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P207

Sigma-Aldrich

Philanthotoxin 433 tris(trifluoroacetate) salt

≥98% (HPLC), powder

Synonyme(s) :

(S)-N-[4-[[3-[(3-Aminopropyl)amino]propyl]amino]butyl]-4-hydroxy-α-[(1-oxobutyl)amino]benzenepropanamide tris(trifluoroacetate) salt, PhTX-433 tris(trifluoroacetate) salt

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About This Item

Formule empirique (notation de Hill):
C23H41N5O3 · 3C2HF3O2
Numéro CAS:
276684-27-6
Poids moléculaire :
777.67
Numéro MDL:
MFCD00661076
Code UNSPSC :
12352202
ID de substance PubChem :
24898269

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

H2O: ≥10 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CCCC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)NCCCCNCCCNCCCN

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

Clé InChI

UROZAUWUTBOQNV-YDULTXHLSA-N

Informations sur le gène

human ... GRIN1(2902)
mouse ... GRIN1(14810)
rat ... GRIN1(24408)

Actions biochimiques/physiologiques

Philanthotoxin 433 is a polyamine-containing toxin, which blocks NMDA-gated ion channels; originally isolated from the venom of the wasp Philanthus triangulum.

Attention

hygroscopic

Reconstitution

Addition of 1 mL of solvent to vial yields a 1 mM solution.

Informations légales

Sold under license from Columbia University.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Conseils de prudence

P301 + P310

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

H Karst et al.
European journal of pharmacology, 270(4), 357-360 (1994-08-03)
The wasp venom philanthotoxin-4.3.3 (PhTX-4.3.3) is an antagonist of glutamate transmission in the insect as well as in the mammalian brain. It was recently shown that PhTX-4.3.3 inhibits the N-methyl-D-aspartate (NMDA) transmission in rat hippocampus. In this study we show
Achmed Mrestani et al.
Cell reports, 37(1), 109770-109770 (2021-10-06)
Neurotransmitter release is stabilized by homeostatic plasticity. Presynaptic homeostatic potentiation (PHP) operates on timescales ranging from minute- to life-long adaptations and likely involves reorganization of presynaptic active zones (AZs). At Drosophila melanogaster neuromuscular junctions, earlier work ascribed AZ enlargement by
J A Benson et al.
Comparative biochemistry and physiology. C, Comparative pharmacology and toxicology, 102(2), 267-272 (1992-06-01)
1. The blocking action of delta-philanthotoxin (PhTX-4.3.3), a wasp toxin composed of a polyamine chain, an aromatic amino acid (tyrosyl) nucleus and an aliphatic (butanoic) acid was studied, together with 33 structural analogues, at the glutamatergic neuromuscular synapse in larvae
P T Brackley et al.
The Journal of pharmacology and experimental therapeutics, 266(3), 1573-1580 (1993-09-01)
Antagonism of rat excitatory amino acid receptors by a synthetic analog [philanthotoxin-343 (PhTX-343)] of a polyamine amide, wasp toxin (philanthotoxin-433) and a structurally related spider toxin, argiotoxin-636 (ArgTX-636), was examined in Xenopus oocytes injected with rat brain RNA or RNA
N B Fedorov et al.
European journal of pharmacology, 228(4), 201-206 (1992-12-01)
A synthetic analog of philanthotoxin-433, philanthotoxin-343 (PhTX-343), was tested in hippocampal pyramidal neurons in vitro. PhTX-343 (2 microM) did not significantly change synaptic transmission mediated by AMPA (alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid)/kainate receptors in the CA1 region of hippocampus. However, PhTX-343 significantly
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