• The Korean Journal of Physiology
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• v.27 no.2
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• pp.151-162
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• 1993

In order to investigate the effect of intracellular cyclic GMP on calcium current the whole-cell patch clamp technique with internal perfusion method was used in isolated ventricular myocytes of the rabbit. Cyclic GMP, 8-bromo-cyclic GMP, cyclic AMP, isoprenaline and forskolin were perfused into cells and their effects on calcium current were analysed by applying depolarizing step pulses of + 10 mV in amplitude far 300 msec from holding potential of - 40 mV. Not only cyclic AMP $(100\;{\mu}M)$ but also cyclic GMF $(100\;{\mu}M)$ increased the basal calcium current. 8-Bromo-cyclic GMP $(100\;{\mu}M)$, a good stimulator of the cyclic GMP-dependent protein kinase, also increased the basal calcium current and its peak amplitude of calcium current was larger than that in the presence of cyclic AMP or cyclic GMP alone. In the presence of $100\;{\mu}M$ cyclic GMP or $100\;{\mu}M$ 8-bromo-cyclic GMP, already augmented calcium current was potentiated by intracellular application of $100\;{\mu}M$ cyclic AMP or $1\;{\mu}M$ isoprenaline or $1\;{\mu}M$ forskolin. In the presence of cyclic GMP, acetylcholine reduced the calcium current only when the calcium current was increased by isoprenaline. From the above results it could be concluded that intracellular perfusion with cyclic GMP increases the basal calcium current via a mechanism involving a cyclic GMP-dependent protein kinase.

• Korean Journal of Fisheries and Aquatic Sciences
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• v.47 no.1
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• pp.45-51
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• 2014

Scuticociliates are regarded as serious pathogens in marine aquaculture worldwide. In Korea, they cause mass-mortalities in fish such as the commercially important olive flounder Paralichthys olivaceus. In particular, mixed infections of scuticociliates with pathogenic bacteria have been commonly reported. During efforts to identify natural marine-algae derived products that possess anti-bacterial and anti-scuticociliate properties, we found that an 80% methanolic extract of the red alga Polysiphonia morrowii Harvey exhibits both anti-scuticociliate activity against Miamiensis avidus, which is a major causative agent of scuticociliatosis, and anti-bacterial activities against fish pathogenic bacteria. Activity-guided fractionation and isolation of the 80% methanolic extract of P. morrowii yielded three bromophenols, which were identified as 3-bromo-4,5-dihydroxybenzyl methyl ether (1), 3-bromo-4,5-dihydroxybenzaldehyde (2) and urceolatol (3) based on spectroscopic analyses. 3-bromo-4,5-dihydroxybenzyl methyl ether (1) showed the highest anti-bacterial and anti-scuticociliate activities, with a minimal inhibitory concentration (MIC) of $62.5{\mu}g/mL$ (against Vibrio anguillarum) and minimal lethal concentration (MLC) of 62.5 ppm (in seawater). Investigations of the anti-bacterial and anti-scuticociliate activities of seventeen bromophenol derivatives, including the three isolated natural bromophenols, showed that the existence of an electron donating group or atom with a non-covalent electron pair at $C_4$ of the 2-bromophenol structure may be important in anti-scuticociliate activity. These findings suggest that the extract and bromophenol derivatives of P. morrowii may provide useful alternatives in aquaculture anti-scuticociliate therapies.

• Journal of the Korean Chemical Society
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• v.36 no.4
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• pp.579-583
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• 1992

Stereoselective synthesis of farnesol, (2E, 6E)-3,7,11-trimethyldodeca-2,6,10-tiren-1-ol(1), was carried out using 5-bromo-2-methylpent-2-ene(2) as a starting material. After conversion of 5-bromo-2-methylpent-2-ene(2) to the corresponding iodide compound, 5-(4-methylpent-3-enyl)-2,3-dihydrofuran(4) was obtained by alkylation of 5-lithio-2,3-dihydrofuran with 5-iodo-2-methylpent-2-ene. Ni(0)-catalyzed coupling reaction of the dihydrofuran 4 with MeMgI was proceeded to give (3E)-4,8-dimethylnona-3,7-dien-1-ol(5) in 72% yield. The resultant homoallylic alcohol 5 was converted to the (5E)-6,10-dimethylundeca-5,9-dien-2-one(8) in 4 steps. Compound 8 was condensed with dimethylmethoxycarbonylmethylphosponate in benzene follwed by $NaBH_4$ reduction in EtOH to yield (2E, 6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol(1). Ni(0)-catalyzed coupling reaction of MeMgI with dihydrofuran 4 was a key step in this synthesis of farnesol(1).

