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P206

Sigma-Aldrich

Philanthotoxin 343 tris(trifluoroacetate) salt

solid

Synonym(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

Empirical Formula (Hill Notation):
C23H41N5O3 · 3C2HF3O2
CAS Number:
Molecular Weight:
777.67
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

form

solid

color

light yellow-green

solubility

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

storage temp.

−20°C

SMILES string

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

InChI key

QTCLKBFOFGTNMC-YDULTXHLSA-N

Gene Information

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.

Biochem/physiol Actions

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).

Caution

Hygroscopic

Reconstitution

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

Legal Information

Sold under license from Columbia University.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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H L Sudan et al.
Invertebrate neuroscience : IN, 1(2), 159-172 (1995-01-01)
The effects of philanthotoxin-343 (PhTX-343; tyrosyl-butanoyl-spermine) and photolabile analogues of this synthetic toxin on locust (Schistocerca gregaria) skeletal muscle have been investigated using whole muscle preparations (twitch contractions), single muscle fibres (excitatory postsynaptic currents (EPSCs)) and muscle membrane patches containing
Denis B Tikhonov et al.
Biophysical journal, 87(1), 159-170 (2004-07-09)
Models of closed and open channel pores of a muscle-type nicotinic acetylcholine receptor (nAChR) channel comprising M1 and M2 segments are presented. A model of the closed channel is proposed in which hydrophobic residues of the Equatorial Leucine ring screen
S D Donevan et al.
Neuroscience, 70(2), 361-375 (1996-01-01)
The effects of the arylalkyamine arthropod toxins argiotoxin 636 and philanthotoxin 343 were studied on N-methyl-D-aspartate receptor currents in cultured rat hippocampal neurons using whole-cell recording techniques. Argiotoxin 636 and philanthotoxin 343 blocked 10 microM N-methyl-D-aspartate (+10 microM glycine) currents
J W Jaroszewski et al.
Journal of medicinal chemistry, 39(2), 515-521 (1996-01-19)
Acid-base properties (pKa values and proton distribution patterns) of philanthotoxin-343(PhTX-343) were investigated by 1H and 13C NMR titration. Chemical shift data and the total ionization shifts were used to assign carbon atoms of the polyamine chain. Nonlinear analysis of the
P Brackley et al.
Neuroscience letters, 114(1), 51-56 (1990-07-02)
The effects of spermine and a synthetic analogue (PhTX-343) of the polyamine amide toxin, delta-philanthotoxin, on the responses of Xenopus oocytes to application of amino acids were examined using voltage clamp. The oocytes were injected with either total rat brain

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