Octanol-water Coefficient Research Articles

Exploring the role of octanol-water partition coefficient and Henry’s law constant in predicting the lipid-water partition coefficients of organic chemicals

Partition coefficients for storage lipid-water (logKlw) and phospholipid-water (logKpw) phases are key parameters to understand the bioaccumulation and toxicity of organic contaminants. However, the published experimental databases of these properties are dwarfs and current estimation approaches are cumbersome. Here, we present partition models that exploit the correlations of logKlw, and of logKpw with the linear combinations of the octanol-water partition coefficient (logKow) and the dimensionless Henry’s law constant (air–water partition coefficient, logKaw). The calibrated partition models successfully describe the variations in logKlw data (n = 305, R2 = 0.971, root-mean-square-error (rmse) = 0.375), and in logKpw data (n = 131, R2 = 0.953, rmse = 0.413). With the inputs of logKow and logKaw estimated from the U.S. EPA’s EPI Suite, our models of logKlw and logKpw have exhibited rmse = 0.52 with respect to experimental values indicating suitability of these models for inclusion in the EPI Suite. Our models perform similar to or better than the previously reported models such as one parameter partition models, Abraham solvation models, and models based on quantum-chemical calculations. Taken together, our models are robust, easy-to-use, and provide insight into variations of logKlw and logKpw in terms of hydrophobicity and volatility trait of chemicals.

Semi-automated harmonization and selection of chemical data for risk and impact assessment.

Chemical data for thousands of substances are available for safety, risk, life cycle and substitution assessments, as submitted for example under the European Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH) Regulation. However, to widely disseminate reported physicochemical properties as well as human and ecological exposure and toxicological data for use in various science and policy fields, systematic methods for data harmonization and selection are necessary. In response to this need, we developed a semi-automated method for deriving appropriate substance property values as input for various assessment frameworks with different requirements for resolution and data quality. Starting with data reported for a given substance and property, we propose a set of aligned data selection and harmonization criteria to obtain a representative mean value and related confidence intervals per chemical-property combination. The proposed method was tested on a set of octanol-water partition coefficients (Kow) for an illustrative set of 20 substances, reported under the REACH regulation as example data source. Our method is generally applicable to any set of substances, and can assess specific distributions in quality and variability across reported data. Further research can likely extend our method for mining information from text fields and adapt it to available data reported or collected from other sources and other substance properties to improve the reliability of input data for risk and impact assessments.

H-beta zeolite-based dispersive solid-phase strategy for the multi-residue determination of pesticides

In this work, electrostatic interactions, hydrogen bonding and other interactions between a variety of pesticides and H-beta zeolite are discussed based on thermodynamics (Gibbs free energy, enthalpy, and entropy). Combined with the physical properties of the target compounds (octanol-water partition coefficient and molar volume), the characteristics of the physical adsorption on the synthetic zeolite were analyzed, the results of H-beta zeolite adsorption showed that the adsorption rate had a nonlinear relationship with the physical properties, and the adsorption reaction was dominated by the adsorption on the surface and in the pores of the H-beta zeolite. Based on the principle of zeolite adsorption, the parameters of absorbent amount, adsorption time, sample pH, ion strength, sample volume and desorption solvent were optimized, a vortex-assisted dispersive solid-phase extraction procedure coupled with liquid chromatography-tandem mass spectrometry was developed for the analysis of multiple pesticides in surface water. The sample was adjusted by phosphate buffer or hydrochloric acid to pH 4, then adsorbed by 50 mg of zeolite within 10 min, adding 2% (g/v) sodium chloride to the solution. The absorbent was eluted with a mixture of acetonitrile-methanol containing 0.5% formic acid after separation, then filtered prior to analysis. The optimized vortex-assisted dispersive solid-phase extraction method simultaneously achieved a low adsorbent dosage, a high enrichment factor of 25, rapid pre-concentration for 30 min, a low solvent usage of 2 mL and multi-target simultaneous analysis. Method performance in terms of accuracy, precision, limit of detection, and limit of quantitation was performed to validate the reliability of the procedure. The proposed protocol achieved acceptable accuracy (recoveries between 62% and 107%), and precision (relative standard deviation < 20%). The limit of detection of the method was below 0.1 μg/L, and the limit of quantitation was 0.08 μg/L or 0.2 μg/L. The results indicated that zeolite is a promising adsorbent with high adsorption capacity. It has the advantages of being a fast, simple, green and economical method for determining residual pesticides in water.

