Propane Dibromide Research Articles

Experimental and theoretical investigation of 1,3-bis(3-hydroxypyridinium)propane dibromide dihydrate, tetrabromozincate hydrate, and tetrabromocuprate

Three gemini hydroxypyridine salts: 1,3-bis(3-hydroxypyridinium)propane dibromide dihydrate (1), 1,3-bis(3-hydroxypyridinium)propane tetrabromozincate hydrate (2), and 1,3-bis(3-hydroxypyridinium)propane tetrabromocuprate (3) were synthesized and characterized by X-ray diffraction, FTIR, Raman, NMR, and DFT methods. The dibromide salt (1) crystallizes with two water molecules. One of the two bromide anions is connected to the hydroxyl group of one pyridinium cation moiety through the O(10)-H(10)···Br(2)− hydrogen bond of 3.146(2) Å, while the other bromide anion, Br(1)− is surrounded by three water molecules. In 1,3-bis(3-hydroxypyridinium)propane tetrabromozincate (2) the water molecule acts as a bridge between the hydroxypyridinium cation and the tetrabromozincate anion, while the tetrabromocuprate anion interacts directly with the hydroxypyridinium cation. The molecular structures of the studied 1,3-bis(3-hydroxypyridinium)propane derivatives 1a, 2a, and 3a were optimized using the APF-D/6–311++G(d,p) method. The optimized structure of salt 1a resembles the crystal structure, while in salts 2a and 3a the structure of 1,3-bis(3-hydroxypyridinium)propane dication is bent to the U-form and the tetrabromomethallate anion is located in a niche. The significant role of the intermolecular interactions and hydrogen bonds was revealed based on IR spectra. The interpretation of 1H and 13C NMR spectra in DMSO-d6 was based on 2D experiments. The quantum theory of atoms in molecules (QTAIM) was employed to classify the strength of hydrogen bonds in salts 1, 2, and 3. Based on the σ-hole concept, intermolecular interactions in 2 and 3 were described.

Preparation and Adsorption Properties of MCM-41 with Novel Gemini Ionic Liquid Surfactants as Template

A mesoporous molecular sieve was prepared by the hydrothermal synthesis method with symmetric Gemini surfactant 1,3-bis(hexadecyldimethylammonio)-propane dibromide, symmetric Gemini ionic liquid surfactant 1,3-bis(3-hexadecylimidazolium-1-yl) propane dibromide and self-designed asymmetric Gemini ionic liquid surfactant 1-(3-(hexadecyldimethylammonio)prop-1-yl)-3-hexadecylimidazolium dibromide as the template agent. The structure characterization results for mesoporous molecular sieves show that the material possesses a hexagonal pore structure with uniform channels. The mesoporous silica that was synthesized with self-designed asymmetric Gemini ionic liquid surfactant as the template agent possesses the largest surface area and its pore size and specific surface area are, respectively, 3.28 nm and 879.37 m2/g. The adsorption properties of the prepared MCM-41 for crystal violet were investigated, and the adsorption thermodynamics and kinetics were investigated. The results show that adsorption equilibrium can be reached under pH = 9 and 35 °C for 50 min, and the quantity of adsorption can reach up to 464.21 mg/g. The adsorption process belongs to Langmuir isothermal adsorption, conforming to second-order adsorption kinetics, and the adsorption process is an endothermic process.

Two supramolecular compounds constructed by polyacid anion clusters: Synthesis, characterization and performance research

In this paper, two novel organic-inorganic hybrid supramolecule compounds {[Cu·L1’·H2O]·(α-Mo8O26)0.5}n 1 and compound {[Cu·L2’·H2O]·(α-Mo8O26)0.5}n 2 have been synthesized [L1’ = 1, 3-bis (4-carboxylpyridine) propane dibromide, L2’ = 1, 4-bis (4-carboxylpyridine) butane dibromide]. Compounds 1 and 2 have been expressly confirmed by PXRD, IR, X-ray single crystal diffraction and TG. Last, the study found that compounds 1 and 2 have obvious adsorption effects on MB and RhB organic dyes, and compound 2 has high adsorption capacity for MB.

