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P206

Sigma-Aldrich

Philanthotoxin 343 tris(trifluoroacetate) salt

solid

Sinónimos:

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

Fórmula empírica (notación de Hill):
C23H41N5O3 · 3C2HF3O2
Número de CAS:
115976-93-7
Peso molecular:
777.67
MDL number:
MFCD00661073
UNSPSC Code:
12352200
PubChem Substance ID:
24898266

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

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.

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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M Nankai et al.
Journal of neurochemistry, 64(5), 2043-2048 (1995-05-01)
NMDA receptor stimulation concomitantly increases the release of [14C]acetylcholine and [3H]-spermidine from rat striatal slices in vitro. The NMDA-induced release of both acetylcholine and spermidine was blocked with equal potency by the NMDA channel blocker phencyclidine (0.1-10 microM). However, certain
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
R Bähring et al.
The Journal of physiology, 509 ( Pt 3), 635-650 (1998-05-23)
1. The action of philanthotoxin 343 (PhTX) on rat homomeric GluR6(Q) recombinant glutamate receptor channels was analysed using concentration-jump techniques and outside-out patches from HEK 293 cells. Both onset and recovery from block by external PhTX were dependent on 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
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
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