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Merck
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P206

Sigma-Aldrich

Philanthotoxin 343 tris(trifluoroacetate) salt

solid

Synonyme(s) :

PhTX-343, S-N-[3-[[4-[(3-Aminopropyl)amino]butyl]amino]propyl]-4-hydroxy-α-[(1-oxobutyl)amino]-benzenepropanamide tris-trifluoroacetate

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About This Item

Formule empirique (notation de Hill):
C23H41N5O3 · 3C2HF3O2
Numéro CAS:
115976-93-7
Poids moléculaire :
777.67
Numéro MDL:
MFCD00661073
Code UNSPSC :
12352200
ID de substance PubChem :
24898266

Forme

solid

Couleur

light yellow-green

Solubilité

methanol: >8 mg/mL (solutions should be freshly prepared.)

Température de stockage

−20°C

Chaîne SMILES 

OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F.CCCC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)NCCCNCCCCNCCCN

InChI

1S/C23H41N5O3.3CHF3O3S/c1-2-7-22(30)28-21(18-19-8-10-20(29)11-9-19)23(31)27-17-6-16-26-14-4-3-13-25-15-5-12-24;3*2-1(3,4)8(5,6)7/h8-11,21,25-26,29H,2-7,12-18,24H2,1H3,(H,27,31)(H,28,30);3*(H,5,6,7)/t21-;;;/m0.../s1

Clé InChI

QTCLKBFOFGTNMC-YDULTXHLSA-N

Informations sur le gène

rat ... Chrm2(81645) , Chrm3(24260)

Application

Philanthotoxin 343 tris(trifluoroacetate) salt has been used as Ca2+-permeable α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors (AMPARs) blocker. It has also been used as an effective glutamate receptors blocker in an acute homeostasis paradigm to examine the speed of the Neto-α-mediated homeostatic response in Drosophila.

Actions biochimiques/physiologiques

Blocks NMDA-gated ion channels; synthetic analog of the wasp polyamine amide toxin δ-philanthotoxin.
Philanthotoxin 343 is a synthetic analog of the wasp polyamine amide toxin δ-philanthotoxin. It blocks the activation of ionotropic receptors such as acetylcholine receptor (AChR) or inhibitory glutamate receptors (iGluRs).

Attention

Hygroscopic

Reconstitution

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

Informations légales

Sold under license from Columbia University.

Code de la classe de stockage

11 - Combustible Solids

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

A light switch controlling Ca2+-permeable AMPA receptors in the retina.
Jeffrey S Diamond
The Journal of physiology, 582(Pt 1), 3-3 (2007-04-28)
D Bowie et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 18(20), 8175-8185 (1998-10-08)
The mechanisms by which polyamines block AMPA and kainate receptors are not well understood, but it has been generally assumed that they act as open-channel blockers. Consistent with this, voltage-jump relaxation analysis of GluR6 equilibrium responses to domoate could be
M Liu et al.
British journal of pharmacology, 122(2), 379-385 (1997-10-06)
1. Block by philanthotoxin-343 (PhTX-343), a neurotoxin from wasps, of ionic currents mediated through neuronal nicotinic acetylcholine (ACh) receptor/channels was characterized in rat phaeochromocytoma PC12 cells, by use of whole cell voltage-clamp techniques. 2. In the cells held at -60
Tim J Brier et al.
Molecular pharmacology, 64(4), 954-964 (2003-09-23)
Whole-cell recordings and outside-out patch recordings from TE671 cells were made to investigate antagonism of human muscle nicotinic acetylcholine receptors (nAChR) by the philanthotoxins, PhTX-343 and PhTX-(12). When coapplied with acetylcholine (ACh), PhTX-343 caused activation-dependent, noncompetitive inhibition (IC50 = 17
Sidsel Frølund et al.
Journal of medicinal chemistry, 53(20), 7441-7451 (2010-09-30)
An array of analogues of the wasp toxin philanthotoxin-433, in which the asymmetric polyamine moiety was exchanged for spermine and the headgroup replaced with a variety of structurally diverse moieties, was prepared using parallel solid-phase synthesis approaches. In three analogues
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