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Copper-Catalyzed Selective Arylations of Benzoxazoles with Aryl Iodides
Kim, Donghae,Yoo, Kwangho,Kim, Se Eun,Cho, Hee Jin,Lee, Junseong,Kim, Youngjo,Kim, Min American Chemical Society 2015 Journal of organic chemistry Vol.80 No.7
<P>A copper-catalyzed direct ring-opening double N-arylation of benzoxazoles with aryl iodides has been developed. The present system exhibits high selectivity despite competition from C-arylation. The selectivity between ring-opening N-arylation and C-arylation was controlled by the choice of reaction vessel. The nitrile bound bis(triphenylphosphine)copper cyanide was identified as the active catalytic species for both reactions, and when combined with a nitrile-containing solvent, enhanced the reaction efficiency.</P>
SoxF Transcription Factors Are Positive Feedback Regulators of VEGF Signaling
Kim, Kangsan,Kim, Il-Kug,Yang, Jee Myung,Lee, Eunhyeong,Koh, Bong Ihn,Song, Sukhyun,Park, Junseong,Lee, Sungsu,Choi, Chulhee,Kim, Jin Woo,Kubota, Yoshiaki,Koh, Gou Young,Kim, Injune Grune & Stratton 2016 Circulation research Vol.119 No.7
<P>Rationale: Vascular endothelial growth factor (VEGF) signaling is a key pathway for angiogenesis and requires highly coordinated regulation. Although the Notch pathway-mediated suppression of excessive VEGF activity via negative feedback is well known, the positive feedback control for augmenting VEGF signaling remains poorly understood. Transcription factor Sox17 is indispensable for angiogenesis, but its association with VEGF signaling is largely unknown. The contribution of other Sox members to angiogenesis also remains to be determined. Objective: To reveal the genetic interaction of Sox7, another Sox member, with Sox17 in developmental angiogenesis and their functional relationship with VEGF signaling. Methods and Results: Sox7 is expressed specifically in endothelial cells and its global and endothelial-specific deletion resulted in embryonic lethality with severely impaired angiogenesis in mice, substantially overlapping with Sox17 in both expression and function. Interestingly, compound heterozygosity for Sox7 and Sox17 phenocopied vascular defects of Sox7 or Sox17 homozygous knockout, indicating that the genetic cooperation of Sox7 and Sox17 is sensitive to their combined gene dosage. VEGF signaling upregulated both Sox7 and Sox17 expression in angiogenesis via mTOR pathway. Furthermore, Sox7 and Sox17 promoted VEGFR2 (VEGF receptor 2) expression in angiogenic vessels, suggesting a positive feedback loop between VEGF signaling and SoxF. Conclusions: Our findings demonstrate that SoxF transcription factors are indispensable players in developmental angiogenesis by acting as positive feedback regulators of VEGF signaling.</P>
( Junseong Kim ),( Youn Kyung Choi ),( Ji-hyeok Lee ),( Seo-young Kim ),( Hyun-soo Kim ),( You-jin Jeon ),( Soo-jin Heo ) 한국키틴키토산학회 2017 한국키틴키토산학회지 Vol.22 No.3
Red tide Heterosigma akashiwo (H. akashiwo), a microscopic alga of the class Raphidophyceae, causes extensive damage to all marine ecosystems. It is essential to reduce the damage to marine ecosystems for them to be used as a resource. In this study, we used organic solvent fractionation to obtain an ethyl acetate-methanol extract from H. akashiwo (HAEM80) and then evaluated its anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells and a zebrafish model. HAME80 markedly inhibited the production of nitric oxide (NO) and prostaglandin E2 (PGE2). It also down-regulated the protein expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) and decreased the secretion of interleukin-1β (IL-1β) in LPS-stimulated RAW 264.7 cells. HAME80 reduced yolk edema and improved the survival rate of LPS-stimulated zebrafish embryos; in addition, the extract significantly reduced the production of ROS and NO and attenuated cell death in this model. Gas chromatography-mass spectrometry (GC-MS) of the extract was used to confirm the identity of peaks 1-20. Taken together, our data suggest that H. akashiwo is a beneficial anti-inflammatory agent.
