- Diol glycidyl ether-bridged cyclens: Preparation and their applications in gene delivery
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Polymeric 1,4,7,10-tetraazacyclododecanes (cyclens) using diol glycidyl ether with different chain length as bridges (5a-e) were designed and synthesized from various diols, 1,7-diprotected cyclen and epichlorohydrin. The molecular weights of the title polymers were measured by GPC with good polydispersity. Agarose gel retardation and fluorescent titration using ethidium bromide showed good DNA-binding ability of 5. They could retard plasmid DNA (pDNA) at an N/P ratio of 4-6 and form polyplexes with sizes around 100-250 nm from an N/P ratio of 10 to 60 and relatively low zeta-potential values (5-22 mV). The cytotoxicity of 5 assayed by MTT is much lower than that of 20 kDa PEI. In vitro transfection against A549 and 293 cells showed that the transfection efficiency (TE) of 5c/DNA polyplexes is close to that of 20 kDa PEI at an N/P ratio of 5. Structure-activity relationship (SAR) of 5 was discussed in their DNA-binding, cytotoxicity, and transfection studies. The TE of 5c/DNA polyplexes could be improved by the introduction of 50 μM of chloroquine, the endosomolytic agents, to pretreated cells. These studies may extend the application areas of macrocyclic polyamines, especially for cyclen.
- Yi, Wen-Jing,Feng, Zhi-Hua,Zhang, Qin-Fang,Zhang, Ji,Li, Ling-Dong,Zhu, Wen,Yu, Xiao-Qi
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- TACN-based oligomers with aromatic backbones for efficient nucleic acid delivery
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Cationic oligomers with a rigid aromatic backbone were first applied as non-viral gene delivery vectors. These materials showed better DNA condensation ability than their flexible analogues. In vitro transfection experiments revealed that the materials with more rigid backbone exhibited considerably higher TE and lower cytotoxicity than 25 kDa PEI. This journal is the Partner Organisations 2014.
- Yi, Wen-Jing,Yu, Xing-Chi,Wang, Bing,Zhang, Ji,Yu, Qing-Ying,Zhou, Xue-Dong,Yu, Xiao-Qi
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- PROCESS FOR PRODUCING EPOXY COMPOUND
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According to the present, invention, a process for producing an epoxy compound, where an epoxy compound can be selectively produced from olefins with good yield at low cost in a safe manner by a simple operation under mild conditions without using a quaternary ammonium salt or a metal compound, is provided. The present invention relates to a process for producing an epoxy compound, comprising epoxidizing a carbon-carbon double bond of an organic compound having a carbon-carbon double bond by using hydrogen peroxide as an oxidant, wherein the epoxidation is carried by out using an organic nitrile compound and an organic amine compound.
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Page/Page column 6-7
(2012/02/06)
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- Dermal penetration and metabolism of five glycidyl ethers in human, rat and mouse skin
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1. Glycidyl ethers (GE), an important class of industrial chemicals, are considered to be potentially mutagenic in vivo because some GE have been shown to be direct mutagens in short-term in vitro tests. 2. The percutaneous penetration and metabolism of representatives of different classes of GE was studied in the fresh, full-thickness C3H mouse, and dermatomed human and Fisher 344 rat skin to determine th apparent permeability constants, lag times and metabolic profiles. 3. Five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol (HDDGE) and the GE of 1-dodecanol (C12GE) and o-cresol (o-CGE), were synthesized by reaction of their alcohols with epichlorohydrin. Their radiolabelled analogues were synthesized with a 14C-label using [U-14C]-epichlorohydrin. 4. There was a large variation (four orders of magnitude) in percutaneous penetration between the five GE. In general, penetration through full-thickness mouse skin was higher than through dermatomed rat skin, whereas dermatomed human skin was the least permeable. The permeability increased in the order YX4000 12GE 12GE and o-CGE penetrated the skin unchanged. For o-CGE, but none of the other GE, the percentage of the applied dose that penetrated the skin unchanged increased over time. 7. The large variation in response observed with the five selected GE indicates that GE should not be considered as a single class of compounds but rather on the basis of their individual properties.
