• Title/Summary/Keyword: $^{1}H$ NMR

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A New Class of Platinum (II) Complexes [Pt (trans-1-daeh) (DPPP)] $2NO_3$ and [Pt (trans-1-daeh)(DPPE)] $2NO_3$ Exhibiting Antitumor Activity and Nephrotoxieity (새로운 Platinum (II) Complex ([Pt (II)(trans-1-dach)(DPPP)] $(NO_3)_2$와 [Pt (II)(trans-1-dach)(DPPE)] $(NO_3)_2$의 항암효과 및 신독성에 관한연구)

  • Jung, Jee-Chang;Yoon, Chin-Hee;Chang, Sung-Goo;Lee, Kyung-Tae;Rho, Young-Soo
    • The Korean Journal of Pharmacology
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    • v.29 no.2
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    • pp.283-295
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    • 1993
  • Pt-complexes is currently one of the most compounds used in the treatment of solid tumors. However, its used is limited by severe side effects such as renal toxicity. Our platinum-based drug discovery program is aimed at developing drugs capable of diminishing toxicity and improving antitumor activity. We synthesized new Pt (II) complex analogues containing 1, 2-diaminocyclohexane (dach) as carrier ligand and 1, 3-bis (diphenylphosphino) propane (DPPP)/1,2-bis (diphenylphosphino) ethane (DPPE) as a leaving group. Furthermore, nitrate was added to improve the solubility. A new series of (KHPC-001) [Pt (trans-1-dach)(DPPP)] $2NO_3$ and (KHPC-002) [Pt (trans-1-dach)(DPPE)] $2NO_3$ were synthesized and characterized by their elemental analysis and by various spectroscopic techniques [infrared (IR), $^{13}carbon$ nuclear magnetic resonance (NMR)]. KHPC-001 and KHPC-002 demonstrated acceptable antitumor activity aganist P-388, L-1210 lymphocytic leukemia cells and significant activity as compared with that of cisplatin. The toxicity of KHPC-001 and KHPC-002 was found quite less than that of cisplatin using MTT, $[^3H]$ thymidine uptake and glucose consumption tests in rabbit proximal tubule cells and human kidney cortical cells.

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Isolation and Identification of Antioxidants from Methanol Extract of Sword Bean (Canavalia gladiata) (작두콩의 메탄올 추출물로부터 항산화 활성 화합물의 분리 및 동정)

  • Kim, Jong-Pil;Lee, Hyang-Hee;Moon, Jae-Hak;Ha, Dong-Ryong;Kim, Eun-Sun;Kim, Jin-Hwan;Seo, Kye-Won
    • Korean Journal of Food Science and Technology
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    • v.45 no.6
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    • pp.777-784
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    • 2013
  • The ethyl acetate (EtOAc) layer of Canavalia gladiata (sword bean) methanol extracts showed higher 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity than other layers. Four phenolic compounds were isolated from the EtOAc layer by silica gel column chromatography and prep-HPLC using a guided DPPH radical-scavenging assay. The isolated compounds were identified as methyl gallate (1), gallic acid (2), 1,6-di-O-galloyl ${\beta}$-$\small{D}$-glucopyranoside (3), and 1,4,6-tri-O-galloyl ${\beta}$-$\small{D}$-glucopyranoside (4) based on MS and NMR analyses. Among the four compounds, no. 4 was isolated from this plant for the first time. Their DPPH radical-scavenging activities based on $SC_{50}$ decreased in the following order: 4 (6.9 ${\mu}M$)>3 (8.3 ${\mu}M$)>2 (10.0 ${\mu}M$)>1 (10.3 ${\mu}M$).

Cobalt(III) Complex of Ethylenediamine-N,N'-di-${\alpha}$-Isobutyric Acid (Ethylenediamine-N,N'-di-${\alpha}$-Isobutyric Acid의 코발트(III) 착물)

  • Moo-Jin Jun;Chang-Yoon Han;Chang-Woo Park;Sung Rack Choi;Kwang-Ha Park
    • Journal of the Korean Chemical Society
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    • v.30 no.1
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    • pp.84-89
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    • 1986
  • A newflexible $N_2O_2$-type tetradentate ligand. Ethylenediamine-N,N'-di-${\alpha}$-isobutyric acid(eddib), has been synthesized, and dichloro cobalt(III) complex of eddib has been prepared via the air-oxidation technique. Only S-cis isomer has been yielded during the preparation of complex. Ring strain and steric hinderance are cited as the cause for the preference for the S-cis geometric configuration. On series of cobalt(III) complexes of eddib, $[Co(eddib)L]^{n+}$ $(L = Cl{\cdot}(H_2O),\;CO_3^{2-},\;(H_2O)_2)$have been prepared in situ. In their electronic absorption spectra, the absorption maxima and their intensities of the above series of complexes are on the ordinary line of the spectrochemical and hyperchromic series. Elemental analysis, IR, NMR and electronic absorption spectra have been used to characterize the complex and geometries of the complex.

