Effect of a nitric oxide synthase inhibitor NG-nitro-L-arginine methyl ester on invasion of human colorectal cancer cell line SL-174T

AIM: To investigate the effect and mechanism of action of the nitric oxide synthase (NOS) inhibitor NG-nitro-L-arginine methyl ester (L-NAME) on invasion and metastasis of human colorectal cancer cell line SL-174T.METHODS: Human colorectal cancer cell line SL-174T was cultured and treated separately with four different dosages of L-NAME for 72 h. Nitric oxide (NO) production was measured with Griess reagent. The effect of L-NAME on invasion and migration of SL-174T cells were evaluated by using Transwell chambers attached with polycarbonate filters and reconstituted basement membrane (Matrigel).RT-PCR was performed to determine the mRNA levels of matrix metalloproteinase-2 (MMP-2) and tissue inhibitor metalloproteinase-2 (TIMP-2).RESULTS: L-NAME could significantly inhibit NO production of SL-174T in a dose-dependent manner. After being treated for 72 h with 0.2, 0.4, 0.8, and 1.0 mmol/L LNAME, respectively, the ability of the L-NAME treated SL174T cells to invade the reconstituted basement membrane decreased significantly (t = 8.056, P＜0.05;t= 14.467, P＜0.01;t= 27.785, P＜0.01;and t= 29.405,P＜0.01, respectively) and the inhibition rates were 10.29%,19.62%, 34.08%, and 42.23%, respectively. Moreover,L-NAME could inhibit migration of SL-174T cells, and the inhibition rates were 20.76%, 24.95%, 39.43%, and 46.85% for L-NAME at 0.2, 0.4, 0.8, and 1.0 mmol/L,respectively (t = 15.116, P＜0.01). In addition, after treatment with L-NAME, expression of MMP-2 mRNA was significantly decreased (t = 71.238, P＜0.01) and that of TIMP-2 mRNA was markedly increased (t = -13.020,P＜O.01).CONCLUSION: L-NAME exerts anti-invasive and antimetastatic effects on SL-174T cell line via downregulating MMP-2 mRNA expression and upregulating TIMP-2 mRNA expression.

Boosted Biodegradability and Tribological Properties of Mineral Base Oil by Methyl Diethanolamine Fatty Acid Esters

Methyl diethanolamine fatty acid esters, viz. methyl diethanolamine octanoate and methyl diethanolamine oleate,were prepared. Their impacts on the biodegradability and tribological properties of mineral base oil 400 SN were evaluated by a tester for fast evaluating the biodegradability of lubricants and by a four-ball tester, respectively. The results showed that methyl diethanolamine octanoate and methyl diethanolamine oleate both could markedly promote the biodegradation of the oil and improved its tribological properties. The improvement of biodegradability was attributed to the enhanced growth and quantity of microbes by methyl diethanolamine fatty acid esters. The worn surfaces were analyzed by a scanning electron microscope(SEM) equipped with an energy dispersive spectrometer(EDS) and an X-ray photoelectron spectroscope(XPS). The results indicated that the enhancement of friction-reducing and anti-wear properties of the mineral oil was attributed to the formation of complicated boundary lubrication films composed of species such as Fe_2O_3, Fe_3O_4 and organic nitrogen-containing compounds with a structure of –C-N-or R-NH_2.

Remarkably reducing carbon loss and H2 consumption on Ni–Ga intermetallic compounds in deoxygenation of methyl esters to hydrocarbons

