• Title/Summary/Keyword: Benzoquinone

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Anticancer Effects of the Hsp90 Inhibitor 17-Demethoxy-Reblastatin in Human Breast Cancer MDA-MB-231 Cells

  • Zhao, Qing;Wu, Cheng-Zhu;Lee, Jae Kyoung;Zhao, Su-Rong;Li, Hong-Mei;Huo, Qiang;Ma, Tao;Zhang, Jin;Hong, Young-Soo;Liu, Hao
    • Journal of Microbiology and Biotechnology
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    • v.24 no.7
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    • pp.914-920
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    • 2014
  • Triple-negative breast cancer (TNBC) possesses a higher rate of distant recurrence and a poorer prognosis than other breast cancer subtypes. Interestingly, most of the heat shock protein 90 (Hsp90) client proteins are oncoproteins, and some are closely related to unfavorable factors of TNBC patients. 17-Demethoxy-reblastatin (17-DR), a novel non-benzoquinone-type geldanamycin analog, exhibited potent Hsp90 ATPase inhibition activity. In this study, the anticancer effects of 17-DR on TNBC MDA-MB-231 cells were investigated. These results showed that 17-DR inhibited cell proliferation, induced apoptosis, and suppressed cell invasion and migration in the MDA-MB-231 cells. Down-regulation of the key Hsp90-dependent tumor-driving molecules, such as RIP1 and MMP-9, by 17-DR may be related to these effects. Taken together, our results suggest that 17-DR has potential as a therapeutic agent for the treatment of TNBC.

Selective Epoxidation and Reduction of Rigid Cyclic ${\alpha},{\beta}$-Unsaturated Carbonyl Compounds (환상 ${\alpha},{\beta}$-불포화 카르보닐 화합물의 선택적 에폭시화 및 환원)

  • Ma, Eun-Sook
    • YAKHAK HOEJI
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    • v.49 no.6
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    • pp.443-448
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    • 2005
  • Diosgenin (25 (R) - spirost-5-en-3$\beta$ -ol) was oxidized with 2,3-dichloro -5,6-dicyano-1,4-benzoquinone to form 25(R)-1,4,6-spirostatrien-3-one (1) as rigid cyclic $\alpha$,$\beta$-unsaturated carbonyl compound. This compound was reacted with $H_{2}O_{2}$, m-chloroperoxybenzoic acid (mCPBA), NaOCl in the presence with (R,R)- or (S,S)-Jacobsen catalyst, tert-butyl-hydroperoxide (TBHP) in Mo$(CO)_{6}$, and in VO $(acac)_{2}$ catalyst, respectively, 25(R) -1,4,6-spirostatrien -3-one (1) was reduced with $NaBH_{4}$ L-Selectride, $LiAIH_{4}$,$BH_{3}$ $\cdot$$(CH_{3})_{2}S$, Superhydride, Red-Al, and lithium tri-tert-butoxyaluminium hydride. And 25(R)-4,6-spirostadien-3$\beta$-ol (4) was treated with $H_{2}O_{2}$, mCPBA, TBHP in D - (-) - and L-(+)-diisopropyltar-trate and $Ti(OiPr)_{4}$ condition (Sharpless asymmetric epoxidation), TBHP in $Mo(CO)_{6}$, and in $VO(acac)_{2}$ catalyst, respectively.

Cure Kinetics of Self-Extinguishing Epoxy Resin Systems with Charge Transfer Complex Type Latent Catalyst for Semiconductor Encapsulation (전하전이착체형 잠재성 촉매를 사용한 반도체 성형용 자소성 에폭시 수지 시스템의 경화 반응속도 연구)

