• Journal of Radiopharmaceuticals and Molecular Probes
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• v.6 no.1
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• pp.53-58
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• 2020

Pretargeting is a two-component strategy often used for tumor targeting to enhance the tumor-to-background ratio in cancer diagnosis as well as therapy. In the multistep strategy, the highly specific unlabeled monoclonal antibodies (mAbs) with the reactive site is allowed to get localized at tumor site first, and then small and fastclearing radiolabeled chelator with counter reactive site is administered which covalently attaches to mAbs via inverse electron demand Diels-Alder reaction (IEDDA). The catalyst-free IEDDA cycloaddition reaction between 1,2,4,5-tetrazines and strained alkene dienophiles aid with properties like selective bioconjugation, swift and high yielding bioorthogonal reactions are emergent in the development of radiopharmaceutical. Due to its fast pharmacokinetics, the in vivo formed radioimmunoconjugates can be imaged at earlier time points by short-lived radionuclides like ¹⁸F and ⁶⁸Ga; it can also reduce radiation damage to the normal cells. Ultimately, this review elucidates the updated status of pretargeting based on antibodies and IEDDA for tumor diagnosis (PET and SPECT) and therapy.

• Biotechnology and Bioprocess Engineering:BBE
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• v.5 no.1
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• pp.61-64
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• 2000

A series of 5-oxaproline peptide derivatives was synthesized and evaluated for its ability to inhibit the prolyl 4-hydroxylase in vitro. Structure-activity studies show that the 5-oxaproline sequences, prepared by the 1,3-dipolar cycloaddition of the C-methoxycarbonyl-N-mannosyl nitrone in the presence of the ethylene, are more active than the corresponding proline derivatives. Prolyl 4-hydroxylase belongs to a family of $Fe^{2+}-dependent$ dioxygenase, which catalyzes the formation of 4-hydroxyproline in collagens by the hydroxylation of proline residues in -Gly-Xaa-Pro-Gly- of procollagen chains. In this paper we discover the more selective N-Cbz-Gly-Phe-Pro-Gly-OEt $(K_m\;=\;520\;{\mu}M)$ sequences which are showed stronger binding than others in vitro. Therefore, we set out to investigate constrained tetrapeptide that was designed to mimic the proline structure of pep tides for the development of prolyl 4-hydroxylase inhibitor. From this result, we found that the most potent inhibitor is N-Dansyl-Gly-Phe-5-oxaPro-Gly-OEt $(K_i\;=\;1.6\;{\mu}M)$. This has prompted attempts to develop drugs which inhibit collagen synthesis. Prolyl 4-hydroxylase would seem a particularly suitable target for antifibrotic therapy.

• Journal of the Korean Applied Science and Technology
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• v.25 no.4
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• pp.469-476
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• 2008

The synthesis of cyclic carbonate from butyl glycidyl ether (BGE) and carbon dioxide was performed in the presence of three different types of ionic liquid : quarternary ammonium salt, alkyl pyridinium salt, and alkylimidazolium salt. Ionic liquids of different alkyl groups ($C_3$, $C_4$, $C_6$ and $C_8$) and anions ($Cl^-$, $Br^-$ and $I^-$) were used for the reaction which was carried out in a batch autoclave reactor at $60{\sim}120^{\circ}C$. The catalytic activity was increased with increasing alkyl chain length in the order of $C_3$ < $C_4$ < $C_6$. But the ionic liquid with longer alkyl chain length ($C_8$) decreased the conversion of BGE because it is too bulky to form an intermediate with BGE. For the counter anion of the ionic liquid catalysts, the BGE conversion decreased in the order $Cl^-$ > $Br^-$ > $I^-$.

