Hydrophilic Groups Research Articles

Qualitative analysis of hydrophilic headgroup water molecular space dependence and wetting effects of solution systems on polluting coal dust

The hydrophilic head groups of the surfactants affect the interfacial tension of surfactant solutions and the internal micelle structure of the bulk surfactants. Because of this, investigating the effect of the hydrophilic head groups on the adsorption performance of surfactants is helpful in terms of revealing the wetting mechanism of surfactants on coal at the molecular level. In this work we combine molecular dynamics simulations and quantum chemistry calculations with a collection of experiments to analyze the interaction patterns between sodium dodecyl sulfonate (SDSO), sodium dodecyl sulfate (SDS), sodium fatty alcohol polyoxyethylene ether carboxylate (SSN), and sodium lauryl phosphate (LSN) with coal. The radial distribution results show that SDSO formed the closest first peak of the hydrated layer at 1.31 Å, with a probability peak of 3.92, which exhibited strong hydrogen bonding interactions that are consistent with the relative concentration and average azimuthal shift trends obtained from molecular trajectory simulations. The priority interaction types between four surfactants and water molecules were determined using the energy difference of molecular orbitals in quantum mechanics. The weak interaction between hydrophilic head groups and water molecules was qualitatively and quantitatively analyzed using the Independent Gradient Model (IGMH), and the fundamental reasons affecting the wetting of long flame coal were obtained.

Self-Assembled Nanocomposite DOX/TPOR4@CB[7]4 for Enhanced Synergistic Photodynamic Therapy and Chemotherapy in Neuroblastoma.

DOX/TPOR4@CB[7]4 was synthesized via self-assembly, and its physicochemical properties and ability to generate reactive oxygen species (ROS) were evaluated. The impact of photodynamic therapy on SH-SY5Y cells was assessed using the MTT assay, while flow cytometry analysis was employed to detect cell apoptosis. Confocal laser scanning microscopy was utilized to observe the intracellular distribution of DOX/TPOR4@CB[7]4 in SH-SY5Y cells. Additionally, fluorescence imaging of DOX/TPOR4@CB[7]4 in nude mice bearing SH-SY5Y tumors and examination of the combined effects of photodynamic and chemical therapies were conducted. The incorporation of CB[7] significantly enhanced the optical properties of DOX/TPOR4@CB[7]4, resulting in increased ROS production and pronounced toxicity towards SH-SY5Y cells. Moreover, both the apoptotic and mortality rates exhibited significant elevation. In vivo experiments demonstrated that tumor growth inhibition was most prominent in the DOX/TPOR4@CB[7]4 group. π-π interactions facilitated the binding between DOX and photosensitizer TPOR, with TPOR's naphthalene hydrophilic groups encapsulated within CB[7]'s cavity through host-guest interactions with CB[7]. Therefore, CB[7] can serve as a nanocarrier to enhance the combined application of chemical therapy and photodynamic therapy, thereby significantly improving treatment efficacy against neuroblastoma tumors.

Regulating room temperature phosphorescence of carbazole quaternization pyridine in polymer through Hofmeister effect

AbstractHofmeister effect is a famous physical chemistry phenomenon that was reported a hundred years ago, which firstly refers to the action of certain salts to decrease the solubility of proteins while others increase. The Hofmeister effect on the luminescent properties of cationic organic fluorophore is still obscure, especially for their room temperature phosphorescence (RTP). Herein, hydrophilic groups (quaternization pyridine) were introduced into carbazole molecules to obtain a series of carbazole derivatives (named CZ‐Py+) with different counter anions in the Hofmeister series. These carbazole derivatives displayed tunable fluorescent color from cyan to yellow in the solid state following the Hofmeister sequence and anti‐Hofmeister behavior in an aqueous solution. Moreover, RTP material with tunable emission color and lifetime was achieved by doping CZ‐Py+ with Hofmeister series anion in polymethyl methacrylate and polyvinyl alcohol, which displayed good performance in time getting information encryption and anti‐counterfeiting.