Ni–Ga alloy(Ni/Ga atomic ratio of 8),Ni3Ga and Ni5Ga3 intermetallic compounds(IMCs)catalysts were prepared from Ni–Mg-Al-Ga layered double hydroxides(LDHs)for the deoxygenation of methyl esters to hydrocarbons.In the alloy and IMCs,the presence of Ga reduced the surface Ni atom density,and the charge transfer from Ga to Ni increased the electron density of Ni.In the deoxygenation of methyl laurate,the Ni catalyst gave a complete hydrogenolysis of methyl laurate to CH4at 330°C and 3.0 MPa,while the presence of Ga promoted the HDO pathway and suppressed C–C bond hydrogenolysis and methanation.The Ni5Ga3 catalyst exhibited the best desired performance.Even at 400°C,it gave the yield of C11 and C12 hydrocarbons of ~99%,and the selectivity to CH4(SCH4) was only 2.4%.In the deoxygenation of methyl octanoate and methyl palmitate,the Ni5Ga3 catalyst also gave the yield of hydrocarbons above95%.Reactivity evaluation and methyl propionate-TPD and TPSR results indicate that the C–OCH3 bond instead of the O–CH3 one was cleaved on both Ni and bimetallic Ni–Ga catalysts.It is highlighted that methanol,derived from the C–OCH3 bond hydrogenolysis,mainly decomposed to CO and H2 on IMCs,while it was converted to methane on metallic Ni and alloy.It is of great significance that H2 could be yielded from the methyl ester itself.In short,the utilization of Ni–Ga IMCs can effectively reduce carbon loss and H2 consumption,all of which are ascribed to the geometric and electronic effects of Ga.

Crystal Structure and Anticancer Properties of Cinobufagin 3-Hemisuberate Methyl Ester

The title compound cinobufagin 3-hemisuberate methyl ester（1） was isolated from the venom of Bufo bufo gargarizans CANTOR. The crystal structure of 1, C35H48O9, was determined by single-crystal X-ray diffraction analysis. It belongs to orthorhombic, space group P212121 with a = 8.9338（3）, b = 16.2970（4）, c = 22.4019（6） , V = 3261.59（16） 3, Mr = 612.73, Z = 4, Dc = 1.248 g/cm3, μ = 0.725 mm-1, F（000） = 1320, S = 1.040, the final R = 0.0374 and wR = 0.0412 for 4458 unique reflections, of which 4088 were observed（I 〉 2σ（I））. In the solid state, short intermolecular C-H...O interactions involving a methine and the ester carbonyl group in cinobufagin moiety and a methyl in the suberate moiety linked adjacent molecules into a three-dimensional network. Detailed analysis of the 1H-NMR data showed that X-ray structure of 1 would be expected to closely resemble the solution conformation in chloroform. Compound 1 was inactive for the inhibition of PC3 and HepG2 cancer cells, but the parent compound cinobufagin showed potent inhibition with IC50 values of 0.145 and 5.48 μM, respectively, indicating that esterification at C（3） decreased the cytotoxic effect of 1.

Interaction of L-Arginine-methyl ester and Sonic hedgehog in liver ischemia-reperfusion injury in the rats

AIM: To investigate the role of Sonic hedgehog (Shh) on the course of liver ischemia and reperfusion (I/R) in rats, and the interaction between treatment with nitric oxide donor L-Arginine-methyl ester (L-Arg) and up-regulation of Shh expression. METHODS: A total of 30 male Sprague-Dawley rats weighing 220-240 g were used in this study. Sham-control group (G1, n = 10): a sham operation was performed (except for liver I/R). I/R-untreated group (G2, n = 10): rats underwent liver ischemia for 1 h followed by reperfusion for 45 min. I/R-L-Arg group (G3, n = 10): after performing the same surgical procedure as in group 2, animals were treated with L-Arg. Liver tissues were taken for determination of malondialdehyde (MDA) levels, and biochemical and histological evaluations were made. RESULTS: Plasma alanine aminotransferase (ALT), aspartate aminotransferase (AST), lactate dehydrogenase (LDH) and γ-glutamyltranspeptidase (GGT) activities were higher in group 2 than in group 3. MDA values and the hepatic injury score decreased in the L-Arg treated group compared to the I/R-untreated group. In group 2, the hepatocytes were swollen with marked vacuolization. Group 3 rats showed well-preserved liver parenchyma, with hepatocytes extending from the central vein. The morphology of the hepatocytes and the sinusoidal structures was normal, without any signs of congestion. Mild Shh positive immunostaining was detected in group 2 animals. The expression of immunoreactive cells was increased markedly in liver tissue from I/R-L-Arg rats.CONCLUSION: Our findings suggest that Shh molecules are critical factors in the pathophysiology of inflammatory liver injury induced by I/R. In addition, NO plays an important role in the immunohistochemical expression of these molecules.