Bioamplification and Biomagnification of Polycyclic Aromatic Hydrocarbons and Halogenated Organic Pollutants in Moths from an Electronic Waste Recycling Site.

Samples of Asota caricae (larvae, pupae, and adults) and its host plant leaf (Ficus hispida), larvae of Aloa lactinea, and mixed adult moths were collected from an electronic waste (e-waste) recycling site in south China. Polycyclic aromatic hydrocarbons, polychlorinated biphenyls, and polybrominated diphenyl ethers were found to exhibit concentrations of 420-1300, 100-860, and 7.6-49 ng/g dry weight, respectively. The different chemical compositions among the samples of the three groups indicated that at least two exposure scenarios occurred among the moths in the study area. A complex relationship between bioamplification factors and the octanol-water partition coefficient (log KOW ) was observed during metamorphosis, in which a positive relationship was evident for 5 < log KOW < 7, whereas an inverse relationship occurred for log KOW values outside of this range. The biomagnification factors (BMFs) calculated from the larvae of Asota caricae to the host plant were negatively correlated with log KOW for all chemicals, differing completely from those obtained in previous studies. However, after metamorphosis, the correlation between BMF and log KOW was found to coincide with that in previous studies. These results indicate that the biotransformation of pollutants in organisms played a key role in determining whether or not biomagnification occurred in organisms and highlight the potential application of the metabolic rate of chemicals in screening-level risk assessments of new chemicals. Environ Toxicol Chem 2022;41:2395-2403. © 2022 SETAC.

Nanocomposite Polymeric Membranes for Organic Micropollutant Removal: A Critical Review.

The prevalence of organic micropollutants (OMPs) and their persistence in water supplies have raised serious concerns for drinking water safety and public health. Conventional water treatment technologies, including adsorption and biological treatment, are known to be insufficient in treating OMPs and have demonstrated poor selectivity toward a wide range of OMPs. Pressure-driven membrane filtration has the potential to remove many OMPs detected in water with high selectivity as a membrane's molecular weight cutoff (MWCO), surface charge, and hydrophilicity can be easily tailored to a targeted OMP's size, charge and octanol-water partition coefficient (Kow). Over the past 10 years, polymeric (nano)composite microfiltration (MF), ultrafiltration (UF), and nanofiltration (NF) membranes have been extensively synthesized and studied for their ability to remove OMPs. This review discusses the fate and transport of emerging OMPs in water, an assessment of conventional membrane-based technologies (NF, reverse osmosis (RO), forward osmosis (FO), membrane distillation (MD) and UF membrane-based hybrid processes) for their removal, and a comparison to the state-of-the-art nanoenabled membranes with enhanced selectivity toward specific OMPs in water. Nanoenabled membranes for OMP treatment are further discussed with respect to their permeabilities, enhanced properties, limitations, and future improvements.

Preparation of an isorhamnetin phospholipid complex for improving solubility and anti-hyperuricemia activity

To improve the solubility and anti-hyperuricemia activity of the insoluble natural flavonoid isorhamnetin (ISO), an isorhamnetin phospholipid complex (ISO-PC) was prepared. ISO-PC was prepared through solvent evaporation and its prescription process was optimized. The formation of ISO-PC was verified via multiple characterization methods. Parameters such as drug loading, solubility, octanol-water partition coefficient, stability, and in vivo anti-hyperuricemia activity of ISO-PC were investigated. The complexation efficiency of ISO-PC was 95.1% ± 0.56%. The characterization results confirmed that ISO-PC was bound by intermolecular interactions between ISO and phospholipids. Compared with ISO, the solubility of ISO-PC in water and 1-octanol increased by 122 and 16.5 times, respectively. In addition, the octanol-water partition coefficient decreased to 1.08. Pharmacodynamic studies have reported that ISO-PC has a more significant effect on reducing serum uric acid levels and renal protection. In conclusion, the findings of this study suggested that ISO-PC could be used as a promising formulation to improve the solubility and the anti-hyperuricemia activity of ISO.

