Guanitoxin
Toxin from strains cyanobacteria Anabaena flos-aquae. This compound is NOT 'Anatoxin a' which is also produced by cyanobacteria and is a potent nicotinic acetylcholine receptor agonist. Fiore et al. suggested a new name Guanitoxin
General
Type : Natural,Organophosphate,Imidazole
Chemical_Nomenclature : [2-amino-5-(dimethylaminomethyl)-4,5-dihydroimidazol-1-yl]oxy-methoxy-phosphinic acid
Canonical SMILES : CN(C)CC1CN=C(N1OP(=O)(O)OC)N
InChI : InChI=1S\/C7H17N4O4P\/c1-10(2)5-6-4-9-7(8)11(6)15-16(12,13)14-3\/h6H,4-5H2,1-3H3,(H2,8,9)(H,12,13)\/t6-\/m1\/s1
InChIKey : FYXHGVMFJYHPFX-ZCFIWIBFSA-N
Other name(s) : AnatoxinAS,AnatoxineAS,Anatoxin-A(S),Anatoxin a(S),Guanitoxin
MW : 252.208
Formula : C7H17N4O4P
CAS_number : 103170-78-1
PubChem : 114989
UniChem : FYXHGVMFJYHPFX-ZCFIWIBFSA-N
IUPHAR :
Wikipedia : Guanitoxin
Target
References (22)
| Title : A systematic review on guanitoxin: General characteristics and ecological risks - Fernandes_2024_Chemosphere__141277 |
| Author(s) : Fernandes KA , Fadul JC , Fiore MF , Pinto E |
| Ref : Chemosphere , :141277 , 2024 |
| Abstract : Fernandes_2024_Chemosphere__141277 |
| ESTHER : Fernandes_2024_Chemosphere__141277 |
| PubMedSearch : Fernandes_2024_Chemosphere__141277 |
| PubMedID: 38307340 |
| Title : Response of Oreochromis niloticus (Teleostei: Cichlidae) exposed to a guanitoxin-producing cyanobacterial strain using multiple biomarkers - Passos_2022_Sci.Total.Environ__155471 |
| Author(s) : Passos LS , Gomes LC , Pereira TM , Sadauskas-Henrique H , Pont GD , Ostrensky A , Pinto E |
| Ref : Sci Total Environ , :155471 , 2022 |
| Abstract : Passos_2022_Sci.Total.Environ__155471 |
| ESTHER : Passos_2022_Sci.Total.Environ__155471 |
| PubMedSearch : Passos_2022_Sci.Total.Environ__155471 |
| PubMedID: 35472340 |
| Title : Guanitoxin, re-naming a cyanobacterial organophosphate toxin - Fiore_2020_Harmful.Algae_92_101737 |
| Author(s) : Fiore MF , de Lima ST , Carmichael WW , McKinnie SMK , Chekan JR , Moore BS |
| Ref : Harmful Algae , 92 :101737 , 2020 |
| Abstract : Fiore_2020_Harmful.Algae_92_101737 |
| ESTHER : Fiore_2020_Harmful.Algae_92_101737 |
| PubMedSearch : Fiore_2020_Harmful.Algae_92_101737 |
| PubMedID: 32113603 |
| Title : Neurotoxic effects of sublethal concentrations of cyanobacterial extract containing anatoxin-a(s) on Nauphoeta cinerea cockroaches - Dos Santos_2018_Ecotoxicol.Environ.Saf_171_138 |
| Author(s) : Dos Santos DS , Rosa ME , Zanatta AP , Oliveira RS , de Almeida CGM , Leal AP , Sanz M , Fernandes KA , de Souza VQ , de Assis DR , Pinto E , Belo CAD |
| Ref : Ecotoxicology & Environmental Safety , 171 :138 , 2018 |
| Abstract : Dos Santos_2018_Ecotoxicol.Environ.Saf_171_138 |
| ESTHER : Dos Santos_2018_Ecotoxicol.Environ.Saf_171_138 |
| PubMedSearch : Dos Santos_2018_Ecotoxicol.Environ.Saf_171_138 |
| PubMedID: 30599431 |
| Title : Anatoxin-a(s): natural organophosphorus anticholinesterase agent - Patocka_2011_Mil.Med.Sci.Lett_80_129 |
| Author(s) : Patocka J , Gupta RC , Kuca K |
| Ref : Military Medical Science Letters , 80 :129 , 2011 |
| Abstract : Patocka_2011_Mil.Med.Sci.Lett_80_129 |
| ESTHER : Patocka_2011_Mil.Med.Sci.Lett_80_129 |
| PubMedSearch : Patocka_2011_Mil.Med.Sci.Lett_80_129 |
| PubMedID: |
| Title : Neurotoxic cyanobacterial toxins - Araoz_2010_Toxicon_56_813 |
| Author(s) : Araoz R , Molgo J , Tandeau de Marsac N |
| Ref : Toxicon , 56 :813 , 2010 |
| Abstract : Araoz_2010_Toxicon_56_813 |
