Octanol-Water Partition Coefficients of Simple Organic Compounds

Sangster, James

doi:10.1063/1.555833

Cited by 848 publications

(671 citation statements)

References 3 publications

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“…Meanwhile, by water→octanol transfer energies, one might expect toluene to bind 0.8 kcal/mol better (20,32), a difference between observed and expected affinities of 0.5 kcal/mol (Table 1). Similarly, n-butylbenzene binds 1.5 kcal/mol better than does benzene, whereas water→octanol transfer free energies would have it binding 2.9 kcal/mol better (20,32) …”

Section: Resultsmentioning

confidence: 99%

Homologous ligands accommodated by discrete conformations of a buried cavity

Merski

Fischer

Balius

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

114

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Conformational change in protein–ligand complexes is widely modeled, but the protein accommodation expected on binding a congeneric series of ligands has received less attention. Given their use in medicinal chemistry, there are surprisingly few substantial series of congeneric ligand complexes in the Protein Data Bank (PDB). Here we determine the structures of eight alkyl benzenes, in single-methylene increases from benzene to n-hexylbenzene, bound to an enclosed cavity in T4 lysozyme. The volume of the apo cavity suffices to accommodate benzene but, even with toluene, larger cavity conformations become observable in the electron density, and over the series two other major conformations are observed. These involve discrete changes in main-chain conformation, expanding the site; few continuous changes in the site are observed. In most structures, two discrete protein conformations are observed simultaneously, and energetic considerations suggest that these conformations are low in energy relative to the ground state. An analysis of 121 lysozyme cavity structures in the PDB finds that these three conformations dominate the previously determined structures, largely modeled in a single conformation. An investigation of the few congeneric series in the PDB suggests that discrete changes are common adaptations to a series of growing ligands. The discrete, but relatively few, conformational states observed here, and their energetic accessibility, may have implications for anticipating protein conformational change in ligand design.

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Section: Resultsmentioning

confidence: 99%

Homologous ligands accommodated by discrete conformations of a buried cavity

Merski

Fischer

Balius

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

114

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“…The K ow is defined as the ratio of the equilibrium concentrations of a dissolved substance in a two-phase octanol and water system, and is expressed by the following equation (Sangster, 1989):…”

Section: Apis/api-ilsmentioning

confidence: 99%

Evaluation of solubility and partition properties of ampicillin-based ionic liquids

Florindo

Araújo

Alves

et al. 2013

International Journal of Pharmaceutics

107

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a b s t r a c tIn order to overcome the problems associated with low water solubility, and consequently low bioavailability of active pharmaceutical ingredients (APIs), herein we explore a modular ionic liquid synthetic strategy for improved APIs. Ionic liquids containing l-ampicillin as active pharmaceutical ingredient anion were prepared using the methodology developed in our previous work, using organic cations selected from substituted ammonium, phosphonium, pyridinium and methylimidazolium salts, with the intent of enhancing the solubility and bioavailability of l-ampicillin forms. In order to evaluate important properties of the synthesized API-ILs, the water solubility at 25 • C and 37 • C (body temperature) as well as octanol-water partition coefficients (K ow 's) and HDPC micelles partition at 25 • C were measured. Critical micelle concentrations (CMC's) in water at 25 • C and 37 • C of the pharmaceutical ionic liquids bearing cations with surfactant properties were also determined from ionic conductivity measurements.

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“…The reported K ow and log K ow for phenol (Fujita et al, 1964;Hansch et al, 1995) are 28.8 and 1.46, respectively, indicating that it is slightly hydrophobic, more so that the SMP derived from it. In contrast, the K ow and log K ow for glucose (Sangster, 1989) are 0.0058 and À3.24, respectively, indicating that it is strongly hydrophilic, even more so than the SMP derived from it. The K ow values clearly indicate that the SMP from each substrate had distinct chemical compositions and contain different functional groups that behave differently in response to changes in the pH.…”

Section: Octanol-water Partition Coefficientmentioning

confidence: 90%

Characterization of soluble microbial products (SMP) derived from glucose and phenol in dual substrate activated sludge bioreactors

Magbanua

Bowers

2006

Biotech & Bioengineering

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Soluble microbial products (SMP) generated by activated sludge cultures receiving a mixed feed of phenol and glucose were characterized with respect to molecular weight (MW) distribution, octanol-water partition coefficient (K ow ), and Microtox 1 toxicity. Short-term batch reactor tests using 14 C-labeled substrates were performed to collect SMP derived from each substrate, while longterm tests were performed with SMP accumulated over multiple feed cycles using fed-batch reactors receiving non-labeled substrates. Yield of SMP in the batch tests, 10%-20% for phenol and 2%-5% for glucose, differed for each substrate and was independent of initial concentration. The MW distribution (MWD) of SMP was independent of feed composition, and was bimodal in the <1 kDa and 10-100 kDa MW ranges for phenol-derived SMP and predominantly <1 kDa for glucose-derived SMP. In the non-labeled tests, the fraction of SMP of MW >100 kDa increased with the proportion of glucose in the feed. The K ow of phenol-derived SMP was higher compared to glucose-derived SMP, indicating that the phenol-derived SMP were more hydrophobic. This was particularly true at an acidic pH, where the K ow was 4.2 AE 1.0 for phenolderived SMP versus 0.13 AE 0.13 for glucose-derived SMP. Toxicity testing indicated that phenol-derived SMP, exerting a mean Microtox 1 inhibition of 1%, were less toxic than phenol itself, and showed little correlation between toxicity and concentration. However, glucosederived SMP were generally more toxic than glucose itself (a non-toxic substrate), and the toxicity increased linearly with the concentration of SMP. ß

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Octanol-Water Partition Coefficients of Simple Organic Compounds

Cited by 848 publications

References 3 publications

Homologous ligands accommodated by discrete conformations of a buried cavity

Homologous ligands accommodated by discrete conformations of a buried cavity

Evaluation of solubility and partition properties of ampicillin-based ionic liquids

Characterization of soluble microbial products (SMP) derived from glucose and phenol in dual substrate activated sludge bioreactors

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