  • Kim, Whan Gun
    • Journal of the Semiconductor & Display Technology
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    • v.13 no.4
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    • pp.27-32
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    • 2014
  • The cure properties of self-extinguishing epoxy resin systems with different charge transfer type latent catalysts were investigated, which are composed of YX4000H as a biphenyl epoxy resin, MEH-7800SS as a hardener, and charge transfer type latent catalysts. We designed and used five kinds of charge transfer type latent catalyst and compared to epoxy resin systems with Triphenylphosphine-Benzoquinone(TPP-BQ) as reference system. The cure kinetics of these systems were analyzed by differential scanning calorimetry with an isothermal approach, the kinetic parameters of all systems were reported in generalized kinetic equations with diffusion effects. The epoxy resin systems with Triphenylphosphine-Quinhydrone(TPP-QH), Triphenylphosphine-Benzanthrone(TPP-BT) and Triphenylphosphine-Anthrone(TPP-AT) as a charge transfer type latent catalyst showed a cure conversion rate of equal or higher rate than those with TPP-BQ. These systems with TPP-QH and Triphenylphosphine-Tetracyanoethylene(TPP-TCE) showed a critical cure reaction conversion of equal or higher conversion than those with TPP-BQ. The increases of cure conversion rates could be explained by the decrease of the activation energy of these epoxy resin systems. It can be considered that the increases of critical cure reaction conversion would be dependent on the crystallinity of the biphenyl epoxy resin systems.

Structural Analysis of Water Soluble Lignin-Carbohydrate Complex(LCC) Isolated from Korean Camellia Mistletoe(Pseudixus japonicus Hayata) (한국산 동백나무겨우살이에서 추출한 수용성 리그닌-탄수화물 복합체의 구조분석)

  • Choi, Joon-Weon;Ahn, Won-Yung
    • Journal of the Korean Wood Science and Technology
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    • v.25 no.3
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    • pp.1-7
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    • 1997
  • 한국산 동백나무겨우살이(Pseudixus japonicus Hayata)에 존재하는 수용성 리그닌-탄수화물 복합체를 구성하는 다당류의 구조를 밝히고 리그닌 성분과 다당류의 결합양식을 구명하고자, 냉 온수 추출한 수용성 리그닌-탄수화물 복합체(M-LCC-WE)를 DEAE Sephadex A-50로 중성분획(M-LCC-N)과 산성분획(M-LCC-A), 나머지분획(M-LCC-R)으로 세분화한 후 M-LCC-N과 M-LCC-A에 대하여 메틸화, 아세틸화, 그리고 DDQ 산화반응을 실시하였다. M-LCC-N을 구성하는 다당류는 ($1{\rightarrow}4$) 글리코시드결합의 arabinan과 ($1{\rightarrow}4$)나 ($1{\rightarrow}6$) 글리코시드결합의 galactan과 glucan으로 M-LCC-A의 다당류는 ($1{\rightarrow}4$) 글리코시드결합의 arabinan과 ($1{\rightarrow}6$) 글리코시드결합의 galactan이 다당류 주성분으로 밝혀졌으며 galacturonic acid가 결합되어 있기 때문에 산성적 성질을 나타내고 있었다. 또한 M-LCC-A에서는 galacturonic acid 의 carboxyl 그룹이 리그닌의 ${\alpha}$-와 ${\gamma}$-위치에서 ester결합이 존재함이 확인되었다.

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Selective Reduction by Lithium Bis- or Tris(dialkylamino)aluminum Hydrides. VIII. Reaction of Lithium Tripiperidinoaluminum Hydride in Tetrahydrofuran with Selected Organic Compounds Containing Representative Functional Groups

