• Biomolecules & Therapeutics
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• v.27 no.5
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• pp.492-501
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• 2019

Nitrogen-containing heterocycles such as quinoline, quinazolinones and indole are scaffolds of natural products and have broad biological effects. During the last years those structures have been intensively synthesized and modified to yield new synthetic molecules that can specifically inhibit the activity of dysregulated protein kinases in cancer cells. Herein, a series of newly synthesized isoquinolinamine (FX-1 to 8) and isoindoloquinazolinone (FX-9, FX-42, FX-43) compounds were evaluated in regards to their anti-leukemic potential on human B- and T- acute lymphoblastic leukemia (ALL) cells. Several biological effects were observed. B-ALL cells (SEM, RS4;11) were more sensitive against isoquinolinamine compounds than T-ALL cells (Jurkat, CEM). In SEM cells, metabolic activity decreased with $10{\mu}M$ up to 26.7% (FX-3), 25.2% (FX-7) and 14.5% (FX-8). The 3-(p-Tolyl) isoquinolin-1-amine FX-9 was the most effective agent against B- and T-ALL cells with IC50 values ranging from 0.54 to $1.94{\mu}M$. None of the tested compounds displayed hemolysis on erythrocytes or cytotoxicity against healthy leukocytes. Anti-proliferative effect of FX-9 was associated with changes in cell morphology and apoptosis induction. Further, influence of FX-9 on PI3K/AKT, MAPK and JAK/STAT signaling was detected but was heterogeneous. Functional inhibition testing of 58 kinases revealed no specific inhibitory activity among cancer-related kinases. In conclusion, FX-9 displays significant antileukemic activity in B- and T-ALL cells and should be further evaluated in regards to the mechanisms of action. Further compounds of the current series might serve as templates for the design of new compounds and as basic structures for modification approaches.

• Applied Chemistry for Engineering
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• v.33 no.5
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• pp.477-481
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• 2022

As a part of improving the quality of crude methylnaphthalene (CMNO), this study was experimentally examined the reduction of nitrogen-containing compounds (NC) present in the CMNO by solvent extraction. The CMNO was composed of three kinds of NC [quinolone (QU), iso-quinoline (IQU), indole (IN)], three kinds of bicyclic aromatic compound [BAC; naphthalene (NA), 1-methylnaphthalene (1MNA), 2-methylnaphthalene (2MNA)] and biphenyl (BP) etc., in addition to an aqueous formamide solution, which were used as raw materials and a solvent, respectively. The increase in the volume fraction of water to the solvent in the initial state (y_w,0) caused a sharp decrease in the distribution coefficient and the yield of NC, but conversely raised the increased selectivity of NC based on 2MNA. The compositions of QU, IQU and IN in the raffinate oil recovered through the equilibrium extraction of batch co-current 5-stage under constant conditions [y_w,0 = 0.1, volume fraction of solvent to feed (CMNO) at the initial state = 1, operating temperature = 303 K, liquid-liquid contacting time = 72 h] were reduced by about 51.5%, 55.2%, and 71.8%, respectively, when compared to those of CMNO. From the excellent reduction rate of NC, the formamide extraction method suggested in this study can be expected to be a useful reduction method for NC contained in the CMNO.

• Applied Chemistry for Engineering
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• v.33 no.4
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• pp.431-435
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• 2022

The reduction of nitrogen-containing compounds (NC) containing the model crude methylnaphthalene oil (CMNO) of 5 compounds system was experimentally studied by solvent extraction. The model CMNO consisting of 3 kinds of NC including quinolone (QU), iso-quinoline (IQU), indole(IN) and 2 kinds of bicyclic aromatic compounds such as 1-methylnaphthalene (1MNA), 2-methylnaphthalene (2MNA) as raw materials, as well as the aqueous solution of formamide as a solvent, were used. The increase in the volume fraction of water to the solvent at the initial state (y_w,0) sharply decreased, but the distribution coefficient and the yield of NC conversely increased the selectivity of NC based on 2MNA, and an increase in the volume fraction of solvent to feed (S/F) simultaneously increased the distribution coefficient, yield and selectivity of NC. The yields of QU, IQU and IN under constant conditions (y_w,0 = 0.1, S/F = 1, equilibrium temperature 303 K) were 30%, 31% and 10%, respectively, and selectivity was 15, 15 and 20, respectively. From the excellent yield and selectivity of NC, the formamide extraction method of this study was expected as a method for reducing the NC contained in the model CMNO.