Kim, Eun-A,Kim, Seo-Young,Ye, Bo-Ram,Kim, Junseong,Ko, Seok-Chun,Lee, Won Woo,Kim, Kil-Nam,Choi, Il-Whan,Jung, Won-Kyo,Heo, Soo-Jin Elsevier 2018 INTERNATIONAL IMMUNOPHARMACOLOGY Vol.59 No.-
<P><B>Abstract</B></P> <P>In this study, we confirmed the anti-inflammatory effect of Apo-9-fucoxanthinone (AF) in <I>in vitro</I> RAW 264.7 cells and <I>in vivo</I> zebrafish model. In lipopolysaccharide (LPS)-stimulated zebrafish, AF significantly decreased the production of reactive oxygen species (ROS), nitric oxide (NO) and cell death. In addition, the mRNA expression of inducible nitric oxide synthase (iNOS), suppressed cyclooxygenase-2 (COX-2) and an inflammatory cytokines; IL-1β, TNF-α were shown reduction. And AF significantly inhibited NO production and expression of iNOS in LPS-stimulated RAW 264.7 cells. Further, AF suppressed COX-2, prostaglandin E2 (PGE<SUB>2</SUB>), and pro-inflammatory cytokines such as interleukin-6 (IL-6), IL-1β, and tumor necrosis factor-α (TNF-α) at 25, 50 and 100 μg/mL, respectively. Further mechanistic studies showed that AF suppressed the nuclear factor-kB (NF-kB) pathway and phosphorylation of mitogen-activated protein kinase (MAPK) pathway molecules such as extracellular signal-regulated kinase (ERK) and c-Jun N-terminal kinase (JNK). According to the results, AF can be used and applied as a useful anti-inflammatory agent of nutraceutical or pharmaceutical.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Anti-inflammatory effect of Apo-9-fucoxanthinone in <I>in vitro</I> RAW 264.7 cells and <I>in vivo</I> zebrafish </LI> <LI> Apo-9-fucoxanthinone suppressed NO production through NF-kB and MAPKs pathway. </LI> <LI> In LPS-stimulated zebrafish, Apo-9-fucoxanthinone significantly decreased ROS, NO, cell death and pro-inflammatory cytokines. </LI> <LI> Apo-9-fucoxanthinone can be extremely useful as an effective anti-inflammatory agent. </LI> </UL> </P>
Kwak, Jiyong,Shim, Jin-Kyoung,Kim, Dong Seok,Lee, Ji-Hyun,Choi, Junjeong,Park, Junseong,Shin, Kyoung-Jin,Kim, Se-Hoon,Kim, Pilnam,Huh, Yong-Min,Kim, Eui Hyun,Chang, Jong Hee,Kim, Sun Ho,Kang, Seok-Gu Spandidos Publications 2016 International journal of oncology Vol.49 No.2
<P>The existence of tumorspheres (TSs) might confer treatment resistance to pineoblastoma (PB). The existence of PB TSs with cellular immortalization potential has not yet been reported. We developed a procedure for isolating TSs from recurrent PB (rPB) and tested whether their properties made them suitable for use as a patient-derived xenograft (PDX). Immunocytochemical staining, RT-PCR and quantitative real-time PCR showed that, among stemness proteins, CD133, musashi and podoplanin were expressed at elevated levels in rPB TSs, but nestin was not. rPB TSs cultured under neuro-glial differentiation conditions expressed TUBB3, but not GFAP, MBP or NeuN. Unlike glioblastoma TSs, rPB TSs showed no clear evidence of invasion in 3D invasion assay or increased expression of genes associated with epithelial-mesenchymal transition. An orthotopic xenograft showed that tumor xenografts replicated the histopathological features of the patient tumor and expressed similar genome profiles, as determined by short tandem repeat genotyping. These data demonstrate the isolation and the characterization of rPB TSs for the first time. Using an orthotopic xenograft, we showed that rPB TSs could replicate the patient tumor, demonstrating their potential as a PDX for precision medicine.</P>
The skin protective effects of compound K, a metabolite of ginsenoside Rb1 from Panax ginseng
Kim, Eunji,Kim, Donghyun,Yoo, Sulgi,Hong, Yo Han,Han, Sang Yun,Jeong, Seonggu,Jeong, Deok,Kim, Jong-Hoon,Cho, Jae Youl,Park, Junseong The Korean Society of Ginseng 2018 Journal of Ginseng Research Vol.42 No.2
Background: Compound K (CK) is a ginsenoside, a metabolite of Panax ginseng. There is interest both in increasing skin health and antiaging using natural skin care products. In this study, we explored the possibility of using CK as a cosmetic ingredient. Methods: To assess the antiaging effect of CK, RT-PCR was performed, and expression levels of matrix metalloproteinase-1, cyclooxygenase-2, and type I collagen were measured under UVB irradiation conditions. The skin hydrating effect of CK was tested by RT-PCR, and its regulation was explored through immunoblotting. Melanin content, melanin secretion, and tyrosinase activity assays were performed. Results: CK treatment reduced the production of matrix metalloproteinase-1 and cyclooxygenase-2 in UVB irradiated NIH3T3 cells and recovered type I collagen expression level. Expression of skin hydrating factors-filaggrin, transglutaminase, and hyaluronic acid synthases-1 and -2-were augmented by CK and were modulated through the inhibitor of ${\kappa}B{\alpha}$, c-Jun N-terminal kinase, or extracellular signal-regulated kinases pathway. In the melanogenic response, CK did not regulate tyrosinase activity and melanin secretion, but increased melanin content in B16F10 cells was observed. Conclusion: Our data showed that CK has antiaging and hydrating effects. We suggest that CK could be used in cosmetic products to protect the skin from UVB rays and increase skin moisture level.