  • 차진순;이재철;주영철
    • Bulletin of the Korean Chemical Society
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    • v.18 no.8
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    • pp.890-895
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    • 1997
  • The approximate rates and stoichiometry of the reaction of excess lithium tripiperidinoaluminum hydride (LTPDA), an alicyclic aminoaluminum hydride, with selected organic compounds containing representative functional groups under the standardized conditions (tetrahydrofuran, 25°) were examined in order to define the reducing characteristics of the reagent for selective reductions. The reducing ability of LTPDA was also compared with those of the parent lithium aluminum hydride (LAH) and lithium tris(diethylamino)aluminum hydride (LTDEA), a representative aliphatic aminoaluminum hydride. In general, the reactivity of LTPDA toward organic functionalities is weaker than LTDEA and much weaker than LAH. LTPDA shows a unique reducing characteristics. Thus, benzyl alcohol, phenol and thiols evolve a quantitative amount of hydrogen rapidly. The rate of hydrogen evolution of primary, secondary and tertiary alcohols is distinctive. LTPDA reduces aldehydes, ketones, esters, acid chlorides and epoxides readily to the corresponding alcohols. Quinones, such as p-benzoquinone and anthraquinone, are reduced to the corresponding diols without hydrogen evolution. Tertiary amides and nitriles are also reduced readily to the corresponding amines. The reagent reduces nitro compounds and azobenzene to the amine stages. Disulfides are reduced to thiols, and sulfoxides and sulfones are converted to sulfides. Additionally, the reagent appears to be a good partial reducing agent to convert primary carboxamides into the corresponding aldehydes.

Reaction of Lithium Gallium Hydride with Selected Organic Compounds Containing Representative Functional Groups

  • Choe, Jeong Hun;Yun, Mun Yeong;Yun, Jong Hun;Jeong, Dong Won
    • Bulletin of the Korean Chemical Society
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    • v.16 no.5
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    • pp.416-421
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    • 1995
  • The approximate rates and stoichiometry of the reaction of excess lithium gallium hydride with selected organic compounds containing representative functional groups were examined under the standard conditions (diethyl ether, 0 $^{\circ}C)$ in order to compare its reducing characteristics with lithium aluminum hydride and lithium borohydride previously reported, and enlarge the scope of its applicability as a reducing agent. Alcohols, phenol, and amines evolve hydrogen rapidly and quantitatively. However lithium gallium hydride reacts with only one active hydrogen of primary amine. Aldehydes and ketones of diverse structure are rapidly reduced to the corresponding alcohols. Conjugated aldehyde and ketone such as cinnamaldehyde and methyl vinyl ketone are rapidly reduced to the corresponding saturated alcohols. p-Benzoquinone is mainly reduces to hydroquinone. Caproic acid and benzoic acid liberate hydrogen rapidly and quantitatively, but reduction proceeds slowly. The acid chlorides and esters tested are all rapidly reduced to the corresponding alcohols. Alkyl halides and epoxides are reduced rapidly with an uptake of 1 equiv of hydride. Styrene oxide is reduced to give 1-phenylethanol quantitatively. Primary amides are reduced slowly. Benzonitrile consumes 2.0 equiv of hydride rapidly, whereas capronitrile is reduced slowly. Nitro compounds consumed 2.9 equiv of hydride, of which 1.9 equiv is for reduction, whereas azobenzene, and azoxybenzene are inert toward this reagent. Cyclohexanone oxime is reduced consuming 2.0 equiv of hydride for reduction at a moderate rate. Pyridine is inert toward this reagent. Disulfides and sulfoxides are reduced slowly, whereas sulfide, sulfone, and sulfonate are inert under these reaction conditions. Sulfonic acid evolves 1 equiv of hydrogen instantly, but reduction is not proceeded.

Synthesis and Characterization of 1-Transition Metal Complex Substituted-2,3,4,5-Tetraphenyl-1-Silacyclopentadienyl Complexes and Generation of Transition Metal Complex-Substituted Silylene

