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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

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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. 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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Fabia Hentschel et al.
Organic & biomolecular chemistry, 10(35), 7120-7133 (2012-08-09)
The symmetrical disulfide psammaplin A from the marine sponge Pseudoceratina sp. was synthesized and structurally altered by replacement of one of the α-(hydroxyimino)acyl units by a fluorescent 4-coumarinacetyl moiety. Thus, the first fluorescent analogs of psammaplin A were obtained. Structural
Carsten Thoms et al.
Journal of chemical ecology, 34(9), 1242-1252 (2008-08-06)
Activated chemical defense, i.e., the rapid conversion of precursor molecules to defensive compounds following tissue damage, has been well documented for terrestrial and marine plants; but evidence for its presence in sessile marine invertebrates remains scarce. We observed a wound-activated
José García et al.
Bioorganic & medicinal chemistry, 19(12), 3637-3649 (2011-01-11)
A collection of analogues of the dimeric natural product psammaplin A that differ in the substitution on the (halo)tyrosine aryl ring, the oxime and the diamine connection has been synthesized. The effects on cell cycle, induction of differentiation and apoptosis
Hak Jae Kim et al.
Radiation oncology (London, England), 7, 39-39 (2012-03-21)
Histone modifications and DNA methylation are two major factors in epigenetic phenomenon. Unlike the histone deacetylase inhibitors, which are known to exert radiosensitizing effects, there have only been a few studies thus far concerning the role of DNA methyltransferase (DNMT)
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
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