Enhanced mechanical strength and water resistance in waterborne polyurethanes through hydroxyl-functionalized MQ silicone resin modification

As an alternative to solvent-based polyurethane, waterborne polyurethane (WPU) uses water as dispersants and can significantly reduce VOC. However, dispersing polyurethanes with hydrophobic backbones in water requires hydrophilic groups, which undermine the water resistance. It remains a challenge to simultaneously improve water resistance and mechanical properties. Here we report a polyurethane with superior mechanical properties and water resistance through the introduction of an organic-inorganic hybrid material, MQ silicone resin. Hydroxyl functionalized MQ silicone resin increases chemical crosslinking and improves the microphase separation and hydrogen bonding strength of polyurethanes. When the MQ-OH content was 10.1 wt%, the tensile strength increased from 27 MPa to 37.3 MPa, and the toughness increased from 74.8 MJ/m3 to 97.4 MJ/m3. Si-O-Si backbones with low surface energy can migrate to the film surface, increasing the surface hydrophobicity. WPU films with MQ silicone resin exhibited remarkable tensile strength retention, with 84.7 % after 40 h hydrolysis in 80 °C water, while WPU retained only 24.6 %. MQ silicone resin offers a novel approach to enhance the hydrophobic properties of WPU without compromising the mechanical properties.

Improving the mechanical properties of heat-treated wood bonding interphase via plasma treatment

Plasma treatment is an eco-friendly and effective way to improve the chemical reactivity of wood surface. This study explores the improvemnet of bonding properties of heat-treated wood for outdoor construction applications through plasma treatment. In this work, the low temperature atmospheric barrier discharge (DBD) plasma was used to modify the surface of heat-treated wood, and then phenol-formaldehyde (PF) resin adhesive and modified wood were applied to prepare bonded wood. The in-situ chemical structure and mechanical properties of the bonding interphase were characterized by Raman spectrum, nanoindentation and digital image correlation technology (DIC) to indicate the effect of DBD modification on the bonding properties of heat-treated wood. Results showed that after plasma treatment, the hydrophilic functional groups in the cell wall were increased and the PF adhesive molecules had chemical interaction with the cell wall. The elastic modulus (Er) and hardness (H) of wood cell wall gradually decreased along the bonding interphase towards wood with the decrease of PF penetration depth, which resulted in the reduction of the mechanical properties difference between the cell wall and PF adhesive at the bonding interphase. As a result, the shear strain was distributed homogeneously due to the effective stress transmission more at the bonding interphase. The shear strength of the control bonded wood decreased by about 35 % after heat treatment at 215 °C for 2 h, while the shear strength of heat-treated wood was increased by up to 34 % after plasma treatment.

Broadband Negative Photoconductive Response in Carbon Nanodots.

Due to the broadband response and low selectivity of external light, negative photoconductivity (NPC) effect holds great potential applications in photoelectric devices. Herein, different photoresponsive carbon nanodots (CDs) are prepared from diverse precursors and the broadband response from the NPC CDs are utilized to achieve the optoelectronic logic gates and optical imaging for the first time. In detail, the mcu-CDs which are prepared by the microwave-assisted polymerization of citric acid and urea possess the large specific surface area and abundant hydrophilic groups as sites for the adsorption of H2O molecules and thereby present a high conductivity in dark. Meanwhile, the low affinity of mcu-CDs to H2O molecules permits the light-induced desorption of H2O molecules by heat effect and thus endow the mcu-CDs with a low conductivity under illumination. The easy absorption and desorption of H2O molecules contribute to the extraordinary NPC of mcu-CDs. With the broadband NPC response in CDs, the optoelectronic logic gates and flexible optical imaging system are established, achieving the applications of "NOR" or "NAND" logic operations and high-quality optical images. These findings unveil the unique optoelectronic properties of CDs, and have the potential to advance the applications of CDs in optoelectronic devices.