• Applied Chemistry for Engineering
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• v.34 no.6
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• pp.665-669
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• 2023

The crude methylnaphthalene oil (CMNO) contains nitrogen compounds (NCs) such as quinoline (QU), isoquinoline (IQU), and indole (IN). These NCs in the CMNO are treated as impurities contained in the CMNO due to contamination of the atmospheric environment and unpleasant odors. In order to improve the quality of CMNO, this study examined the effect of extraction experimental factors on the reduction of NCs contained in CMNO using CMNO as a raw material and an aqueous formamide solution as a solvent, respectively. The increase in the volume ratio of solvent to feed in initial (S/F)₀ in initial increased the distribution coefficient of NCs and the selectivity of NCs in reference to 2-methylnaphthalene (2MNA). Additionally, an increase in operating temperature (T) increased the distribution coefficient of NCs but conversely decreased selectivity. The compositions of QU, IQU, and IN in the raffinate oil recovered through equilibrium extraction under a constant condition (volume fraction of water to solvent in initial (y_w,0) = 0.1, (S/F)₀ = 9, T = 303 K, liquid-liquid contacting time = 72 h) were reduced by about 58.5 wt%, 61.9 wt%, and 73.4 wt%, respectively, compared to those of CMNO. The formamide extraction method in this study was expected to be an effective reduction method for NCs contained in CMNO.

• Korean Journal of Weed Science
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• v.15 no.1
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• pp.54-62
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• 1995

Acetolactate synthase activity inhibition and herbicidal activities were investigated with 2 sulfonylureas [chlorsulfuron{2-chloro-N-{{(4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino} carboxyl} benzenesulfonamide}, metsulfuron-methyl{methyl-2{{{{(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino}carbonyl}amino}sulfonyl}benzoic acid}, and 2 imidazoli-nones [imazethapyr{2-{4,5-dihydro-4-methyl-4-(1-methyl)-5-oxo-1H-imidazol-2-yl}-5-ethyl-3-pyridinecarboxylicacid}, imazaquin{2-{4,5-dihydro-4-methyl-4-(1-methyl)-5-oxo-1H-imidazol-2-yl}-3-quinoline carboxylic acid} herbicides. A broad weeding spectrum was observed with the treated herbicides at low application rates. Both corn(Zea mays L.) and sorghum(Sorghum bicolor Moench) were very sensitive to the two herbicide groups. Although legumes, such as soybean(Glycine max Merr.), clover(Trifolium repense L.), and indian jointvetch(Aeschnomene indica L.) were sensitive to the sulfonylureas, they were tolerant to the imidazolinones. On the contrary, wheat(Triticum aestivum L.) and barley(Hoderum sativum Jess.) showed the reverse responses of the legumes to the two herbicide groups. Quackgrass(Agropyron repens(L.) P. Beauv.). however, was commonly tolerant to the two herbicide groups. Degrees of crop injury and acetolactate synthase inhibition also varied with the crops examined. The 50% inhibition concentrations of sulfonylureas on acetolactate synthase in vitro activity($IC_{50}$) from corn, wheat, and soybean did not relate to the greenhouse herbicidal activities ($GI_{50}$). With chlorsulfuron, for example, wheat had more than 100 times higher $GI_{50}$ than corn and soybean, but the $IC_{50}$ was 4 to 10 times lower. Similar observation was made with metsulfuron-methyl. However, closer relationships between $IC_{50}$ and $GI_{50}$ were found with the imidazolinones. When imazethapyr was applied, the order of $GI_{50}$ values against com, wheat, and soybean was the same as that of $IC_{50}$.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.53 no.1
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• pp.75-84
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• 2008

