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MedKoo Cat#: 555559 | Name: PhTX-343 TFA

Description:

WARNING: This product is for research use only, not for human or veterinary use.

PhTX-343, also known as Philanthotoxin 343, is synthetic analogue of Philanthotoxin 433. PhTX-343 blocks NMDA-gated ion channels; synthetic analog of the wasp polyamine amide toxin δ-philanthotoxin.

Chemical Structure

PhTX-343 TFA
PhTX-343 TFA
CAS#115976-93-7 (TFA)

Theoretical Analysis

MedKoo Cat#: 555559

Name: PhTX-343 TFA

CAS#: 115976-93-7 (TFA)

Chemical Formula: C29H44F9N5O9

Exact Mass:

Molecular Weight: 777.68

Elemental Analysis: C, 44.79; H, 5.70; F, 21.99; N, 9.01; O, 18.52

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
115976-93-7 (free base) 115976-93-7 (TFA)
Synonym
(S)-PTX 343; (S)-PhTX 343; (S)-Philanthotoxin 343; PhTX-343 TFA; PhTX-343; PhTX= 343; PhTX343;
IUPAC/Chemical Name
(S)-N-(1-((3-((4-((3-aminopropyl)amino)butyl)amino)propyl)amino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)butyramide tris(2,2,2-trifluoroacetate)
InChi Key
ACIUBIMDIUIKBJ-YDULTXHLSA-N
InChi Code
InChI=1S/C23H41N5O3.3C2HF3O2/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*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
SMILES Code
O=C(NCCCNCCCCNCCCN)[C@@H](NC(CCC)=O)CC1=CC=C(O)C=C1.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Philanthotoxin 433, is a polyamine-containing toxin, which blocks NMDA-gated ion channels; originally isolated from the venom of the wasp Philanthus triangulum.