- Boogaard,Denneman,Van Sittert
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p. 469 - 483
(2007/10/03)
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- Metabolic inactivation of five glycidyl ethers in lung and liver of humans, rats and mice in vitro
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1. Some glycidyl ethers (GE) have been shown to be direct mutagens in short-term in vitro tests and consequently GE are considered to be potentially mutagenic in vivo. However, GE may be metabolically inactivated in the body by two different enzymatic routes: conjugation of the epoxide moiety with the endogenous tripeptide glutathione (GSH) catalysed by glutathione S-transferase (GST) or hydrolysis of the epoxide moiety catalysed by epoxide hydrolase (EH). 2. The metabolic inactivation of five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol (HDDGE) and the GE of 1-dodecanol (C12GE) and o-cresol (o-CGE), has been studied in subcellular fractions of human, C3H mouse and F344 rat liver and lung. 3. All GE were chemically very stable and resistant to aqueous hydrolysis, but were rapidly hydrolysed by EH in cytosolic and microsomal fractions of liver and lung. The aromatic GE were very good substrates for EH. In general, microsomal EH is more efficient than cytosolic EH in hydrolysis of GE, and human microsomes are more efficient than rodent microsomes. 4. The more water-soluble GE, o-CGE and HDDGE, were good substrates for GST whereas the more lipophilic GE, YX4000 and C12GE, were poor substrates for GST. In general, rodents are more efficient in GSH conjugation of GE than humans. 5. In general, the epoxide groups of YX4000 are the most and those of HDDGE the least efficiently inactivated of the five GE under study. For the other three GE no general trend was observed: the relative efficiency of inactivation varied with organ and species. 6. The large variation in metabolism observed with five representative GE indicate that GE have variable individual properties and should not be considered as a single, homogenous class of compounds.
- Boogaard,De Kloe,Bierau,Kuiken,Borkulo,VanSittert
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p. 485 - 502
(2007/10/03)
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- Synthesis of [14C]-Labelled glycidyl and glycerol ethers of aliphatic and aromatic alcohols.
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The synthesis of [14C]-labelled glycidyl ethers and the corresponding glycerol ethers is described for the monofunctional compounds 1-dodecanol and ortho-cresol and the bifunctional compounds 4,4'-dihydroxy-3,3',5,5'-tetramethyl biphenyl and 1,6-hexanediol. The synthesis is based on reaction between the alcohol and [U-14C]-epichlorohydrin. The aromatic compounds have been converted to the corresponding glycidyl ethers by using sodium hydroxide and the aliphatic compounds by using tin(IV) chloride as a catalyst. Thus radio-labelled glycidyl ethers were obtained in yields between 50-80, with a chemical purity of > 92 and a radiochemical purity of > 95 by HPLC. The specific activities of the glycidyl ethers were approximately 0.2 mCi/mmol for the monofunctional compounds and approximately 0.4 mCi/mmol for the bifunctional compounds.
- Van Elburg,Ormskerk,De Kloe,Boogaard
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p. 147 - 167
(2007/10/03)
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- Synthesis of alkyloxy (di)alkylamino propanols, hydroxy alkyloxy (di)alkylamino propanols, and the dimer compounds for use as fuel additives
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Alkyl glycidyl ethers and bis glycidyl ethers, synthesized in a heterogeneous weakly hydrous medium, were condensed with primary or secondary amines to obtain 3-alkyloxy propanolaminesor bis alkyloxy propanolamines in a regioselective manner. The compounds were characterized by conventional spectroscopic methods, and complete nuclear magnetic resonance data are given. Their high-temperature stability, their good emulsifying power, their oxidation, and corrosion inhibition make these compounds suitable for solubilizing ethanol-diesel fuel blends.
- Satge De Caro, Pascale,Mouloungui, Zephirin,Gaset, Antoine
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p. 235 - 240
(2007/10/03)
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