Preparation of 2D supramolecular material doping with TiO2 for degradation of tetracycline

Anatase TiO2 photocatalyst supported on [BMPP]2[2D-Mo18O56] (BMPP = 1, 3-bis(4-methylpyridine) propane dibromide) was successfully prepared by hydrothermal method. The composites were characterized by field emission scanning electron microscopy (SEM), X-ray diffractometer (XRD), infrared spectroscopy (IR) and energy-dispersive X-ray spectrometer (EDS). The results show that the high content anatase nanoparticles are uniformly loaded on the polyacid supramolecules to form the composite material. The photocatalytic activity of TiO2/Mo9O28-BMPP towards the tetracyclines (TCs), a model pollutant, has been investigated. The results show that under a 500W high-pressure xenon lamp, 0.15 g TiO2/MoB can degrade 97% of 20 mL (25 mg/L) Tc after 115 min, showing high catalytic activity. In addition, 0.15-TiO2/MoB can be easily separated from the reaction system by centrifugation, and the catalyst still maintains high photocatalytic activity after 3 cycles of tests under the same conditions. This shows that it has the potential for recycling. This research provides a new way for the development of new supported catalysts.

Spectroscopic, structural and theoretical investigation of 1,3-bis(3-hydroxymethylpyridinium)propane dibromide, tetrabromozincate and tetrabromocuprate

The structures of 1,3-bis(3-hydroxymethylpyridinium)propane dibromide (1), 1,3-bis(3-hydroxymethylpyridinium)propane tetrabromozincate (2) and 1,3-bis(3-hydroxymethylpyridinium)propane tetrabromocuprate (3) have been studied by X-ray diffraction, DFT, FTIR, NMR and UV–vis methods. The crystal structures of three analogous compounds are significantly different: 1 is orthorhombic, space group Fdd2, Z = 8, 2 is triclinic, space group P1¯, Z = 2 and 3 is monoclinic, space group C2/c, Z = 8. The bispyridinium dication in 1 lies on the special position on the 2-fold axis. Each 3-hydroxymethyl group forms an OH⋯Br hydrogen bond, and the dications combine into three-dimensional networks through numerous CH⋯Br bonds. The IR spectra of the dibromide of 1,3-bis(3-hydroxymethylpyridinium)propane (1) and its tetrabromometallates (2 and 3) were compared and their interpretation was confirmed by calculated spectra. UV–vis spectra for tetrabromocuprate salt (3) showed significant differences between solid-phase and water solution.

Highly Efficient Separation of Phenolic Compounds from Oil Mixtures by Imidazolium-Based Dicationic Ionic Liquids via Forming Deep Eutectic Solvents

The separation of phenolic compounds from oil mixtures is an important step for further refining or applications of the oil mixtures. In this work, three imidazolium-based dicationic ionic liquids (DILs; 1,2-bis[N-(N′-methylimidazolium)]ethane dibromide, DIL1; 1,3-bis[N-(N′-methylimidazolium)]propane dibromide, DIL2; and 1,4-bis[N-(N′-methylimidazolium)]butane dibromide, DIL3) were synthesized and used to separate phenolic compounds from oil mixtures. The effects of time, temperature, DIL:phenol mole ratio, and initial phenol concentration on separation performance were investigated in detail. It was found that the removal efficiency of phenol followed the order DIL1 < DIL2 < DIL3. DIL3 showed the maximum phenol removal efficiency of 96.6% and the minimum ultimate phenol concentration of 3.9 g/dm3. Initial phenol concentration had little influence on the ultimate phenol concentration. Less than 0.4 in DIL:phenol mole ratio was needed to obtain the highest phenol removal efficiency, and the separation proc...

Effect of imidazolium-based ionic liquids on the aggregation behavior of twin-tailed cationic gemini surfactant in aqueous solution

ABSTRACTMicellization behavior of the twin-tailed surfactants can be modulated by the addition of various modifiers. Ionic liquids (ILs) are one of them and are documented here. The beauty of these environmentally benign neoteric molecules lies in their structural versatility. Here, we have investigated the effect of three ILs: 1-butyl-3-methylimidazolium bromide ([C4mim][Br]), 1-hexyl-3-methylimidazolium bromide ([C6mim][Br]), and 1-octyl-3-methylimidazolium bromide ([C8mim][Br]) on the aggregation and surface adsorption behavior of cationic gemini surfactant, bis(hexadecyldimethyl ammonium)propane dibromide (16-3-16) through experimentally measured electrical conductivities, surface tensions, and by spectral methods (UV-vis absorbance and fluorescence measurements). The main focus of the study is to observe the effect of added ILs on the critical micelle concentration (cmc), various surface parameters, aggregation number, and size of the aggregates of gemini surfactant. The results show that the more hydrophobic ILs, that is, [C6mim][Br] and [C8mim][Br] behave as electrolyte at lower concentration and cosurfactant at higher concentration, whereas moderately hydrophobic IL [C4mim][Br] acts as an electrolyte at all concentration ranges studied. The modulating effects of ILs were also compared with conventional electrolyte (NaBr) at similar conditions.