Synthesis and Crystal Structure of 4-(4,6-dimethoxyl -pyrimidin-2-yl)-3-thiourea Carboxylic Acid Methyl Ester

The title compound 4-（4,6-dimethoxylpyrimidin-2-yl）-3-thiourea carboxylic acid methyl ester was synthesized by the reaction of 2-amino-4,6-dimethoxyl pyrimidine, potassium thiocyanate and methyl chloroformate in ethyl acetate. Single crystals suitable for X-ray measurement were obtained by recrystallization with the solvent of dimethyl formamide at the room temperature. The structure was characterized by elemental analysis and IR and determined by X-ray diffraction analysis＇ Crystallographic data： C9H12N4O4S, Mr = 272.29, monoclinic, space group C2/m with a = 1.6672（3）, b = 0.66383（12）, c = 1.1617（2） nm, β = 109.275（2）°, V = 1.2136（4） nm^3, Dc = 1.490 g/cm^3,μ = 0.281 mm^-1, F（000） = 568, Z = 4, R1 = 0.0341and wR2 = 0.1042.

Epoxidation of Unsaturated Fatty Acid Methyl Esters in the Presence of SO_3H-functional Brφnsted Acidic Ionic Liquid as Catalyst

The epoxidation of unsaturated fatty acid methyl esters(FAMEs)by peroxyacetic acid generated in situ from hydrogen peroxide and acetic acid was studied in the presence of SO3H-functional Brnsted acidic ionic liquid (IL)[C3SO3HMIM][HSO4]as catalyst.The effects of hydrogen peroxide/ethylenic unsaturation ratio,acetic acid concentration,IL concentration,recycling of the IL catalyst,and temperature on the conversion to oxirane were studied.The kinetics and thermodynamics of unsaturated FAMEs epoxidation and the kinetics of oxirane cleavage of the epoxidized FAMEs by acetic acid were also studied.The conversion of ethylenic unsaturation group to oxirane, the reaction rate of the conversion to oxirane,and the rate of hydrolysis(oxirane cleavage)were higher by using the IL catalyst.

Effects of Yttrium Doping on the Performance of Ru-Based Catalysts for Hydrogenation of Fatty Acid Methyl Ester

The highly dispersed supported ruthenium-yttrium (Ru-Y) bimetallic catalysts were prepared by impregnation method and their catalytic performance for hydrogenation of ester was fully investigated. The catalyst was characterized by X-ray diffraction and field emission scanning electron microscopy. The results show that the average particle diameter of the bimetallic crystallites was less than 10 nm. The effects of the reaction temperature, the hydrogen pressure, the amount of catalyst and the proportion of yttrium in catalyst on the hydrogenation of ester were studied. The experimental results show that the introduction of yttrium not only changed the chemical and textural properties of ruthenium-based catalyst but also controlled the formation of Ru-Y alloy. The Ru-Y catalyst (Ru-2%Y/TiO2) exhibited high catalytic activity and good selectivity towards the higher alcohols. Under optimal reaction conditions of 240°C and 5 MPa hydrogen pressure, the conversion of palm oil esters was above 93.4% while the selectivity towards alcohol was above 99.0%.

Chiral Separation of N-Benzoyl Phenylalanine Methyl Ester by Nonaqueous Capillary Electrophoresis

A successful chiral separation of N-benzoyl phenylalanine methyl ester has been achieved by nonaqueous capillary electrophoresis (NACE) using P-CD as chiral selector in formamide (FA). Some experimental parameters influencing the chiral separation such as concentration of P-CD, ionic strength and apparent pH (pH*) are discussed.

