Psammaplin A
Product Code: AG-CN2-0088
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0088-C100 | 100 ug | £120.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
+4°C
Documents
Further Information
Alternate Names/Synonyms:
Bisprasin; NSC-614495
Appearance:
Off-white solid.
CAS:
110659-91-1
EClass:
32160000
Form (Short):
solid
GHS Symbol:
GHS07
Handling Advice:
Keep cool and dry.
Hazards:
H315, H319, H335
InChi:
InChI=1S/C22H24Br2N4O6S2/c23-15-9-13(1-3-19(15)29)11-17(27-33)21(31)25-5-7-35-36-8-6-26-22(32)18(28-34)12-14-2-4-20(30)16(24)10-14/h1-4,9-10,29-30,33-34H,5-8,11-12H2,(H,25,31)(H,26,32)/b27-17-,28-18-
InChiKey:
LMAFSGDNHVBIHU-HJTNQMAYSA-N
Long Description:
Chemical. CAS: 110659-91-1. Formula: C22H24Br2N4O6S2. MW: 664.4. Isolated from Psammaplysilla purpurea. Antibiotic. Caffeine-like Ca2+ releaser in heavy sarcoplasmic reticulum (HSR). Antifungal. Chitinase inhibitor. DNA methyltransferase inhibitor. Histone deacetylase (HDAC) inhibitor. Anticancer compound. Angiogenesis suppressor.
MDL:
MFCD11045304
Molecular Formula:
C22H24Br2N4O6S2
Molecular Weight:
664.4
Package Type:
Vial
Precautions:
P261, P280, P302, P352, P312
Product Description:
Antibiotic [1]. Caffeine-like Ca2+ releaser in heavy sarcoplasmic reticulum (HSR) [2]. Antifungal [3]. Chitinase inhibitor [3]. DNA methyltransferase inhibitor [4]. Histone deacetylase (HDAC) inhibitor [4, 5]. Anticancer compound. Angiogenesis suppressor [5].
Purity:
>98% (HPLC)
Signal Word:
Warning
SMILES:
ON=C(CC1=CC(Br)=C(O)C=C1)C(=O)NCCSSCCNC(=O)C(CC1=CC(Br)=C(O)C=C1)=N/O
Solubility Chemicals:
Soluble in DMSO, MeOH/H2O(40:60) or CH3CN/H2O(40:60). Insoluble in water.
Source / Host:
Isolated from Psammaplysilla purpurea.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
Psammaplin A, a natural bromotyrosine derivative from a sponge, possesses the antibacterial activity against methicillin-resistant Staphylococcus aureus and the DNA gyrase-inhibitory activity: D. Kim, et al.; Arch. Pharm. Res. 22, 25 (1999) | Bisprasin, a novel Ca(2+) releaser with caffeine-like properties from a marine sponge, Dysidea spp. acts on Ca(2+)-induced Ca(2+) release channels of skeletal muscle sarcoplasmic reticulum: A. Suzuki, et al.; J. Pharmacol. Exp. Ther. 292, 725 (2000) | Psammaplin A, a chitinase inhibitor isolated from the Fijian marine sponge Aplysinella rhax: J.N. Tabudravu, et al.; Bioorg. Med. Chem. 10, 1123 (2002) | Psammaplins from the sponge Pseudoceratina purpurea: inhibition of both histone deacetylase and DNA methyltransferase: I.C. Pina, et al.; J. Org. Chem. 68, 3866 (2003) | Psammaplin A, a marine natural product, inhibits aminopeptidase N and suppresses angiogenesis in vitro: J.S. Shim, et al.; Cancer Lett. 203, 163 (2004) | Psammaplin A is a natural prodrug that inhibits class I histone deacetylase: D.H. Kim, et al.; Exp. Mol. Med. 39, 47 (2007) | Defining the mechanism of action and enzymatic selectivity of psammaplin A against its epigenetic targets: M.B. Baud, et al.; J. Med. Chem. 55, 1731 (2012)