• Title/Summary/Keyword: Pyrrole

Search Result 222, Processing Time 0.023 seconds

meso-Substituted Dipyrromethanes from Vinylogous Aromatic Heterocycles and Their Utilization to the Synthesis of meso-Functionalized Porphyrins

  • Hong, Seong-Jin;Lee, Mi-Hye;Lee, Chang-Hee
    • Bulletin of the Korean Chemical Society
    • /
    • v.25 no.10
    • /
    • pp.1545-1550
    • /
    • 2004
  • meso-Functionalized dipyrromethanes 6-10 were synthesized by acid-catalyzed addition of pyrrole to ${\alpha}$-position of 2-alkenyl pyrroles. The regiochemistry of the reaction can be explained by either the formation of more stable carbocation intermediate or ${\beta}$-addition of ${\alpha},{\beta}$-unsaturated carbonyl compounds. The starting 2-alkenyl pyrroles were synthesized by Aldol condensation of 2-formylpyrrole with active methylene compounds such as nitromethane, diethylmalonate and malononitrile. Attempted ‘2+2' condensation of meso-diethylmalonyldipyrromethane, meso-(p-tolyl)dipyrromethane and p-tolualdehyde afforded three different porphyrins 12, 13 and 14 in reasonable yields. On the other hand, meso-(nitromethyl)dipyrromethane with p-(tbutyl) benzaldehyde resulted in the formation of three different porphyrins such as 5,15-dicyano-10,20-diarylporphyrin (16), 5-cyano-15-formyl-10,20-diarylporphyrin (17) and 5,15-diformyl-10,20-diarylporphyrin (18) in low yields. Conversion of nitromethyl groups to nitrile and (or) formyl group was observed under the porphyrin forming conditions.

Photo-Induced Cytotoxicity of Prodigiosin Analogues

  • Park, Gyung-Se;Tomlinson, John T.;Misenheimer, Jacob A.;Kucera, Gregory L.;Manderville, Richard A.
    • Bulletin of the Korean Chemical Society
    • /
    • v.28 no.1
    • /
    • pp.49-52
    • /
    • 2007
  • Prodigiosin (1) is the parent member of a class of polypyrrole natural products that exhibit promising anticancer activities. They can facilitate copper-promoted oxidative DNA damage by binding to copper ions, and this activity is thought to represent their mechanism of cytotoxicity in the dark. They also possess photoinduced cytotoxicity, although 1 is too toxic in the dark to be used effectively for the treatment of cancer by photodynamic therapies. To circumvent dark toxicity by prodigiosins, the semi-synthetic analogue 2, in which the N-pyrrolic atoms of 1 are methylated to block copper coordination, and the synthetic phenyl analogues 3 and 4, which lack the copper-coordinating A-pyrrole ring of 1, were tested for their ability to inhibit colony formation of HL-60 cancer cells in the absence and presence of visible light (λ > 495 nm). Our results show that 2-4 lack cytotoxicity in the dark, but are able to inhibit colony formation of HL-60 cells following irradiation for 30 min. The synthetic derivative 4 exhibits photo-induced cytotoxicity similar to that of the natural product 1, demonstrating the potential use of prodigiosin-based compounds for treatment of cancers following irradiation with visible light.

Characteristics of Enhanced Current by Polypyrrole under Illumination (폴리피롤에 빛을 쪼일 때 증가되는 전류의 특성)

  • Chae, Won Seok;Jang, Yeah Suk;Lee, Beom Gyu;Kim, Kang Jin
    • Journal of the Korean Chemical Society
    • /
    • v.39 no.4
    • /
    • pp.294-300
    • /
    • 1995
  • The photoelectrochemical behavior of polypyrrole films on Pt, glassy-C and indium tin oxide(ITO) under illumination was studied in aqueous solution containing a redox couple such as I-/I2 or Fe(CN)64-/Fe(CN)63-. Polypyrrole(PPy) was coated on Pt, glassy-C and ITO electrodes using electrochemical polymerization of pyrrole by potentiostatic method. Illumination of the PPy film results in the increase of cathodic and anodic currents at redox potentials of the redox species. These enhanced currents are caused both by the semiconductor characteristics of PPy and by the photothermal acceleration of redox reaction at PPy-electrode surface, and are dependent on the pH of redox solutions and the dopants in PPy.