Research on the application of hydrophilic modified covalent organic framework membranes in seawater desalination

Given the global challenge of freshwater scarcity, the importance of seawater desalination technology has grown. This study examines the efficiency and role of hydrophilic-modified covalent organic framework (COF) membranes in seawater desalination through molecular simulations. Incorporating hydrophilic groups like -SO3H into N2COF membranes and optimizing their structure significantly improved water permeability and salt ion retention. Non-equilibrium molecular dynamics (NEMD) simulations showed that hydrophilic modifications enhance water permeability while preserving salt ion interception efficacy. Furthermore, adjusting the membrane's stacking method could further enhance its seawater desalination performance. The simulations confirm the high-efficiency desalination capability of hydrophilic-modified COF membranes and offer crucial theoretical guidance for designing and preparing high-performance desalination materials.

Interaction of anthocyanins, soluble dietary fiber and waxy rice starch: Their effect on freeze-thaw stability, water migration, and pasting, rheological and microstructural properties of starch gels

This study aimed to investigate the effect of the interaction of black rice anthocyanins (BRA), soluble dietary fiber from extruded rice bran (ES) and waxy rice starch (WRS) on the physicochemical properties of starch gels, including gelatinization properties, rheological properties, freeze-thaw stability, water migration, molecular structure and gel microstructure. The results showed that the pasting temperature (PT) of the mixtures was increased, and the peak viscosity (PV), trough viscosity (TV), final viscosity (FV) and setback viscosity (SV) were significantly reduced when ES and BRA were added to WRS in different proportions (ES:BRA, 4:0, 4:0.4, 4:1, 4:2, 8:0, 8:0.8, 8:2, 8:4). Both ES and BRA could enhance the viscosity of WRS gels, and ES exhibited strong ability on improving the strength of gels. The presence of ES and BRA improved the water retaining capacity of WRS gels, but weakened the freeze-thaw stability. ES, BRA and WRS formed non-covalent bonds (hydrogen bonds) through hydrophilic groups during gelatinization, which improved the gel properties. In addition, the steric hindrance formed by ES and BRA inhibited starch retrogradation. These results might contribute to the development of starch-based food formulations with good quality.

All-in-one, gas-permeable, ultrathin, flexible, and self-adhesive epidermal electrode for biopotential recording and muscle theranostics

Epidermal electronics have attracted extensive attention owing to their potential in personal healthcare and human–machine interactions (HMIs). However, their low conductivity and poor ability to conform to the human skin impede their practical application. Herein, a multifunctional flexible dry epidermal electrode for biopotential recording and muscle thermotherapy was developed based a conductive polymer (poly(3,4-ethylenedioxythiophene) doped with polystyrene sulfonic acid (PEDOT:PSS)). PEDOT:PSS was modified using poly(vinyl alcohol) (PVA) with hydrophobic groups. The electrode is able to self-adhere to human skin through a hydrophobic interaction with the skin. Moreover, the hydrophilic groups can absorb the humidity under the skin and move it by the hydrophobic groups, which allows the electrode exhibits good gas-permeability. The ultrathin electrode conforms well to the topography of the human skin and, thus, can form a stable and intimate interface with it, resulting in a low electrode–skin contact impedance that allows the recording of biopotentials with high quality. Moreover, the electrode exhibits rapid Joule heating performance at a low voltage (up to 53.8 °C in 12 s at 1.5 V), which is suitable for the electrothermal therapy of muscle. On-body measurements confirm that our electrode could detect muscle fatigue via electromyography (EMG) and perform electrothermal therapy to relieve muscle fatigue. This study offers an efficient method for developing all-in-one wearable flexible epidermal electrode for biopotential recording and muscle theranostics.

Cellular and Molecular Insights into the Divergence of Neural Stem Cells on Matrigel and Poly-l-lysine Interfaces.