Polychlorinated naphthalenes (PCNs) in soils and plants from Svalbard, Arctic: Levels, distribution, and potential sources

As persistent organic pollutants (POPs) newly banned by the Stockholm Convention, polychlorinated naphthalenes (PCNs) have been widely detected in various environmental matrices. To date, however, the occurrence of PCNs in soils and plants in the Arctic environment has not been reported. In the current study, the concentrations and distribution of PCNs in Arctic soils and plants from Svalbard were analyzed. Total PCN concentrations ranged from 5.3 to 2550 pg/g dry weight (dw) in soils and 77 to 870 pg/g dw in plants. The higher levels of PCNs near the research stations and Longyearbyen town highlighted the significant influence of local anthropogenic emission sources. The composition of PCNs in Arctic soils and plants was dominated by lower chlorinated homologues, especially mono- to trichlorinated naphthalenes, which accounted for over 80 % of total PCNs in the soil and plant samples. The correlation analysis indicated the potential influences of total organic carbon (TOC) content on PCN concentrations in the soil, and octanol-air partition coefficients (KOA) or octanol-water partition coefficients (KOW) on PCN accumulation from soils to plants. To the best of our knowledge, this is the first study to report on the concentration and distribution of PCNs in Arctic soils and plants.

Percutaneous absorption and exposure risk assessment of organophosphate esters in children’s toys

The percutaneous penetration and exposure risk of organophosphate esters (OPEs) from children’s toys remains largely unknown. Percutaneous penetration of OPEs was evaluated by EPISkin™ model. Chlorinated OPEs (Cl-OPEs) and alkyl OPEs, except tris(2-ethylhexyl) phosphate, exhibited a fast absorption rate and good dermal penetration ability with cumulative absorptions of 57.6–127 % of dosed OPEs. Cumulative absorptions of OPEs through skin cells were inversely associated with their molecular weight and log octanol-water partition coefficient. Additionally, a quantitative structure-activity relationship model indicated that topological charge and steric features of OPEs were closely related to the transdermal permeability of these chemicals. With the clarification of the factors affecting the transdermal penetration of OPEs, the level and exposure risk of OPEs in actual toys were studied. The summation of 18 OPE concentrations in 199 toy samples collected from China ranged from 6.82 to 228,254 ng/g, of which Cl-OPEs presented the highest concentration. Concentrations of OPEs in toys exhibited clear type differences. Daily exposure to OPEs via dermal, hand-to-mouth contact, and mouthing was evaluated, and dermal contact was a significant route for children’s exposure to OPEs. Hazard quotients for noncarcinogenic risk assessment were below 1, indicating that the health risk of OPEs via toys was relatively low.

Acylating blueberry anthocyanins with fatty acids: Improvement of their lipid solubility and antioxidant activities.

Aimed at exploring the impact of fatty acid side chains on the anthocyanins, n-valeric acid, n-decanoic acid and myristic acid were used to grafting onto the blueberry anthocyanins, and the acylating degree value of the of n-valeric acid acylated anthocyanins (Va-An), n-decanoic acid acylated anthocyanins (De-An) and myristic acid acylated anthocyanins (My-An) reached 6.43 %, 7.56% and 8.38 %, respectively. After acylation modification, the octanol-water partition coefficient of the anthocyanins increased from -0.20 (native anthocyanins, Na-An) to 0.65 (Va-An), 0.66 (De-An) and 0.72 (My-An), respectively, indicating the increasement of the lipid solubility. Besides, although the DPPH clearance of acylated anthocyanins was lower than that of native anthocyanins, the inhibition ratio of β-carotene bleaching and malonaldehyde reduction effect of the acylated blueberry anthocyanins in Caenorhabditis elegans were both stronger than that of native anthocyanins, which might be caused by the improvement of lipid solubility of the anthocyanins.