• Bulletin of the Korean Chemical Society
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• v.35 no.10
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• pp.3001-3004
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• 2014

A series of hydroxyl-derivatized quaternized polymers were successfully synthesized by atom transfer radical polymerization (ATRP) and Cu(I)-catalyzed 1,3-dipolar cycloaddition of azide and alkynes (click chemistry), followed by quaternization reactions. ATRP was employed to synthesize poly(2-hydroxyethyl methacrylate) (PHEMA), followed by introduction of alkyne groups using pentynoic acid, leading to HEMA-Alkyne. 2-Azido-1-ethanol and 3-azido-1-propanol were combined with the HEMA-Alkyne backbone via click reaction, resulting in triazole-ring containing hydroxyl-derivatized polymers. Quaternization reactions with methyl iodide were conducted on the triazole ring of each polymer. Molecular weight, molecular weight distribution, and the degree of quaternization (DQ) were determined by gel permeation chromatography (GPC) and $^1H$ NMR spectroscopy. The average molecular weight ($M_n$) of the resulting polymers ranged from $5.9{\times}10^4$ to $1.05{\times}10^5g/mol$ depending on the molecular architecture. The molecular weight distribution was low ($M_w/M_n$ = 1.26-1.38). The transmission spectra of the 0.1 wt % aqueous solutions of the resulting quaternized polymers at 650 nm were measured as a function of temperature. Results showed that the upper critical solution temperature (UCST) could be finely controlled by the level of DQ.

• Macromolecular Research
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• v.15 no.2
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• pp.142-146
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• 2007

Poly[(1-(9-carbazoly1)ethylene)-co-(3-cinnamoyloxyoctyl-9-carbazolyl)] ethylene (PVK-Cin) was prepared by tethering cinnamate pendants to a carbazole group via an octylene spacer. The photopatternability of the new PVK based-polymer was investigated using a photocrosslinking reaction under UV light illumination $(\lambda=254nm)$. Blends of the PVK-Cin and a soluble poly(phenylene vinylene) (CzEh-PPV) were employed to study the photocrosslinking behavior. Well resolved lithographic patterns were observed in these polymer systems. PVK-Cin produced a blue light emitting pattern both before and after the photocrosslinking reaction. The blends of PVK-Cin and CzEh-PPV also showed corresponding emissions at 398 and 525 (560) nm in the film state.

• Bulletin of the Korean Chemical Society
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• v.32 no.1
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• pp.229-238
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• 2011

A series of novel glucose derived benzyl and alkyl 1,2,3-triazoles and their hydrochlorides have been synthesized via Cu(I)-catalyzed 1,3-dipolar cycloaddition. All the new compounds were characterized by MS, IR and NMR spectra. The DEPT, APT, $^1H$-$^1H$ and $^1H-^{13}C$ 2D NMR spectra for some compounds were also recorded. These compounds were evaluated for their in vitro antibacterial activities against Staphylococcus aureus ATCC 29213, Bacillus subtilis, Bacillus proteus, Pseudomonas aeruginosa, Escherichia coli ATCC 25922, and antifungal activities against Candida albicans and Aspergillus fumigatus. The bioactive data revealed that (3R,4S,5S,6S)-2-(hydroxymethyl)-6-methoxy-4,5-bis((1-octyl-1H-1,2,3-triazol-4-yl)methoxy)-tetrahydro-2H-pyran-3-ol 8a exhibited excellent antifungal activity against A. fumigatus with an MIC value of 0.055 mM compared to Fluconazole. It also showed broad inhibitory efficacy against tested bacterial strains with MIC values ranging from 0.049 mM to 0.39 mM.