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Mixed Intramolecular Hydrogen Bonding in Dihydroxythiophene-based Units and Boron and Technetium Chelation

  • Ko, Sang-won;Park, Sang-Hyun;Gwon, Hui-Jeong;Lee, Jun-seong;Kim, Min-Jeong;Kwak, Yeon-ju;Do, Young-kyu;Churchill, David G.
    • Bulletin of the Korean Chemical Society
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    • v.27 no.2
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    • pp.243-250
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    • 2006
  • Three novel potential metal ion chelating units have been synthesized and characterized: 5-hexylcarbamoyl-3,4-dihydroxythiophene-2-carboxylic acid methyl ester (5), 3-benzyloxy-4-hydroxythiophene-2,5-dicarboxylic acid bis-hexylamide (6), and 3,4-dihydroxythiophene-2,5-dicarboxylic acid bis-hexylamide (7). The crystal structure of 6 was obtained and suggests the presence of three distinct intramolecular hydrogen bonds, namely $[N_{amide}-H{\cdot}{\cdot}{\cdot}O]$ $[O-H{\cdot}{\cdot}{\cdot}O_{amide}]$ and $[N_{amide}-H{\cdot}{\cdot}{\cdot}S]$. Boron chelation with 5, 6 and 7 through the use of $BF_3, \;B(OH)_3 \;or \;B(OMe)_3$ was probed by $^1H$, $^{11}B$, and $^{13}C$ NMR spectroscopy. Technetium (I) chelation with 5, 6 and 7 was also studied via HPLC elutions using $[^{99m}Tc(CO)_3(OH_2)_3]^+$.

Synthesis, Characterization and Cosmetic Application of Self-Assembled Sericin-PEG Nanoparticle

  • E. S. Choung;S. Y. Eom;Kim, J. H.;Kim, K. S.;Kim, K. H.;Lee, K. G.;Lee, Y. W.;C. S. Cho
    • Proceedings of the SCSK Conference
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    • 2003.09a
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    • pp.501-519
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    • 2003
  • Silk Sericin(SS) is a natural protein extracted from cocoon of bombix mori and shows moisturizing effect to the skin due to a number of hydroxyl groups in the structure. But its application to cosmetics is limited due to its poor solubility in water. In order to solve this drawback and expand its application to cosmetics, polyethyleneglycol(PEG) was conjugated with sericin by reacting activated polyethyleneglycol(ActPEG). Reaction site of sericin is tyrosine residue, which was determined by using $^1$H-NMR. Random coil structure of sericin was transformed to beta-sheet structure by conjugating polyethyleneglycol. It was confirmed that melting point of sericin-PEG conjugate was lowered compared to that of each sericin and PEG due to the interaction between sericin and PEG in crystalline structure. Self-assembled sericin-PEG nanoparticle was obtained by dialyzing with alcohol solution of sericin-PEG conjugate against water. The particle is spherical and has 200-400nm of size. The moisturizing ability of sericin-PEG nanoparticle was much higher than that of sericin itself. Incorporation of vitamin A into sericin-PEG nanoparticle was carried out by diafiltration method. The content of incorporated Vitamin A in sericin-PEG nanoparticle was 8.9 wt%. Releasing behaviour of vitamin A incorporated into nanoparticle was tested in phosphate buffer, pH 7.4 at 37$^{\circ}C$. and half-life of Vitamin A release was 43hrs. Sericin-PEG nanoparticle exhibited higher moisturing effect than sericin itself and distilled water, respectively. No toxicity and irritation were observed in animal tests. It can be expected that the self-assembled sericin-PEG nanoparticle can be developed for cosmetics.