Evaluation of possible inhibition of human liver drug metabolizing cytochromes P450 by two new acetylcholinesterase oxime-type reactivators

Two non-symmetric bispyridine oxime – based reactivators of acetylcholinesterase enzyme (AChE), labeled as K027 (1-(4-carbamoylpyridinium)-3-(4-hydroxyiminomethylpyridinium)-propane dibromide) and K203 ((E)-1-(4- carbamoylpyridinium)-4-(4-hydroxyiminomethylpyridinium)-but-2-ene dibromide) were tested for their potential to inhibit activities of human liver microsomal cytochromes P450 (CYP). Both oximes are very potent reactivators of organophosphate-inhibited AChE.An interaction of both compounds with CYP in human liver microsomal preparation was detected using difference spectroscopy. The compounds were shown to bind to CYP enzymes with spectral binding constants of 5.04 ± 1.79 nM (K027) and 5.2 ± 2.6 nM (K203). Enzymology studies were subsequently performed aimed at determining which of the nine most important CYP involved in drug is affected by this interaction. The results have shown no prominent inhibition of individual CYP activities with either compounds except in the case of CYP2E1 and K203. Diagnostic Dixon plot revealed that K203 acted as an uncompetitive inhibitor of CYP2E1. Inhibition of this activity however is not as prominent as to make a potent drug interaction likely. Hence, the interaction of K027 and K203 oxime-type AChE reactivators with human liver microsomal CYP enzymes does not seem to be of prominent clinical importance and both compounds could be safely used in this respect as antidotes with low risk of drug interactions.

Phenol Adsorption Characteristics of Two Novel Gemini Surfactants Modified Organ-bentonites

Bentonite was modified by means of ion exchange with two Gemini surfactants(1, 3- bis(dodecyldimethylammonio)-propane dibromide(BDP) and 1, 3-bis(dodecyldimethylammonio)-2-hydroxypropane dichloride(BDHP)) respectively to prepare two organ- bentonites BDP-B and BDHP-Bt. The organ-bentonites were characterized by X-ray diffraction(XRD) and FT-IR spectroscopy. Then their adsorption ability of phenol from aqueous solutions was examined in terms of the p H value and contact time.The results show that the adsorption of phenol increases with of the increasing p H value. The adsorption kinetics was found to follow the pseudo- second- order kinetic model and the equilibrium data fitted the Langmuir and Temkin equations better than Freundlich equation for both BDP modified bentonite(BDPBt) and BDHP modified bentonite(BDHP-Bt). The results also show that BDHP-Bt containing one hydroxyl in the Gemini surfactant molecule was more effective than BDP-Bt for the sorption of phenol from aqueous solutions. Thus, a new idea was put forward for the selection of high efficient modified agent, i.e., hydroxyl-containing Gemini surfactants. The negative values of ΔG° and ΔH° obtained from thermodynamic study of adsorption process indicated the spontaneous and exothermic nature for the two organ- bentonites.

A comparative study and evaluation of sulfamethoxazole adsorption onto organo-montmorillonites

Three organo-montmorillonites were prepared using surfactants, and their adsorption behaviors toward sulfamethoxazole (SMX) were investigated. The surfactants used were cetyltrimethyl ammonium bromide (CTMAB), 3-(N,N-dimethylhexadecylammonio) propane sulfonate (HDAPS) and 1,3-bis(hexadecyldimethylammonio)-propane dibromide (BHDAP). The properties of the organo-montmorillonites were characterized by X-ray diffraction, scanning electron microscopy and N2 adsorption–desorption isotherm measurements. Results showed that the interlayer spacing of montmorillonite was increased and the surface area as well as the morphology were changed. Batch adsorption experiments showed that the surfactant loading amount had a great effect on the adsorption of SMX. The adsorption process was pH dependent and the maximum adsorption capacity was obtained at pH3 for HDAPS-Mt, while CTMAB-Mt and BHDAP-Mt showed a high removal efficiency at 3–11. The adsorption capacity increased with the initial SMX concentration and contact time but decreased with increasing solution ionic strength. Kinetic data were best described by the pseudo second-order model. Equilibrium data were best represented by the Langmuir model, and the Freundlich constant (n) indicated a favorable adsorption process. The maximum adsorption capacity of SMX was 235.29mg/g for CTMAB-Mt, 155.28mg/g for HDAPS-Mt and 242.72mg/g for BHDAP-Mt. Thermodynamic parameters were calculated to evaluate the spontaneity and endothermic or exothermic nature. The adsorption mechanism was found to be dominated by electrostatic interaction, while hydrophobic interaction played a secondary role.

