Psammaplysene A

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

MedKoo CAT#: 526110

CAS#: 850013-02-4

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

Chemical Structure

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Psammaplysene A
CAS# 850013-02-4
Instruction

Theoretical Analysis

MedKoo Cat#: 526110
Name: Psammaplysene A
CAS#: 850013-02-4
Chemical Formula: C27H35Br4N3O3
Exact Mass: 764.94
Molecular Weight: 769.211
Elemental Analysis: C, 42.16; H, 4.59; Br, 41.55; N, 5.46; O, 6.24

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.