Poly-l-lysine (PLL) and Matrigel, both classical coating materials for culture substrates in neural stem cell (NSC) research, present distinct interfaces whose effect on NSC behavior at cellular and molecular levels remains ambiguous. Our investigation reveals intriguing disparities: although both PLL and Matrigel interfaces are hydrophilic and feature amine functional groups, Matrigel stands out with lower stiffness and higher roughness. Based on this diversity, Matrigel surpasses PLL, driving NSC adhesion, migration, and proliferation. Intriguingly, PLL promotes NSC differentiation into astrocytes, whereas Matrigel favors neural differentiation and the physiological maturation of neurons. At the molecular level, Matrigel showcases a wider upregulation of genes linked to NSC behavior. Specifically, it enhances ECM-receptor interaction, activates the YAP transcription factor, and heightens glycerophospholipid metabolism, steering NSC proliferation and neural differentiation. Conversely, PLL upregulates genes associated with glial cell differentiation and amino acid metabolism and elevates various amino acid levels, potentially linked to its support for astrocyte differentiation. These distinct transcriptional and metabolic activities jointly shape the divergent NSC behavior on these substrates. This study significantly advances our understanding of substrate regulation on NSC behavior, offering novel insights into optimizing and targeting the application of these surface coating materials in NSC research.

Mechanism Involved in Polyvinyl Chloride Nanoplastics Induced Anaerobic Granular Sludge Disintegration: Microbial Interaction Energy, EPS Molecular Structure, and Metabolism Functions.

Nanoplastics (NPs) are emerging pollutants and have been reported to cause the disintegration of anaerobic granular sludge (AnGS). However, the mechanism involved in AnGS disintegration was not clear. In this study, polyvinyl chloride nanoplastics (PVC-NPs) were chosen as target NPs and their long-term impact on AnGS structure was investigated. Results showed that increasing PVC-NPs concentration resulted in the inhibition of acetoclastic methanogens, syntrophic propionate, and butyrate degradation, as well as AnGS disintegration. At the presence of 50 μg·L-1 PVC-NPs, the hydrophobic interaction was weakened with a higher energy barrier due to the relatively higher hydrophilic functional groups in extracellular polymeric substances (EPS). PVC-NPs-induced ROS inhibited quorum sensing, significantly downregulated hydrophobic amino acid synthesis, whereas it highly upregulated the genes related to the synthesis of four hydrophilic amino acids (Cys, Glu, Gly, and Lys), resulting in a higher hydrophily degree of protein secondary structure in EPS. The differential expression of genes involved in EPS biosynthesis and the resulting protein secondary structure contributed to the greater hydrophilic interaction, reducing microbial aggregation ability. The findings provided new insight into the long-term impact of PVC-NPs on AnGS when treating wastewater containing NPs and filled the knowledge gap on the mechanism involved in AnGS disintegration by PVC-NPs.

Carbon dots as a sustainable electrolyte enhancer in aqueous alkaline electrochemical capacitors

In the endeavour to increase the energy density and to widen the potential window of aqueous alkaline electrochemical capacitors (EC), this study explores the role of carbon dots (CDs) as an additive in potassium hydroxide electrolyte. The CDs with an average size of ∼2.2 nm and negative surface potential are synthesized from a dispersion of palm kernel shell powder in water using a low-temperature hydrothermal process. Electrochemical measurements show that the CD–electrolyte ion (K+) interaction has improved counter ion adsorption in porous carbon electrodes via lowering the characteristic resistances and time constants, which significantly improved the fraction of adsorbed charges than diffusively stored. The improved ionic conductivity is attributed to the improved wettability introduced by the hydrophilic functional groups in the CDs. These parametric changes widened the potential window and marked an 80 % increase in the specific energy and over a 10 % increase in specific power in a practical EC with similar mass-loading as commercial devices. The device with CDs demonstrated superior cycling stability and Coulombic efficiency than the control device without them. These findings underscore the potential of CDs as a promising avenue for advancing the performance parameters of aqueous electrolyte EC, aligning with the overarching goal of realising economical, environmentally friendly, and sustainable energy storage solutions.