Self-assembly of cucurbit[8]uril-based polypseudorotaxanes using host–guest interactions

Two inclusion complexes formed on self-assembly of the Q[8] host with dihexyl-4,4′-bipyridinium (HV2+) dibromide and 1,3-bis(4-butylpiperazin-1-yl)-propane (C3PA2+) dibromide guests have been characterized by X-ray crystallography, which clearly shows how the hosts and the guests interlock with each other using supramolecular interactions, eventually generating novel polypseudorotaxanes.

Preparation and Thermal Stability of Oil-based Au Nanofluids

Two cationic surfactants,N-cetyl-N-(hydroxyethyl)-N,N-dimethyl ammonium bromide(CHDAB) and 1,4-bis(cetyldimethylammonium) propane dibromide(G16-4-16),were used as surface-modified reagents for preparation of hydrophobic gold nanoparticles from reduction of HAuCl4 with KBH4 in mixture of petroleum ether/n-butanol/H2O.The results show that gemini surfactant G16-4-16 is better for coating and dispersing,and the gold nanoparticles coated by the gemini surfactant G16-4-16 have a narrow size distribution with an average diameter of 5.2 nm.Stable nanofluids containing gold nanoparticles with hydrocarbon(toluene) as base liquids were prepared.The thermal stability of the nanofluids as a function of time was monitored using UV-Vis absorption method.It is shown that the gold nanofluid has good thermal stability,which has a stable time of 20 h at 130 ℃.The thermal conductivity of the gold nanofluids was performed by point heat source method.The enhancements of thermal conductivity of the gold nanofluids containing 1.5%(mass fraction) gold nanoparticles can reach 17%.

The removal of p-nitrophenol from aqueous solutions by adsorption using gemini surfactants modified montmorillonites

Montmorillonites modified by two gemini surfactants (1,3-bis(dodecyldimethylammonio)-propane dibromide (BDP) and 1,3-bis(dodecyldimethylammonio)-2-hydroxypropane dichloride (BDHP)) via ion exchange were used to remove p-nitrophenol (PNP) from aqueous solutions. The organo-montmorillonites were characterized by X-ray diffraction (XRD) and FT-IR spectroscopy. The effects of the concentration of modified agent, adsorbent mass, pH and contact time were investigated in detail. The results showed that as the concentration of modified agent increased, the adsorption amount increased accordingly and reached maximum adsorption when the concentration of modified agent approached and exceeded 1.0CEC. The removal percentages of PNP increased with the increasing of adsorbent mass at constant initial PNP concentration (100mg/L). The results revealed that the adsorption of PNP increases with an increase in pH. The adsorption kinetics was found to follow the pseudo-second-order kinetic model and the equilibrium data fitted the Langmuir, Redlich–Peterson and Temkin equations better than Freundlich equation for both BDP modified montmorillonite (BDP-Mt) and BDHP modified montmorillonite (BDHP-Mt). The results also showed that BDHP-Mt containing one hydroxyl in the gemini surfactant molecule was more effective than BDP-Mt for the sorption of PNP from aqueous solutions. Thus, a new idea was provided for the selection of high efficient modified agent, i.e., hydroxyl-containing gemini surfactants. The negative values of ΔG° and ΔH° obtained from thermodynamic study of adsorption process indicated the spontaneous and exothermic nature of the two processes.

Pharmacokinetic study of two acetylcholinesterase reactivators, trimedoxime and newly synthesized oxime K027, in rat plasma

