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The crystal structure of anthraquinone-2-carboxylic acid has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional theory techniques. Anthraquinone-2-carboxylic acid crystallizes in space group P -1 (#2) with a = 3.7942(2), b = 13.266(5), c = 22.835(15) Å, α = 73.355(30), β = 89.486(6), γ = 86.061(1)°, V = 1098.50(7) Å3, and Z = 4. The crystal structure contains two independent molecules of anthraquinone-2-carboxylic acid. Although the expected hydrogen-bonded dimers are present, the dimers are not centrosymmetric. The dimer contains one molecule of each planar low-energy conformation. The crystal structure consists of a herringbone array of centrosymmetric pairs of molecules parallel to the bc -plane. The molecules stack along the short a -axis. The powder pattern has been submitted to ICDD® for inclusion in the Powder Diffraction File™ (PDF®). [ABSTRACT FROM AUTHOR]

Infections linked to Staphylococcus spp. are difficult to treat with current antibiotic therapy, resulting in increased antibiotic resistance populations. One of the leading strategies to overcome this issue is the novel combination of antibacterial nanoparticles (NPs) and sustainable natural compounds. This study reported the identification of a new synergistic combination of copper oxide (CuO) NPs, a well-known antibacterial agent against Staphylococcus spp., and anthraquinone-2-carboxylic acid (AQ), a plant-derived antimicrobial compound, with a potent and specific fashion in killing Staphylococcus spp. CuO NPs were synthesized using the one-pot coprecipitation method and characterized by using X-ray diffraction and transmission electron microscopy. Further checkerboard analysis showed that CuO NPs and AQ increased the antibacterial activity of individual agents against Staphylococcus aureus among Staphylococcus spp. by four- to eightfold compared to individual materials. Additional mechanistic studies on the synergy revealed that the inhibition of biofilm formation and loss of cytoplasmic volume with cell shrinkage are the major actions of the combination in expressing the phenotype. This study clearly showed that the combination of CuO NPs and AQ would be a novel strategy to eradicate S. aureus infections. [ABSTRACT FROM AUTHOR]

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Anthraquinone-2-carboxlic acid (9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid, AQCA) was identified as one of the major anthraquinones in Brazilian taheebo. Since there was no report explaining its immunopharmacological actions, in this study, we aimed to investigate the molecular mechanism of AQCA-mediated anti-inflammatory activity using reporter gene assays, kinase assays, immunoblot analyses, and overexpression strategies with lipopolysaccharide (LPS)-treated macrophages. AQCA was found to suppress the release of nitric oxide (NO) and prostaglandin (PG) E2 from LPS-treated peritoneal macrophages without displaying any toxic side effects. Molecular analysis revealed that AQCA was able to inhibit the activation of the nuclear factor (NF)-ĸB and activator protein (AP)-1 pathways by direct suppression of upstream signaling enzymes including interleukin-1 receptor-associated kinase 1 (IRAK1) and spleen tyrosine kinase (Syk). Therefore, our data strongly suggest that AQCA-mediated suppression of inflammatory responses could be managed by a direct interference of signaling cascades including IRAK and Syk, linked to the activation of NF-ĸB and AP-1. [ABSTRACT FROM AUTHOR]

Metal-free and several metallo-porphyrazines (M = Mg, 2H, Co, Cu, or Zn) carrying eight (3-thiopropyl anthraquinone-2-carboxylate) groups at the peripheral positions were synthesized from octakis(3-hydroxypropylthio)porphyrazinato] Mg(II). Symmetrically functionalized porphyrazines with eight ester units were soluble in common organic solvents. Chloro-octakis(3-thiopropyl anthraquinone-2-carboxylate) porphyrazinato iron(III) (FePzCl) was prepared by the reaction of metal-free porphyrazine with iron(II) acetate and further treatment with hydrochloric acid solution. The oligomeric structure [FePz(pyz)]nand the monomeric compound [FePz(py)2] were formed as stable complexes by reacting FePzCl with pyrazine and pyridine, respectively. The porphyrazine compounds were characterized by different spectroscopic methods. Metal-free and metallo-porphyrazines (M = Mg, 2H, Co, Cu, Zn, or ClFe) with eight (3-thiopropyl anthraquinone-2-carboxylate) units appending on the periphery through flexible alkylthio-bridges have been synthesized through esterification of octakis(hydroxypropylthio) porphyrazinato magnesium with anthraquinone-2-carboxylic acid in the presence of dicyclohexylcarbodiimide (DCCI) and toluene-p-sulfonic acid. The synthesized compounds were characterized by FT-IR, UV–vis,1H and13C NMR, mass spectrometry, and elemental analysis. [ABSTRACT FROM AUTHOR]

β-Cyclodextrin (CD) derivatives containing an aromatic triazole ring were studied as potential carriers of the following drugs containing an anthraquinone moiety: anthraquinone-2-sulfonic acid (AQ2S); anthraquinone-2-carboxylic acid (AQ2CA); and a common anthracycline, daunorubicin (DNR). UV-Vis and voltammetry measurements were carried out to determine the solubilities and association constants of the complexes formed, and the results revealed the unique properties of the chosen CDs as effective pH-dependent drug complexing agents. The association constants of the drug complexes with the CDs containing a triazole and lipoic acid (βCDLip) or galactosamine (βCDGAL), were significantly larger than that of the native βCD. The AQ2CA and AQ2S drugs were poorly soluble, and their solubilities increased as a result of complex formation with βCDLip and βCDGAL ligands. AQ2CA and AQ2S are negatively charged at pH 7.4. Therefore, they were less prone to form an inclusion complex with the hydrophobic CD cavity than at pH 3 (characteristic of gastric juices) when protonated. The βCDTriazole and βCDGAL ligands were found to form weaker inclusion complexes with the positively charged drug DNR at an acidic pH (pH 5.5) than in a neutral medium (pH 7.4) in which the drug dissociates to its neutral, uncharged form. This pH dependence is favorable for antitumor applications. [ABSTRACT FROM AUTHOR]