  • Paek Cheolki;Ko Jaejung;Kong Youngkun;Kim, Chang Hwan;Lee Myong Euy
    • Bulletin of the Korean Chemical Society
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    • v.15 no.6
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    • pp.460-465
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    • 1994
  • New silicon-monosubstituted (${\eta}^4$-2,3,4,5-tetraphenyl-l-silacyclopentadiene)transi tion metal complexes are described. (7-Alkyl-7-silanorbornadienyl)MLn(Alkyl=Methyl: MLn=CpRu$(CO)_2$: Alkyl=Methyl: MLn=CpNi(CO): Alkyl=Ethyl: MLn=CpNi(CO)) complexes were prepared from the corresponding silole-transition metal complexes with dimethylacetylenedicarboxylate. Cycloaddition products were obtained with 2,3-dimethyl-1,3-butadiene, 2,3-butanedione, and 1,4-benzoquinone through the ruthenium-substituted silylene. We have determined the crystal structure of (1-methyl-2,3,4,5-tetraphenyl-l-silacyclopentadien yl)cyclopentadienyldicarbonylruthenium by using graphite monochromated Mo-Ka radiation. The compound was crystallized in the monoclinic space group $P2_{1/c}$ with a = 9.838(l), b = 15.972(3), c = 18.327(3) ${\AA}$, and ${\beta}= 94.28(l)^{circ}$. The ruthenium moiety CpRu$(CO)_2$ on silicon is in an axial position.

Characterization of Anthraquinone-Based Electron Acceptors for Organic Solar Cells (유기태양전지용 안트라퀴논 기반 전자 받게 분자의 특성 분석)

  • Hyun, Chang-Seok;An, Byeong-Kwan
    • Journal of the Korean Institute of Electrical and Electronic Material Engineers
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    • v.35 no.4
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    • pp.366-371
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    • 2022
  • Recently many efforts have been made to develop a novel class of non-fullerene electron acceptor materials for high-performance organic solar cells. In this work, anthraquinone derivatives, TMAQ and THAQ, were prepared and their availability as electron acceptor materials for organic solar cells were investigated in terms of optical, thermal, electrochemical properties, and solar cell devices. Compared to TMAQ, a significant bathochromic shift of absorption band was observed for THAQ owing to intramolecular hydrogen-bond-assisted CT interactions. Thanks to the fused aromatic ring structure and benzoquinone unit, both TMAQ and THAQ exhibited a high thermal stability and an efficient electron reduction process. In particular, the intramolecular O-H---O=C hydrogen bond of THAQ plays an important role in improving the thermal stability and electron reduction properties. In the P3HT:acceptor solar cell system, THAQ-based devices had more than ca. 6 times higher power conversion efficiency than TMAQ -based devices. These results serve as a guide for developing high-efficient anthraquinone-based electron acceptor materials.

The Relationship between Prohibitin 1 Expression, Hepatotoxicity Induced by Acetaminophen, and Hepatoprotection by S-Adenosylmethionine in AML12 Cells

  • Eunhye Cho;Soohan Jung;Jina Kim;Kwang Suk Ko
    • Journal of Microbiology and Biotechnology
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    • v.32 no.11
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    • pp.1447-1453
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    • 2022
  • Prohibitin 1 (Phb1) is a pleiotropic protein, located mainly in the mitochondrial inner membrane and involved in the regulation of cell proliferation and the stabilization of mitochondrial protein. Acetaminophen (APAP) is one of the most commonly used over-the-counter analgesics worldwide. However, at high dose, the accumulation of N-acetyl-p-benzoquinone imine (NAPQI) can lead to APAP-induced hepatotoxicity. In this study, we sought to understand the regulation of mRNA expression in relation to APAP and GSH metabolism by Phb1 in normal mouse AML12 hepatocytes. We used two different Phb1 silencing levels: high-efficiency (HE, >90%) and low-efficiency (LE, 50-60%). In addition, the siRNA-transfected cells were further pretreated with 0.5 mM of Sadenosylmethionine (SAMe) for 24 h before treatment with APAP at different doses (1-2 mM) for 24 h. The expression of APAP metabolism-related and antioxidant genes such as Cyp2e1 and Ugt1a1 were increased during SAMe pretreatment. Moreover, SAMe increased intracellular GSH concentration and it was maintained after APAP treatment. To sum up, Phb1 silencing and APAP treatment impaired the metabolism of APAP in hepatocytes, and SAMe exerted a protective effect against hepatotoxicity by upregulating antioxidant genes.