12), p.1741-1743
Main Authors: Cho, Arthur, Ochoa Lara, Karen L, Yatsimirsky, Anatoly K, Eliseev, Alexey V
Format: Article
Language:English
Subjects:
Alkaline Phosphatase - pharmacology
Antineoplastic Agents - metabolism
Binding Sites
Cyclodextrins - chemical synthesis
Cyclodextrins - metabolism
Diminazene - analogs & derivatives
Diminazene - metabolism
Half-Life
Hydrolysis
Indoles - metabolism
Intercalating Agents - metabolism
Ligands
Magnetic Resonance Spectroscopy
Models, Chemical
Models, Molecular
Molecular Mimicry
Phosphorus Compounds - chemical synthesis
Phosphorylation
Titrimetry
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Summary:A synthetic supramolecular system is described that models the effect of phosphoryl transfer in molecular recognition. β-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 β-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol005915x