MedKoo Cat#: 526110 | Name: Psammaplysene A

Description:

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

Psammaplysene A is a naturally occurring inhibitor of FOXO1a nuclear export.

Chemical Structure

Psammaplysene A
Psammaplysene A
CAS#850013-02-4

Theoretical Analysis

MedKoo Cat#: 526110

Name: Psammaplysene A

CAS#: 850013-02-4

Chemical Formula: C27H35Br4N3O3

Exact Mass: 764.9412

Molecular Weight: 769.21

Elemental Analysis: C, 42.16; H, 4.59; Br, 41.55; N, 5.46; O, 6.24

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.
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Related CAS #
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Synonym
Psammaplysene A
IUPAC/Chemical Name
(E)-N-[3-[2,6-Dibromo-4-[2-(dimethylamino)ethyl]phenoxy]propyl]-3-[3,5-dibromo-4-[3-(dimethylamino)propoxy]phenyl]prop-2-enamide
InChi Key
PKWUEPCKAUUBLY-BQYQJAHWSA-N
InChi Code
InChI=1S/C27H35Br4N3O3/c1-33(2)11-6-14-37-27-21(28)15-19(16-22(27)29)7-8-25(35)32-10-5-13-36-26-23(30)17-20(18-24(26)31)9-12-34(3)4/h7-8,15-18H,5-6,9-14H2,1-4H3,(H,32,35)/b8-7+
SMILES Code
O=C(NCCCOC1=C(Br)C=C(CCN(C)C)C=C1Br)/C=C/C2=CC(Br)=C(OCCCN(C)C)C(Br)=C2
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
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 769.21 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: Obrador-Hevia A, Serra-Sitjar M, Rodríguez J, Villalonga P, Fernández de Mattos S. The tumour suppressor FOXO3 is a key regulator of mantle cell lymphoma proliferation and survival. Br J Haematol. 2012 Feb;156(3):334-45. doi: 10.1111/j.1365-2141.2011.08951.x. Epub 2011 Nov 23. PubMed PMID: 22107151. 2: Mojsilovic-Petrovic J, Nedelsky N, Boccitto M, Mano I, Georgiades SN, Zhou W, Liu Y, Neve RL, Taylor JP, Driscoll M, Clardy J, Merry D, Kalb RG. FOXO3a is broadly neuroprotective in vitro and in vivo against insults implicated in motor neuron diseases. J Neurosci. 2009 Jun 24;29(25):8236-47. doi: 10.1523/JNEUROSCI.1805-09.2009. PubMed PMID: 19553463; PubMed Central PMCID: PMC2748231. 3: Hoekstra AV, Sefton EC, Berry E, Lu Z, Hardt J, Marsh E, Yin P, Clardy J, Chakravarti D, Bulun S, Kim JJ. Progestins activate the AKT pathway in leiomyoma cells and promote survival. J Clin Endocrinol Metab. 2009 May;94(5):1768-74. doi: 10.1210/jc.2008-2093. Epub 2009 Feb 24. PubMed PMID: 19240153; PubMed Central PMCID: PMC2684476. 4: Berry E, Hardt JL, Clardy J, Lurain JR, Kim JJ. Induction of apoptosis in endometrial cancer cells by psammaplysene A involves FOXO1. Gynecol Oncol. 2009 Feb;112(2):331-6. doi: 10.1016/j.ygyno.2008.10.017. Epub 2008 Nov 28. PubMed PMID: 19041124; PubMed Central PMCID: PMC2662924. 5: Fernández de Mattos S, Villalonga P, Clardy J, Lam EW. FOXO3a mediates the cytotoxic effects of cisplatin in colon cancer cells. Mol Cancer Ther. 2008 Oct;7(10):3237-46. doi: 10.1158/1535-7163.MCT-08-0398. PubMed PMID: 18852127; PubMed Central PMCID: PMC2748241. 6: Georgiades SN, Clardy J. Preparation of a psammaplysene-based library. Org Lett. 2006 Sep 14;8(19):4251-4. PubMed PMID: 16956199; PubMed Central PMCID: PMC2522302. 7: Georgiades SN, Clardy J. Total synthesis of psammaplysenes A and B, naturally occurring inhibitors of FOXO1a nuclear export. Org Lett. 2005 Sep 15;7(19):4091-4. PubMed PMID: 16146359. 8: Schroeder FC, Kau TR, Silver PA, Clardy J. The psammaplysenes, specific inhibitors of FOXO1a nuclear export. J Nat Prod. 2005 Apr;68(4):574-6. PubMed PMID: 15844952.