- Expanding the structural diversity of hydrophobic ionic liquids: physicochemical properties and toxicity of Gemini ionic liquids
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Ionic liquids (ILs) have been labeled as a promising green alternative to traditional materials; however, many ILs have been discovered to be toxic, especially hydrophobic ILs (HILs). HILs are limited in their structural diversity as most are composed of heteroaromatic cations with long alkyl chains and paired with [BF4], [PF6], or [NTf2] anions. This study aims to diversify HILs by synthesizing two sets of HILs with unique cations and anions. The first set of HILs contain cholinium- and dicholinium-based cations paired with the [NTf2] anion. The [DC-ether] cation is identified as a promising cation and is paired with an array of asymmetric bis(sulfonyl)amide anions to form the second set of HILs. In total, twenty HILs are synthesized. Each HIL is characterized using traditional physicochemical techniques and is evaluted for toxicity usingin vitroandin vivomethods.
- Berdusco, Nicole,Bertz, Colin,Mecozzi, Sandro,Padilla, Marshall S.
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- High-Resolution Solid-State Nuclear Magnetic Resonance and X-ray Structure Study of Choline Chloride, Bromide, and Iodide
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13C and 2H high-resolution solid-state NMR studies of choline chloride and bromide in their radiation-sensitive α phases indicate the onset of reorientational motions at temperatures preceding the transition to their radiation-stable (higher-temperature) β phases.These motions are effectively isotropic both below and above the α-to-β phase transitions.The early onset of the rotational motion and the accompanying drop in the radiation sensitivity strongly suggest that the extreme difference in radiation sensitivity between the α and β phases is principally due to processes affected by the rotational motions and not to crystallographic differences.Choline iodide, which is radiation normal at all temperatures so far studied, shows motions of the two methylene carbons even at room temperature.An X-ray study of the latter compound at ambient temperature indicates P21/m at the possible space group with appreciable disordering between the symmetric positions related by the reflection plane defined by the O, N, and one of the methyl carbons.The reorientational motion in choline iodide becomes completely isotopic only at temperatures close to its third phase transition (ca. 163 deg C).An analysis of the low-temperature spectra shows that in choline chloride and bromide the chemical shift tensor of the N-13CH2 carbon is directed with ?33 approximately parallel to the N-CH2 bond.The 2H spectra (OH position) show that the electric field gradient tensors of all three compounds have similar principal values, are approximately axial, and show the same effects of motion as the 13C.
- Wemmer, D.,Petrouleas, V.,Panaglotopoulos, N.,Filippakis, S. E.,Lemmon, R. M.
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- Hydrophilic quaternary ammonium type ionic liquids. Systematic study of the relationship among molecular structures, osmotic pressures, and water-solubility
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This Letter examines the relationship between the structures of ionic liquids and their water-solubility or osmotic pressure with a number of synthesized quaternary ammonium type ionic liquids and organic salts containing a hydroxyl group as hydrophilic substituted groups on ammonium group cations, and bromide or methylsulfonate as anions. The study found a linear relation between the amount and osmotic pressure of the water-soluble ionic liquids synthesized here, strongly indicating that these water-soluble ionic liquids are perfectly ionized in water like inorganic salts with small diameter ions.
- Kawai, Koji,Kaneko, Kotaro,Yonezawa, Tetsu
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- PH-sensitive self-propelled motion of oil droplets in the presence of cationic surfactants containing hydrolyzable ester linkages
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Self-propelled oil droplets in a nonequilibrium system have drawn much attention as both a primitive type of inanimate chemical machinery and a dynamic model of the origin of life. Here, to create the pH-sensitive self-propelled motion of oil droplets, we synthesized cationic surfactants containing hydrolyzable ester linkages. We found that n-heptyloxybenzaldehyde oil droplets were self-propelled in the presence of ester-containing cationic surfactant. In basic solution prepared with sodium hydroxide, oil droplets moved as molecular aggregates formed on their surface. Moreover, the self-propelled motion in the presence of the hydrolyzable cationic surfactant lasted longer than that in the presence of nonhydrolyzable cationic surfactant. This is probably due to the production of a fatty acid by the hydrolysis of the ester-containing cationic surfactant and the subsequent neutralization of the fatty acid with sodium hydroxide. A complex surfactant was formed in the aqueous solution because of the cation and anion combination. Because such complex formation can induce both a decrease in the interfacial tension of the oil droplet and self-assembly with n-heptyloxybenzaldehyde and lauric acid in the aqueous dispersion, the prolonged movement of the oil droplet may be explained by the increase in heterogeneity of the interfacial tension of the oil droplet triggered by the hydrolysis of the ester-containing surfactant.
