• Title/Summary/Keyword: carboxylic acid

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Inhibitory Effects of Momordin I Derivatives on the Formation of Fos-Jun-AP-1 DNA Complex

  • Lee, Ju-hyung;Park, Chi-Hoon;Kim, Wook-Hwan;Hwang, Yun-Ha;Jeong, Kyung-chae;Yang, Chul-Hak
    • Bulletin of the Korean Chemical Society
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    • v.27 no.4
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    • pp.535-538
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    • 2006
  • In our previous studies, we have observed that curcumin and momordin I isolated from Ampelopsis radix inhibit the formation of Fos-Jun-activation protein-1 (AP-1) DNA complex. We have screened more effective compounds which have a 5-membered ring framework like momordin I and have modified disaccharide or carboxylic acid portions in momordin I. We synthesized momordin I derivatives according to the published method with slight modification. Synthetic momordin I derivatives showed remarkable inhibitory activities on Fos-Jun-AP-1 DNA complex formation results in in vitro assays. The $IC_{50}$ values of momordin I derivatives were about 4.0 $\mu$M in an electrophoretic mobility shift assay (EMSA). This value is about 125 times higher than that of curcumin and about 12 times higher than that for curcumin derivative C1, and moreover about 30 times higher than that for momordin I. We found momordin I derivatives (a) and (b) are the strongest inhibitory compound for Fos-Jun-AP-1 DNA complex formation.

Conjugation of Ginsenoside Rg3 with Gold Nanoparticles

  • Park, You-Mie;Im, A-Rang;Joo, Eun-Ji;Lee, Ji-Hye;Park, Hyeung-Geun;Kang, Young-Hwa;Linhardt, Robert J.;Kim, Yeong-Shik
    • Bulletin of the Korean Chemical Society
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    • v.32 no.1
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    • pp.286-290
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    • 2011
  • Ginsenoside Rg3 was reported to have important biological activities. We demonstrate conjugation and quantification procedures of ginsenoside Rg3 to gold nanoparticles for future biological and medical applications. Ginsenoside Rg3 was conjugated to spherical gold nanoparticles using a bifunctional heptaethylene glycol linker. The sulfhydryl group of heptaethylene glycol was adsorbed onto gold nanoparticles, and carboxylic acid end of heptaethylene glycol was bonded through a hydroxyl group of Rg3 via ester bond formation. The conjugation of Rg3 was characterized with various spectroscopic techniques, high resolution-transmission electron microscopy, and using Rg3 monoclonal antibody. The Rg3- functionalized gold nanoparticles were $4.7{\pm}1.0$ nm in diameter with a surface charge of -4.12 mV. The total number of Rg3 molecules conjugated to a 3.6 mL solution of gold nanoparticle was determined to be $9.5{\times}10^{14}$ corresponding to ~6 molecules of Rg3/gold nanoparticle. These results suggest that ginsenoside Rg3 is successfully conjugated to gold nanoparticles via heptaethylene glycol linker. The quantification was performed by using Rg3 monoclonal antibody without interference of gold's intrinsic color.

IQGAP1, a signaling scaffold protein, as a molecular target of a small molecule inhibitor to interfere with T cell receptor-mediated integrin activation

  • Li, Lin-Ying;Nguyen, Thi Minh Nguyet;Woo, Eui Jeon;Park, Jongtae;Hwang, Inkyu
    • Korean Journal of Agricultural Science
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    • v.47 no.2
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    • pp.361-373
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    • 2020
  • Integrins such as lymphocyte function-associated antigen -1 (LFA-1) have an essential role in T cell immunity. Integrin activation, namely, the transition from the inactive conformation to the active one, takes place when an intracellular signal is generated by specific receptors such as T cell receptors (TCRs) and chemokine receptors in T cells. In an effort to explore the molecular mechanisms underlying the TCR-mediated LFA-1 activation, we had previously established a high-throughput cell-based assay and screened a chemical library deposited in the National Institute of Health in the United States. As a result, several hits had been isolated including HIKS-1 (Benzo[b]thiophene-3-carboxylic acid, 2-[3-[(2-carboxyphenyl) thio]-2,5-dioxo-1-pyrrolinyl]-4,5,6,7-tetrahydro-,3-ethyl ester). In an attempt to reveal the mode of action of HIKS-1, in this study, we did drug affinity responsive target stability (DARTS) assay finding that HIKS-1 interacted with the IQ motif containing GTPase activating protein 1 (IQGAP1), a 189 kDa multidomain scaffold protein critically involved in various signaling mechanisms. Furthermore, the cellular thermal shift assay (CETSA) provided compelling evidence that HIKS-1 also interacted with IQGAP1 in vivo. Taken together, it can be concluded that HIKS-1 interferes with the TCR-mediated LFA-1 activation by interacting with IQGAP1 and thereby disrupting the signaling pathway for LFA-1 activation.