K027 [1-(4-hydroxyiminomethylpyridinium)-3-(4-carbamoylpyridinium)-propane dibromide] is a promising new reactivator of organophosphate- or organophosphonate-inhibited acetylcholinesterase (AChE) with low acute toxicity and broad spectrum efficacy. The aim of the present study was to compare the pharmacokinetics of both compounds. Male Wistar rats (body weight = 320 ± 10 g) were administered a single intramuscular dose of K027 (22.07 mg kg(-1)) and an equimolar dose of trimedoxime. Blood was collected at various time intervals until 180 min. Plasma samples were analyzed by reversed-phase HPLC with ultraviolet (UV) detection. The recovery of both oximes from the plasma was approximately 90% and a linear relationship (R(2) > 0.998) was observed between the peak areas and concentrations of calibrated standards in the range 1-100 µg ml(-1). Near-identical plasma profiles were obtained for both compounds. No differences were found in the mean ± SD values of C(max) (18.6 ± 2.5 vs 20.0 ± 6.3 µg ml(-1), P = 0.72) and AUC(0-180min) (2290 ± 304 vs 2269 ± 197 min µg ml(-1), P = 0.84). However, the percentage coefficient of variation of the first-order rate constant of absorption (k(a)) was 3-fold higher (P < 0.01) providing evidence for more erratic absorption of intramuscular trimedoxime as compared with K027. In conclusion, oxime K027 might have superior pK properties that may be translated in its faster absorption and subsequent tissue distribution.

Kinetic and spectroscopic investigations of aqueous micelles of cationic surfactants

Abstract The aqueous micellar solutions of monocationic surfactants N-hexadecyl-N,N,N-trimethylammonium bromide (CTABr), N-hexadecyl-N,N,N-trimethylammonium nitrate (CTANO3), N,N,N-tributyl-N-hexadecylammonium bromide (CTBABr) and gemini surfactants 1,4-bis(N-hexadecyl-N,N-dimethylammonium)ethane dibromide (C-E-C2Br), 1,4-bis(N-hexadecyl-N,N-dimethylammonium)propane dibromide (C-P-C2Br), and 1,4-bis(N-hexadecyl-N,N-dimethylammonium)butane dibromide (C-B-C2Br) were studied with a solvatochromic probe, 2,6-diphenyl-4-(2,4,6-triphenylpyridinium-1-yl)phenolate, better known as Reichard’s ET-30 dye. The local polarity at the probe site (ET) was calculated from the wavelength maximum of the lowest-energy intramolecular charge-transfer ϖ-ϖ* absorption band of ET-30. The results were compared with a kinetic investigation of the cyclization of 2-(3-bromopropyloxy)phenoxide (PhBr7) in micelles; this reaction is a model for SN2 reactions and it depends on medium polarity.

The antidotal efficacy of the bispyridinium oximes K027 and TMB-4 against tabun poisoning in mice

A toxic effect of highly toxic nervous agents is irreversible inhibition of vitally important enzyme acethylcholinesterase (AChE). Inhibition of AChE results in accumulation of acetylcholine (ACh) at the synaptic cleft of the cholinergic neurons, leading to overstimulation of cholinergic receptors. The highly toxic nature of tabun has been known for many years, but there are still serious limitations to the antidotal therapy. In this paper a bispyridinium compound K027 [1-(4-hydroxyiminomethylpyridinium)-3-(-4-carbamoylpyridinium) propane dibromide] was tested as potential antidote in tabun poisoned mice. Oxime TMB-4 was included for comparison. The therapeutic efficacy of applied antidotal regimens was tested as pretreatment given 15 min before tabun poisoning and/or as therapy given 1 min after tabun poisoning. Using oxime K027 (25% of its LD 50) plus atropine as both, pretreatment and therapy, we showed that this combination can protect mice 8 times better than the therapy alone. Under these experimental conditions we confirmed good antidotal efficacy of K027. Moreover, its low acute toxicity is as much as beneficial effect in contrast to high toxicity of currently used TMB-4.

Novel Gemini Cationic Surfactants Based on N, N-Dimethyl Fatty Hydrazide and 1,3-Dibromopropane: Synthesis, Evaluation of Surface and Antimicrobial Properties

A fatty hydrazide based cationic gemini surfactants, 1,3-bis (N'-acyl-N,N-dimethylhydrazinium) propane dibromide which possess hydrolyzable amido moieties in the lipophilic portions, were prepared by reacting 1,3-bromopropane with N,N-dimethyl fatty hydrazide. The surface properties were explained and discussed based on the effect of their chemical structures. The micelle-forming ability, foaming ability, and foam stability were evaluated. The prepared surfactants also showed some antimicrobial activity against gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus) but they were not active against gram negative bacteria (Escherichia coli, P. aeruginosa), yeast (Candida albicans), and molds (Aspergillus niger).

