Piperafizine A
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| Category | Others |
| Catalog number | BBF-03965 |
| CAS | 130603-59-7 |
| Molecular Weight | 304.34 |
| Molecular Formula | C19H16N2O2 |
| Purity | >99% by HPLC |
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Description
It is a methylated diketopiperazine formed by the condensation of phenylalanine and is produced by many species in the genus Streptomyces. It exhibits little activity in vitro but potentiates vincristine antitumour potency.
Specification
| Synonyms | 3,6-Dibenzylidene-1-methyl-2,5-dioxopiperazine |
| Storage | Store at -20°C |
| IUPAC Name | (3Z,6Z)-3,6-dibenzylidene-1-methylpiperazine-2,5-dione |
| Canonical SMILES | CN1C(=CC2=CC=CC=C2)C(=O)NC(=CC3=CC=CC=C3)C1=O |
| InChI | InChI=1S/C19H16N2O2/c1-21-17(13-15-10-6-3-7-11-15)18(22)20-16(19(21)23)12-14-8-4-2-5-9-14/h2-13H,1H3,(H,20,22)/b16-12-,17-13- |
| InChI Key | DILBTCUXPAXMSM-MCOFMCJXSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Light Yellow Solid |
| Boiling Point | 613.1±55.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1. Antiproliferative and antiplasmodial compounds from selected Streptomyces species
Jie Li, Carla Slebodnik, L Harinantenaina Rakotondraibe, Yongchun Shen, Hyun-Young Park, Leah C Blasiak, Peggy J Brodie, Karen TenDyke, David G I Kingston, Maria B Cassera, Rado Rasolomampianina, Russel Hill, Felicite Rejo Bioorg Med Chem Lett . 2015 Dec 1;25(23):5646-9. doi: 10.1016/j.bmcl.2015.07.103.
In continuation of our ongoing search for bioactive compounds from microbial extracts, we performed antiproliferative and/or antimalarial assays on extracts of 806 microbial species isolated from Madagascan marine organisms, on 1317 species isolated from Madagascan soil samples and on a Streptomyces species (S.4) from a marine sponge collected from the Florida Keys. This work identified active extracts from four Streptomyces isolates (S.1, S.2, S.3 and S.4). The extracts of Streptomyces S.1 and S.2 showed antiproliferative activity against the A2780 ovarian cancer cell line, while those of S.3 and S.4 displayed both antiproliferative and antimalarial activity. Bioassay-guided fractionation coupled with dereplication of the active extracts led to the identification and isolation of nonactin (1), monactin (2), dinactin (3), ±-nonactic acid (4), toyocamycin (5), piperafizine A (6) and a new dipeptide named xestostreptin (7). The structures of all isolated compounds 1-7 were elucidated by analyses of their NMR spectroscopic and mass spectrometric data, and were confirmed by comparison with the data reported in the literature. Compound 6 was crystallized and subjected to X-ray diffraction analysis to confirm its structure as piperafizine A (6). Compounds 1-3 displayed strong antiproliferative activity against A2780 ovarian cancer cells (IC50 values of 0.1, 0.13 and 0.2 μM, respectively), A2058 melanoma cells (IC50 values of 0.2, 0.02 and 0.02 μM, respectively), and H522-T1 non small-cell cancer lung cells (IC50 values of 0.1, 0.01 and 0.01 μM, respectively), while compounds 4 and 7 exhibited weak antiplasmodial activity against the Dd2 strain of Plasmodium falciparum, with IC50 values of 6.5 and 50 μM, respectively.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