Action of Rodgersia podophylla Root Extracts on Melanin Biosynthesis in Skin (도깨비 부채 뿌리 추출물의 피부 과다색소침착에 미치는 영향)

  • Kong, Yeon-Hee;Lee, Pyeong-Jae;Choi, Sang-Yoon
    • Korean Journal of Medicinal Crop Science
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    • v.15 no.6
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    • pp.434-436
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    • 2007
  • In the previous study, we reported the inhibitory effects of Rodgersia podophylla root extract on tyrosinase activity and melanin production in melan-a cells. However, mechanism of the inhibitory activity and in vivo assay were not yet examined. This study performed the examination of the effects of Rodgersia podophylla root extract on protein expression and in vivo depigmenting activity using melan-a cells and brown guinea pigs. As the results of western immunoblotting analysis, treatment of Rodgersia podophylla root extract reduced tyrosinase expression rates in 10 and 100 ppm concentrations, dose dependently. Moreover, Rodgersia podophylla root extract exhibited depigmenting activity on UV-B induced hyperpigmentation in brown guinea pig skin. These results suggested that Rodgersia podophylla root extract could act as whitening agent for the skin via not only direct tyrosinase activity inhibition but also reducing of tyrosinase expression.

Properties of Synthesis (BaSr)$(CoFe)O_3$ Cathode for IT-SOFC by GNP (GNP 법을 이용한 저온형 SOFC용 (BaSr)$(CoFe)O_3$ 공기극의 제조 및 특성 평가)

  • Lee, Mi-Jai;Moon, Ji-Woong;Kim, Sei-Ki;Ji, Mi-Jung;Hwang, Hae-Jin;Lim, Yong-Ho;Choi, Byung-Hyun
    • 한국신재생에너지학회:학술대회논문집
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    • 2006.06a
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    • pp.51-54
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    • 2006
  • Cathode material, $(Ba_{0.5}Sr_{0.5})_{0.99}Co_{0.8}Fe_{0.2}O_{3-{\delta}}$, for low temperature SOFC was prepared by the glycine-nitrate synthesis process (GNP). The characteristics of the synthesized powders were studied with controlling pH of a precursor. The synthesis BSCF powders with pH were agglomeration state and calcinations temperature has not influence on particles. Highly acidicprecursor solution increased a single phase forming the temperature. Also, synthesis BSCF powder was show result for thermal analysis and alteration of difference crystal with pH. It is considered that Ba and Sr cannot complex by carboxylic acid group of glycine, because under highly acidic condition the caboxylic group mainly combined with $H^+$ insead of alkali and alkaline earth cations. In case of using precursor solution with pH $2{\sim}3$, a single perovskite phase was obtained at $1000^{\circ}C$. Polarization resistance of $(Ba_{0.5}Sr_{0.5})_{0.99}Co_{0.8}Fe_{0.2}O_{3-{\delta}}$ was measured by AC impedance spectroscopy from the two electrode symmetric cell. Area specific resistance of the $(Ba_{0.5}Sr_{0.5})_{0.99}Co_{0.8}Fe_{0.2}O_{3-{\delta}}$ air electrode at $500^{\circ}C\;and\;600^{\circ}C$ were $0.96{\Omega}?cm^2$ and $0.16{\Omega}?cm^2$, respectively.

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Physicochemical Properties of Antioxidant Fractions Extracted from Freeze-Dried Coffee by Various Solvents (동결건조 커피의 순차용매 분획별 특성과 항산화 효과)

  • Rhi, Ju-Won;Shin, Hyo-Sun
    • Korean Journal of Food Science and Technology
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    • v.28 no.1
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    • pp.109-116
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    • 1996
  • The relationship between antioxidant activities and physicochemical properties of several fractions obtained from freeze-dried (FD) coffee were investigated. The nine kinds of fraction were consecutively extracted from FD coffee with solvents in increasing order of polarity, and the higher polarity of the solvent the higher extraction yield of the fraction. The antioxidant activities of the fractions were determined by Rancimat and oven test on edible oils. The antioxidant activities of the fractions increased in the order of acetone>ethanol>methanol>50% methanol/water>water fraction, and the antioxidant activities of them were higher on lard than on soybean oil. The antioxidant activity of each fraction was strongly related to the contents of total phenol, total nitrogen content and acidity, whereas color intensity, reducing power, carboxylic acid content showed little contribution to the activity. All fractions had three peaks maxima at 208, 275 and 324 nm on UV-visible spectra, but the only one at 324 nm was linealy proportional to the antioxidant activities of the fractions.

