• Title/Summary/Keyword: ${\beta}$-Naphthol

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Enhancement of radiation effect using beta-lapachone and underlying mechanism

  • Ahn, Ki Jung;Lee, Hyung Sik;Bai, Se Kyung;Song, Chang Won
    • Radiation Oncology Journal
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    • v.31 no.2
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    • pp.57-65
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    • 2013
  • Beta-lapachone (${\beta}$-Lap; 3,4-dihydro-2, 2-dimethyl-2H-naphthol[1, 2-b]pyran-5,6-dione) is a novel anti-cancer drug under phase I/II clinical trials. ${\beta}$-Lap has been demonstrated to cause apoptotic and necrotic death in a variety of human cancer cells in vitro and in vivo. The mechanisms underlying the ${\beta}$-Lap toxicity against cancer cells has been controversial. The most recent view is that ${\beta}$-Lap, which is a quinone compound, undergoes two-electron reduction to hydroquinone form utilizing NAD(P)H or NADH as electron source. This two-electron reduction of ${\beta}$-Lap is mediated by NAD(P)H:quinone oxidoreductase (NQO1), which is known to mediate the reduction of many quinone compounds. The hydroquinone forms of ${\beta}$-Lap then spontaneously oxidizes back to the original oxidized ${\beta}$-Lap, creating futile cycling between the oxidized and reduced forms of ${\beta}$-Lap. It is proposed that the futile recycling between oxidized and reduced forms of ${\beta}$-Lap leads to two distinct cell death pathways. First one is that the two-electron reduced ${\beta}$-Lap is converted first to one-electron reduced ${\beta}$-Lap, i.e., semiquinone ${\beta}$-Lap $(SQ)^{{\cdot}-}$ causing production of reactive oxygen species (ROS), which then causes apoptotic cell death. The second mechanism is that severe depletion of NAD(P)H and NADH as a result of futile cycling between the quinone and hydroquinone forms of ${\beta}$-Lap causes severe disturbance in cellular metabolism leading to apoptosis and necrosis. The relative importance of the aforementioned two mechanisms, i.e., generation of ROS or depletion of NAD(P)H/NADH, may vary depending on cell type and environment. Importantly, the NQO1 level in cancer cells has been found to be higher than that in normal cells indicating that ${\beta}$-Lap may be preferentially toxic to cancer cells relative to non-cancer cells. The cellular level of NQO1 has been found to be significantly increased by divergent physical and chemical stresses including ionizing radiation. Recent reports clearly demonstrated that ${\beta}$-Lap and ionizing radiation kill cancer cells in a synergistic manner. Indications are that irradiation of cancer cells causes long-lasting elevation of NQO1, thereby sensitizing the cells to ${\beta}$-Lap. In addition, ${\beta}$-Lap has been shown to inhibit the repair of sublethal radiation damage. Treating experimental tumors growing in the legs of mice with irradiation and intraperitoneal injection of ${\beta}$-Lap suppressed the growth of the tumors in a manner more than additive. Collectively, ${\beta}$-Lap is a potentially useful anti-cancer drug, particularly in combination with radiotherapy.

Development of Susceptible Functional Fibers using the Microcapsule of Susceptible Materials(II) ―Photochromic functional fibers― (감성물질의 마이크로캡슐화에 의한 감성기능 섬유의 개발(II) -감광변색 기능섬유-)

  • Kim, Moon Sik;Park, Sun Ju;Lee, Shin Hee;Park, Soo Min
    • Textile Coloration and Finishing
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    • v.8 no.1
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    • pp.73-82
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    • 1996
  • The photochromic dye(spiroxazine, Blue) as a susceptible material was synthesized by condensing 1-nitroso-$\beta$-naphthol with indoline. The melting point of the synthesized spiroxazine dye was 254$^{\circ}C$. Irradiation with ultraviolet light had effect on reversible coloration reaction. The photochromic dye microcapsules were produced by in situ polymerization using urea-formaldehyde prepolymer. The average diameter of the microcapsule was 2.94$\mu$m. The dyeability and washing fastness of the photochromic microcapsule fibers were increased by the pretreatment of cationic agent.

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Synthesis of Super Hydrophobic Orange Dyes Having Maximum Absorption at 450-500nm for Pure Polyolefin Fibers (450-500nm의 최대흡수를 가지는 순수 폴리올레핀 소재용 초소수성 오렌지 염료의 합성)

  • Kim, Taekyeong;Ryu, Myeonghwa
    • Textile Coloration and Finishing
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    • v.26 no.3
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    • pp.165-172
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    • 2014
  • Novel super hydrophobic orange dyes having maximum absorption band at 450-500nm were synthesized to dye polyolefin fibers such as polypropylene and ultra high molecular weight polyethylene fibers, using 4-alkylanilines and ${\beta}$-naphthol. Their absorption spectra at visible range showed almost the same, which meant that the alkyl substituents introduced to chromophore did not affect on color appearance of the dyes. Considering both color strength and wash fastness, the decyl-substituted dye was determined as the optimum one practically. From the dyeing results at various conditions, the optimum dyeing was $130^{\circ}C$ for 1 hour with 5% owf of dyes. The good fastness ratings to washing, rubbing were obtained showing 4-5 for both fibers. Light fastness was also acceptable giving rating 3-4 for polypropylene fibers and rating 3 for ultra high molecular weight polyethylene fibers.