• Bulletin of the Korean Chemical Society
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• v.35 no.4
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• pp.1144-1148
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• 2014

Here we report a facile synthesis of ruthenium (Ru) Nanoparticles (NPs) by chemical co-precipitation method. The calcination of ruthenium hydroxide samples at $500^{\circ}C$ under hydrogen atmosphere lead to the formation of $Ru^0$ NPs. The size and aggregation of Ru NPs depends on the pH of the medium, and type of surfactant and its concentration. The X-ray diffraction (XRD), scanning electron microscope (SEM) and transmission electron microscope image (TEM) analyses of particles indicated the formation of $Ru^0$ NPs, and have 10 to 20 nm sizes. As-synthesized $Ru^0$ NPs are characterized and investigated their catalytic ability in click chemistry (azidealkyne cycloaddition reactions), showing good results in terms of reactivity. Interestingly, small structural differences in triazines influence the catalytic activity of $Ru^0$ nanocatalysts. Click chemistry has recently emerged to become one of the most powerful tools in drug discovery, chemical biology, proteomics, medical sciences and nanotechnology/nanomedicine. In addition, preliminary tests of recycling showed good results with neither loss of activity or significant precipitation.

• Macromolecular Research
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• v.9 no.6
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• pp.327-331
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• 2001

A new soluble photosensitive poly(amide-co-imide) containing p-phenylenediacryloyl moiety was synthesized and its photoreactivity was characterized. The copolymer was synthesized fromp-phenylenediacryloyl chloride, 4,4-(hexafluoroisopropylidene)diphthalic anhydride and two equivalents of bis(4-aminophenyl) ether in NMP with a subsequent chemical imidization of the resulting poly[amide$\xi$ο-(amic acid)] by acetic anhydride and pyridine. The structure and thermal properties of the polymer were characterized by spectroscopic methods and thermal analyses. The polymer was stable up to 350$\^{C}$, showed good solubility in polar aprotic solvents, and became insoluble after UV irradiation due to the[2+2] cycloaddition of phenylenediacryloyl moiety. Photoreactivity of the polymer was investigated in solution or as a film with respect to the various exposure conditions by UV/Vis spectroscopy. The photosensitivity was noticeably increased with the irradiation temperature, especially in the presense of photosensitizer. The reason for the increased sensitivity was speculated based on the flexibilization of main chain at elevated temperature. Exposure characteristic curves were obtained from the gel fraction experiments after UV irradiation. The sensitivity and contrast at 160$\^{C}$ were measured to be 293 mJ/㎠ and 1.64, respectively.

• Polymer(Korea)
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• v.33 no.1
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• pp.67-71
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• 2009

The stitching method for the synthesis of $Fr\acute{e}chet$-type dendrimers was elaborated using click chemistry between an alkyne and an azide. The core building block, 4,4'-(3,5-bis(azidopropyloxy)benzyloxy)bisphenyl, was designed to serve as the azide functionalities for dendrimer growth via click reactions with the alkyne-dendrons. The synthetic strategy involved an 1,3-dipolar cycloaddition reaction between an azide and an alkyne-functionalized $Fr\acute{e}chet$-type dendrons in the presence of Cu(I) species which is known as the best example of click chemistry.

• Bulletin of the Korean Chemical Society
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• v.8 no.2
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• pp.102-105
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• 1987

2-Methoxy-6-methyl-3,4-dihydro-2H-pyran ($1_a$), 2-ethoxy-3,6-dimethyl-3,4-dihydro-2H-pyran ($1_b$), and 2-ethoxy-3-methyl-6-ethyl-3,4-dihydro-2H-pyran ($1_c$) were prepared by (4 + 2) cycloaddition reaction from the corresponding vinyl ketones and alkyl vinyl ethers. Compounds $1_{a-c}$ were ring-open polymerized by cationic catalyst to obtain alternating head-to-head (H-H) copolymers. For comparison, copolymer of head-to-tail (H-T) was also prepared by free radical copolymerization of the mixture of the corresponding monomers. The H-H copolymer exhibited some differences in its $^1H$ NMR and IR spectra. However, significant differences were showed between the H-H and H-T copolymers in the $^{13}C$ NMR spectra. Also noteworthy was that$T_g$ value of H-H copolymer was higher than that of the corresponding H-T structure. Decomposition temperature of the H-H copolymer was lower than that of the H-T copolymer. All the H-H and H-T copolymers were soluble in common solvents.