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Traitements sur $R\'{e}sines$ des Euax de Purge de $G\'{e}n\'{e}rateur$ de P. W. R. $Condition\'{e}es$ $\`{a}$ L' Ammoniaque (P.W.R 형(型) 원자로(原子爐)의 증기발생기배수(蒸氣發生器排水)의 Ion 교환처리(交換處理) 연구(硏究))

  • Lee, Sang-Hoon;Park, Sang-Hoon
    • Journal of Radiation Protection and Research
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    • v.2 no.1
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    • pp.24-30
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    • 1977
  • Les eaux de $g\'{e}n\'{e}rateur$ de vapeur d'un $r\'{e}acteur$ P. W. R peuvent $\^{e}tre$ $contamin\'{e}es$ par des $radio-\'{e}lements$. Ces eaux sont habituellement $condition\'{e}es$ 'phosphate' pour limiter leur $agressivit\'{e}$ et la tendence actuelle est de remplacer les phosphate par un conditionment 'Amoniaques'. La $pr\'{e}sente$ $\'{e}tude$ a pour but de definir la $possibilit\'{e}$ $d'{\'{e}}purer$ des eaux $condition\'{e}es$ $\'{a}$ l'ammoniaque $\'{a}$ l'aide $d'{\'{e}}changeurs$ d'ion organiques. Des Facteurs de $D\'{e}contamination$ (F. D) en Cesium 137 et Strontium 90 et la $dur\'{e}e$ du cycle $d'{\'{e}}puration$ ont $d\^{u}$ $\^{e}tre$ bien meilleurs avec une colonne de 10 ml de $r\'{e}sine$ Carborylique Duolite $CC_4$ mise sous forme acide, suivie d'une colonne de 10 ml de $r\'{e}sine$ cationique Amberlite IR 120 mise sous forme acide et suivie d'une colonne de 10 ml de $r\'{e}sine$ anionique Amberlite IRA 400 mise sous forme hydroxyde.

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Reaction of Lithium n-Butylborohydride with Selected Organic Compounds Containing Representative Functional Groups

  • Chong-Suh Pyun;Jong-Chan Son;Nung-Min Yoon
    • Bulletin of the Korean Chemical Society
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    • v.4 no.1
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    • pp.3-9
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    • 1983
  • Lithium n-butylborohydride was prepared from borane-dimethylsulfide (BMS) and n-butyllithium, and the approximate rates and stoichiometrics of its reactions with selected organic compounds containing representative functional groups were studied in THF at room temperature. Phenol and benzenetiol liberated hydrogen quickly and quantitatively, and the reactions of primary alcohols, 2,6-di-ter-butylphenol and 1-hexanethiol liberated hydrogen quantitatively within 3 hrs, whereas the reactions of secondary and tertiary alcohols were very slow. Aldehydes and ketones were reduced rapidly and quantitatively to the corresponding alcohols. Cinnamaldehyde utilized 1 equiv. of hydride rapidly, suggesting the reduction to cinnamyl alcohol. Carboxylic acids evolved 1 equiv. of hydrogen rapidly and further reduction was not observed. Anhydrides utilized 2 equiv. of hydride rapidly but further hydride uptake was very slow, showing a half reduction. Acid chlorides were reduced to the alcohol stage very rapidly. All the esters examined were reduced to the corresponding alcohol rapidly. Lactones were also reduced rapidly. Expoxides took up 1 equiv. of hydride at a moderate rate to be reduced to the corresponding alcohols. Nitriles and primary amides were inert to this hydride system, whereas tertiary amide underwent slow reduction. Nitroethane and nitrobenzene were reduced slowly, however azobenzene and azoxybenzene were quite inert. Cyclohexanone oxime evolved 1 equiv. of hydrogen rapidly, but no further reduction was observed. Phenyl isocyanate and pyridine N-oxide were proceeded slowly, showing 1.74 and 1.53 hydride uptake, respectively in 24 hours. Diphenyl disulfide was reduced rapidly, whereas di-n-butyl disulfide, sulfone and sulfonic acids were inert or sluggish. n-Hexyl iodide and benzyl bromide reacted rapidly, but n-octyl bromide, n-octyl chloride, and benzyl chloride reacted very slowly.

