Hydrophobic Properties of Chromones and Flavones. Relationships Between Octanol/Water Partition Coefficients and RP‐HPLC Capacity Factors

Recanatini, Maurizio

doi:10.1002/qsar.19870060104

Cited by 13 publications

(6 citation statements)

References 28 publications

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“…The term polyphenols is increasingly being used in a broader sense and now includes a large variety of compounds produced in plants, via either the shikimate or the acetate pathway, and comprising several thousand molecules . A number of these compounds are outlined in Table …”

Section: Introductionmentioning

confidence: 99%

Dietary factors affecting polyphenol bioavailability

Bohn¹

2014

Nutr Rev

444

327

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While many epidemiological studies have associated the consumption of polyphenols within fruits and vegetables with a decreased risk of developing several chronic diseases, intervention studies have generally not confirmed these beneficial effects. The reasons for this discrepancy are not fully understood but include potential differences in dosing, interaction with the food matrix, and differences in polyphenol bioavailability. In addition to endogenous factors such as microbiota and digestive enzymes, the food matrix can also considerably affect bioaccessibility, uptake, and further metabolism of polyphenols. While dietary fiber (such as hemicellulose), divalent minerals, and viscous and protein-rich meals are likely to cause detrimental effects on polyphenol bioaccessibility, digestible carbohydrates, dietary lipids (especially for hydrophobic polyphenols, e.g., curcumin), and additional antioxidants may enhance polyphenol availability. Following epithelial uptake, polyphenols such as flavonoids may reduce phase II metabolism and excretion, enhancing polyphenol bioavailability. Furthermore, polyphenols may act synergistically due to their influence on efflux transporters such as p-glycoprotein. In order to understand polyphenol bioactivity, increased knowledge of the factors affecting polyphenol bioavailability, including dietary factors, is paramount.

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Section: Introductionmentioning

confidence: 99%

Dietary factors affecting polyphenol bioavailability

Bohn¹

2014

Nutr Rev

444

327

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“…The quality of eq 2 is some what decreased because of the different partitioning behavior of hydrogen-bonding substituents , and the relative acidity of methanol, the modifier in RP-HPLC measurement, compared to octanol . Figure shows the Collander plot.…”

Section: Resultsmentioning

confidence: 99%

In Vivo Activity and Hydrophobicity of Cytostatic Aziridinyl Quinones

et al. 1996

J. Med. Chem.

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For a series of 3,6-disubstituted bisaziridinylbenzoquinones the in vivo and in vitro activities against murine tumors, as well as the in vivo toxicity, are analyzed. Properties describing biochemical and physicochemical reactions are also incorporated in the analyses. The important 1-octanol/water partition coefficients were determined, using a fast variation of the shake flask method. New pi'-values were calculated for the substituents in this series. These quinone pi'-values deviate strongly from the standard pi-values, especially for hydrogen-bonding substituents. To discriminate between the toxic and therapeutic activity of the compounds, principal components and partial least squares analyses were applied. Evidence is presented for selective antitumor action of the investigated compounds. The L1210 clonogenic assay only seems to relate to the general cytotoxicity and has no predictive value for in vivo activity for these compounds. The activity is correlated to the hydrophobicity of the quinones. The toxicity correlates with the ease of reduction, contrary to the hypothesis of bioreductive activation as a mechanism for selectivity.

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“…Also, the hydrophobic interactions employed by the substituents of the chromone ligand help in the insertion of complex 1 within the bases of tRNA, leading to the disruption of secondary structure of tRNA. [41,42] Fluorescence titration studies Emission spectral titrations were conducted to further substantiate the interaction affinities of complex 1 with ct-DNA/tRNA. By exciting 1 with 310 nm wavelength (λ ex ), a perceptible fluorescence was demonstrated at ca.…”

Section: Absorption Titration Studiesmentioning

confidence: 99%

Chromone‐Appended Zn(II) tRNA‐Targeted Potential Anticancer Chemotherapeutic Agent: Structural Details, in vitro ct‐DNA/tRNA Binding, Cytotoxicity Studies And Antioxidant Activity

et al. 2022

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A 3-formyl-chromone-appended zinc(II) intercalator drug candidate of the formulation [bis(chromone)(H 2 O) 2 Zn(II)] was prepared as a potent anticancer agent and thoroughly characterized by multi-spectroscopic and single X-ray crystallographic studies. Preliminary binding studies of complex 1 with ct-DNA/tRNA were carried out employing various complementary biophysical techniques and the corroborative results of these experiments suggested strong binding propensity via intercalation binding mode towards ct-DNA/tRNA therapeutic targets, with higher preference for tRNA as quantified by binding constant { K b , K and K sv } parameters. The cleavage studies with pBR322 DNA were performed which implied that 1 cleaved the DNA by hydrolytic cleavage pathway which was further validated by T4 religation assay. Moreover, 1 was found to exhibit the tRNA cleavage behavior in a concentration and time-dependent manner. The cytotoxicity of complex 1 was evaluated against Huh-7, DU-145 and the PNT2 cell lines by MTT assay. A dose-dependent growth inhibition of the Huh-7 and DU-145 cells at low micromolar concentrations was observed and in another set of experiments, lipid peroxidation & glutathione (GSH) depletion were induced in the presence of the tested drug candidate. Interestingly, drug candidate 1 demonstrated selective cytotoxic activity for the DU-145 cancer cell line with LC 50 value of 3.2 μM which was further visualized by confocal microscopy.

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Hydrophobic Properties of Chromones and Flavones. Relationships Between Octanol/Water Partition Coefficients and RP‐HPLC Capacity Factors

Cited by 13 publications

References 28 publications

Dietary factors affecting polyphenol bioavailability

Dietary factors affecting polyphenol bioavailability

In Vivo Activity and Hydrophobicity of Cytostatic Aziridinyl Quinones

Chromone‐Appended Zn(II) tRNA‐Targeted Potential Anticancer Chemotherapeutic Agent: Structural Details, in vitro ct‐DNA/tRNA Binding, Cytotoxicity Studies And Antioxidant Activity

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