• Biomolecules & Therapeutics
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• v.7 no.3
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• pp.227-233
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• 1999

The effects of 2-bromo-3-(3,5-tert-butyl-4-hydroxylphenyl)-1,4-naphthalenedione(TPN2), a synthetic vitamin K derivative, on platelet aggregation and its action mechanisms were investigated in rat platelet. TPN2 inhibited the platelet aggregation induced by collagen($10\mu\textrm{g}$/ml), thrombin(0.1 U/ml), A23187($10\mu\textrm{M}$) and arachidonic acid($100\mu\textrm{M}$) in concentration-dependent manner with $IC_{50}$ values of 6.5$\pm$1.3, 59.3$\pm$4.5, 13.0$\pm$2.37 and 2.9$\pm$$1.0\mu\textrm{M}$, respectively. Collagen-induced serotonin release was significantly reduced by TPN2. The elevation of intracellular free $Ca^{2+}$ concentration ([$Ca^{2+}$]i) by collagen stimulation was greatly decreased by the pretreatment of TPN2, which was due to the inhibition of calcium release from intracellular store and influx from outside of the cell. TPN2 also significantly reduced the thromboxane $A_2$($TXA_2$) formation in a concentration-dependent manner. The collagen-induced arachidonic acid (AA) release in [$^3H$]-AA incorporated platelet, an indicative of the phospholipase $A_2$ activity, was decreased by TPN2 pretreatment. TPN2 significantly inhibited the activity of thromboxane synthase, but did not affect the cyclooxygenase activity. From these results. it is suggested that TPN2 exert its antiplatelet activity through the inhibition of the intra-cellular $Ca^{2+}$ mobilization and the decrease of the $TXA_2$ synthesis.

• Bulletin of the Korean Chemical Society
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• v.30 no.10
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• pp.2318-2328
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• 2009

Massive deadenylation of adenine based-nucleosides induced by halogenated alkanes at the physiological condition have been observed. For the study of deadenylation effects by the different substituents and/or functionality in halogenated alkanes, diverse kinds of halogenated alkanes were incubated with adenine based-nucleosides (ddA, dA and adenosine) for 48 h at the physiological condition (pH 7.4, $37\;{^{\circ}C}$), which were analyzed by HPLC and further confirmed by LC-MS. Among the sixteen different halogenated alkanes, we observed massive deadenylation of nucleosides by 2-bromo-2-methylpropane, 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane. The order of deadenylation rate was highest in 2-bromo-2-methylpropane followed by 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane. In addition, time and dose response relationship of deadenylation in adenine based-nucleosides induced by 2-bromo-2-methylpropane, 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane at the physiological condition were investigated. In addition, deadenylation of calf thymus DNA induced by halogenated alkanes was also investigated. These results suggest that the toxic effect of certain halogenated alkanes might be from the depurination of nucleosides.

• Journal of the Korean Chemical Society
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• v.31 no.1
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• pp.94-97
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• 1987

In a converting reaction of $p-bromo-\alpha-diethylaminoacetophenone$ (1a) and $p-bromo-\alpha-piperidinoacetophenone$ (1b) with KCN and $(NH_4)_2CO_3$, to hydantoin, the expected 5-(p-bromophenyl)-5-diethylaminomethylhydantion (2a) and 5-(p-bromophenyl)-5-piperidinomethylhydantoin (2b) were not formed. Diethylaminomethyl group and piperidinomethyl group were eliminated and p,p'-dibromodiphenylhydantil (4), which might be formed through dimerization of 5-(bromophenyl)-hydantoin (3), and p-bromobenzoic acid (5), which was formed through a degradation of 5-(bromophenyl)-hydantoin, were obtained. In the case of $p-bromo-\alpha-morpholinoacetophenone$ (1c), the expected 5-(p-bromophenyl)-5-morpholinomethylhydantoin (2c) was formed.

