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Carbamates with Differential Mechanism of Inhibition Toward Acetylcholinesterase and Butyrylcholinesterase

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Department of Medicine (Neurology), Dalhousie University, Halifax, Nova Scotia, Canada, Department of Anatomy and Neurobiology, Dalhousie University, Halifax, Nova Scotia, Canada, Department of Chemistry, Mount Saint Vincent University, Halifax, Nova Scotia, Canada, Eppley Institute, University of Nebraska Medical Center, Omaha, Nebraska
* To whom correspondence should be addressed. Phone: 902-473-2490. Fax: 902-473-7133. E-mail: [email protected]. Address: Room 1308, Camp Hill Veterans’ Memorial Building 1, 5955 Veterans’ Memorial Lane, Halifax, Nova Scotia, Canada, B3H 2E1.
†Department of Medicine (Neurology), Dalhousie University.
‡Department of Anatomy and Neurobiology, Dalhousie University.
§Department of Chemistry, Mount Saint Vincent University.
∥Eppley Institute, University of Nebraska Medical Center.
Cite this: J. Med. Chem. 2008, 51, 14, 4200–4212
Publication Date (Web):June 21, 2008
Copyright © 2008 American Chemical Society

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    Abstract Image

    Most carbamates are pseudoirreversible inhibitors of cholinesterases. Phenothiazine carbamates exhibit this inhibition of acetylcholinesterase but produce reversible inhibition of butyrylcholinesterase, suggesting that they do not form a covalent bond with the catalytic serine. This atypical inhibition is attributable to π−π interaction of the phenothiazine moiety with F329 and Y332 in butyrylcholinesterase. These residues are in a helical segment, referred to here as the E-helix because it contains E325 of the catalytic triad. The involvement of the E-helix in phenothiazine carbamate reversible inhibition of butyrylcholinesterase is confirmed using mutants of this enzyme at A328, F329, or Y332 that show typical pseudoirreversible inhibition. Thus, in addition to various domains of the butyrylcholinesterase active site gorge, such as the peripheral anionic site and the π-cationic site of the Ω-loop, the E-helix represents a domain that could be exploited for development of specific inhibitors to treat dementias.

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