Preparing Stock Solutions

The following data is based on the product molecular weight 777.68 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kachel HS, Patel RN, Franzyk H, Mellor IR. Block of nicotinic acetylcholine receptors by philanthotoxins is strongly dependent on their subunit composition. Sci Rep. 2016 Nov 30;6:38116. doi: 10.1038/srep38116. PubMed PMID: 27901080; PubMed Central PMCID: PMC5128878. 2: Franzyk H, Grzeskowiak JW, Tikhonov DB, Jaroszewski JW, Mellor IR. The effects of conformational constraints in the polyamine moiety of philanthotoxins on AMPAR inhibition. ChemMedChem. 2014 Aug;9(8):1725-31. doi: 10.1002/cmdc.201402109. Epub 2014 Jul 8. PubMed PMID: 25044789. 3: McClymont DW, Harris J, Mellor IR. Open-channel blockade is less effective on GluN3B than GluN3A subunit-containing NMDA receptors. Eur J Pharmacol. 2012 Jul 5;686(1-3):22-31. doi: 10.1016/j.ejphar.2012.04.036. Epub 2012 Apr 27. PubMed PMID: 22564863; PubMed Central PMCID: PMC3657159. 4: Frølund S, Bella A, Kristensen AS, Ziegler HL, Witt M, Olsen CA, Strømgaard K, Franzyk H, Jaroszewski JW. Assessment of structurally diverse philanthotoxin analogues for inhibitory activity on ionotropic glutamate receptor subtypes: discovery of nanomolar, nonselective, and use-dependent antagonists. J Med Chem. 2010 Oct 28;53(20):7441-51. doi: 10.1021/jm100886h. PubMed PMID: 20873775. 5: Diamond JS. A light switch controlling Ca2+-permeable AMPA receptors in the retina. J Physiol. 2007 Jul 1;582(Pt 1):3. Epub 2007 Apr 26. PubMed PMID: 17463033; PubMed Central PMCID: PMC2075293. 6: Osswald IK, Galan A, Bowie D. Light triggers expression of philanthotoxin-insensitive Ca2+-permeable AMPA receptors in the developing rat retina. J Physiol. 2007 Jul 1;582(Pt 1):95-111. Epub 2007 Apr 12. PubMed PMID: 17430992; PubMed Central PMCID: PMC2075288. 7: Strømgaard K, Piazzi L, Olsen CA, Franzyk H, Jaroszewski JW. Protolytic properties of polyamine wasp toxin analogues studied by 13C NMR spectroscopy. Magn Reson Chem. 2006 Nov;44(11):1013-22. PubMed PMID: 16941578. 8: Jørgensen MR, Olsen CA, Mellor IR, Usherwood PN, Witt M, Franzyk H, Jaroszewski JW. The effects of conformational constraints and steric bulk in the amino acid moiety of philanthotoxins on AMPAR antagonism. J Med Chem. 2005 Jan 13;48(1):56-70. PubMed PMID: 15634001. 9: Tikhonov DB, Mellor IR, Usherwood PN. Modeling noncompetitive antagonism of a nicotinic acetylcholine receptor. Biophys J. 2004 Jul;87(1):159-70. PubMed PMID: 15240454; PubMed Central PMCID: PMC1304339. 10: Brier TJ, Mellor IR, Tikhonov DB, Neagoe I, Shao Z, Brierley MJ, Strømgaard K, Jaroszewski JW, Krogsgaard-Larsen P, Usherwood PN. Contrasting actions of philanthotoxin-343 and philanthotoxin-(12) on human muscle nicotinic acetylcholine receptors. Mol Pharmacol. 2003 Oct;64(4):954-64. PubMed PMID: 14500752. 11: Shinada T, Nakagawa Y, Hayashi K, Corzo G, Nakajima T, Ohfune Y. Synthesis and paralytic activities of squaryl amino acid-containing polyamine toxins. Amino Acids. 2003 Apr;24(3):293-301. PubMed PMID: 12707812. 12: Kerschbaum HH, Kozak JA, Cahalan MD. Polyvalent cations as permeant probes of MIC and TRPM7 pores. Biophys J. 2003 Apr;84(4):2293-305. PubMed PMID: 12668438; PubMed Central PMCID: PMC1302796. 13: Wellendorph P, Jaroszewski JW, Hansen SH, Franzyk H. A sequential high-yielding large-scale solution-method for synthesis of philanthotoxin analogues. Eur J Med Chem. 2003 Jan;38(1):117-22. PubMed PMID: 12593922. 14: Mellor IR, Brier TJ, Pluteanu F, Strømgaard K, Saghyan A, Eldursi N, Brierley MJ, Andersen K, Jaroszewski JW, Krogsgaard-Larsen P, Usherwood PN. Modification of the philanthotoxin-343 polyamine moiety results in different structure-activity profiles at muscle nicotinic ACh, NMDA and AMPA receptors. Neuropharmacology. 2003 Jan;44(1):70-80. PubMed PMID: 12559123. 15: Lei S, McBain CJ. Distinct NMDA receptors provide differential modes of transmission at mossy fiber-interneuron synapses. Neuron. 2002 Mar 14;33(6):921-33. PubMed PMID: 11906698. 16: Li Y, Popaj K, Lochner M, Geneste H, Budriesi R, Chiarini A, Melchiorre C, Hesse M. Analogues of polyamine alkaloids and their synthetic advantages. Farmaco. 2001 Jan-Feb;56(1-2):127-31. PubMed PMID: 11347953. 17: Tikhonov DB, Magazanik LG, Mellor IR, Usherwood PN. Possible influence of intramolecular hydrogen bonds on the three-dimensional structure of polyamine amides and their interaction with ionotropic glutamate receptors. Receptors Channels. 2000;7(3):227-36. PubMed PMID: 11342390. 18: Armstrong JN, MacVicar BA. Theta-frequency facilitation of AMPA receptor-mediated synaptic currents in the principal cells of the medial septum. J Neurophysiol. 2001 Apr;85(4):1709-18. PubMed PMID: 11287493. 19: Strømgaard K, Brier TJ, Andersen K, Mellor IR, Saghyan A, Tikhonov D, Usherwood PN, Krogsgaard-Larsen P, Jaroszewski JW. Solid-phase synthesis and biological evaluation of a combinatorial library of philanthotoxin analogues. J Med Chem. 2000 Nov 16;43(23):4526-33. PubMed PMID: 11087577. 20: Usherwood PN. Natural and synthetic polyamines: modulators of signalling proteins. Farmaco. 2000 Mar;55(3):202-5. Review. PubMed PMID: 10919083.