Paeciloquinone A

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Category Enzyme inhibitors
Catalog number BBF-02340
CAS 162797-33-3
Molecular Weight 356.28
Molecular Formula C18H12O8

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Description

It is produced by the strain of Paecilomyces carneus P-177. It can inhibit the epidermal growth factor receptor protein tyrosine kinase. Paeciloquinone A inhibits the V-abl protein tyrosine kinase with IC50 of 0.59 μmol/L.

Specification

Synonyms 9,10-Anthracenedione, 1,3,6,8-tetrahydroxy-2-(tetrahydro-2-oxo-3-furanyl)-
IUPAC Name 1,3,6,8-tetrahydroxy-2-(2-oxooxolan-3-yl)anthracene-9,10-dione
Canonical SMILES C1COC(=O)C1C2=C(C=C3C(=C2O)C(=O)C4=C(C3=O)C=C(C=C4O)O)O
InChI InChI=1S/C18H12O8/c19-6-3-8-13(10(20)4-6)17(24)14-9(15(8)22)5-11(21)12(16(14)23)7-1-2-26-18(7)25/h3-5,7,19-21,23H,1-2H2
InChI Key CCJBPPLPVJLTRD-UHFFFAOYSA-N

Properties

Appearance Yellow Crystal
Melting Point >350°C
Solubility Soluble in Methanol

Reference Reading

1. Paeciloquinones A, B, C, D, E and F: new potent inhibitors of protein tyrosine kinase produced by Paecilomyces carneus. II. Characterization and structure determination
A Fredenhagen, P Hug, H Sauter, H H Peter J Antibiot (Tokyo). 1995 Mar;48(3):199-204. doi: 10.7164/antibiotics.48.199.
Paeciloquinones A to F and versiconol have been isolated as inhibitors of protein tyrosine kinases from the culture broth of the fungus Paecilomyces carneus P-177. The structures of the new anthraquinones were determined by spectroscopic methods, mainly 1H NMR and 13C NMR. The substitution pattern was established by investigation of the respective methylated derivatives.
2. Paeciloquinones A, B, C, D, E and F: new potent inhibitors of protein tyrosine kinases produced by Paecilomyces carneus. I. Taxonomy, fermentation, isolation and biological activity
F Petersen, A Fredenhagen, H Mett, N B Lydon, R Delmendo, H B Jenny, H H Peter J Antibiot (Tokyo). 1995 Mar;48(3):191-8. doi: 10.7164/antibiotics.48.191.
Paeciloquinones A to F as well as versiconol have been isolated as inhibitors of protein tyrosine kinase from the culture broth of the fungus Paecilomyces carneus P-177. The novel anthraquinones inhibit epidermal growth factor receptor protein tyrosine kinase in the micromolar range. Two compounds, paeciloquinones A and C, are potent and selective inhibitors of the v-abl protein tyrosine kinase with an IC50 of 0.4 microM. Dependent on the fermentation conditions, partially different sets of paeciloquinones may be produced. An HPLC method allows separation of all major active components.

Bio Calculators

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L

* 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
g/mol
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