Brønsted Acidic Ionic Liquids as Efficient Catalysts for Clean Synthesis of Carbamatoalkyl Naphthols

  • Tavakoli-Hoseini, Niloofar;Heravi, Majid M.;Bamoharram, Fatemeh F.;Davoodnia, Abolghasem
    • Bulletin of the Korean Chemical Society
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    • v.32 no.3
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    • pp.787-792
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    • 2011
  • Under mild conditions and without any additional organic solvent, synthesis of carbamatoalkyl naphthols could be carried out in the present of two halogen-free Br${\phi}$nsted acidic ionic liquids, 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate and N-(4-sulfonic acid)butylpyridinium hydrogen sulfate. A wide range of aromatic aldehydes easily undergo condensation with $\beta$-naphthol and methyl or benzyl carbamate to afford the desired products of good purity in excellent yields. The present methodology offers several advantages such as a simple procedure with an easy work-up, short reaction times, and excellent yields. The catalysts could be recycled and reused for several times without substantial reduction in their catalytic activities.

A DABCO Derived Ionic Liquid Based on Tetrafluoroborate Anion: Preparation, Characterization and Evaluation of its Catalytic Activity in the Synthesis of 14-Aryl-14H-dibenzo[a, j]xanthenes

  • Atefeh, Zare-Bidaki;Davoodnia, Abolghasem
    • Bulletin of the Korean Chemical Society
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    • v.33 no.4
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    • pp.1154-1158
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    • 2012
  • A room-temperature ionic liquid (RTIL) derived from 1,4-diazabicyclo[2.2.2]octane (DABCO) consisting of tetrafluoroborate anion, 1-butyl-4-(4-sulfonylbutyl)-1,4-diazoniabicyclo[2.2.2]octane hydrogen sulfate tetrafluoroborate ($[C_4DABCOC_4SO_3H][BF_4][HSO_4]$) was synthesized and catalytically evaluated in the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes by cyclocondensation reaction of ${\beta}$-naphthol and aryl aldehydes. This novel RTIL with an acidic $SO_3H$ group showed high catalytic activity with good to excellent yields of the desired products in short reaction times. Moreover, the catalyst could be recovered and reused at least three times with only slight reduction in its catalytic activity.

Development of Susceptible Functional Fibers using Microcapsule of Susceptible Materials(I) ―Photochromic functional fibers― (감성물질의 마이크로캡슐화에 의한 감성기능 섬유이 개발(I) ―감광변색 기능섬유―)

  • Kim, Moon Sik;Park, Sun Ju;Park, Soo Min
    • Textile Coloration and Finishing
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    • v.7 no.4
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    • pp.97-104
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    • 1995
  • The photochromic dyes(spiroxazine) as a susceptible material were synthesized by condensing 1-nitroso-$\beta$-naphthol with piperidine. The melting point of the synthesized spiroxazine dye was 245$^{\circ}C$. Irradiation with ultraviolet light had effect on reversible coloration reaction. The photochromic dye microcapsules were produced by interfacial precipitation method using polyvinylalcohol and ethylcellulose. The average diameter of microcapsules was 5.4$\mu$m. The dyeability and fastness of dyeings of the microcapsule fibers were increased by pretreatment of the cationic agent.

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A comparison of the hydrolase activities of excretory-secretory products and somatic extracts from fish parasitic nematodes, Anisakis simplex sensu stricto and Anisakis pegreffii larvae (어류 기생성 선충 Anisakis simplex sensu stricto와 Anisakis pegreffii 유충의 excretory-secretory products 및 somatic extracts의 가수분해효소 활성 비교)

  • Jeon, Chan-Hyeok;Wi, Seong;Kim, Jeong-Ho
    • Journal of fish pathology
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    • v.27 no.1
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    • pp.25-33
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    • 2014
  • Hydrolase activities of excretory-secretory products (ESP) and somatic extracts (SE) from Anisakis simplex sensu stricto (s.s.) and Anisakis pegreffii larvae were investigated by using API ZYM kit. In esterase group, acid phosphatase showed high activity from both of A. simplex (s.s.) and A. pegreffii. Esterase (C4) showed activity only from SE and A. simplex (s.s.) showed higher activity than A. pegreffii. Alkaline phosphatase, acid phosphatase and naphthol-AS-BI-phosphohydrolase showed higher activity in 3rd stage larvae than in 4th stage larvae of both species. In aminopeptidase group, only leucine arylamidase showed remarkable activity in SE of both anisakid species, and A. simplex (s.s.) SE showed higher activity than A. pegreffii SE. In glycosidase group, N-acetyl-${\beta}$-glucosaminidase, ${\alpha}$-mannosidase, ${\alpha}$-fucosidase showed higher activity in A. simplex (s.s.) than A. pegreffii, and 4th larvae showed higher activity than 3rd larvae. These differences in hydrolase activity of anisakid nematodes larvae are thought to be due to different metabolism such as growth, moulting, digestion and feeding.

