PhTX-433 TFA

• CAT Number: I034709
• CAS Number: 276684-27-6
• Molecular Formula: C29H44F9N5O9
• Molecular Weight: 777.68
• Purity: 98%
• Synonyms: PhTX-433; PhTX 433; PhTX433; Philanthotoxin 433; Philanthotoxin-433; Philanthotoxin433
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (S)-N-(1-((4-((3-((3-aminopropyl)amino)propyl)amino)butyl)amino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)butyramide tris(2,2,2-trifluoroacetate)
• InChI: InChI=1S/C23H41N5O3.3C2HF3O2/c1-2-7-22(30)28-21(18-19-8-10-20(29)11-9-19)23(31)27-17-4-3-13-25-15-6-16-26-14-5-12-24;3*3-2(4,5)1(6)7/h8-11,21,25-26,29H,2-7,12-18,24H2,1H3,(H,27,31)(H,28,30);3*(H,6,7)/t21-;;;/m0.../s1
• InChIKey: UROZAUWUTBOQNV-YDULTXHLSA-N
• SMILES: CCCC(N[C@@H](CC1=CC=C(O)C=C1)C(NCCCCNCCCNCCCN)=O)=O.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F

PhTX-433 (Cat.No:I034709), also known as Philanthotoxin 433, is a polyamine-containing toxin, which blocks NMDA-gated ion channels; originally isolated from the venom of the wasp Philanthus triangulum.