Dinuclear Metallocenes with a Modulated Biphenylene Bridge for Olefin Polymerization
Kim, Seong Kyun,Kim, Hwa Kyu,Lee, Min Hyung,Yoon, Seung Woong,Han, Yonggyu,Park, Sungjin,Lee, Junseong,Do, Youngkyu WILEY-VCH Verlag 2007 European journal of inorganic chemistry Vol. No.
<P>Dinuclear group 4 metallocene catalysts linked by a biphenylene or 1,2-diphenylethylene bridge, namely [4,4′-(C<SUB>5</SUB>Me<SUB>4</SUB>)<SUB>2</SUB>(C<SUB>6</SUB>H<SUB>4</SUB>)<SUB>2</SUB>][CpZrCl<SUB>2</SUB>]<SUB>2</SUB> (2a), [p-(C<SUB>5</SUB>Me<SUB>4</SUB>)C<SUB>6</SUB>H<SUB>4</SUB>CH<SUB>2</SUB>]<SUB>2</SUB>[CpZrCl<SUB>2</SUB>]<SUB>2</SUB> (2b), [p-(3,4-Me<SUB>2</SUB>C<SUB>5</SUB>H<SUB>2</SUB>)C<SUB>6</SUB>H<SUB>4</SUB>CH<SUB>2</SUB>]<SUB>2</SUB>[CpZrCl<SUB>2</SUB>]<SUB>2</SUB> (2c), [(C<SUB>5</SUB>Me<SUB>4</SUB>)<SUB>2</SUB>(C<SUB>6</SUB>H<SUB>4</SUB>)<SUB>2</SUB>][TiCl<SUB>3</SUB>]<SUB>2</SUB> (3a), [p-(C<SUB>5</SUB>Me<SUB>4</SUB>)C<SUB>6</SUB>H<SUB>4</SUB>CH<SUB>2</SUB>]<SUB>2</SUB>[TiCl<SUB>3</SUB>]<SUB>2</SUB> (3b), and [p-(3,4-Me<SUB>2</SUB>C<SUB>5</SUB>H<SUB>2</SUB>)C<SUB>6</SUB>H<SUB>4</SUB>CH<SUB>2</SUB>]<SUB>2</SUB>[TiCl<SUB>3</SUB>]<SUB>2</SUB> (3c), have been prepared and the crystal structures of 2b and 3b determined by X-ray diffraction methods. The crystal structures reveal that these complexes consist of two equivalent metal units inverted with respect to the center of the bridge. All the complexes were tested for the polymerization of ethylene and styrene in the presence of methylaluminoxane (MAO), and direct comparisons of their catalytic properties with those of the corresponding mononuclear analogues [(PhC<SUB>5</SUB>Me<SUB>4</SUB>)CpZrCl<SUB>2</SUB>] (4a), [(p-TolC<SUB>5</SUB>Me<SUB>4</SUB>)CpZrCl<SUB>2</SUB>] (4b), [(1-p-Tol-3,4-Me<SUB>2</SUB>C<SUB>5</SUB>H<SUB>2</SUB>)CpZrCl<SUB>2</SUB>] (4c), [(PhC<SUB>5</SUB>Me<SUB>4</SUB>)TiCl<SUB>3</SUB>] (5a), [(p-TolC<SUB>5</SUB>Me<SUB>4</SUB>)TiCl<SUB>3</SUB>] (5b), and [(1-p-Tol-3,4-Me<SUB>2</SUB>C<SUB>5</SUB>H<SUB>2</SUB>)TiCl<SUB>3</SUB>] (5c) were performed. The dinuclear zirconocenes show a high activity in ethylene polymerization comparable with those of the corresponding mononuclear catalysts and give an increased molecular weight of polyethylene. The dinuclear half-sandwich titanocenes exhibit similar or slightly lower activity and molecular weight in styrene polymerization compared with their mononuclear analogues. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)</P> <B>Graphic Abstract</B> <P> <img src='wiley_img/14341948-2007-2007-4-EJIC200600833-fig000.gif' alt='wiley_img/14341948-2007-2007-4-EJIC200600833-fig000'> </P>