68Ga-Labeled Maleimide for Blood Pool and Lymph PET Imaging through Covalent Bonding to Serum Albumin In Vivo

This study aims to develop a novel 68Ga-labeled tracer, which can covalently bind to albumin in vivo based on the maleimide–thiol strategy, and to evaluate its potential applications using positron emission tomography (PET). 68Ga-labeled maleimide-monoamide-DOTA (denoted as [68Ga]Ga-DM) was prepared conveniently with a high radiochemical yield (>90%) and radiochemical purity (>99%). Its molar activity was calculated as 249.60 ± 68.50 GBq/μmol, and the octanol–water partition coefficient (LogP) was −3.15 ± 0.08 with good stabilities. In vitro experiments showed that [68Ga]Ga-DM can bind to albumin efficiently and rapidly, with a binding fraction of over 70%. High uptake and excellent retention in blood were observed with a long half-life (t1/2Z) of 190.15 ± 24.14 min, which makes it possible for blood pool PET imaging with high contrast. The transient micro-bleeding in the rat model was detected successfully with PET imaging. In addition, the uptakes of [68Ga]Ga-DM in the inflammatory popliteal lymph nodes depend on the severity (5.90% ID/g and 2.32% ID/g vs 1.01% ID/g for healthy lymph nodes at 0.5 h post-injection) indicating its feasibility for lymphatic imaging. In conclusion, a novel 68Ga-labeled tracer was prepared with high efficiency and yield in mild conditions. Based on the promising properties of bonding covalently to albumin, great stability, high blood contrast with a long half-life, and well environmental tolerance, [68Ga]Ga-DM could be developed as a potential tracer for PET imaging of blood pool, bleeding, and vascular permeability alteration diseases in the clinic.

Anticancer activity and QSAR study of sulfur-containing thiourea and sulfonamide derivatives

Sulfur-containing compounds are considered as attractive pharmacophores for discovery of new drugs regarding their versatile properties to interact with various biological targets. Quantitative structure-activity relationship (QSAR) modeling is one of well-recognized in silico tools for successful drug discovery. In this work, a set of 38 sulfur-containing derivatives (Types I–VI) were evaluated for their in vitro anticancer activities against 6 cancer cell lines. In vitro findings indicated that compound 13 was the most potent cytotoxic agent toward HuCCA-1 cell line (IC50 = 14.47 μM). Compound 14 exhibited the most potent activities against 3 investigated cell lines (i.e., HepG2, A549, and MDA-MB-231: IC50 range = 1.50–16.67 μM). Compound 10 showed the best activity for MOLT-3 (IC50 = 1.20 μM) whereas compound 22 was noted for T47D (IC50 = 7.10 μM). Subsequently, six QSAR models were built using multiple linear regression (MLR) algorithm. All constructed QSAR models provided reliable predictive performance (training sets: Rtr range = 0.8301–0.9636 and RMSEtr = 0.0666–0.2680; leave-one-out cross validation sets: RCV range = 0.7628–0.9290 and RMSECV = 0.0926–0.3188). From QSAR modeling, chemical properties such as mass, polarizability, electronegativity, van der Waals volume, octanol-water partition coefficient, as well as frequency/presence of C–N, F–F, and N–N bonds in the molecule are essential key predictors for anticancer activities of the compounds. In summary, a series of promising fluoro-thiourea derivatives (10, 13, 14, 22) were suggested as potential molecules for future development as anticancer agents. Key structure-activity knowledge obtained from the QSAR modeling was suggested to be advantageous for suggesting the effective rational design of the related sulfur-containing anticancer compounds with improved bioactivities and properties.

In silico prediction of boiling point, octanol-water partition coefficient, and retention time index of polycyclic aromatic hydrocarbons through machine learning.

