2508 Phalloidin Phalloidin is one of a group of toxins from the death cap (Amanita phalloides) known as phallotoxins. The phallotoxins consist of at least seven compounds, all of which have seven similar peptide rings, isolated from the death cap (Amanita phalloides). Though highly toxic to liver cells, it has since been found to have little input into the death cap's toxicity as it is not absorbed through the gut. Furthermore, it is also found in the edible (and sought after) Blusher (Amanita rubescens). (L996) 17466-45-4 4752 3301.7000000000007 Clear solution. 5 mg/mL at 0°C [MERCK INDEX (1996)] Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) It binds actin, preventing its depolymerization and poisoning the cell. Phalloidin binds specifically at the interface between F-actin subunits, locking adjacent subunits together. Phalloidin, a bicyclic heptapeptide, binds to actin filaments much more tightly than to actin monomers, leading to a decrease in the rate constant for the dissociation of actin subunits from filament ends, which essentially stabilizes actin filaments through the prevention of filament depolymerization. Moreover, phalloidin is found to inhibit the ATP hydrolysis activity of F-actin (L1183). Phalloidin was suggested to undergo bioactivation in the liver (A649). Free toxin may be removed by opsonization via the reticuloendothelial system (primarily the liver and kidneys) or it may be degraded through cellular internalization via the lysosomes. Lysosomes are membrane-enclosed organelles that contain an array of digestive enzymes, including several proteases. LD50: 2 mg/kg (Mouse) (T258) No indication of carcinogenicity (not listed by IARC). (L135) The property of phalloidin is a useful tool for investigating the distribution of F-actin in cells by labeling phalloidin with fluorescent analogs and using them to stain actin filaments for light microscopy (L996). Liver lesions, tachycardia, hypoglycemia, hypotension and electrolyte imbalance with acid- base disturbance (L1160). Hypovolemic shock; Gastrointestinal symptoms occur after a latent period and include abdominal pain, vomiting, and watery diarrhea. Neurologic symptoms are related to hepatic failure and may include encephalopathy, somnolence, confusion, coma and seizures (L1160). Consider gastric lavage and activated charcoal. (A678) 2009-07-03T21:46:55Z 2014-12-24T20:25:33Z http://en.wikipedia.org/wiki/Phalloidin A8W7P3 C08439 8040 D010590 Phalloidin true CC(O)C1N=C(O)C(C)N=C(O)C(CC(C)(O)CO)N=C(O)C2CC3=C(NC4=CC=CC=C34)SCC(N=C1O)C(=O)N1CC(O)CC1C(O)=NC(C)C(O)=N2 C35H48N8O11S InChI=1/C35H48N8O11S/c1-15-27(47)38-22-10-20-19-7-5-6-8-21(19)41-33(20)55-13-24(34(53)43-12-18(46)9-25(43)31(51)37-15)40-32(52)26(17(3)45)42-28(48)16(2)36-30(50)23(39-29(22)49)11-35(4,54)14-44/h5-8,15-18,22-26,41,44-46,54H,9-14H2,1-4H3,(H,36,50)(H,37,51)(H,38,47)(H,39,49)(H,40,52)(H,42,48) InChIKey=KPKZJLCSROULON-UHFFFAOYNA-N 788.868 788.316325108 Exogenous Liquid CHEMBL502682 23340042 Phalloidin.png image/png 70627 2014-10-14T18:12:31Z BSEQ0008416