Hydrophobicity partition coefficient

In practice, the above equation is valid only if the organic carbon content is the primary sorbent, for organic pollutants with molecular weights less than 400, and when the organic pollutant does not have special-function groups that could promote ion exchange or complexation. In other words, when hydrophobic partition is the sole adsorption mechanism, Koc is strongly correlated with the hydrophobic partition coefficient (Koa,). The octanol/ water partition coefficient is defined as follows ... 

Tanaka, A., Nakamura, K., Nakanishi, I. and Fujiwara, H. (1994). A Novel and Useful Descriptor for Hydrophobicity, Partition Coefficient Micellar-Water, and Its Application to a QSAR Study of Antiplatelet Agents. J.Med.Chem., 37,4563-4566. 

Note that the relative spatial arrangement of the phenyl, amine, and hydroxyl functionahties are identical for (R)-alprenolol and (5)-sotalol. In addition to P-blocking activities, some of these compounds also possess potent local anaesthetic activity (see Anesthetics). The membrane stabilizing activity, however, is not stereoselective and correlates directly with the partition coefficient (hydrophobicity) of the compound. 

In subsequent studies attempting to find a correlation of physicochemical properties and antimicrobial activity, other parameters have been employed, such as Hammett O values, electronic distribution calculated by molecular orbital methods, spectral characteristics, and hydrophobicity constants. No new insight on the role of physiochemical properties of the sulfonamides has resulted. Acid dissociation appears to play a predominant role, since it affects aqueous solubiUty, partition coefficient and transport across membranes, protein binding, tubular secretion, and reabsorption in the kidneys. An exhaustive discussion of these studies has been provided (10). 

The partition coefficient P, defined as the equilibrium concentration of the compound in n-octanol divided by that in the aqueous phase, has been measured for pyrazole and indazole (B-79MI40416). It was found that log F = 0.13-0.26 for pyrazole and 1.82 for indazole, clearly showing the greater hydrophobicity (lipophilicity) of the indazole ring, due to the benzenoid moiety. 

The comparison of predicting capabilities of two kinds of hydrophobicity evaluations is of interest. For these purpose partition coefficients P and P for a number of benzodiazepines gidazepam (I), medazepam (II), nitrazepam (III), oxazepam (IV), lorazepam (V) and diazepam (VI) were determined. 

The lipophilicity (7 m value) and specific hydrophobic surface area of pyrido[l,2-a]pyrazinium-l-olates 342 and -3-olate 343, and l-(4-chlorophe-nyl)-l-hydroxy-l,2-dihydropyrazino[2,l-a]isoquinolinium salt (344) has been measured by reversed-phase thin-layer chromatography (98MI13). Partition coefficient (log/ ) of 9-bromo-5-[(A-phenylaminocarbonyl)-methyl]-l,2,3,5,6,7-hexahydropyrido[l,2,3- fc]quinoxaline-2,3-dione was calculated to be 2.78 (97JMC4053). 

The pFL-dependent partitioning of the ionizable, cationic dye thymol blue has also been investigated [6]. In its neutral, zwitterionic, and monoanionic forms, the dye preferentially partitions into the IL phase (from acidic solution), the partition coefficient to the IL increasing with increasing IL hydrophobicity. Under basic conditions, the dye is in the dianionic form and partitions into water (Figure 3.3-9). 

An alternative, single mechanism for both bases may be formulated, however, by taking into account the differences in basicity (piCa = 5.25 and 11.01, for Py and EtsN, respectively [148]), and hydrophobicity between the two bases. A quantitative measure of the latter property is given by logP, the partition coefficient of the solute between n-octanol and water (logP = log([solute] octanol/[solute]water)> 0.65 and 1.45 for Py and EtsN, respectively [149]. This unified mechanism is shown in Fig. 4, where B refers to the base employed. 

Compounds with high values are of low polarity and are described as being lipophilic and hydrophobic. Compounds with high values are of high polarity and are hydrophilic. Although the partition coefficient between octanol and water is... 

The solubilization of amino acids in AOT-reversed micelles has been widely investigated showing the importance of the hydrophobic effect as a driving force in interfacial solubihzation [153-157]. Hydrophilic amino acids are solubilized in the aqueous micellar core through electrostatic interactions. The amino acids with strongly hydrophobic groups are incorporated mainly in the interfacial layer. The partition coefficient for tryptophan and micellar shape are affected by the loading ratio of tryptophan to AOT [158],... 

Despite the work of Overton and Meyer, it was to be many years before structure-activity relationships were explored further. In 1939 Ferguson [10] postulated that the toxic dose of a chemical is a constant fraction of its aqueous solubility hence toxicity should increase as aqueous solubility decreases. Because aqueous solubility and oil-water partition coefficient are inversely related, it follows that toxicity should increase with partition coefficient. Although this has been found to be true up to a point, it does not continue ad infinitum. Toxicity (and indeed, any biological response) generally increases initially with partition coefficient, but then tends to fall again. This can be explained simply as a reluctance of very hydrophobic chemicals to leave a lipid phase and enter the next aqueous biophase [11]. An example of this is shown by a QSAR that models toxicity of barbiturates to the mouse [12] ... 

Clog P Calculated hydrophobicity of the whole molecule (calculated logarithm of partition coefficient (P) in M-octanol/water) ji Calculated hydrophobicity of the substituent... 

Nys, G. G., Rekker, R. F. Statistical analysis of a series of partition coefficients with special reference to the predictability of folding of drug molecules. Introduction of hydrophobic fragmental constants (/-values). Chim. Therap. 1973, 8, 521-535. 

In general, there is a positive correlation between hydrophobicity of solvents and nontoxicity for biocatalysts. The log P value was demonstrated to be a suitable parameter for characterization of solvent hydrophobicity (Table 1). Log P is the logarithm of the partition coefficient of a solvent in a water-l-octanol two-phase system [11,12,41,77]. Solvents with log P > A are very hydrophobic and generally nontoxic for biocatalysts. 

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