Electrospray Ionization Mass Spectra of Amino Acid Methyl Ester 5′-Phosphoramidates of 2′,3′-Isopropylideneuridine

Amino acid methyl ester phosphates were synthesized and determined by using positive-ion mode dectrospmy ionization mass spectrometry（ESIMS） in combination with multistage tandem mass spectrometry. The fragmentation pathways were investigated, and it was observed that most fragment ions contained the phosphoryl group. It was interesting to observe that the fragmentation pathways of the protonated molecule show some differences when compared with those of the sodium ion adduct. The methoxy group of amino acid methyl ester can migrate from the carbonyl group to the phosphoryl group in the sodium ion adduct.

Methyl Ester Type Produced by Catalytic Transesterification:From Various Oil Feedstock to Biodiesel Products

Biodiesel research has been carried out via transesterification.However,biodiesel products(methyl esters)have not encountered new insights,because feedstocks have been explored and studied.Various optimum conditions on transesterification reaction could produce different methyl ester type with different compound.So,this review describes various oil feedstock that were to find new insights about methyl ester type.The review took the results of study that has been published with experience for 10 years.The results of the study reviewed on the transesterification method,characterization of methyl esters,and its components.The component reviewed and correlated to the literature,structure,and GC-MS analysis.The review can provide challenges for methyl ester research in future research.

Comparative Evaluation of the Thermal Aging of Solid Insulation in Mineral Oil and Methyl Ester of Palm Kernel Oil

The purpose of this work is to determine the impact of thermal aging on the dielectric and physicochemical properties of the oil/paper mixed insulation. We performed a comparative analysis of dielectric paper dipped in two cooling fluids: palm kernel oil methyl ester (MEPKO) and mineral oil (MO). Two types of dielectric paper were used: Thermally Upgraded Kraft paper (TUK) and Nomex-910 paper (NP-910). An accelerated aging test was realized at 110°C during a total of 96 hours. Samples of oil and paper were collected after 0, 48, 72 and 96 hours for analyses purposes. The analyses performed included the measurement of the Breakdown voltage (BDV) of the dielectric papers, the Total Acid Number (TAN) and the Decay Dissolved Products (DDP) of the liquid dielectrics. The BDV of NP-910 is greater than the BDV of TUK. Concerning the type of oil, the BDV of dielectric papers impregnated with MEPKO is greater than the BDV of similar papers impregnated with MO, indicating a better preservation of paper when dipped in methyl esters. The analyses of TAN and DDP revealed that Nomex-910 improves the oxidation stability of MO, but reduces the oxidation stability of MEPKO. These results prove that methyl esters can be used as a substitute to replace mineral oils in power transformers. Furthermore, they show that NP can be used mainly in areas of transformer where solid insulation is subjected to high thermal and electrical stress, and TUK other places where solid insulation is required. Such combination could assure money savings and a better preservation of the oil viscosity.

Kinetic Resolution of DL-Phenylalanine Methyl Ester by α-Chymotrypsin Immobilized on Porous Silica Beads

Kinetic resolution of DL-phenylalanine methyl ester was carried out using drimobilized α -chymotrypsin (IC) as catalyst. The effects of temperatUre, pH, concentration of substrate and reactionvessels on the resolution were investigated. High quality L-phenylalanine was obtained in good yieldby an IC column.

Study on the Total Synthesis of 3-Oxo-9β-Acetoxyilicic Acid─The Synthesis of 9β-Acetoxy-3(4),11(13)-Dien-5αH,7αH-12-Eudesmanoic Acid Methyl Ester

The synthesis of 99-acetoxy-3(4), 11(13)-dien-5αH 7αH-12-eudesmanoic acid methyl ester (2) was achieved from oxycarvone. The key step is the p-toluenesulfonhydrazide assisted reductiv rearrangement reaction

Optimization of Injection Timing and Injection Duration of a Diesel Engine Running on Pure Biodiesel SME (Soya Methyl Ester)

