The Chemistry and Pharmacology of Anatoxin-a and Related Homotropanes with respect to Nicotinic Acetylcholine Receptors

@article{Wonnacott2006TheCA,
  title={The Chemistry and Pharmacology of Anatoxin-a and Related Homotropanes with respect to Nicotinic Acetylcholine Receptors},
  author={Susan Wonnacott and Timothy Gallagher},
  journal={Marine Drugs},
  year={2006},
  volume={4},
  pages={228 - 254}
}
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. 
A two-directional approach to the anatoxin alkaloids: second synthesis of homoanatoxin and efficient synthesis of anatoxin-a.
Total syntheses of the potent neurotoxins, environmental hazards, and biochemical probes anatoxin-a and homoanatoxin have been achieved from a common intermediate using a combined two-directional
Molecular modelling and quantitative structure-activity relationship studies of anatoxin-a and epibatidine derivatives with affinity to rodent nAChR receptors
TLDR
Structural analyses of anatoxin-a and epibatidine and a set of their derivatives indicated that the geometric and steric features are important determinants of the compound’s activities.
A Pharmacological Comparison of Two Isomeric Nicotinic Receptor Agonists: The Marine Toxin Isoanatabine and the Tobacco Alkaloid Anatabine
TLDR
An initial in vitro investigation of the actions of two isomeric tetrahydropyridyl ring-containing anabasine analogs reveals an ability to stimulate both α4β2 and α7 nAChRs, a property that may be useful in developing more efficacious drugs to treat neurodegenerative and other medical disorders.
Nicotinic acetylcholine receptor partial antagonist polyamides from tunicates and their predatory sea slugs
TLDR
Molleamine C (3) is a partial antagonist, reaching a maximum block of 76-82% of the acetylcholine signal and showing no partial agonist response, and may provide a lead compound for the development of neuroactive compounds with unique biological properties.
Nicotinic Acetylcholine Receptor Partial Antagonist Polyamides from Tunicates and Their Predatory Sea Slugs.
TLDR
Molleamine C (3) is a partial antagonist, reaching a maximum block of 76-82% of the acetylcholine signal and showing no partial agonist response, and may provide a lead compound for the development of neuroactive compounds with unique biological properties.
PdII -Mediated Oxidative Amination for Access to a 9-Azabicyclo[4.2.1]nonane Compound Library and Anatoxin-a
Intramolecular oxidative amination of readily accessible aminocyclooct-4-enes provides rapid and regioselective access to the 9-azabicyclo[4.2.1]nonane framework characteristic of the natural product
Evidence that biosynthesis of the neurotoxic alkaloids anatoxin-a and homoanatoxin-a in the cyanobacterium Oscillatoria PCC 6506 occurs on a modular polyketide synthase initiated by L-proline.
TLDR
GC-MS and NMR analyses of homoanatoxin-a produced by Oscillatoria PCC 6506 using labeled precursors confirm that proline is very likely the starter of these polyketide synthases, and it is shown that the anaC, anaE, anaF, and anaG genes are always present in the genome of cyanobacteria producing anat toxin-a and homoan atoxin- a and absent in nonproducing strains.
Biosynthesis of anatoxin-a and analogues (anatoxins) in cyanobacteria.
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