Psammaplin A

Psammaplin A is a marine metabolite. Psammaplin A is a selective HDAC1 (IC50: 45 nM), DNA methyltransferases (IC50: 18.6 nM) and aminopeptidase N (APN) (IC50: 18 μM) inhibitor. Psammaplin A also inhibits DNA topoisomerase and farnesyl protein transferase. Psammaplin A is a PPARγ activator and induces apoptosis. Psammaplin A has antitumor and anti-inflammatory activities. Psammaplin A has antibacterial activity against Gram-positive bacteria and inhibits DNA synthesis and DNA gyrase activity. Psammaplin A inhibits angiogenesis[1][2][3][4][5][6][7][8].

Product Specifications

CAS Number

[110659-91-1]

UNSPSC

12352005

Hazard Statement

H315-H319-H335

Target

Aminopeptidase; Apoptosis; Bacterial; DNA Methyltransferase; DNA/RNA Synthesis; Farnesyl Transferase; HDAC; PPAR

Type

Natural Products

Related Pathways

Anti-infection; Apoptosis; Cell Cycle/DNA Damage; Epigenetics; Metabolic Enzyme/Protease; Vitamin D Related/Nuclear Receptor

Applications

COVID-19-anti-virus

Field of Research

Cancer; Infection; Inflammation/Immunology

Assay Protocol

https://www.medchemexpress.com/psammaplin-a.html

Purity

96.0

Solubility

DMSO : 33.3 mg/mL (ultrasonic; warming)

Smiles

O=C(NCCSSCCNC(/C(CC1=CC(Br)=C(O)C=C1)=N/O)=O)/C(CC2=CC(Br)=C(O)C=C2)=N/O

Molecular Formula

C22H24Br2N4O6S2

Molecular Weight

664.39

Precautions

P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P362+P364-P403+P233-P405-P501

References & Citations

[1]Hong S, et al. Efficient synthesis and biological activity of Psammaplin A and its analogues as antitumor agents. Eur J Med Chem. 2015;96:218-30.|[2]Shim JS, et al. Psammaplin A, a marine natural product, inhibits aminopeptidase N and suppresses angiogenesis in vitro. Cancer Lett. 2004 Jan 20;203 (2) :163-9.|[3]Lee BC, et al. In vitro and in vivo anti-Vibrio vulnificus activity of psammaplin A, a natural marine compound. Mol Med Rep. 2016 Sep;14 (3) :2691-6.|[4]Piña IC, et al. Psammaplins from the sponge Pseudoceratina purpurea: inhibition of both histone deacetylase and DNA methyltransferase. J Org Chem. 2003 May 16;68 (10) :3866-73.|[5]Baud MG, et al. Defining the mechanism of action and enzymatic selectivity of psammaplin A against its epigenetic targets. J Med Chem. 2012 Feb 23;55 (4) :1731-50.|[6]Jiang Y, et al. Cytotoxicity of psammaplin A from a two-sponge association may correlate with the inhibition of DNA replication. BMC Cancer. 2004 Sep 30;4:70.|[7]Jongheon S, et al, New Bromotyrosine Metabolites from the Sponge Aplysinella rhax, Tetrahedron, Volume 56, Issue 46, 2000, Pages 9071-9077, ISSN 0040-4020|[8]Mora FD, et al. Bioassay for the identification of natural product-based activators of peroxisome proliferator-activated receptor-gamma (PPARgamma) : the marine sponge metabolite psammaplin A activates PPARgamma and induces apoptosis in human breast tumor cells. J Nat Prod. 2006 Apr;69 (4) :547-52.