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In Vitro Antitumor Activity and Nephrotoxicity of the Novel Platinum(II) Coordination Complex Containing Cis-dach/Diphosphine (새로운 Platinum(II)Complex ([Pt(II)(cis-dach)(DPPP)].$(NO_3)_2$의 항암효과 및 신독성)

  • Jung, Jee-Chang;Yim, Sung-Vin;Park, Seung-Joon;Chung, Joo-Ho;Ko, Kye-Chang;Chang, Sung-Goo;Rho, Young-Soo
    • The Korean Journal of Pharmacology
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    • v.32 no.1
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    • pp.93-102
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    • 1996
  • Platinum coordination complexes are currently one of the most compounds used in the treatment of solid tumors. However, its use is limited by severe side effects such as nephrotoxicity. Our platinum-based drug discovery program is aimed at developing drugs capable of diminishing toxicity and broadening the clinical spectrum of activity of cisplatin. We synthesized new Pt(II) complex analogue containing 1,2-diaminocyclohexane (dach) as carrier ligand and 1,3-bis(diphenyl phosphino)propane (DPPP) as a leaving group. Furthermore, nitrate was added to improve the solubility. A new series of PC-1 [Pt(cis-dach) (DPPP)]. $2NO_3_2$ was synthesized and characterized by their elemental analysis and by various spectroscopic techniques [infrared (IR), $^{13}carbon$ nuclear magnetic resonance (NMR)]. PC-1 was demonstrated acceptable antitumor activity aganist SKOV -3, OVCAR-3 human ovarian adenocarcinomacells and significant activity as compared with that of cisplatin. The toxicity of PC-1 was found quite less than that of cisplatin using MTT, $[^3H]thymidine$ uptake and glucose consumption tests in rabbit proximal tubule cells, human kidney cortical cells and human renal cortical tissues. Based on these results, this novel platinum compound represent a valuable lead in the development of a new anticancer chemotherapeutic agent capable of improving antitumor activity and low toxicity.

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Synthesis and Spectroscopic Characterization of Manganese(II), Iron(III) and Cobalt(III) Complexes of Macrocyclic Ligand. Potential of Cobalt(III) Complex in Biological Activity

  • El-Tabl, Abdou S.;Shakdofa, Mohamad M.E.;El-Seidy, Ahmed M.A.
    • Journal of the Korean Chemical Society
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    • v.55 no.6
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    • pp.919-925
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    • 2011
  • A new series of manganese(II), iron(III) and cobalt(III) complexes of 14-membered macrocyclic ligand, (3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosane-1,8-diamine) have been prepared and characterized by elemental analyses, IR, UV-VIS, $^1H$- and $^{13}C$- NMR spectra, magnetic susceptibilities, conductivities, and ESR measurements. Molar conductance measurements in DMF solution indicate that the complexes are electrolytes. The ESR spectrum for cobalt(III) complex in $CD_3OD+10%D_2O$ after exposure to $^{60}Co-{\gamma}$-rays at 77 K using a 0.2217 M rad $h^{-1}$ vicrad source showed $g_{\perp}$ > $g_{\parallel}$ > $g_e$, indicating that, the unpaired electron site is mainly present in the $d_z2$ orbital with covalent bond character. In this case, the ligand hyperfine tensors are nearly collinear with ${\gamma}$-tensors, so there is no major tendency to bend. Therefore, little extra delocalization via the ring lobe of the $dz^2$ orbital occurs. However, the ESR spectrum in solid state after exposure to $^{60}Co-{\gamma}$-rays at 77 K showed $g_{\parallel}$ > $g_{\perp}$ > $g_e$, indicating that, the unpaired electron site is mainly present in the $d_x2_{-y}2$ ground state as the resulting spectrum contains a large number of randomly oriented molecules provided that, the principle directions of g and A tensors. Manganese (II) complex 2, $[H_{12}LMn]Cl_4.2H_2O$, showed six isotropic lines characteristic to an unpaired electron interacting with a nucleus of spin 5/2, however, iron(III) complex 3, $[H_{12}LFe]Cl_5.H_2O$, showed spectrum of a high spin $^{57}Fe$ (I=1/2), $d^5$ configuration. The geometry of these complexes was supported by elemental analyses, IR, electronic and ESR spectral studies. Complex 1 showed exploitation in reducing the amount of electron adducts formed in DNA during irradiation with low radiation products.