• Bulletin of the Korean Chemical Society
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• v.30 no.12
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• pp.2949-2958
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• 2009

Massive deguanylation of guanine based-nucleosides induced by halogenated alkanes at the physiological condition have been observed. For the study of deguanylation effects by the different substituents and/or functionality in halogenated alkanes, diverse kinds of halogenated alkanes were incubated with guanine based-nucleosides (ddG, dG and guanosine) for 48 h at the physiological condition (pH 7.4, 37$^{\circ}C$), which were analyzed by HPLC and further confirmed by LC-MS. Among the sixteen different halogenated alkanes, we observed massive deguanylation of nucleosides by 2-bromo-2-methylpropane, 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane. The order of deguanylation rate was highest in 2-bromo-2-methylpropane followed by 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane. In addition, time and dose response relationship of deguanylation in guanine basednucleosides induced by 2-bromo-2-methylpropane, 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane at the physiological condition were investigated. Deguanylation of calf thymus DNA induced by halogenated alkanes was also investigated. These results suggest that the toxic effect of certain halogenated alkanes might be from the depurination of nucleosides.

• The Korean Journal of Nuclear Medicine
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• v.33 no.3
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• pp.298-305
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• 1999

Purpose: N-(3-[$^{18}F$]Fluoropropyl)-$2{\beta}$-carbomethoxy-$3{\beta}$-(4-iodophenyl)nortropane [$^{18}F$]FP-CIT) has been shown to be very useful for imaging the dopamine transporter. However, synthesis of this radiotracer is somewhat troublesome. In this study, we used a new method for the preparation of [$^{18}F$]FP-CIT to increase radiochemical yield and effective specific activity. Materials and Methods: [$^{18}F$]FP-CIT was prepared by N-alkylation of nor-${\beta}$-CIT (2 mg) with 3-bromo-1-[$^{18}F$]fluoropropane in the presence of $Et_3N$ (5-6 drops of $DMF/CH_3CN$, $140^{\circ}C$, 20 min). 3-Bromo-1-[$^{18}F$]fluoropropane was synthesized from $5{\mu}L$ of 3-bromo-1-trifluoromethanesulfonyloxypropane (3-bromopropyl-1-triflate) and $nBu_4N^{18}F$ at $80^{\circ}C$. The final compound was purified by reverse phase HPLC and formulated in 13% ethanol in saline. Results: 3-Bromo-1-[$^{18}F$]fluoropropane was obtained from 3-bromopropyl-1-triflate and $nBu_4N^{18}F$ in 77-80% yield. N-Alkylation of nor-${\beta}$-CIT with 3-bromo-1-[$^{18}F$]fluoropropane was carried out at $140^{\circ}C$ using acetonitrile containing a small volume of DMF as the solvents. The overall yield of [$^{18}F$]FP-CIT was 5-10% (decay-corrected) with a radiochemical purity higher than 99% and effective specific activity higher than the one reported in the literature based on their HPLC data. The final [$^{18}F$]FP-CIT solution had the optimal pH (7.0) and it was pyrogen-free. Conclusion: In this study, 3-bromopropyl-1-triflate was used as the precursor for the [$^{18}F$]fluorination reaction and new conditions were developed for purification of [$^{18}F$]FP-CIT by HPLC. We established this new method for the preparation of [$^{18}F$]FP-CIT, which gave high effective specific activity and relatively good yield.

• Bulletin of the Korean Chemical Society
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• v.18 no.2
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• pp.129-130
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• 1997

• Journal of the Korean Chemical Society
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• v.10 no.2
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• pp.51-53
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• 1966

A new conventional method for the preparation of 5-iodo, chloro-, and bromo-6-methyluracil by Sandmeyer reaction was described. According to this procedure, 5-halo-6-methyluracils have been prepared in high yields (up to 70%) without any difficulties to obtain highly pure products. No appreciable competing reaction was observed.