Polycyclic aromatic hydrocarbons (PAHs), a special class of persistent organic pollutants (POPs) with two or more aromatic rings, have received extensive attention owing to their carcinogenic, mutagenic, and teratogenic effects. Quantitative structure-property relationship (QSPR) is powerful chemometric method to correlate structural descriptors of PAHs with their physicochemical properties. In this manuscript, a QSPR study of PAHs was performed to predict their boiling point (bp), octanol-water partition coefficient (LogKow ), and retention time index (RI). In addition to traditional molecular descriptors, structural fingerprints play an important role in the correlation of the above properties. Three regression methods, partial least squares (PLS), multiple linear regression (MLR), and genetic function approximation (GFA), were used to establish QSPR models for each property of PAHs. The correlation coefficient (R2 test ) and root mean square error (RMSE) of best model were 0.980 and 24.39% (PLS), 0.979 and 35.80% (GFA), 0.926 and 22.90% (MLR) for bp, LogKow, and RI, respectively. The model proposed here can be used to estimate physicochemical properties and inform toxicity prediction of environmental chemicals.

Uptake and photoinduced degradation of phthalic acid esters (PAEs) in Ulva lactuca highlight its potential application in environmental bioremediation

The bioaccumulation of phthalates was studied in fragments of Ulva lactuca exposed for a maximum of 31 days at different concentrations of a solution of six phthalic acid esters (PAEs). The algal matrix showed rapid uptake since the first sampling, which increased over the time of the experimental period, at the end of which seaweed’s bioaccumulation potential was also evaluated. After the uptake, the algal matrix was subjected to UV irradiation in order to verify the removal of the phthalates. PAEs with higher octanol–water partition coefficients (logKow) and molecular weights were preferentially uptaken by U. lactuca in all the exposure experiments. It was observed that both accumulation (biota-sediment accumulation factor (log10BSAF) ranging from 3.75 to 4.02) and photodegradation (higher than 70% removal for all phthalates in 8 h) are more efficient at lower concentration levels. These results suggest the potential use of the algal matrices for environmental bioremediation, in order to mitigate the impact of pollution from ubiquitous pollutants such as PAEs.

Characterization and Interpolation of Sediment Polychlorinated Biphenylsand Polybrominated Diphenyl Ethersin Resident Killer Whale Habitat along the Coast of British Columbia, Canada.

The northeastern Pacific northern and southern resident killer whale (Orcinus orca) populations are listed as threatened and endangered in Canada, respectively, with persistent, bioaccumulative contaminants, such as polychlorinated biphenyls (PCBs) and polybrominated diphenyl ethers (PBDEs), posing threats to their recovery. Concentrations of PCBs and PBDEs in subtidal surface sediments collected from 97 sites along the British Columbia (BC) coast were used to identify their distribution and profiles, and to assess killer whale habitat quality. Victoria Harbour (VH3(site ID: 1) ) sediments exhibited the highest PCB and PBDE concentrations. For PCBs, PCB-138 was found at the highest concentration, followed by PCB-153, PCB-110, PCB-149, PCB-101, and PCB-118. For PBDEs, individual congeners were ranked as follows: BDE-209 > BDE-207 > BDE-206 > BDE-208 > BDE-47 > BDE-99. Principal component analyses (PCA) illustrated the variations in contaminant profiles, with PC1 for PCBs and PBDEs correlated with the octanol-water partition coefficient (log KOW , p < 0.003). Based on the PCA, sediment particle size, total organic carbon (TOC), and water depth at collection were other factors associated with the distribution of PBDEs, while PCB profiles were associated with TOC. Total PCB and PBDE concentrations at 100% and 34% of the sites, respectively, exceeded the recently adopted British Columbia's Ministry of Environment and Climate Change Strategy Working Sediment Quality Guidelines (PCBs 3.7 pg/g dry wt and PBDEs 1000 pg/g dry wt), considered protective of killer whales. Our findings suggest that the legacy of banned PCBs and PBDEs has the potential to constrain the recovery of killer whales as a result of their mobilization from sediments and consequent uptake by marine food webs. Environ Toxicol Chem 2022;41:2139-2151. © 2022 SETAC.

