This product is isolated and purified from the roots of Rubia cordifolia L.
9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid/Anthraquinone-2-Carboxylic Acid/2-Anthracenecarboxylic acid, 9,10-dihydro-9,10-dioxo-/9,10-dioxoanthracene-2-carboxylic acid/9,10-Dioxo-9,10-dihydro-2-anthracenecarboxylic acid
518.3±39.0 °C at 760 mmHg
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For Reference Standard and R&D, Not for Human Use Directly.
provides coniferyl ferulate(CAS#:117-78-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
The physicochemical properties of 9,10-anthraquinone-2-carboxylic acid (AQCA) were investigated by thermal analysis, powder X-ray diffraction pattern, solubility, and partition coefficient. The chemical structure of AQCA was confirmed by the data from UV, Fourier transform IR (FTIR), and NMR analyses. Solubility and partition coefficient data were pH dependent. A new methanolic solvate of AQCA that lost 9.34% of its initial weight from 70 to 100 degrees C was found by thermogravimetric analysis. Sublimation of AQCA occurred at temperatures > 250 degrees C and needle-like crystals (Form I) were formed. The water solubility of AQCA increased with temperature; its heat of solution was 32.7 kJ/mol. A differential scanning calorimetry-FTIR microscopic system correlated a thermal phase transition with structural changes due to loss of methanol from the solvate, and three-dimensional FTIR spectra indicated that the process was complete by 100 degrees C. The kinetics of desolvation and sublimation from each crystal form of AQCA were determined. The activation energy of desolvation of methanol from solvate was 425.8 kJ/mol, and the activation energy of sublimation from Form I or desolvated crystals was 182.7 kJ/mol.
Physicochemical Characterization of 9,10-anthraquinone 2-carboxylic Acid
S Y Tsai 1, S C Kuo, S Y Lin
Although prolidase [E.C.188.8.131.52] is found in normal cells, substantially increased levels are found in some neoplastic tissues. Prolidase evokes the ability to hydrolyse the imido-bond of various low molecular weight compounds coupled to L-proline. The synthesis of three proline analogues of anthraquinone-2-carboxylic acid (1-3) has been performed. Treatment of these prodrugs with prolidase generated L-proline and the free drug, demonstrating their substrate susceptibility prolidase. The concentrations of 1, 2 and 3 needed to inhibit [1H]thymidine incorporation into DNA by 50% (IC50) in breast cancer MCF-7 cells were found to be 185 +/- 5 microM, 107 +/- 6 microM and 87 +/- 6 microM, respectively, suggesting a lower cytotoxic potency of these compounds compared to Hoechst 33228 (IC50 = 55 +/- 6 microM).
Cytotoxicity Activity of L-proline Analogues of anthraquinone-2-carboxylic Acid in Breast Cancer MCF-7 Cells
A Bielawska 1, K Bielawski, J Pałka
Background: The genome is constantly assaulted by oxidation reactions which are likely to be associated with oxygen metabolism, and oxidative lesions are generated by many types of oxidants. Such genotoxin-induced alterations in the genomic message have been implicated in aging and in several pathophysiological processes, particularly those associated with cancer. The guanine base (G) in genomic DNA is highly susceptible to oxidative stress due to having the lowest oxidation potential. Therefore, G-C–>T-A and G-C–>C-G transversion mutations frequently occur under oxidative conditions. One typical lesion of G is 8-oxo-7,8-dihydro-guanine (8-oxoG), which can pair with A. This pairing may cause G-C–>T-A transversion mutations. Although the number of G-C–>C-G transversions is rather high under specific oxidation conditions such as riboflavin photosensitization, the molecular basis of G-C–>C-G transversions is not known.
Results: To determine which oxidative products are responsible for G-C–>C-G transversion mutations, we photooxidized 5′-d(AAAAAAGGAAAAAA)/5′-d(TTTTTTCCTTTTTT) using either riboflavin or anthraquinone (AQ) carboxylate under UV irradiation. Prolonged low-temperature (4 degrees C) enzymatic digestion of photoirradiated sample indicated that under both conditions the amount of 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodG) initially increased with decreasing amounts of 2′-deoxyguanosine (dG), then decreased with the formation of 2-amino-5-[(2-deoxy-beta-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one (dIz), suggesting that nascent 8-oxoG was further oxidized to 2,5-diamino-4H-imidazol-4-one (Iz) in duplex DNA. Photoirradiation of an AQ-linked oligomer with a complementary strand containing 8-oxoG indicated that 8-oxoG residues were oxidized to Iz. These results indicate that Iz is formed from 8-oxoG through long-range hole migration. Primer extension experiments using a template containing Iz demonstrated that only dGTP is specifically incorporated opposite Iz suggesting that specific Iz-G base pairs are formed. The ‘reverse’ approach consisting of DNA polymerization using dIzTP showed that dIzTP is incorporated opposite G, further confirming the formation of a Iz-G base pair.
Conclusions: HPLC product analysis demonstrated that Iz is a key oxidation product of G through 8-oxoG in DNA photosensitized with riboflavin or anthraquinone. Photoreaction of AQ-linked oligomer confirmed that Iz is formed from 8-oxoG through long-range hole migration. Two sets of primer extension experiments demonstrated that Iz can specifically pair with G in vitro. Specific Iz-G base pair formation can explain the G-C–>C-G transversion mutations that appear under oxidative conditions.
Possible Cause of G-C-->C-G Transversion Mutation by Guanine Oxidation Product, Imidazolone