Structure-Activity Relationship between the Hydrophobicity of Alkali Metal Salts of Warfarin [3-(<i>α</i>-Acetonyl-benzyl)-4-hydroxycoumarin] and the Effectiveness of the Taste Response to These Salts in Mice

Ohnishi, Michihiro; Sugawara, Ryozo; Kusano, Tyuzi

doi:10.1271/bbb.59.995

Cited by 3 publications

(4 citation statements)

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“…This suggests an increase in the lipophilicity of these salts in the same order. A similar increase in the lipophilicity of alkali metal salts of warfarin (except for lithium salt) was shown in [ 59 ]. The lipophilicity parameters obtained for the CN and PHE phases ( Table 5 ) are closely correlated to each other (the square of the correlation coefficient for the linear relationship is R 2 = 0.9742).…”

Section: Resultssupporting

confidence: 80%

“…The lithium cation is smaller than the other alkali metal ions and the interactions between water molecules and lithium ions seems to be different than that between the water molecules and other alkali metal cations. There are data in the literature that shows that the hydration of the lithium cation from the salt molecule affects its properties and causes that lithium to not follow the period low, e.g., in the studies of hydrophobicity of alkali metal salts of warfarin and the taste response to these salts in mice [ 59 ]. According to Mähler and Persson, who studied the hydration of alkali metal ions in aqueous solution, the lithium cation may form a second hydration sphere in contrast to sodium ion and probably other heavier alkali metal cations [ 60 ].…”

Section: Resultsmentioning

confidence: 99%

“…Besides this, the presence of the catechol moiety, the type of metal in the carboxylate group of chlorogenate is crucial for the pro-oxidative properties of tested compounds. The pro-/antioxidative activity of phenolic compounds or their alkali metal salts is sometimes correlated with the increase in their lipophilicity [ 59 ].…”

Section: Resultsmentioning

confidence: 99%

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The Study of Anti-/Pro-Oxidant, Lipophilic, Microbial and Spectroscopic Properties of New Alkali Metal Salts of 5-O-Caffeoylquinic Acid

Kalinowska

Bajko

Matejczyk

et al. 2018

IJMS

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Lithium, sodium, potassium, rubidium and caesium salts of 5-O-caffeoylquinic acid (chlorogenic acid, 5-CQA) were synthesized and described by FT-IR (infrared spectroscopy), FT-Raman (Raman spectroscopy), UV (UV absorption spectroscopy), 1H (400.15 MHz), 13C (100.63 MHz) NMR (nuclear magnetic resonance spectroscopy). The quantum–chemical calculations at the B3LYP/6-311++G** level were done in order to obtain the optimal structures, IR spectra, NBO (natural bond orbital) atomic charges, HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) orbitals and chemical reactivity parameters for 5-CQA and Li, Na and K 5-CQAs (chlorogenates). The DPPH (α, α-diphenyl-β-picrylhydrazyl) and FRAP (ferric reducing antioxidant power) assays were used for the preliminary estimation of the antioxidant properties of alkali metal chlorogenates and chlorogenic acid. In the DPPH assay the EC50 parameter were equal to 7.39 μM for 5-CQA and was in the range of 4.50–5.89 μM for salts. The FRAP values for two different concentrations (5 and 2.5 μM) of the studied compounds were respectively 114.22 and 72.53 μM Fe2+ for 5-CQA, whereas for salts they were 106.92–141.13 and 78.93–132.00 μM Fe2+. The 5-CQA and its alkali metal salts possess higher antioxidant properties than commonly applied antioxidants (BHA, BHT, l-ascorbic acid). The pro-oxidant action of these compounds on trolox oxidation was studied in the range of their concentration 0.05–0.35 μM. The lipophilicity (logkw) of chlorogenates and chlorogenic acid was determined by RP-HPLC (reverse phase—high performance liquid chromatography) using five different columns (C8, PHE (phenyl), CN (cyano), C18, IAM (immobilized artificial membrane)). The compounds were screened for their in vitro antibacterial activity against E. coli, Bacillus sp., Staphylococcus sp., Streptococcus pyogenes and antifungal activity against Candida sp. The 5-CQA possessed lower antibacterial (minimal inhibitory concentration, MIC = 7.06 mM) and antifungal (MIC = 14.11 mM) properties than its alkali metal salts (MIC values: 6.46–2.63 mM and 12.91–5.27mM, respectively). The synthesized chlorogenates possessed better antioxidant, lipophilic, antimicrobial as well as lower pro-oxidant properties than the ligand alone. Moreover, a systematic change of the activity of alkali metal salts along the series Li→Cs suggests that there are correlations between the studied biological properties. The type of metal cation in the carboxylate group of chlorogenate is crucial for the activity of studied compounds.

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Section: Resultssupporting

confidence: 80%

Section: Resultsmentioning

confidence: 99%

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The Study of Anti-/Pro-Oxidant, Lipophilic, Microbial and Spectroscopic Properties of New Alkali Metal Salts of 5-O-Caffeoylquinic Acid

Kalinowska

Bajko

Matejczyk

et al. 2018

IJMS

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“…12) Although the taste concentration of potassium warfarin with the weakest bitterness is l.455 mM (0.048%), the decrease of the bitterness of the poison substance is required further for the practical control of rodents. It had been reported that the toxicity of the S body was larger than the R body in the optical isomers of warfarin.…”

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confidence: 99%