High-throughput determination of octanol/water partition coefficients using a shake-flask method and novel two-phase solvent system

Morikawa, Go; Suzuka, Chihiro; Shoji, Atsushi; Shibusawa, Yöichi; Yanagida, Akio

doi:10.1016/j.jpba.2015.09.019

Cited by 24 publications

(14 citation statements)

References 32 publications

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“…Notably, the water solubility (>10 000 mg L −1 ) of carbanion‐decorated BODIPY 3 a‐Na was over 10 000 times greater than that of simple BODIPYs 2 a and 11 (<1 mg L −1 ). Also, we found that the log D (distribution coefficient in an octan‐1‐ol/pH 7.4 phosphate buffer biphasic system) of 3 a‐Na was 6.8 by applying Yanagida's protocol [17] using a biphasic system containing acetonitrile, 0.1 M phosphate buffer, and octan‐1‐ol in a ratio of 25:25:4 v/v/v (see the Supporting Information). In contrast, a known water‐soluble BODIPY 12 [10a] bearing two sulfonato groups showed remarkable hydrophilic character with −0.9 of log D (entry 5).…”

Section: Figurementioning

confidence: 99%

A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes

et al. 2021

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Installation of a carbanionic substituent, that is strongly stabilized by two (trifluoromethyl)sulfonyl (Tf = SO 2 CF 3) groups, into several fluorescence dyes including boron-dipyrromethenes (BODIPYs), fluoresceins, and aminocoumarins has been achieved by the 2,2-bis(triflyl)ethylation reaction of the dye frameworks with highly electrophilic Tf 2 C = CH 2 , followed by neutralization with NaHCO 3. Despite the contradiction between water solubility and lipophilicity, the carbanion-decorated dyes thus obtained showed significant enhancement of not only water solubility but also lipophilicity. This work clearly demonstrates that the fluorinated, highly stabilized carbanionic substituent is a new option for controlling the macroscopic property of chemical materials. Water solubility (and aqueous solubility) is a key macroscopic property for chemical materials directed towards biorelevant applications. [1] The most common way to improve the water solubility of less soluble compounds is introduction of ionic groups such as the sulfonato group into the molecular structure (Figure 1 A). However, such ionic functionalities

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Section: Figurementioning

confidence: 99%

A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes

et al. 2021

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“…Octanol-water partition coefficient (Poct) value was obtained by equilibrating the NA aqueous solution with 1-octanol in a shaker bath at 25ºC overnight [29]. Distribution of NA between the aqueous and the organic phase was estimated by the differences between the NA concentration at the beginning and at the equilibrium step, according to the following equation (Eq.1):…”

Section: Partition Coefficient Determinationmentioning

confidence: 99%

A novel ultradeformable liposomes of Naringin for anti-inflammatory therapy

Pleguezuelos-Villa

Mir-Palomo

Dı́ez-Sales

et al. 2018

Colloids and Surfaces B: Biointerfaces

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The article has 4636 words including ackwonledgment and references. The abstract has 127 words. There are 5 figures and 2 tables. Highlights Nanovesicles were small in size and monodispersed independently of the NA concentration. No citotoxity effects were observed in 3T3 fibroblasts treated with ultradeformable liposomes. Ultradeformable liposomes have the ability to reduce skin inflammation. Graphical abstract AbstractUltradeformable liposomes were formulated using naringin (NA), a flavanone glycoside, at different concentrations (3, 6 and 9 mg/mL). Nanovesicles were small size (~100 nm), regardless of the NA concentration used, and monodisperse (PI < 0.30). All formulations showed a high entrapment efficiency (~88%) and a highly negative zeta potential (around -30 mV). The selected formulations were highly biocompatible as confirmed by in vitro studies using 3T3 fibroblasts.In vitro assay showed that the amounts (%) of NA accumulated in the epidermis (~ 10%) could explain the anti-inflammatory properties of ultradeformable liposomes. In vivo studies confirmed the higher effectiveness of ultradeformable liposomes respect to betamethasone cream and NA dispersion in reducing skin inflammation in mice. Overall, it can conclude that NA ultradeformable liposomes can be considered as a promising formulation for the treatment of skin inflammatory diseases.

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“…Physicochemical properties such as solubility, lipophilicity, hydrophilicity, cytotoxicity, thermosensitivity are important approaches for drug development therefore great emphasis has been taken improving these properties of drug‐like compounds [6–8] . Recently, the studies have been interested on solubility and lipophilicity of compounds because, major obstacle in drug delivery systems is hydrophobicity leading to poor bioavailability [9–12] . Especially, lipophilicity is a key physicochemical property that plays crucial role in determining the overall suitability of drug candidates, thus there have been of growing evidence to suggest that control of lipophilicity can improve compound quality and the likelihood of therapeutic success [9–12] .…”

Section: Introductionmentioning

confidence: 99%

“…Recently, the studies have been interested on solubility and lipophilicity of compounds because, major obstacle in drug delivery systems is hydrophobicity leading to poor bioavailability [9–12] . Especially, lipophilicity is a key physicochemical property that plays crucial role in determining the overall suitability of drug candidates, thus there have been of growing evidence to suggest that control of lipophilicity can improve compound quality and the likelihood of therapeutic success [9–12] . Lipophilicity (logP o/w ) is directly related to the ability of a molecule to cross cell membranes in biomedicine and is defined octanol (lipid bilayer of cell membrane)‐water (the solvent in/out of cells) partition coefficient of the chemical structures.…”

Section: Introductionmentioning

confidence: 99%

Effect of the Hydrophilic/Hydrophobic Pendants on Physicochemical Properties: Applications Based on Cyclotriphosphazene Core

Özcan

Uslu

2021

ChemistrySelect

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This study focused on investigating the effect of hydrophilic and hydrophobic substituents on the physicochemical properties for medical applications. In this study, to understand the effect of hydrophilic and hydrophobic substituents on physicochemical parameters such as lipophilicity and thermosensitivity, a series of cis‐tris nongeminal [N3P3(R1‐4)3(Ra‐f)3] cyclotriphosphazenes [R1‐4=diethylene glycol monomethyl ether (DEGME), triethylene glycol monomethyl ether (TEGME), methoxypolyethylene glycol (mPEG350), methoxypolyethylene glycol‐550 (mPEG550); (2–5) respectively; Ra‐f=pyrazole, 3,5‐dimethylpyrazole, imidazole, 2‐methyl imidazole, benzimidazole, 5,6‐dimethyl benzimidazole, [2(a–f), 3(a–f), 4(a–f), 5(a–f)] respectively] were synthesized and fully characterized by mass, 31P and 1H NMR spectroscopies. Solubility and thermosensitivity based on substituent dependent LCST (lower critical solution temperature) behaviour of all synthesized molecules are investigated. Each compound analysed by HPLC to determine the lipophilicity values (logPo/w) between n‐octanol and water. A good correlation (r=0.9975 and R2=0.9948) was observed between the experimentally determined logPo/w and estimated milogP values. The results showed that LCST values of the reported compounds were linearly correlated with their lipophilicity values.

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High-throughput determination of octanol/water partition coefficients using a shake-flask method and novel two-phase solvent system

Cited by 24 publications

References 32 publications

A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes

A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes

A novel ultradeformable liposomes of Naringin for anti-inflammatory therapy

Effect of the Hydrophilic/Hydrophobic Pendants on Physicochemical Properties: Applications Based on Cyclotriphosphazene Core

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