- Banno, Taisuke,Kuroha, Rie,Toyota, Taro
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- Preparation method and application of near-infrared dye functionalized intelligent super-molecule vesicle
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The invention discloses a preparation method and an application of a near-infrared dye functionalized intelligent super-molecule vesicle. According to the preparation method, water solubility column [5] aromatic hydrocarbon (WP5) serves as a main body, a biquaternary ammonium salt functionalized near-infrared dye G based on perylene diimide serves as an objective body, the intelligent super-molecule vesicle is constructed by the aid of acting force of the main body and the objective body between the water solubility column [5] aromatic hydrocarbon and the near-infrared dye, and efficient loading of a drug (hydrophobic anticancer drug adriamycin) can be achieved in the self-assembly process. The near-infrared dye G has excellent near-infrared photo-thermal conversion performance and can serve as a photo-thermal treatment reagent of a tumor. The super-molecule drug load vesicle constructed by the aid of the acting force of the main body and the objective body between the WP5 and the near-infrared dye can stably exist in physiology environments and can rapidly and efficiently release a photo-thermal treatment reagent and a chemotherapy drug in tumor acidic micro-environments, collaborative treatment of photo-thermal treatment/chemotherapy is achieved, the super-molecule drug load vesicle is provided with a good drug delivery system, treatment effect of the tumor is greatly improved, and the super-molecule drug load vesicle has an excellent clinical application prospect.
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Paragraph 0046; 0054; 0055
(2018/10/11)
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- Continuous fluorometric assays for acetylcholinesterase activity and inhibition with conjugated polyelectrolytes
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(Figure Presented) Quick but sensitive: A super-quenched fluorogenic complex of a cationic acetylcholine (ACh) derivative with an energy-acceptor tag and an anionic water-soluble conjugated polymer forms the basis of a highly effective fluorescence turn-on assay for studying the enzyme kinetics and inhibition of acetylcholinesterase (AChE; see schematic representation of the assay). FRET = fluorescence resonant energy transfer.
- Feng, Fude,Tang, Yanli,Wang, Shu,Li, Yuliang,Zhu, Daoben
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p. 7882 - 7886
(2008/09/18)
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- Inactivation of acetylcholine esterase under the action of active oxygen species generated by reaction of nitrite ion with hydrogen peroxide
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Inactivation of acetylcholine esterase under the action of hydroxyl radical generated by reaction of nitrite ion with hydrogen peroxide was studied. The inactivating effect of the system nitrite ion-hydrogen peroxide is independent of the nitrite ion concentration and pH and depends on the hydrogen peroxide concentration, with a minimum observed at the molar ratio of hydrogen peroxide to nitrite ion of 2 : 1. The results were explained in terms of the mechanism of radical reactions in the system nitrite ion-hydrogen peroxide. The inactivating effect of this system on acetylcholine esterase is considered to result from peroxide damage of this protein with hydroxyl radical formed by reaction of nitrite ion with hydrogen peroxide.
- Shugalei,Tselinskii,Golubkova,Mikhailova
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p. 655 - 659
(2007/10/03)
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- Dependence of in vitro enzymic hydrolysis of alkyl(2-benzoyl-oxyethyl)dimethylammonium bromides on the alkyl length
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Microsomal esterases were used in (he study of the m vitro enzymic hydrolysis of the ester bond in alkyl(2-benzoyloxyethyl)dimethylammonium bromides. These compounds are potential "soft" disinfectants, easily biodegradable to nontoxic biologically inactive hydrolytic products, namely substituted choline and benzoic acid. Formation of the latter product was used to monitor the kinetics of the reaction. It has been found that the rate of enzymic hydrolysis is substantially influenced by different length of the alkyl chain on the ammonium nitrogen. At the same time, interspecies (rat-mouse) and interorgan (liver-kidney) variability has been observed.
- Olaszova, Eva,Paulikova, Ingrid,Helia, Otto,Svajdlenka, Emil,Devinsky, Ferdinand,Lacko, Ivan
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p. 245 - 251
(2007/10/03)
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