  • PDF

Impregnation of Nitrogen Functionalities on Activated Carbon Fiber Adsorbents for Low-level CO2 Capture (저농도 이산화탄소 포집용 활성탄소섬유 흡착제의 질소작용기 함침연구)

  • Hwang, Su-Hyun;Kim, Dong-Woo;Jung, Dong-Won;Jo, Young-Min
    • Journal of Korean Society for Atmospheric Environment
    • /
    • v.32 no.2
    • /
    • pp.176-183
    • /
    • 2016
  • Activated carbon fibers (ACFs) for $CO_2$ adsorption were prepared from polyacrylonitrile (PAN) fiber through the systematic processes such as oxidation, activation and amination with the focus on the formation of nitration functional groups. Textural analysis of test samples revealed the decrease of specific surface area and pore volume by chemical activation including amination. The ratio of micropores to the total volume was 0.85 to 0.91, which was high enough with the pore size of 1.57 to 1.77 nm. Nitrogen compounds such as imine, pyridine and pyrrole presenting favorable interforces to $CO_2$ molecules were formed throughout the whole preparation steps. The aminated ACF adsorbent showed the enhanced adsorption capacity, 0.40 mmol/g for low-level $CO_2$ flow (3000 ppm) at room temperature. Selectivity of $CO_2$ against dry air ($O_2$ & $N_2$) also increased from 1.00 to 4.66 by amination.

Electrochemical Analysis of Biosensor using Bio-MEMS Technologies for the Detection of Serotonin (바이오멤스기술을 이용한 세로토닌 검출용 바이오센서의 전기화학적 특성 분석)

  • Yun, Dong-Hwa;Song, Min-Jung;Kim, Jong-Hoon;Min, Nam-Ki;Hong, Suk-In
    • Proceedings of the KIEE Conference
    • /
    • 2003.07c
    • /
    • pp.1932-1934
    • /
    • 2003
  • 본 논문은 신경전달물질 중 우울증, 신부전증의 지표 물질인 세로토닌의 농도를 극미량의 시료를 사용하여 정량할 수 있는 방법을 개발하기 위해 초소형 효소 고정화 전극을 개발하였다. 전극은 실리콘 웨이퍼 상에 반도체 공정을 이용하여 마이크로 크기의 Pt 박막 전극을 제작하였고, 전기화학적 방법으로 pyrrole 단량체를 Pt 전극 상에 순환전압전류법을 이용하여 산화적으로 전기 중합하였다. 효소의 고정은 일정 전압을 인가한 시간대 전류법으로 고정화하였다. 제작된 전극은 시간대 전류법으로 세로토닌의 농도에 따른 감도를 측정하였다. 세로토닌의 농도 범위 $1.0{\mu}mol/L{\sim}10mmol/L$에서의 감도는 $7.0{\mu}$A/decade를 나타내었으며, 실험결과에 따라 전극의 표면에서 발생하는 전류는 세로토닌의 농도에 비례함을 알 수 있었다. 전극의 표면분석은 Scanning Electron Microscopy(SEM), Energy Dispersive X-ray Spectroscopy(EDX) 그리고 Auger Electron Spectroscopy(AES)를 이용하여 분석하였다.

  • PDF

CROX (Cluster Regulation of RUNX) as a Potential Novel Therapeutic Approach

  • Kamikubo, Yasuhiko
    • Molecules and Cells
    • /
    • v.43 no.2
    • /
    • pp.198-202
    • /
    • 2020
  • Comprehensive inhibition of RUNX1, RUNX2, and RUNX3 led to marked cell suppression compared with inhibition of RUNX1 alone, clarifying that the RUNX family members are important for proliferation and maintenance of diverse cancers, and "cluster regulation of RUNX (CROX)" is a very effective strategy to suppress cancer cells. Recent studies reported by us and other groups suggested that wild-type RUNX1 is needed for survival and proliferation of certain types of leukemia, lung cancer, gastric cancer, etc. and for their one of metastatic target sites such as born marrow endothelial niche, suggesting that RUNX1 often functions oncogenic manners in cancer cells. In this review, we describe the significance and paradoxical requirement of RUNX1 tumor suppressor in leukemia and even solid cancers based on recent our findings such as "genetic compensation of RUNX family transcription factors (the compensation mechanism for the total level of RUNX family protein expression)", "RUNX1 inhibition-induced inhibitory effects on leukemia cells and on solid cancers through p53 activation", and "autonomous feedback loop of RUNX1-p53-CBFB in acute myeloid leukemia cells". Taken together, these findings identify a crucial role for the RUNX cluster in the maintenance and progression of cancers and suggest that modulation of the RUNX cluster using the pyrrole-imidazole polyamide gene-switch technology is a potential novel therapeutic approach to control cancers.