| ESTHER : Araoz_2010_Toxicon_56_813 |
| PubMedSearch : Araoz_2010_Toxicon_56_813 |
| PubMedID: 19660486 |
| Title : Methods for detection of anatoxin-a(s) by liquid chromatography coupled to electrospray ionization-tandem mass spectrometry - Dorr_2010_Toxicon_55_92 |
| Author(s) : Dorr FA , Rodriguez V , Molica R , Henriksen P , Krock B , Pinto E |
| Ref : Toxicon , 55 :92 , 2010 |
| Abstract : Dorr_2010_Toxicon_55_92 |
| ESTHER : Dorr_2010_Toxicon_55_92 |
| PubMedSearch : Dorr_2010_Toxicon_55_92 |
| PubMedID: 19632258 |
| Title : Detection of anatoxin-a(s) in environmental samples of cyanobacteria by using a biosensor with engineered acetylcholinesterases - Devic_2002_Appl.Environ.Microbiol_68_4102 |
| Author(s) : Devic E , Li D , Dauta A , Henriksen P , Codd GA , Marty JL , Fournier D |
| Ref : Applied Environmental Microbiology , 68 :4102 , 2002 |
| Abstract : Devic_2002_Appl.Environ.Microbiol_68_4102 |
| ESTHER : Devic_2002_Appl.Environ.Microbiol_68_4102 |
| PubMedSearch : Devic_2002_Appl.Environ.Microbiol_68_4102 |
| PubMedID: 12147513 |
| Title : A disposable acetylcholinesterase-based electrode biosensor to detect anatoxin-a(s) in water - Villatte_2002_Anal.Bioanal.Chem_372_322 |
| Author(s) : Villatte F , Schulze H , Schmid RD , Bachmann TT |
| Ref : Anal Bioanal Chem , 372 :322 , 2002 |
| Abstract : Villatte_2002_Anal.Bioanal.Chem_372_322 |
| ESTHER : Villatte_2002_Anal.Bioanal.Chem_372_322 |
| PubMedSearch : Villatte_2002_Anal.Bioanal.Chem_372_322 |
| PubMedID: 11936106 |
| Title : Radioreceptor assays for sensitive detection and quantitation of saxitoxin and its analogues from strains of the freshwater cyanobacterium, Anabaena circinalis - Llewellyn_2001_Environ.Sci.Technol_35_1445 |
| Author(s) : Llewellyn LE , Negri AP , Doyle J , Baker PD , Beltran EC , Neilan BA |
| Ref : Environ Sci Technol , 35 :1445 , 2001 |
| Abstract : Llewellyn_2001_Environ.Sci.Technol_35_1445 |
| ESTHER : Llewellyn_2001_Environ.Sci.Technol_35_1445 |
| PubMedSearch : Llewellyn_2001_Environ.Sci.Technol_35_1445 |
| PubMedID: 11348083 |
| Title : 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_1997_Toxicon_35_901 |
| Author(s) : Henriksen P , Carmichael WW , An J , Moestrup O |
| Ref : Toxicon , 35 :901 , 1997 |
| Abstract : Henriksen_1997_Toxicon_35_901 |
| ESTHER : Henriksen_1997_Toxicon_35_901 |
| PubMedSearch : Henriksen_1997_Toxicon_35_901 |
| PubMedID: 9241784 |
| Title : Effects of a homoanatoxin-a-containing extract from Oscillatoria formosa (Cyanophyceae\/cyanobacteria) on neuromuscular transmission - Lilleheil_1997_Toxicon_35_1275 |
| Author(s) : Lilleheil G , Andersen RA , Skulberg OM , Alexander J |
| Ref : Toxicon , 35 :1275 , 1997 |
| Abstract : Lilleheil_1997_Toxicon_35_1275 |
| ESTHER : Lilleheil_1997_Toxicon_35_1275 |
| PubMedSearch : Lilleheil_1997_Toxicon_35_1275 |
| PubMedID: 9278976 |
| Title : The toxins of Cyanobacteria - |
| Author(s) : Carmichael WW |
| Ref : Sci Am , 270 :64 , 1994 |
| PubMedID: 8284661 |
| Title : Anatoxin-a(s), a naturally occurring organophosphate, is an irreversible active site-directed inhibitor of acetylcholinesterase (EC 3.1.1.7) - Hyde_1991_J.Biochem.Toxicol_6_195 |
| Author(s) : Hyde EG , Carmichael WW |
| Ref : Journal of Biochemical Toxicology , 6 :195 , 1991 |
| Abstract : Hyde_1991_J.Biochem.Toxicol_6_195 |
| ESTHER : Hyde_1991_J.Biochem.Toxicol_6_195 |
| PubMedSearch : Hyde_1991_J.Biochem.Toxicol_6_195 |
| PubMedID: 1770503 |