Green vortex-assisted emulsification microextraction using a ternary deep eutectic solvent for extraction of tetracyclines in infant formulas

A novel green alternative vortex-assisted emulsification liquid–liquid microextraction based on a new hydrophobic deep eutectic solvent (DES) was developed to extract tetracyclines in infant formulas. Five new ternary DESs were synthesized and tested in this regard. Among them [thymol]:[ethylene glycol]:[benzyl alcohol] (2:2:1) DES demonstrated the highest extraction efficiency. The analyzes were performed by HPLC. The DES was characterized by attenuated total reflectance-FTIR, nuclear magnetic resonance spectroscopy, and octanol–water partition coefficient. The effect of type, mole ratio, and volume of DES, dispersing agent, pH, and ionic strength was studied. The limits of quantification and linear range were 3–9.32 and 3–500 μg kg−1, respectively. The method was applied to detect tetracyclines in infant formulas, and the recoveries were obtained as 68.9–102.0 % with relative standard deviations < 9 %. The procedure greenness was assessed using the Analytical Eco-Scale. This paper represents the first application of a novel ternary DES to analyze tetracyclines in infant formulas.

Identification of Novel Organophosphate Esters in Hydroponic Lettuces (Lactuca sativa L.): Biotransformation and Acropetal Translocation.

The absorption, translocation, and biotransformation behaviors of organophosphate esters (OPEs) and diesters (OPdEs) in a hydroponic system were investigated. The lateral root was found as the main accumulation and biotransformation place of OPEs and OPdEs in lettuce. The nontarget analysis using high-resolution mass spectrometry revealed five hydroxylated metabolites and five conjugating metabolites in the OPE exposure group, among which methylation, acetylation, and palmitoyl conjugating OPEs were reported as metabolites for the first time. Particularly, methylation on phosphate can be a significant process for plant metabolism, and methyl diphenyl phosphate (MDPP) accounted for the majority of metabolites. The translocation factor values of most identified OPE metabolites are negatively associated with their predicted logarithmic octanol-water partitioning coefficient (log Kow) values (0.75-2.45), indicating that hydrophilicity is a dominant factor in the translocation of OPE metabolites in lettuce. In contrast, palmitoyl conjugation may lead to an enhanced acropetal translocation and those with log Kow values < 0 may have limited translocation potential. Additionally, OPE diesters produced from the biotransformation of OPEs in lettuce showed a higher acropetal translocation potential than those exposed directly. These results further emphasize the necessity to consider biotransformation as an utmost important factor in the accumulation and acropetal translocation potential of OPEs in plants.

Toward revealing the role of the cation in the phytotoxicity of the betaine-based esterquats comprising dicamba herbicide

In this study, two homologous series of esterquats comprising alkyl (from ethyl to octadecyl) betainate cations and bromide as well as dicamba anions were successfully synthesized, starting from a renewable raw material – glycine betaine. Due to the favorable octanol-water partition coefficient and utilization of biodegradable cations of natural origin, synthesized esterquats can be considered promising alternatives to currently applied dicamba-based formulations. In addition, the obtained results allowed us to verify whether the organic cations in quaternary ammonium salts containing herbicidally active anions (such as dicamba) play the role of biologically inactive adjuvants that only enhance the efficiency of the active ingredient or if they simultaneously exhibit a significant degree of phytotoxicity. Analysis of the influence of alkyl betainate esterquats containing nonherbicidal (bromide) anions on seedlings of white mustard revealed that alkyl betainate cations promote the germination of white mustard seeds; however, the subsequent growth of the seedlings was significantly inhibited. Further studies performed on white mustard and cornflower plants in a stage of 4–6 leaves allowed us to conclude that in the case of sensitive plants, the high phytotoxicity can be attributed to the presence of the dicamba anion, whereas for more resistant plants the additional influence of the cation on the phytotoxic effect is visible. Esterquats comprising a dodecyl substituent or longer had high surface active properties. Nonetheless, their contact angle values were not correlated with phytotoxicity data, indicating an additional influence of the cation on this stage of plant development. Interestingly, subsequent dose–response experiments conducted for two selected dicamba–based products confirmed that the greatest phytotoxicity was expressed by compounds containing a decyl substituent.