Screening of Lactobacilli Derived from Chicken Feces and Partial Characterization of Lactobacillus acidophilus A12 as Animal Probiotics

  • Lee, Na-Kyoung;Yun, Cheol-Won;Kim, Seung-Wook;Chang, Hyo-Ihl;Kang, Chang-Won;Paik, Hyun-Dong
    • Journal of Microbiology and Biotechnology
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    • v.18 no.2
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    • pp.338-342
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    • 2008
  • This study was performed to screen and select Lactobacillus strains from chicken feces for probiotic use in animals. Of these strains, strain AU had the highest immunostimulatory effect. Therefore, strain A12 was characterized as a potential probiotic. Strain A12 was tentatively identified as Lactobacillus acidophilus A12, using the API 50 CHL kit based on a 99.9% homology. L. acidophilus A12 was highly resistant to artificial gastric juice (pH 2.5) and bile acid (oxgall). Based on results from the API ZYM kit, leucine arylamidase, crystine arylamidase, acid phosphatase, naphthol-AS-BI-phosphohydrolase, ${\alpha}$-galactosidase, ${\beta}$-galactosidase, ${\alpha}$-glucosidase, ${\beta}$-glucosidase, and N-acetyl-${\beta}$-glucosamidase were produced by strain A12. L. acidophilus A12 showed resistance to several antibiotics (nisin, gentamicin, and erythromycin). The amount of interleukin $(IL)-1{\alpha}$ in $20{\times}$ concentrated supernatant from L. acidophilus A12 was approximately 156pg/ml. With regard to antioxidant activity, L. acidophilus A12 supernatant showed 60.6% DPPH radical scavenging activity. These results demonstrate the potential use of L. acidophilus A12 as health-promoting probiotics.

Cellular Biomarker of Membrane Stability and Hydrolytic Enzyme Activity in the Hemocytes of Benzo(a)pyrene-exposed Pacific oyster, Crassostrea gigas

  • Jo Qtae;Choy Eun-Jung;Park Doo Won;Jee Young-Ju;Kim Sung Yeon;Kim Yoon
    • Fisheries and Aquatic Sciences
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    • v.5 no.4
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    • pp.263-270
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    • 2002
  • The Pacific oysters, Crassostrea gigas, were stressed with different concentrations of benzo(a) pyrene and depurated to determine the hemocyte lysosomal membrane stability and hydrolytic enzymatic activity as a biomarker candidate to the chemical, using NRR (neutral red retention) and API ZYM System, respectively. The membrane damage measured as NRR decrease was significant with the increase of chemical concentration and exposure time (P<0.05), providing a possible tool for biomarker. Interestingly, the control showed intrinsic stress probably due to captive life in the laboratory, and a recovering trend was also found during the depuration. The benzo(a)pyrene-exposed oysters showed increased enzyme activities in alkaline phosphatase, esterase (C4), acid phosphatase, naphthol-AS-BI-phospho­hydrolase, $\beta$-galactosidase, $\beta$-glucuronidase, and N-acetyl- $\beta$-glucosaminidase. Of them, only two enzymes, acid phosphatase and alkaline phosphatase, showed some potential available for the generation of enzymatic biomarker in the oyster. The results are suggestive of the potential availability of the cellular and enzymatic properties as a biomarker. However, considering that a robust biomarker should be insensitive to natural stress coming from normal physiological variation, but sensitive to pollutants, a concept of intrinsic stress the animal possesses should be taken into consideration. This reflects the necessity of further research on the intrinsic stress affecting the cellular and enzymatic properties of the chemical­stressed oysters prior to using the data as a biomarker.

Synthesis of Super Hydrophobic Disazo Red Dyes using Alkylanilines as Diazo Components (알킬아닐린을 디아조성분으로 활용한 디스아조계 초소수성 적색염료의 합성)

  • Kim, Taekyeong;Ryu, Myeonghwa;Jang, Youngjae
    • Textile Coloration and Finishing
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    • v.27 no.1
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    • pp.27-34
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    • 2015
  • Novel super hydrophobic disazo red dyes were synthesized to improve light fastness of the primary monoazo red dye of previous study on polyolefin fibers such as polypropylene and ultra high molecular weight polyethylene fibers. 4-Alkylanilines were diazotized and then coupled to 2,5-dimethylaniline to produce dye intermediates which were then further used to synthesize final disazo red dyes by diazoization and coupling to ${\beta}$-naphthol. Considering both affinity of the dyes toward both polyolefin fibers and color fastnesses, the decyl-substituted dye was determined as the optimum dye. The decyl-substituted disazo red dye exhibited good dyeability on both polyolefin fibes and almost the same color values as the previous primary monoazo red dye. Light fastness on ultra high molecular weight polyethylene fibers was improved up to rating 3~4 compared to rating 2~3 of the previous primary monoazo red dye.