Isolation of Dextran-producing Leuconostoc Zactis from Kimchi

  • Kim, Bong-Joon;Min, Bong-Hee;Kim, Jeongho;Han, Hong-Ui
    • Journal of Microbiology
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    • v.39 no.1
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    • pp.11-16
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    • 2001
  • Tentative identification of Leuconostoc lactis IH23 isolated from kimchi (a fermented vegetable product) has been described previously with 16S rDNA sequencing (Choi, 1., M. Sc. Thesis Inha Univ.1999). This strain produced the slime identified as dextran based on IR, $\^$13/C- and $^1$H-NMR spectroscopic results. Further study proved that the isolate IH23 belongs to a homogeneous genetic group with L. lactis DSM 20202$\^$T/ and L. argentinum DSM 8581$\^$T/. The results showed DNA-DNA homology of 99-100%, 16S rDNA gene sequence similarity (97.7% ), and a phylogenetic relationship although L. argentinum DSM 8581$\^$T/ had lower homology (80-91%). These data indicate that L. argentinum DSM 8581$\^$T/ and the isolate IH23 belong to an identical species with L. lactis DSM 20202$\^$T/at the genetic level, although in carbohydrate fermentation, the isolate IH23 was mast closely related to L. argentinum DSM 8581$\^$T/ and quite different from L. lactis DSM 20202$\^$T/. Here we first report the isolation of consistent phenotypic variation in Leuconostoc lactis. We also emphasize that the nomenclature of subspecies needs to be differentiated into the three strains mentioned above in Leuconostoc lactis.

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The Chirality Conversion Reagent for Amino Acids Based on Salicyl Aldehyde

  • Yoon, Hoe-Jin;Jung, Hein;Ahn, Yun-Soo;Nandhakumar, Raju;Kim, Jun-Soo;Kim, Kwan-Mook
    • Bulletin of the Korean Chemical Society
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    • v.33 no.5
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    • pp.1715-1718
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    • 2012
  • 2-Hydroxy-6-(1-(3-phenylurylphenyl)ethoxy)-benzaldehyde ($\mathbf{2}$) has been synthesized in racemic form from 1,3-Dihydroxybenzene via formylation and reaction with 3-phenyluryl-methylbenzylbromide. The optically pure form of $\mathbf{2}$ was separated by normal silica column chromatography from the imine diastreomer which was obtained by the reaction of racemic mixture of $\mathbf{2}$ with optically pure leucinol. The absolute configuration of the separated enantiomer of $\mathbf{2}$ was decided from the energy calculation of the corresponding imine diastereomers. The activity of $\mathbf{2}$ as a chirality conversion reagent (CCR) for amino acids was determined by $^1H$ NMR analysis. The efficiency of $\mathbf{2}$ is not better than the previous CCRs based on binaththol. Compound $\mathbf{2}$, however, has lower molecular weight compared to other CCRs. This work demonstrates that asymmetric carbon can control the selectivity of amino acids.

Promotion and Inhibition Phenomenon of Natural Gas Hydrates (촉진 및 저해 현상에 의한 천연가스 하이드레이트의 상평형)

  • Lee, Seungmin;Park, Sungmin;Lee, Youngjun;Kang, Boram;Seo, Yongwon
    • 한국신재생에너지학회:학술대회논문집
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    • 2010.06a
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    • pp.217.1-217.1
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    • 2010
  • 본 연구에서는 실제 천연가스 구성성분인 메탄 (90%)+에탄 (7%)+프로판 (3%) 혼합기체를 사용하여 심해저 퇴적부에 존재하는 천연가스 하이드레이트 개발과 가스 하이드레이트 형성법을 이용한 천연가스 수송 및 저장법 개발을 위한 열역학적 특성을 살펴보았다. 천연가스 하이드레이트 개발 연구에서는 심해저 퇴적층의 영향을 살펴보기 위해 기공의 직경이 6.0, 15.0, 30.0, 100.0 nm인 다공성 실리카 젤을 사용하여 기공 직경에 따른 3상(하이드레이트 (H)-물 (LW)-기상 (V)) 평형을 측정하였다. 천연가스 하이드레이트 수송/저장법 연구에서는 천연가스 하이드레이트 형성 압력을 낮추어 줄 수 있는 열역학적 촉진제인 TBAB(농도: 5, 10, 40, 60 wt%)와 THF(농도: 1, 5.56, 10 mol%)를 첨가하여 각각의 농도에 따른 혼합 가스 하이드레이트의 3상 평형을 측정하였다. 그 결과 다공성 매질인 실리카 젤의 경우 기공 직경의 크기가 작아질수록 벌크상태의 하이드레이트에 비해 평형 온도는 낮아지고, 평형 압력은 높아져 저해효과가 커짐을 알 수 있었고, 열역학적 촉진제를 첨가했을 경우 TBAB의 농도가 40 wt%, THF의 농도가 5.56 mol%일 경우 촉진 정도가 가장 크게 나타났으며, 그 이상의 농도일 경우 가스 하이드레이트 형성 반응에 참여하지 않은 TBAB와 THF에 의해 오히려 촉진 정도가 감소하는 것을 알 수 있었다. 또한 $^{13}C$ NMR 분석을 통해 혼합 가스 하이드레이트의 격자 형성과 기체 포집에 따른 구조적인 변화에 대해서도 살펴보았다.

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