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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

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
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
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
Yuan Ge et al.
Nature communications, 10(1), 4089-4089 (2019-09-11)
The α-amino-3-hydroxy-5-methylisoxazole-4-propionic acid subtype glutamate receptors (AMPARs) mediate the fast excitatory synaptic transmission in the mammalian brain and are important for synaptic plasticity. In particular, the rapid insertion of the GluA1 homomeric (GluA1-homo) AMPARs into the postsynaptic membrane is considered
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