Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

P8749

Sigma-Aldrich

Psammaplin A

≥97% (HPLC), solid

Synonym(s):

Bisprasin, N,N"-(dithiodi-2,1-ethanediyl)bis[3-bromo-4-hydroxy-a-(hydroxyimino)-benzenepropanamide

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C22H24Br2N4O6S2
CAS Number:
110659-91-1
Molecular Weight:
664.39
UNSPSC Code:
12352200

Assay

≥97% (HPLC)

form

solid

solubility

DMSO: >10 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

O\N=C(\Cc1ccc(O)c(Br)c1)C(=O)NCCSSCCNC(=O)C(\Cc2ccc(O)c(Br)c2)=N/O

Biochem/physiol Actions

Psammaplin A is an antibiotic, anti-tumor, DNA methyltransferase inhibitor.
Psammaplin A is an antibiotic, anti-tumor, DNA methyltransferase inhibitor. It is a bromotyrosine-derived, symmetrical conjugate of cystamine, which was first isolated from the Psammaplinaplysilla sponge. Psammaplin A impedes angiogenesis as well as bacterial and tumor cell growth. Psammaplin A inhibits the activities of several key enzymes in prokaryotic and eukaryotic systems including those involved in epigenetic control of gene expression, DNA replication, angiogensis, and microbial detoxification.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
077K46101
077K4610

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Natural product family 18 chitinase inhibitors.
Ole A Andersen et al.
Natural product reports, 22(5), 563-579 (2005-09-30)
Raquel Pereira et al.
Journal of medicinal chemistry, 55(22), 9467-9491 (2012-10-04)
A SAR study has been carried out around a modified scaffold of the natural product psammaplin A obtained by replacing the o-bromophenol unit by an indole ring. A series of indole psammaplin A constructs were generated in a short synthetic
Julien Saguez et al.
Pest management science, 62(12), 1150-1154 (2006-09-06)
Four chitinase inhibitors, cyclo-(Proline-Tyrosine), cyclo-(Histidine-Proline), allosamidin and psammaplin A, were selected for in vitro feeding experiments with the peach-potato aphid, Myzus persicae (Sulzer), under controlled photoperiod and temperature conditions. Artificial diets were used to provide chitinase inhibitors at 10, 50
Hak Jae Kim et al.
Archives of pharmacal research, 35(10), 1849-1854 (2012-11-10)
This study reports the pharmacokinetics and tissue distribution of a novel histone deacetylase and DNA methyltransferase inhibitor, psammaplin A (PsA), in mice. PsA concentrations were determined by a validated LC-MS/MS assay method (LLOQ 2 ng/mL). Following intravenous injection at a
Matthias G J Baud et al.
Organic & biomolecular chemistry, 9(3), 659-662 (2010-11-30)
New synthetic routes towards the natural product psammaplin A were developed with the particular view to preparing diverse analogues for biological assessment. These routes utilize cheap and commercially available starting materials, and allowed access to psammaplin A analogues not accessible
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service