Reaction of Sodium Tris(diethylamino)aluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups

  • Cha, Jin-Soon;Jeoung, Min-Kyoo;Kim, Jong-Mi;Kwon, Oh-Oun;Lee, Keung-Dong;Kim, Eun-Ju
    • Bulletin of the Korean Chemical Society
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    • v.15 no.10
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    • pp.881-888
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    • 1994
  • The approximate rates and stoichiometry of the reaction of excess sodium tris(diethylamino)aluminum hydride (ST-DEA) with selected organic compounds containing representative functional groups under standardized conditions(tetrahydrofuran, $0{\circ}$) were studied in order to characterize the reducing characteristics of the reagent for selective reductions. The reducing ability of STDEA was also compared with those of the parent sodium aluminum hydride (SAH) and lithium tris(diethylamino)aluminum hydride (LTDEA). The reagent appears to be milder than LTDEA. Nevertheless, the reducing action of STDEA is very similar to that observed previously for LTDEA, as is the case of the corresponding parent sodium and lithium aluminum hydrides. STDEA shows a unique reducing characteristics. Thus, benzyl alcohol, phenol and 1-hexanol evolved hydrogen slowly, whereas 3-hexanol and 3-ethyl-3-pentanol, secondary and tertiary alcohols, were essentially inert to STDEA. Primary amine, such as n-hexylamine, evolved only 1 equivalent of hydrogen slowly. On the other hand, thiols examined were absolutely stable. STDEA reduced aidehydes and ketones rapidly to the corresponding alcohols. The stereoselectivity in the reduction of cyclic ketones by STDEA was similar to that by LTDEA. Quinones, such as p-benzoquinone and anthraquinone, were reduced to the corresponding 1,4-dihydroxycyclohexadienes without evolution of hydrogen. Carboxylic acids and anhydrides were reduced very slowly, whereas acid chlorides were reduced to the corresponding alcohols readily. Esters and epoxides were also reduced readily. Primary carboxamides consumed hydrides for reduction slowly with concurrent hydrogen evolution, but tertiary amides were readily reduced to the corresponding tertiary amines. The rate of reduction of aromatic nitriles was much faster than that of aliphatic nitriles. Nitrogen compounds examined were also reduced slowly. Finally, disulfide, sulfoxide, sulfone, and cyclohexyl tosylate were readily reduced without evolution of hydrogen. In addition to that, the reagent appears to be an excellent partial reducing agent: like LTDEA, STDEA converted ester and primary carboxamides to the corresponding aldehydes in good yields. Furthermore, the reagent reduced aromatic nitriles to the corresponding aldehydes chemoselectively in the presence of aliphatic nitriles. Consequently, STDEA can replace LTDEA effectively, with a higher selectivity, in most organic reductions.

Reducing Characteristics of Potassium Tri-sec-butylborohydride

  • Yoon, Nung-Min;Hwang, Young-Soo;Yang, Ho-Seok
    • Bulletin of the Korean Chemical Society
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    • v.10 no.4
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    • pp.382-388
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    • 1989
  • The approximate rates and stoichiometry of the reaction of excess potassium tri-sec-butylborohydride ($K_s-Bu_3BH$) with selected organic compounds containing representative functional groups were determined under the standard conditions (0$^{\circ}C$, THF) in order to define the characteristics of the reagent for selective reductions. Primary alcohols evolve hydrogen in 1 h, but secondary and tertiary alcohols and amines are inert to this reagent. On the other hand, phenols and thiols evolve hydrogen rapidly. Aldehydes and ketones are reduced rapidly and quantitatively to the corresponding alcohols. Reduction of norcamphor gives 99.3% endo- and 0.7% exo-isomer of norboneols. The reagent rapidly reduces cinnamaldehyde to the cinamyl alcohol stage and shows no further uptake of hydride. p-Benzoquinone takes up one hydride rapidly with 0.32 equiv hydrogen evolution and anthraquinone is cleanly reduced to the 9,10-dihydoxyanthracene stage. Carboxylic acids liberate hydrogen rapidly and quantitatively, however further reduction does not occur. Anhydrides utilize 2 equiv of hydride and acyl chlorides are reduced to the corresponding alcohols rapidly. Lactones are reduced to the diol stage rapidly, whereas esters are reduced moderately (3-6 h). Terminal epoxides are rapidly reduced to the more substituted alcohols, but internal epoxides are reduced slowly. Primary and tertiary amides are inert to this reagent and nitriles are reduced very slowly. 1-Nitropropane evolves hydrogen rapidly without reduction and nitrobenzene is reduced to the azoxybenzene stage, whereas azobenzene and azoxybenzene are inert. Cyclohexanone oxime evolves hydrogen without reduction. Phenyl isocyanate utilizes 1 equiv of hydride to proceed to formanilide stage. Pyridine and quinoline are reduced slowly, however pyridine N-oxide takes up 1.5 equiv of hydride in 1 hr. Disulfides are rapidly reduced to the thiol stage, whereas sulfide, sulfoxide, sulfonic acid and sulfone are practically inert to this reagent. Primary alkyl bromide and iodide are reduced rapidly, but primary alkyl chloride, cyclohexyl bromide and cyclohexyl tosylate are reduced slowly.