Efficacy of two new asymmetric bispyridinium oximes (K-27 and K-48) in rats exposed to diisopropylfluorophosphate: comparison with pralidoxime, obidoxime, trimedoxime, methoxime, and HI-6

Introduction. The new K-oximes, K-27 [1-(4-hydroxyimino-methylpyridinium)-4-(4-carbamoylpyridinium) propane dibromide] and K-48 [1-(4-hydroxyimino-methylpyridinium)-4-(4-carbamoylpyridinium) butane dibromide], show good in vitro efficacy in protecting acetylcholinesterase from inhibition by different organophosphorus compounds (OPCs), including nerve agents. To assess their efficacy in vivo, the extent of oxime-conferred protection from mortality induced by diisopropylfluorophosphate (DFP) was quantified and compared with that of five established oximes. Materials and Methods. Rats received DFP intraperitoneally in a dosage of 6, 8, or 10 μmol/rat and immediately thereafter intraperitoneal injections of K-27, K-48, pralidoxime, obidoxime, trimedoxime, methoxime, or HI-6. The relative risk (RR) of death over time (48 h) was estimated by Cox survival analysis, comparing results with the no-treatment group. Results. Best protection was observed when K-27 was used, reducing the RR of death to 19% of control RR (p ≤ 0.005), whereas obidoxime (RR = 26%, p ≤ 0.01), K-48 (RR = 29%, p ≤ 0.005) and methoxime (RR = 26%, p ≤ 0.005) were comparable. The RR of death was reduced only to about 35% of control by HI-6, to 45% by trimedoxime, and to 59% by 2-PAM (p ≤ 0.005). Whereas the differences between the best oximes (K-27, obidoxime, methoxime, and K-48) were not statistically significant; these four oximes were significantly more effective than 2-PAM (p ≤ 0.05). The efficacy of K-27 was also significantly higher than that of HI-6, trimedoxime, and 2-PAM (p ≤ 0.05). Conclusion. Our data provide further evidence that K-27 is a very promising candidate for the treatment of intoxication with a broad spectrum of OPCs.

Direct electrochemistry of hemoglobin based on Gemini surfactant protected gold nanoparticles modified glassy carbon electrode

Gold nanoparticle stabilized by Gemini surfactant (GEM16-3-16-Au) was synthesized in aqueous solution of 1,3-bis(cetyldimethylammonium) propane dibromide (GEM16-3-16) by the reduction of HAuCl4 with UV irradiation and characterized by UV–vis absorption spectroscopy, X-ray diffraction (XRD), and transmission electron microscopy (TEM). The size of AuNPs is uniform and the average diameter is about 20 nm. The direct electrochemistry of hemoglobin (Hb) can be facilely achieved by incorporated into the GEM16-3-16-Au film on the glassy carbon electrode. A couple of quasi-reversible redox peaks of Hb were observed on the Hb/GEM16-3-16-Au/GC electrode at about −0.256 V and −0.206 V in phosphate buffer solution (pH 7.0). The results indicated that GEM16-3-16-Au film on GC electrode provided a favorable microenvironment both for immobilization of Hb and for electron transfer between Hb and electrode.

The Influence of Acetylcholinesterase Reactivators on Selected Hepatic Functions in Rats

The aim of our study was to evaluate the impact of acetylcholinesterase reactivators--K027 [1-(4-carbamoyl pyridinium)-3-(4-hydroxyiminomethyl pyridinium) propane dibromide], HI-6 [1-(4-carbamoylpyridinium)-3-(2-hydroxyimino methylpyridinium) oxapropane dichloride] and obidoxime [1,3-bis(4-hydroxyiminomethyl pyridinium)oxapropane dichloride] on hepatic functions in vivo. Male Wistar rats were randomly divided to seven groups and intramuscularly administered with saline and acetylcholinesterase reactivators (K027, HI-6 and obidoxime) at doses of 5% LD(50) and 50% LD(50). Liver tissue samples were taken 24 hr after administration. Histochemical detection of lipid droplets and immunohistochemical detection of multidrug resistance protein 2 (Mrp2) were provided. Lipid droplet count in rat liver did not show any significant differences in animals administered with K027, HI-6 and obidoxime in comparison with the control group. Mrp2 protein expression significantly decreased when animals were administered with K027 at a dose of 50% LD(50) and HI-6 and obidoxime at doses of 5% LD(50) and 50% LD(50), when compared to the controls. No statistical differences of Mrp2 expression were measured when animals were administered with K027 at a dose of 5% LD(50) in comparison with control animals. We found impaired hepatic transporter function after administration of HI-6, obidoxime and higher concentration of K027, which might be the underlying mechanism of acetylcholinesterase reactivators' hepatotoxicity.