Prediction of polarity-dependent environmental behaviors of humic substances (HS) using a HS hydrophobicity index based on hydrophilic interaction chromatography

A variety of analytical methods have been applied to describe the properties of aquatic humic substances (HS). However, there are only a few methods available to probe HS hydrophobicity because of the heterogeneous character of HS. In this study, hydrophilic interaction chromatography (HILIC) equipped with a UV detector was employed to describe the heterogeneous distribution of HS with respect to its hydrophobicity and to suggest a representative HS hydrophobicity index. To this end, various mobile phases were explored to achieve the optimal separation capability of HILIC. The highest resolution was obtained with a mobile phase comprising acetonitrile and water at a ratio of 70:30 (v:v). A calibration curve was successfully constructed using eight different HS precursor compounds, which allowed for the successful conversion of the retention time (RT) into the octanol-water partition coefficient (Kow) (log Kow = −2.83 × (RT) + 17.44, R2 = 0.950). Several possible HS hydrophobicity indices were derived from the HILIC chromatogram. Among those, the weight-average log KOW value exhibited the strongest negative correlation with the well-known polarity index, (O + N)/C ratios, of seven reference HS samples. This new HILIC-based index (i.e., average log KOW) also presented a good relationship with the HS binding coefficients with pyrene as well as the extent of HS adsorption onto kaolinite at a given solution chemistry (i.e., at a high ionic strength and a neutral pH), both of which are known to be largely governed by the hydrophobic nature of HS. This study demonstrated that the average KOW value based on HILIC is an intuitive and robust HS hydrophobicity index to fully represent the heterogeneous distribution of hydrophobicity within a bulk HS and could be applied to predict many environmental behaviors related to HS hydrophobicity or HS polarity.

Octanol-Water Partition Coefficients of Fluorinated Drug Molecules with Continuum Solvation Models.

In this work, we have examined the efficiency of continuum solvation models, used with density functional theory methods, in calculating octanol-water partition coefficients (logP) of 56 fluorine containing drug molecules. The solvation model based on density model computed logP values that are in good agreement with the benchmark values. The conductor-like polarizable continuum models computed results have issues in predicting correct trend, often with reversal of sign from benchmark. The choice of basis set does not show significant effect, and the selection of atomic radii affects geometry convergence during calculations.

Occurrence and ecological risks of PAHs in the dissolved and particulate phases of coastal surface water of Taiwan

Surface seawater were collected from seven sites along the coast of Taiwan. A total of 100 L seawater was pre-concentrated from each site and the concentrations of 16 polycyclic aromatic hydrocarbons (PAHs) in the dissolved and particulate phases were analyzed. The characteristics, potential sources, and ecological risks of PAHs in seawater were assessed. The concentration of total PAHs (TPAHs) in the dissolved phases ranged between 3.3–25.8 ng/L, with an average of 14.7 ± 8.9 ng/L, classified as slightly contaminated, while the particulate phase ranged between 3.3–22.4 ng/L (8.5 ± 6.8 ng/L). The TPAHs concentrations in seawater are mainly dominated in the dissolved phase (60.4 ± 22.0%). The partition coefficients of PAHs in the particulate and dissolved phases were linearly correlated significantly with octanol–water partition coefficient (r = 0.744; p<0.01), indicating that hydrophobicity plays a key role in the partitioning behavior of PAHs. The dissolved phase PAHs in seawater were dominated by 3-ring PAHs (84.8 ± 3.9%), while the particulate phase was dominated by 5-ring PAHs (88.4 ± 9.1%). According to the diagnostic ratio, coal and biomass combustion are the main sources of PAHs, while petroleum and petroleum combustion sources also contributed to the northeast coast. The results of toxic equivalence quotients and mean risk quotient showed that the toxicity and risks of PAHs in the particulate phases were higher than those in the dissolved phases. Furthermore, the proportion of 5-ring PAHs in the dissolved phase was low (5.9 ± 4.3%), but relatively contributed high potential toxicity.