• 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.

• Journal of the Korean Chemical Society
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• v.42 no.1
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• pp.69-77
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• 1998

(3S,4S)-1-(t-Butoxycarbonylmethyl)-3-[(S)-1-(t-butyldimethylsilyloxy)ethyl]-4-(2-diazo-2-ethoxycarbonyl-1-oxoethyl)-2-azetidinone (14) was prepared from 4-styryl-2-azetidinone 7b via a sequence of reactions involving N-alkylation with bromoacetate, ozonolysis, oxidation, condensation with magnesium ethyl malonate, and diazo transfer reaction. (3S,4S)-3-[(S)-1-(t-Butyldimethylsilyloxy)ethyl]-4-(3-diazo-3-ethoxycarbonyl1-hydroxypropyl)-2-azetidinone (21) was also prepared from 4-formyl-2-azetidinone 5b via a sequence of reactions involving Wittig reaction, 1,3-dipolar cycloaddition with ethoxycarbonylformonitrile oxide, catalytic hydrogenation, and diazotization. However, the final cyclization of 14 or 21 to 1-hydroxycarbapenem or 1-hydroxycarbapenam by treating with $Rh_2(OAc)_4$ was unsuccessful.

• Journal of the Korean Chemical Society
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• v.26 no.3
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• pp.172-178
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• 1982

A psoralen-DNA monoadduct analogue, 4',5'-dihydropsoralen (DHP) is synthesized and its photophysical properties such as fluorescence quantum yield (0.08), phosphorescence quantum yield (0.013), fluorescence lifetime (0.95ns), and phosphorescence lifetime(0.039s) were measured in ether solution and in frozen matrix state at 77K. The photocycloaddition reaction of DHP with tetramethylethylene(TME) was carried out in solution and in the frozen state. The major photoadduct was isolated and characterized by elemental analysis and physical methods such as UV, IR, NMR, and mass spectrometry. The major DHP-TME photoadduct was proved to be an 1 : 1 $C_4$-cycloadduct formed through 2 + 2 cycloaddition of the pyrone double bond of DHP to TME.

• 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.

• 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.

• Bulletin of the Korean Chemical Society
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• v.8 no.2
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• pp.96-101
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• 1987

2-Ethoxy-6-methoxy-5-cyano-3,4-dihydro-2H-pyran (1_a$), 2-n-butoxy-6-methoxy-5-cyano-3,4-dihydro-2H-pyr an (1b), 2-isobutoxy-6-methoxy-5-cyano-3,4-dihydro-2H-py ran ($1_c$), and 2-ethoxy-6-methoxy-3-methyl-5-cyano-3,4-dihydro -2H-pyran ($1_d$) were prepared by (4 + 2) cycloaddition reaction of methyl $\alpha$-cyanoacrylate with the corresponding alkyl vinyl ethers. Compounds $1_{a-d}$ were ring-open polymerized by cationic catalyst to obtain alternating head-to-head (H-H) copolymers. For comparison, head-to-tail (H-T) copolymer $3_a$ was also prepared by free radical copolymerization of the corresponding monomers. The H-H copolymer exhibited minor differences in its $1_H% NMR and IR spectra, but in the $^{13}C$ NMR spectra significant differences were observed between the H-H and H-T copolymers. Glass transition temperature ($T_g$) of H-H copolymer was higher than that of the H-T copolymer, but thermal decomposition temperature of the H-H copolymer was lower than that of the H-T copolymer. Compounds $1_a$, $a_b$, and $1_c$, copolymerized well with styrene by cationic catalyst, but compound 1d failed to copolymerize with styrene. All of the H-H and H-T copolymers were soluble in common solvents and the inherent viscosities were in the range 0.2-0.4 dl/g.

• Bulletin of the Korean Chemical Society
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• v.33 no.7
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• pp.2193-2199
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• 2012

A series of novel polytriazoleimides were prepared from various aromatic dianhydrides and a new kind of 1,2,3-triazole-containing aromatic diamine synthesized by the Cu (I)-catalyzed 1,3-dipolar cycloaddition reaction in DMAc, and characterized by FT-IR, $^1H$-NMR, XRD, DSC and TGA techniques. The results show the polytriazoleimides are soluble in most of strong polar solvents and have inherent viscosity values of 0.51-0.62 dL/g(DMAc). The polytriazoleimide films exhibit a tensile strength of 62.3-104.5 MPa and an elongation at breakage of 4.0-8.1%, a glass transition temperature ($T_g$) of $257-275^{\circ}C$, a decomposition temperature (at 5% weight loss) of $350-401^{\circ}C$ in $N_2$ atmosphere, and a dielectric constant of 2.47-3.01 at 10 MHz, which depend on the structure of the polymers. The polytriazoleimides perform good resistance to acid and alkali solution.