Facile dip-coating of silk fibroin/tannic acid@CaCO3 hybrid film with superhydrophilicity on the surface of polypropylene nonwovens for oil–water separation

Superhydrophilic membrane materials are widely used for oil/water separation due to their excellent resistance to anti-fouling underwater. The key factors for realizing superhydrophilicity of membranes are the introduction of hydrophilic groups and the construction of surface micro/nano roughness structures. Herein, we propose a simple, mild, and green dip-coating method to prepare silk fibroin (SF)-tannic acid (TA)@CaCO3 hybrid film to achieve superhydrophilicity of polypropylene nonwovens (PP). Specifically, the hydrophobic interactions between SF and hydrophobic materials were used to create the pre-coatings. TA molecules were deposited onto the surface of SF via hydrogen bonding to provide phenolic hydroxyl groups for achieving the hydrophilicity of PP membranes. Then, the CaCO3 was synthesized in situ by introducing Ca2+ into the pre-coating while depositing TA to construct micro/nano-roughness structures on the PP membrane surface for obtaining superhydrophilicity. PP-SF-TA@CaCO3 membranes exhibit outstanding superhydrophilicity and underwater superoleophobicity, with separation efficiencies exceeding 99 % for a variety of oil–water mixtures and oil-in-water emulsions, and water fluxes ranging from 4000 L m-2h−1 to 5500 L m-2h−1. The separation efficiencies remained above 99 % throughout 50 separation cycles, indicating the excellent separation stability of the modified membranes. Moreover, no significant loss of separation efficiency was observed when separating oil mixtures from harsh water sources, including acidic, alkaline, cold, and hot water. Therefore, the membranes modified by the above process have a promising application in the practical separation of oily wastewater.

Evaluation of surface structure, water sorption properties, water plasticizing effect, and color stability of dried chrysanthemums

The storage stability of two varieties of chrysanthemum (Chrysanthemum morifolium Ramat. cv. HSGJ and C. morifolium Ramat. cv. JSHJ)was evaluated in this study through an analysis of their water binding behavior. This involved examining the surface structure of the powdered dried chrysanthemums, studying the water sorption characteristics, and quantifying the water plasticizing effect. In comparison to JSHJ, powdered HSGJ had a smaller particle size and more hydrophilic groups on its surface. Additionally, it exhibited significantly higher characteristic values of adsorbed water, excluding the number of adsorbed monolayers (Nam). The sorption of water by the powdered chrysanthemums conformed to a type II isotherm. The Guggenheim–Anderson–deBoer (GAB) model was trustworthy for predicting water sorption within the range of aw from 0.112 to 0.907 and temperatures between 20 and 40 °C. The exothermic interactions between water molecules and the primary sorption sites of the powdered samples became more powerful when the temperature decreased. Powdered chrysanthemums can be preserved at 30 °C if the humidity is below 0.0852 g/g for HSGJ and 0.0766 g/g (d.b) for JSHJ. The color changes of powdered samples were not significantly affected when stored in a glassy state. This study is significant for identifying the drying endpoint, predicting shelf life, and choosing suitable packaging materials for dried chrysanthemums.

Comprehensive analysis of water vapor sorption kinetics and mechanisms using biosorbent pellets from canola meal and oat hull