This study was carried out to predict the impact of injection timing and injection duration on engine brake power and Nitrogen Oxides emissions in a diesel engine using biofuel Soya Methyl Ester (SME). Predictions were accomplished at three different injection timings 10°, 5° Crank Angle (CA) before Top Dead Center (bTDC) and 0° CA at Top Dead Center (TDC) and four injection durations 20°, 25°, 30°, 35° CA. The study was conducted using a simulation software (Diesel-RK). The predicted results showed that the powers produced by all the setups of the different injection timings are almost equal, but they differ in injection durations, e.g. the power at setup (10° CA-bTDC) duration 20° CA and 2500 rpm equal to 52 kW, at setup (5° CA-bTDC) duration 25° CA and same engine speed the power is equal to 51 kW, and at setup (0° CA-TDC) durations 30° the power is equal to 51 kW. The power in all setups are decreased as the injection duration increased, e.g. at setup 0° CA TDC durations 25°, 35°, and 40° CA and at 4000 rpm, the brake powers are equal 71, 65, and 59 kW respectively, thus the reduction percentages are 9% and 17% when compared to the 25° injection duration. The nitrogen oxides emissions decreased as the injection duration is increased, e.g. the emissions at setup (10° CA-bTDC) durations 25°, 30°, and 40° CA and at 2500 rpm are equal 852, 589, 293 ppm respectively, the reduction percentages are 30% and 72%. The variations of injection timing and injection duration have taken a weighty influence on engine performance and emissions. The results are considered as a novelty in the field of using pure biofuel Soya Methyl Ester in diesel engine according to our information.

Evaluation of methyl ester sulphonate spacer fluid additive for efficient wellbore clean-up

Oil-based drilling fluid(OBDF)is used to drill through high permeable pay zone to prevent possible damage to the formation.However,the oil based drilling fluid leaves behind filter cake residue and oilwet surfaces which hinder cement bonding.Spacer fluid is usually introduced to clean up the wellbore prior to cementing job.This work presents a spacer fluid designed with environment-friendly anionic methyl ester sulphonate(MES)surfactant and evaluated through a series of experimental tests to ascertain its effectiveness to clean wellbore.Addition of methyl ester sulphonate to confected waterbased drilling fluid at high amount(0.15 g and 0.20 g)showed good rheological properties,compatibility with OBDF and cement and low contact angle on steel and sandstone in the range of 21.9°-34.7°.Furthermore,results show that it requires less amount of MES spacer fluid to revert oil-wet OBDF aqueous phase to water external continuous phase,validating the low contact angle measurements.Cleaning efficiencies for two best performing MES spacer fluids achieved 83.27%and 94.3%respectively.Shear bond strength were measured to be 1.3 MPa and 1.05 MPa for steel and sandstone respectively,above the minimum allowable shear bond strength for oil well cementing.Hence,MES spacer fluid can be used to clean up wellbores in high permeable formations and in well completion,where strong cement bonding is required.

Levodopa methyl ester increases nerve growth factor expression in visual cortex area 17 in a feline model of strabismic amblyopia

In the present study, a feline model of strabismic amblyopia was established during a sensitive developmental period, and the influence of levodopa methyl ester and levodopa on nerve growth factor expression in the visual cortex (area 17) was compared. Pattern visual-evoked potential and immunohistochemistry results showed that levodopa methyl ester and levodopa treatment shortened P100 wave latency, increased P100 amplitude, and increased the number of endogenous nerve growth factor-positive cells in visual cortex levels. In particular, the effects of levodopa methyl ester were superior to levodopa treatment.

Ternary Liquid-Liquid Equilibrium for Systems of Fatty Acid Methyl Ester(Methyl Palmitate/Methyl Stearate)+Ethanol+Glycerol at Atmospheric Pressure

Liquid-liquid equilibrium data of two ternary systems methyl palmitate+ethanol+glycerol and methyl stearate+ethanol+glycerol at(318.2 and 333.2)K and atmospheric pressure were measured. The values of distribution coefficient and selectivity were calculated, which indicates that glycerol can be separated from fatty acid ester by using ethanol as an extraction solvent. The consistency of the isothermal tie-line data were checked by the Othmer-Tobias equation. The correlation coefficients R2 are higher than 0.993,9 for all the fitted curves. The NRTL activity coefficient model was applied to the correlation of the measured tie-line data. The root mean square deviation(RMSD)values are less than 0.007 for all the systems, which shows a good predictive capability of this model for such systems.