Colored potatoes are an excellent source of dietary polyphenols including anthocyanins. Generally, anthocyanins from fruits and vegetables exhibit anti-carcinogenesis and anti-cancer properties in vitro test. This experiment was conducted to know the effects of colored potato extracts contained anthocyanins on antimutagenic activity and anticancer activity to six human cancer cell lines containing LNCaP (androgen-dependent) prostate cancer cells. Extracts of three colored potatoes ('Hongyoung', 'Jayoung' and 'Jasim') and the white potato ('Superior') cultivars were used in this study. The extracts of three colored potatoes inhibited the mutagenicities induced by direct mutagen such as 4-nitro-quinoline-1-oxide (4-NQO) and another indirect mutagens of bezo(a)pyrene (BaP). Also, the extracts of 'Hoyoung' and 'Jayoung' showed higher antimutagenic activity than 'Jasim' and 'Superior' against to direct or indirect mutagen on both strains of TA98 and TA100. The activity of growth-inhibitory of extract of four potato cultivars were screened by SRB (sulphorhodamine B) method on diverse human cancer cells representing different types of cancers. Among the extract of four potato cultivars, the extract of 'Jasim' showed moderate inhibition on proliferation of LNCaP, ACHN and MOLT-4F cells and did not inhibit the proliferation of other cancer cells. On the other hand, extract of 'Superior' did not inhibit the proliferation of any tested cancer cell lines. However, the extracts of 'Hongyoung and Jayoung' inhibited the proliferation of cancer cells with $GI_{50}$ values ranging from 2.5 to $30\;{\mu}g/mL$. On the basis of the $GI_{50}$ values, it is clear that LNCaP cells were more sensitive to extracts of colored potato cultivars than other cancer cells. The extract of 'Jayoung' at $30\;{\mu}g/mL$ were more active and inhibited cell proliferation, and induced apoptosis in LNCaP cells. This result revealed that the extracts of colored potatoes are expected to be good candidate for development into source of antimutagenic and anticancer agent.

• Horticultural Science & Technology
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• v.28 no.5
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• pp.790-795
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• 2010

This experiment was conducted to clarify the effects of cycloheximide and holding solution on vase life of cut 'Blue Magic' iris. The vase life of iris flowers held in 3% sucrose (S) + $100mg{\cdot}L^{-1}$ hydroxy quinoline sulfate (HQS) + $50mg{\cdot}L^{-1}$ $AgNO_3$ + $100mg{\cdot}L^{-1}$ Benzylaminopurine (BA), 3% S + $100mg{\cdot}L^{-1}$ HQS + $10{\mu}M$ cycloheximide (CHI), or 3% S + $100mg{\cdot}L^{-1}$ HQS + $50{\mu}M$ CHI were much longer than those held in distilled water. Squeeze stem phenomenon that showed at a holding solution containing $200mg{\cdot}L^{-1}$ HQS disappeared at a holding solution containing $100mg{\cdot}L^{-1}$ HQS. The holding solution containing 3% S + $100mg{\cdot}L^{-1}$ HQS + $50mg{\cdot}L^{-1}$ $AgNO_3$ + $100mg{\cdot}L^{-1}$ BA extended the most effective treatments on vase life, fresh weight, water balance, and flowering of cut iris flowers. However, the holding solution containing 3% S + $100mg{\cdot}L^{-1}$ HQS + $10{\mu}M$ CHI and 3% S + $100mg{\cdot}L^{-1}$ HQS + $50{\mu}M$ CHI was not effective in solution uptake or transpiration, but did result in high water balance. Iris flowers treated with CHI at the half-open flower stage showed increases in ornamental value, such as full flower opening and extended vase life. To improve flower quality and prolonging vase life of cut iris flowers, a holding solution containing $50{\mu}M$ CHI can be used continuously from the half-open stage.

• Journal of Food Hygiene and Safety
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• v.34 no.2
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• pp.140-147
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• 2019

An analytical method was developed for the determination of quinoxyfen in agricultural products using the QuEChERS (Quick, Easy, Cheap, Effective, Rugged and Safe) method by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The samples were extracted with 1% acetic acid in acetonitrile and water was removed by liquid-liquid partitioning with $MgSO_4$ (anhydrous magnesium sulfate) and sodium acetate. Dispersive solid-phase extraction (d-SPE) cleanup was carried out using $MgSO_4$, PSA (primary secondary amine), $C_{18}$ (octadecyl) and GCB (graphitized carbon black). The analytes were quantified and confirmed by using LC-MS/MS in positive mode with MRM (multiple reaction monitoring). The matrix-matched calibration curves were constructed using six levels ($0.001-0.25{\mu}g/mL$) and the coefficient of determination ($R^2$) was above 0.99. Recovery results at three concentrations (LOQ, 10 LOQ, and 50 LOQ, n=5) were in the range of 73.5-86.7% with RSDs (relative standard deviations) of less than 8.9%. For inter-laboratory validation, the average recovery was 77.2-95.4% and the CV (coefficient of variation) was below 14.5%. All results were consistent with the criteria ranges requested in the Codex guidelines (CAC/GL 40-1993, 2003) and Food Safety Evaluation Department guidelines (2016). The proposed analytical method was accurate, effective and sensitive for quinoxyfen determination in agricultural commodities. This study could be useful for the safe management of quinoxyfen residues in agricultural products.