Agricultural residues, specifically canola meal (CM) and oat hull (OH), have been innovatively utilized to develop biosorbents for sorbing water vapor from the air. These biomaterials are comprised of hydrophilic functional groups that effectively perform air dehydration. Air, being non-polar, was used as a model gas in this study to simulate gas dehydration. In the current research, these materials were formed into pellets to produce high-quality biosorbents with controlled size, shape, and enhanced moisture uptake capacity. CM (309.48 mg/g) and OH (233.07 mg/g) pellets had higher or comparable water sorption capacities than commercialized adsorbents used for drying gases. The mixed-order kinetic model described the sorption process well and identified both mass transfer and sorption on active site steps (R 2 > 0.991 and χ 2 < 16.0). Regarding the OH pellet, sorption on active sites was the predominant kinetic mechanism at the beginning, followed by intraparticle diffusion until equilibrium. However, sorption on CM pellets was delayed at 4.2 min at the initial stage, owing to the external mass transfer resistance; then, intraparticle diffusion controlled the process until equilibrium. Adding sodium lignosulfonate (LSNa) lowered the initial sorption rate but enhanced the water uptake and strength of pellets. The addition of LSNa resulted in a 25% and 14% increase in the water uptake capacity of oat hull and canola meal pellets, respectively; conversely, it also caused an increase in the delay time for sorption on CM pellets at the beginning of the process, extending it to 9.50 min.

Biodegradable Plastics from Mango Seed Starch for Sustainable Food Packaging‐Effect of Citric Acid and Fillers

AbstractStarch based bioplastics were prepared and characterized with fillers carboxy methyl cellulose (CMC), chitosan (CS) and nanochitosan (NCS); plasticizer sorbitol and cross‐linking agent citric acid (CA) at different loading levels. Structural, water resistance, water vapor permeability, solubility, mechanical, antimicrobial and biodegradation properties of the bioplastics were investigated. FTIR confirmed bonding of starch with cross‐linking agent, fillers and plasticizer. The water uptake of the CMC bioplastics was decreased up to 70 % with 20 % CA addition. Bioplastics with CS and NCS showed lesser water uptake, only 12.5 % for CS bioplastic. The water vapour permeability (WVP) of all bioplastics was low in the range 2.16×10−7–6.29×10−7 gday−1 m−1 Pa−1. The CA addition increased water resistance and lowered WVP of the bioplastics by restricting the hydrophilic functional groups and forming more tight structures. The fillers CS and NCS additions enhanced the mechanical strength attributing to more hydrogen bonding between NH3+ of chitosan and OH− of starch. All bioplastics demonstrated good antimicrobial activities. These bioplastics offer an attractive alternative to non‐biodegradable plastics used in food packaging due to its enhanced water resistance, antibacterial properties and biodegradability.

Biodegradable MXene Quantum Dots with High Near-Infrared Photothermal Performance for Cancer Treatment.

Photothermal therapy (PTT) offers significant potential in cancer treatment due to its short, simple, and less harmful nature. However, obtaining a photothermal agent (PTA) with good photothermal performance and biocompatibility remains a challenge. MXenes, which are PTAs, have shown promising results in cancer treatment. This study presents the preparation of Ti3C2 MXene quantum dots (MXene QDs) using a simple hydrothermal and ultrasonic method and their use as a PTA for cancer treatment. Compared to conventional MXene QDs synthesized using only the hydrothermal method, the ultrasonic process increased the degree of oxidation on the surface of the MXene QDs. This resulted in the presence of more hydrophilic groups such as hydroxyl groups on the MXene QD surfaces, leading to excellent dispersion in the aqueous system and biocompatibility of the prepared MXene QDs without the need for surface modification. The MXene QDs showed great photothermal performance with a photothermal conversion efficiency of 62.5%, resulting in the highest photothermal conversion efficiency among similar materials reported thus far. Both in vitro and in vivo experiments have proved the potent tumor inhibitory effect of the MXene QD-mediated PTT, with minimal harm to mice. Therefore, these MXene QDs hold a significant promise for clinical applications.

Preparation, Characterization, and Antioxidant Properties of Self-Assembled Nanomicelles of Curcumin-Loaded Amphiphilic Modified Chitosan.