Comparison of Volatile Components in Fresh and Dried Red Peppers (Capsicum annuum L.)

  • Jun, Hae-Roung;Cho, In-Hee;Choi, Hyung-Kyoon;Kim, Young-Suk
    • Food Science and Biotechnology
    • /
    • v.14 no.3
    • /
    • pp.392-398
    • /
    • 2005
  • Fresh, and sun- and oven-dried red peppers were analyzed for volatile components. Also, their odor-active compounds were determined using gas chromatography-olfactometry (GC-O). More diverse volatile components, such as aldehydes, ketones, acids, and esters, were found in dried samples than in fresh ones. They included hexanal, ethyl acetate, ${\alpha}$-ionone, and ${\beta}$-ionone. Some Strecker aldehydes, 2-methyl butanal and 3-methyl butanal, were found only in dried red peppers. More hydrocarbons of high volatility and terpene-type components, such as ${\gamma}$-terpinene and aromadendrene, were detected only in fresh red peppers. A considerable amount of naphthalene was formed during sun-drying, whereas 2-furancarboxaldehyde, 1-methyl-1H-pyrrole and benzeneethanol were detected only in oven-dried red peppers. Characteristic odor of fresh ones could be attributed to 3-penten-2-o1, 2-methyl-2-butenal, 2-methoxy phenol, 2-hydroxy-methyl-benzoate, and 2-phenoxy ethanol, whereas some odorants, including 2-pentyl furan, naphthalene, hexyl hexanoate, and ${\alpha}$-ionone, could be responsible for distinctive odor property of sun-dried red peppers. 2-Furancarboxaldehyde, benzeneethanol, 4-vinyl-2-methoxy phenol, and unknown played important roles in odor property of oven-dried red peppers.

Synthesis of Mesostructured Conducting Polymer-Carbon Nanocomposites and Their Electrochemical Performance

  • Choi, Moon-Jung;Lim, Byung-Kwon;Jang, Jyong-Sik
    • Macromolecular Research
    • /
    • v.16 no.3
    • /
    • pp.200-203
    • /
    • 2008
  • A conducting polymer layer was introduced into the pore surface of mesoporous carbon via vapor infiltration of a monomer and subsequent chemical oxidative polymerization. The polypyrrole, conducting polymer has attracted considerable attention due to the high electrical conductivity and stability under ambient conditions. The mesoporous carbon-polypyrrole nanocomposite exhibited the retained porous structure, such as mesoporous carbon with a three-dimensionally connected pore system after intercalation of the polypyrrole layer. In addition, the controllable addition of pyrrole monomer can provide the mesoporous carbon-polypyrrole nanocomposites with a tunable amount of polypyrrole and texture property. The polypyrrole layer improved the electrode performance in the electrochemical double layer capacitor. This improved electrochemical performance was attributed to the high surface area, open pore system with three-dimensionally interconnected mesopores, and reversible redox behavior of the conducting polypyrrole. Furthermore, the correlation between the amount of polypyrrole and capacitance was investigated to check the effect of the polypyrrole layer on the electrochemical performance.

Effect of Coated Polypyrrole Content on the Properties of Polypyrrole Coated Fabrics (폴리피롤 코팅 직물의 성질에 미치는 폴리피롤 함량의 영향)

  • Son, Seong-Ho;Lee, Young-Hee;Lee, Dong-Jin;Kim, Sung Yeol;Kim, Han-Do
    • Textile Coloration and Finishing
    • /
    • v.28 no.2
    • /
    • pp.92-100
    • /
    • 2016
  • To chemically prepare polypyrrole(pPy) coated fabrics(silk, cotton and nylon fabrics), the fabrics were first soaked in 0.4M oxidant $FeCl_3$/0.06M dopant anthraquinone-2-sulfonic acid solution for 5min at room temperature, and subsequently soaked in a 0.4M monomer pyrrole aqueous solution for 5min at room temperature. The content(wt%) of coated pPy in the coated fabrics was controlled by the number of treatments(these two steps). This study examined the effect of the number of treatments/pPy content on the sheet resistance, mechanical/bending properties and color behaviors of pPy coated fabrics. The coated pPy content, sheet resistance(${\Omega}$/square) and color strength(K/S) of pPy coated fabrics increased sharply with increasing number of treatments up to 20 times, while the increase slowed down afterward. The tensile strength, elongation at break and lightness($L^*$) decreased with increasing number of treatments. The tensile modulus and bending rigidity of coated fabrics increased significantly with increasing number of treatments/coated pPy content. This indicated that the flexibility of coated fabrics decreased considerably.