Reference

1: Kachel HS, Patel RN, Franzyk H, Mellor IR. Block of nicotinic acetylcholine receptors by philanthotoxins is strongly dependent on their subunit composition. Sci Rep. 2016 Nov 30;6:38116. doi: 10.1038/srep38116. PubMed PMID: 27901080; PubMed Central PMCID: PMC5128878.
2: Park P, Sanderson TM, Amici M, Choi SL, Bortolotto ZA, Zhuo M, Kaang BK, Collingridge GL. Calcium-Permeable AMPA Receptors Mediate the Induction of the Protein Kinase A-Dependent Component of Long-Term Potentiation in the Hippocampus. J Neurosci. 2016 Jan 13;36(2):622-31. doi: 10.1523/JNEUROSCI.3625-15.2016. PubMed PMID: 26758849; PubMed Central PMCID: PMC4710778.
3: McGee TP, Bats C, Farrant M, Cull-Candy SG. Auxiliary Subunit GSG1L Acts to Suppress Calcium-Permeable AMPA Receptor Function. J Neurosci. 2015 Dec 9;35(49):16171-9. doi: 10.1523/JNEUROSCI.2152-15.2015. PubMed PMID: 26658868; PubMed Central PMCID: PMC4682783.
4: Franzyk H, Grzeskowiak JW, Tikhonov DB, Jaroszewski JW, Mellor IR. The effects of conformational constraints in the polyamine moiety of philanthotoxins on AMPAR inhibition. ChemMedChem. 2014 Aug;9(8):1725-31. doi: 10.1002/cmdc.201402109. Epub 2014 Jul 8. PubMed PMID: 25044789.
5: Mattison HA, Bagal AA, Mohammadi M, Pulimood NS, Reich CG, Alger BE, Kao JP, Thompson SM. Evidence of calcium-permeable AMPA receptors in dendritic spines of CA1 pyramidal neurons. J Neurophysiol. 2014 Jul 15;112(2):263-75. doi: 10.1152/jn.00578.2013. Epub 2014 Apr 23. PubMed PMID: 24760782; PubMed Central PMCID: PMC4064414.
6: Younger MA, Müller M, Tong A, Pym EC, Davis GW. A presynaptic ENaC channel drives homeostatic plasticity. Neuron. 2013 Sep 18;79(6):1183-96. doi: 10.1016/j.neuron.2013.06.048. Epub 2013 Aug 22. PubMed PMID: 23973209; PubMed Central PMCID: PMC3784986.
7: Bellone C, Mameli M, Lüscher C. In utero exposure to cocaine delays postnatal synaptic maturation of glutamatergic transmission in the VTA. Nat Neurosci. 2011 Oct 2;14(11):1439-46. doi: 10.1038/nn.2930. PubMed PMID: 21964489.
8: Jackson AC, Milstein AD, Soto D, Farrant M, Cull-Candy SG, Nicoll RA. Probing TARP modulation of AMPA receptor conductance with polyamine toxins. J Neurosci. 2011 May 18;31(20):7511-20. doi: 10.1523/JNEUROSCI.6688-10.2011. PubMed PMID: 21593335; PubMed Central PMCID: PMC3164836.
9: Sara Y, Bal M, Adachi M, Monteggia LM, Kavalali ET. Use-dependent AMPA receptor block reveals segregation of spontaneous and evoked glutamatergic neurotransmission. J Neurosci. 2011 Apr 6;31(14):5378-82. doi: 10.1523/JNEUROSCI.5234-10.2011. PubMed PMID: 21471372; PubMed Central PMCID: PMC3086544.
10: Jackson AC, Nicoll RA. Stargazin (TARP gamma-2) is required for compartment-specific AMPA receptor trafficking and synaptic plasticity in cerebellar stellate cells. J Neurosci. 2011 Mar 16;31(11):3939-52. doi: 10.1523/JNEUROSCI.5134-10.2011. PubMed PMID: 21411637; PubMed Central PMCID: PMC3104604.
11: Müller M, Pym EC, Tong A, Davis GW. Rab3-GAP controls the progression of synaptic homeostasis at a late stage of vesicle release. Neuron. 2011 Feb 24;69(4):749-62. doi: 10.1016/j.neuron.2011.01.025. PubMed PMID: 21338884; PubMed Central PMCID: PMC3059509.
12: Frølund S, Bella A, Kristensen AS, Ziegler HL, Witt M, Olsen CA, Strømgaard K, Franzyk H, Jaroszewski JW. Assessment of structurally diverse philanthotoxin analogues for inhibitory activity on ionotropic glutamate receptor subtypes: discovery of nanomolar, nonselective, and use-dependent antagonists. J Med Chem. 2010 Oct 28;53(20):7441-51. doi: 10.1021/jm100886h. PubMed PMID: 20873775.
13: He K, Song L, Cummings LW, Goldman J, Huganir RL, Lee HK. Stabilization of Ca2+-permeable AMPA receptors at perisynaptic sites by GluR1-S845 phosphorylation. Proc Natl Acad Sci U S A. 2009 Nov 24;106(47):20033-8. doi: 10.1073/pnas.0910338106. Epub 2009 Nov 5. PubMed PMID: 19892736; PubMed Central PMCID: PMC2785287.
14: Frade JG, Barbosa RM, Laranjinha J. Stimulation of NMDA and AMPA glutamate receptors elicits distinct concentration dynamics of nitric oxide in rat hippocampal slices. Hippocampus. 2009 Jul;19(7):603-11. doi: 10.1002/hipo.20536. PubMed PMID: 19115375.
15: Galván EJ, Calixto E, Barrionuevo G. Bidirectional Hebbian plasticity at hippocampal mossy fiber synapses on CA3 interneurons. J Neurosci. 2008 Dec 24;28(52):14042-55. doi: 10.1523/JNEUROSCI.4848-08.2008. PubMed PMID: 19109487; PubMed Central PMCID: PMC2660276.
16: Mathew SS, Hablitz JJ. Calcium release via activation of presynaptic IP3 receptors contributes to kainate-induced IPSC facilitation in rat neocortex. Neuropharmacology. 2008 Jul;55(1):106-16. doi: 10.1016/j.neuropharm.2008.05.005. Epub 2008 May 14. PubMed PMID: 18508095; PubMed Central PMCID: PMC2580077.
17: Szinyei C, Narayanan RT, Pape HC. Plasticity of inhibitory synaptic network interactions in the lateral amygdala upon fear conditioning in mice. Eur J Neurosci. 2007 Feb;25(4):1205-11. PubMed PMID: 17331216.
18: Kukley M, Capetillo-Zarate E, Dietrich D. Vesicular glutamate release from axons in white matter. Nat Neurosci. 2007 Mar;10(3):311-20. Epub 2007 Feb 11. PubMed PMID: 17293860.
19: Andersen TF, Tikhonov DB, Bølcho U, Bolshakov K, Nelson JK, Pluteanu F, Mellor IR, Egebjerg J, Strømgaard K. Uncompetitive antagonism of AMPA receptors: Mechanistic insights from studies of polyamine toxin derivatives. J Med Chem. 2006 Sep 7;49(18):5414-23. PubMed PMID: 16942015.
20: Strømgaard K, Piazzi L, Olsen CA, Franzyk H, Jaroszewski JW. Protolytic properties of polyamine wasp toxin analogues studied by 13C NMR spectroscopy. Magn Reson Chem. 2006 Nov;44(11):1013-22. PubMed PMID: 16941578.