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P206

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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Acerca de este artículo

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


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.[1] 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.[2]

Biochem/physiol Actions

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).[3]
Blocks NMDA-gated ion channels; synthetic analog of the wasp polyamine amide toxin δ-philanthotoxin.

Preparation Note

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

Legal Information

Sold under license from Columbia University.

Disclaimer

Hygroscopic


Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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Malene R Jørgensen et al.
Journal of medicinal chemistry, 48(1), 56-70 (2005-01-07)
Philanthotoxin-343 (PhTX-343), a synthetic analogue of wasp toxin PhTX-433, is a noncompetitive antagonist at ionotropic receptors (e.g., AChR or iGluR). To determine possible effects of variations of the amino acid side chain, a library consisting of seventeen PhTX-343 analogues was
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
A C Green et al.
Brain research, 717(1-2), 135-146 (1996-04-22)
Primary cultures of rat cerebellar granule cells have been used to assess the potential neuroprotective effects of philanthotoxins and argiotoxin-636 (ArgTX-636). These polyamine amides are potent antagonists of ionotropic L-glutamate (L-Glu) receptors. In granule cells loaded with fluo-3, ArgTX-636 and