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the chemistry and pharmacology of anatoxin-a and related homotropanes with respect to nicotinic acetylcholine receptorsanatoxin-a和相关的化学和药理学homotropanes烟碱乙酰胆碱受体
Mar. Drugs 2006, 4, 228-254
Marine Drugs
ISSN 1660-3397
© 2006 by MDPI
/marinedrugs
Special Issue on “Marine Drugs and Ion Channels” Edited by Hugo Arias
Review
The Chemistry and Pharmacology of Anatoxin-a and Related
Homotropanes with respect to Nicotinic Acetylcholine Receptors
Susan Wonnacott 1,* and Timothy Gallagher 2
1 Department of Biology and Biochemistry, University of Bath, Bath BA2 7AY, United Kingdom
E-mail: bsssw@bath.ac.uk
2 School of Chemistry, University of Bristol, Bristol BS8 1TS, United Kingdom
E-mail: T.Gallagher@bristol.ac.uk
* Author to whom correspondence should be addressed.
Received: 25 January 2006 / 31 January 2006 / Published: 6 April 2006
Abstract: This chapter covers the chemistry and nicotinic pharmacology of naturally
occurring homotropane alkaloids, with an emphasis of anatoxin-a. In addition to anatoxin-a,
homoanatoxin and pinnamine, as well as the major classes of synthetic derivatives of
anatoxin-a including UB-165, are discussed.
Keywords: anatoxin-a, homoanatoxin, UB165, pinnamine, homotropane, nicotinic
acetylcholine receptor, pharmacophore
Abbreviations: nAChR, nicotinic acetylcholine receptors; PHT, pyrido[3,4-b]-homotropane;
QSAR, quantitative structure activity relationship; VDW, van der Waals.
Introduction
This chapter aims to cover the chemistry and nicotinic pharmacology of naturally occurring
homotropane alkaloids and their synthetic derivatives, with particular emphasis on anatoxin-a – first
isolated from freshwa
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