Curcumin (Cur) is a phytochemical with various beneficial properties, including antioxidant, anti-inflammatory, and anticancer activities. However, its hydrophobicity, poor bioavailability, and stability limit its application in many biological approaches. In this study, a novel amphiphilic chitosan wall material was synthesized. The process was carried out via grafting chitosan with succinic anhydride (SA) as a hydrophilic group and deoxycholic acid (DA) as a hydrophobic group; 1H-NMR, FTIR, and XRD were employed to characterize the amphiphilic chitosan (CS-SA-DA). Using a low-cost, inorganic solvent-based procedure, CS-SA-DA was self-assembled to load Cur nanomicelles. This amphiphilic polymer formed self-assembled micelles with a core-shell structure and a critical micelle concentration (CMC) of 0.093 mg·mL-1. Cur-loaded nanomicelles were prepared by self-assembly and characterized by the Nano Particle Size Potential Analyzer and transmission electron microscopy (TEM). The mean particle size of the spherical Cur-loaded micelles was 770 nm. The drug entrapment efficiency and loading capacities were up to 80.80 ± 0.99% and 19.02 ± 0.46%, respectively. The in vitro release profiles of curcumin from micelles showed a constant release of the active drug molecule. Cytotoxicity studies and toxicity tests for zebrafish exhibited the comparable efficacy and safety of this delivery system. Moreover, the results showed that the entrapment of curcumin in micelles improves its stability, antioxidant, and anti-inflammatory activity.

Daidzein‐Based Amphiphilic Small Molecular Antimicrobial Peptidomimetics as Novel Antimicrobial Agents with Anti‐Biofilm Activity

AbstractA new series of daidzein‐based short peptidomimetic compounds were developed. In this study, we incorporated an alkyl chain with different chain lengths as hydrophobic groups, various amino acids and their respective guanidinium salts as hydrophilic groups. The most potent compound 9 a showed excellent antibacterial activity with minimum inhibitory concentration (MIC) of 8 μM against S. aureus and 32 μM against Escherichia coli. Furthermore, 9 a inhibited more than 65 % S. aureus biofilm formation at sub‐MIC, it also disrupted 69 % pre‐established S. aureus at 64 μM. The cytoplasmic membrane permeability study of 9 a revealed that the depolarization of membrane could be the possible mechanism of action. However, 9 a exhibited moderate toxicity against human erythrocytes.

Metabolism of alcohol ethoxylates (AEs) in rat, hamster, and human hepatocytes and liver S9: a pilot study for metabolic stability, metabolic pathway, and metabolites identification in vitro and in silico

Alcohol ethoxylates (AEs) are a well-known class of non-ionic surfactants widely used by the personal care market. The aim of this study was to evaluate and characterize the in vitro metabolism of AEs and identify metabolites. Five selected individual homologue AEs (C8EO4, C10EO5, C12EO4, C16EO8, and C18EO3) were incubated using human, rat, and hamster liver S9 fraction and cryopreserved hepatocytes. LC–MS was used to identify metabolites following the incubation of AEs by liver S9 and hepatocytes of all three species. All AEs were metabolized in these systems with a half-life ranging from 2 to 139 min. In general, incubation of AE with human liver S9 showed a shorter half-life compared to rat liver S9. While rat hepatocytes metabolized AEs faster than human hepatocytes. Both hydrophobic alkyl chain and hydrophilic EO head group groups of AEs were found to be target sites of metabolism. Metabolites were identified that show primary hydroxylation and dehydrogenation, followed by O-dealkylation (shortening of EO head groups) and glucuronidation. Additionally, the detection of whole EO groups indicates the cleavage of the ether bond between the alkyl chain and the EO groups as a minor metabolic pathway in the current testing system. Furthermore, no difference in metabolic patterns of each individual homologue AE investigated was observed, regardless of alkyl chain length or the number of EO groups. Moreover, there is an excellent agreement between the in vitro experimental data and the metabolite profile simulations using in silico approaches (OECD QSAR Toolbox). Altogether, these data indicate fast metabolism of all AEs with a qualitatively similar metabolic pathway with some quantitative differences observed in the metabolite profiles. These metabolic studies using different species can provide important reference values for further safety evaluation.