Lipophilicity Study of Salicylic and Acetylsalicylic Acids Using Both Experimental and Calculations Methods

Dołowy, Małgorzata; Pyka, Alina

doi:10.1080/10826076.2014.913527

Cited by 16 publications

(9 citation statements)

References 27 publications

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“…When C w is higher than C P4VB , there is so much acid that the enhanced partitioning associated with the dye becomes negligible, as can be seen from the flattening of the curves toward the expected value at high C w in Figure 6b and its eventual saturation at P O/W = ∼260, which is fairly close to the previously published value of 224. 50 However, when C P4VB ≫ C w , the presence of excess np-P4VB appears to enhance the partitioning of the acid into the droplet.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Ultrasensitive Picomolar Detection of Aqueous Acids in Microscale Fluorescent Droplets

et al. 2021

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We report on a fluorescent-droplet-based acid-sensing scheme that allows limits of detection below 100 pM for weak acids. The concept is based on a strong partitioning of acid from an aqueous phase into octanol droplets. Using salicylic acid as a demonstration, we show that at a high concentration, the acid partitions into the organic phase by a factor of 260, which is approximately consistent with literature values. However, at lower concentrations, we obtain a partition coefficient as high as 10 6 , which is partly responsible for the excellent sensing performance. The enhanced equilibrium partitioning is likely due to the interaction of the dissociated acid phase with the sensor dye employed for this work. The effect of droplet size was determined, after which we derived a simple model to predict the time dependence of the color change as a function of droplet size. This work shows that color-change fluorescent-droplet-based detection is a promising avenue that can lead to exceptional sensing performance from an aqueous analyte.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Ultrasensitive Picomolar Detection of Aqueous Acids in Microscale Fluorescent Droplets

et al. 2021

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Section: Introductionmentioning

confidence: 99%

“…Our previous papers demonstrate the utility and efficiency of certain topological indices for the prediction of chromatographic retention data in various separation techniques, including the TLC method [36,37]. Some topological indices correlated well with the lipophilicity of various biologically active compounds, including pharmaceutically important compounds, such as salicylic/acetylsalicylic acid and spironolactone [36,37]. A wide application of topological indices in the prediction of the lipophilicity of active pharmaceutical ingredients is also shown in our book chapter titled Topological Indices in Modeling of Chromatographic Retention [38].…”

Section: Introductionmentioning

confidence: 99%

A Comparative Study of the Lipophilicity of Metformin and Phenformin

2021

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The results presented in this paper confirm the beneficial role of an easy-to-use and low-cost thin-layer chromatography (TLC) technique for describing the retention behavior and the experimental lipophilicity parameter of two biguanide derivatives, metformin and phenformin, in both normal-phase (NP) and reversed-phase (RP) TLC systems. The retention parameters (RF, RM) obtained under different chromatographic conditions, i.e., various stationary and mobile phases in the NP-TLC and RP-TLC systems, were used to determine the lipophilicity parameter (RMW) of metformin and phenformin. This study confirms the poor lipophilicity of both metformin and phenformin. It can be stated that the optimization of chromatographic conditions, i.e., the kind of stationary phase and the composition of mobile phase, was needed to obtain the reliable value of the chromatographic lipophilicity parameter (RMW) in this study. The fewer differences in the RMW values of both biguanide derivatives were ensured by the RP-TLC system composed of RP2, RP18, and RP18W plates and the mixture composed of methanol, propan-1-ol, and acetonitrile as an organic modifier compared to the NP-TLC analysis. The new calculation procedures for logP of drugs based on topological indices 0χν, 0χ, 1χν, M, and Mν may be a certain alternative to other algorithms as well as the TLC procedure performed under optimized chromatographic conditions. The knowledge of different lipophilicity parameters of the studied biguanides can be useful in the future design of novel and more therapeutically effective metformin and phenformin formulations for antidiabetic and possible anticancer treatment. Moreover, the topological indices presented in this work may be further used in the QSAR study of the examined biguanides.

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“…[2][3][4] Linear relationships between the retention factors, and the standard lipophilicity parameter, logP, can be expected. Taking into account the same retention mechanism in HPLC and thin-layer chromatography (TLC), in numerous instances the fast, simple and reliable RPTLC method was used for determination of lipophilicity.…”

Section: Introductionmentioning

confidence: 99%

Estimation of Lipophilicity of Some Polyoxygenated Steroids by the Means of Normal-Phase Thin-Layer Chromatography

Tosti

Šegan

Milić

et al. 2015

Journal of Liquid Chromatography & Related Technologies

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Unmodified silica gel in combination with two mobile phases, acetone -n-hexane andacetonitrile -dichloromethane, was used in order to evaluate the capability of normalphase (NP) chromatography on bare silica gel in estimation of lipophilicity of some polyoxygenated steroids. Soczewinski equation coefficients were employed as a measure of lipophilicity. The R M 0 values obtained in NP-systems were correlated with those derived by extrapolation from reversed-phase (RP) systems. In addition, retention data, i.e. lipophilicity parameters determined in NP systems were compared with logP values calculated by use of several commercial computer programs. The results showed that chromatographic parameters R M 0 , and m obtained in NP system consisted of silica gel as stationary phase and acetone -n-hexane as mobile phase, are acceptable as the measures of lipophilicity of polyoxygenated steroids. The mechanism of retention was discussed. Downloaded by [Massachusetts PRIM Board] at 16:21 05 April 2015 2

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Lipophilicity Study of Salicylic and Acetylsalicylic Acids Using Both Experimental and Calculations Methods

Cited by 16 publications

References 27 publications

Ultrasensitive Picomolar Detection of Aqueous Acids in Microscale Fluorescent Droplets

Ultrasensitive Picomolar Detection of Aqueous Acids in Microscale Fluorescent Droplets

A Comparative Study of the Lipophilicity of Metformin and Phenformin

Estimation of Lipophilicity of Some Polyoxygenated Steroids by the Means of Normal-Phase Thin-Layer Chromatography

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