| Title : Reversal of cholinesterase inhibition and clinical signs and the postmortem findings in mice after intraperitoneal administration of anatoxin-a(s), paraoxon or pyridostigmine - Cook_1991_Vet.Hum.Toxicol_33_1 |
| Author(s) : Cook WO , Dahlem AM , Harlin KS , Beasley VR , Hooser SB , Haschek WM , Carmicheal WW |
| Ref : Vet Hum Toxicol , 33 :1 , 1991 |
| Abstract : Cook_1991_Vet.Hum.Toxicol_33_1 |
| ESTHER : Cook_1991_Vet.Hum.Toxicol_33_1 |
| PubMedSearch : Cook_1991_Vet.Hum.Toxicol_33_1 |
| PubMedID: 2017858 |
| Title : Pathophysiologic effects of anatoxin-a(s) in anaesthetized rats: the influence of atropine and artificial respiration - Cook_1990_Pharmacol.Toxicol_67_151 |
| Author(s) : Cook WO , Iwamoto GA , Schaeffer DJ , Carmichael WW , Beasley VR |
| Ref : Pharmacol Toxicol , 67 :151 , 1990 |
| Abstract : Cook_1990_Pharmacol.Toxicol_67_151 |
| ESTHER : Cook_1990_Pharmacol.Toxicol_67_151 |
| PubMedSearch : Cook_1990_Pharmacol.Toxicol_67_151 |
| PubMedID: 2255668 |
| Title : Regional brain cholinesterase activity in rats injected intraperitoneally with anatoxin-a(s) or paraoxon - Cook_1989_Toxicol.Lett_49_29 |
| Author(s) : Cook WO , Dellinger JA , Singh SS , Dahlem AM , Carmichael WW , Beasley VR |
| Ref : Toxicol Lett , 49 :29 , 1989 |
| Abstract : Cook_1989_Toxicol.Lett_49_29 |
| ESTHER : Cook_1989_Toxicol.Lett_49_29 |
| PubMedSearch : Cook_1989_Toxicol.Lett_49_29 |
| PubMedID: 2815113 |
| Title : 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_1989_J.Environ.Pathol.Toxicol.Oncol_9_393 |
| Author(s) : Cook WO , Iwamoto GA , Schaeffer DJ , Beasley VR |
| Ref : J Environ Pathol Toxicol Oncol , 9 :393 , 1989 |
| Abstract : Cook_1989_J.Environ.Pathol.Toxicol.Oncol_9_393 |
| ESTHER : Cook_1989_J.Environ.Pathol.Toxicol.Oncol_9_393 |
| PubMedSearch : Cook_1989_J.Environ.Pathol.Toxicol.Oncol_9_393 |
| PubMedID: 2517795 |
| Title : Anticholinesterase poisonings in dogs from a cyanobacterial (blue-green algae) bloom dominated by Anabaena flos-aquae - Mahmood_1988_Am.J.Vet.Res_49_500 |
| Author(s) : Mahmood NA , Carmichael WW , Pfahler D |
| Ref : American Journal of Veterinary Research , 49 :500 , 1988 |
| Abstract : Mahmood_1988_Am.J.Vet.Res_49_500 |
| ESTHER : Mahmood_1988_Am.J.Vet.Res_49_500 |
| PubMedSearch : Mahmood_1988_Am.J.Vet.Res_49_500 |
| PubMedID: 3132068 |
| Title : Comparison of effects of anatoxin-a(s) and paraoxon, physostigmine and pyridostigmine on mouse brain cholinesterase activity - Cook_1988_Toxicon_26_750 |
| Author(s) : Cook WO , Beasley VR , Dahlem AM , Dellinger JA , Harlin KS , Carmichael WW |
| Ref : Toxicon , 26 :750 , 1988 |
| Abstract : Cook_1988_Toxicon_26_750 |
| ESTHER : Cook_1988_Toxicon_26_750 |
| PubMedSearch : Cook_1988_Toxicon_26_750 |
| PubMedID: 3188065 |
| Title : Anatoxin-a(s), an anticholinesterase from the cyanobacterium Anabaena flos-aquae NRC-525-17 - Mahmood_1987_Toxicon_25_1221 |
| Author(s) : Mahmood NA , Carmichael WW |
| Ref : Toxicon , 25 :1221 , 1987 |
| Abstract : Mahmood_1987_Toxicon_25_1221 |
| ESTHER : Mahmood_1987_Toxicon_25_1221 |
| PubMedSearch : Mahmood_1987_Toxicon_25_1221 |
| PubMedID: 3124299 |
| Title : Toxicology and pharmacological action of anabaena flos-aquae toxin. - Carmichael_1975_Science_187_542 |
| Author(s) : Carmichael WW , Biggs DF , Gorham PR |
| Ref : Science , 187 :542 , 1975 |
| Abstract : Carmichael_1975_Science_187_542 |
| ESTHER : Carmichael_1975_Science_187_542 |
| PubMedSearch : Carmichael_1975_Science_187_542 |
| PubMedID: 803708 |