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Chemical Compound Review:

Anatoxin-A(S) [(5S)-2-amino-5- (dimethylaminomethyl)-4,5...

Synonyms: Anatoxin a(s), LS-19301, AC1L3GC5, C19998, 103170-78-1

Hyde, E.G. et al., Henriksen, P. et al., Mahmood, N.A. et al., Devic, E. et al., Cook, W.O. et al., et al.

Hitzfeld, Höger, Dietrich,

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Disease relevance of Anatoxin-A(S)

Anabaena flos-aquae NRC 525-17 produces a very potent neurotoxin, anatoxin-a(s) [1].
Anatoxin-a(s), a neurotoxin produced by some freshwater cyanobacteria, was detected by measuring the inhibition of acetylcholinesterase activity [2].
These toxins (microcystins, nodularins, saxitoxins, anatoxin-a, anatoxin-a(s), cylindrospermopsin) are structurally diverse and their effects range from liver damage, including liver cancer, to neurotoxicity [3].
The stomach contents contained colonies and single trichomes of Anabaena, and anticholinesterase activities equivalent to 2.1-89.7 micrograms anatoxin-a(s) kg-1 body weight and microcystins (53-95 ng kg-1) were also detected [4].

High impact information on Anatoxin-A(S)

Unlike paraoxon, anatoxin-a(s) did not cause detectable inhibition of cholinesterase in the central nervous system, but did cause inhibition of cholinesterase in blood, suggesting that anatoxin-a(s) is strictly a peripheral cholinesterase inhibitor [5].
Anatoxin-a(s) did not inhibit brain cholinesterase activity suggesting that this toxin is unable to cross the blood-brain barrier [6].
Further comparison of the semipurified bloom toxin with an irreversible anticholinesterase anatoxin-a(s), produced by A flos-aquae strain NRC-525-17, revealed the bloom toxin and anatoxin-a(s) had similar properties on high-performance liquid chromatography and on the inhibition of electric eel acetylcholinesterase (EC 3.1.1.7) [7].
In the present study the interaction of anatoxin-a(s) with AChE was investigated by protection studies and since similarities have been noted between anatoxin-a(s) and the synthetic organophosphate anticholinesterases, the ability of reactivators to reactivate the inhibited enzyme was investigated [8].
Even when survival time of rats was increased by pretreatment with atropine, phrenic nerve amplitude increased, indicating a lack of a depressive effect of anatoxin-a(s) on central mediation of respiration [9].

Biological context of Anatoxin-A(S)

Effect of anatoxin-a(s) from Anabaena flos-aquae NRC-525-17 on blood pressure, heart rate, respiratory rate, tidal volume, minute volume, and phrenic nerve activity in rats [10].

Gene context of Anatoxin-A(S)

Previous work has shown anatoxin-a(s) to be a potent irreversible inhibitor of electric eel acetylcholinesterase (EC 3.1.1.7, AChE) [8].

Analytical, diagnostic and therapeutic context of Anatoxin-A(S)

Detection of anatoxin-a(s) in environmental samples of cyanobacteria by using a biosensor with engineered acetylcholinesterases [2].
Gel filtration profiles indicated similarity between the toxic component from the Lake Knud sø 1994 bloom with registered bird-kills and anatoxin-a(s) isolated from Anabaena flos-aquae NRC-525-17 [4].
Anatoxin-a(s) was administered by continuous intravenous infusion [10].

References

Microcystins from Anabaena flos-aquae NRC 525-17. Harada, K., Ogawa, K., Kimura, Y., Murata, H., Suzuki, M., Thorn, P.M., Evans, W.R., Carmichael, W.W. Chem. Res. Toxicol. (1991) [Pubmed]
Detection of anatoxin-a(s) in environmental samples of cyanobacteria by using a biosensor with engineered acetylcholinesterases. Devic, E., Li, D., Dauta, A., Henriksen, P., Codd, G.A., Marty, J.L., Fournier, D. Appl. Environ. Microbiol. (2002) [Pubmed]
Cyanobacterial toxins: removal during drinking water treatment, and human risk assessment. Hitzfeld, B.C., Höger, S.J., Dietrich, D.R. Environ. Health Perspect. (2000) [Pubmed]
Detection of an anatoxin-a(s)-like anticholinesterase in natural blooms and cultures of cyanobacteria/blue-green algae from Danish lakes and in the stomach contents of poisoned birds. Henriksen, P., Carmichael, W.W., An, J., Moestrup, O. Toxicon (1997) [Pubmed]
Regional brain cholinesterase activity in rats injected intraperitoneally with anatoxin-a(s) or paraoxon. Cook, W.O., Dellinger, J.A., Singh, S.S., Dahlem, A.M., Carmichael, W.W., Beasley, V.R. Toxicol. Lett. (1989) [Pubmed]
Comparison of effects of anatoxin-a(s) and paraoxon, physostigmine and pyridostigmine on mouse brain cholinesterase activity. Cook, W.O., Beasley, V.R., Dahlem, A.M., Dellinger, J.A., Harlin, K.S., Carmichael, W.W. Toxicon (1988) [Pubmed]
Anticholinesterase poisonings in dogs from a cyanobacterial (blue-green algae) bloom dominated by Anabaena flos-aquae. Mahmood, N.A., Carmichael, W.W., Pfahler, D. Am. J. Vet. Res. (1988) [Pubmed]
Anatoxin-a(s), a naturally occurring organophosphate, is an irreversible active site-directed inhibitor of acetylcholinesterase (EC 3.1.1.7). Hyde, E.G., Carmichael, W.W. J. Biochem. Toxicol. (1991) [Pubmed]
Pathophysiologic effects of anatoxin-a(s) in anaesthetized rats: the influence of atropine and artificial respiration. Cook, W.O., Iwamoto, G.A., Schaeffer, D.J., Carmichael, W.W., Beasley, V.R. Pharmacol. Toxicol. (1990) [Pubmed]
Effect of anatoxin-a(s) from Anabaena flos-aquae NRC-525-17 on blood pressure, heart rate, respiratory rate, tidal volume, minute volume, and phrenic nerve activity in rats. Cook, W.O., Iwamoto, G.A., Schaeffer, D.J., Beasley, V.R. J. Environ. Pathol. Toxicol. Oncol. (1989) [Pubmed]

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