13044-38-7Relevant academic research and scientific papers
Design and synthesis of amphiphilic 2-hydroxybenzylphosphonium salts with antimicrobial and antitumor dual action
Lyubina, Anna P.,Mironov, Vladimir F.,Pashirova, Tatiana N.,Sapunova, Anastasiia S.,Shaihutdinova, Zukhra M.,Tatarinov, Dmitry A.,Terekhova, Natalia V.,Voloshina, Alexandra D.,Zakharova, Lucia Ya.
, (2020)
Here we report the synthesis and biological evaluation of a series of new 2-hydroxybenzylphosphonium salts (QPS) with antimicrobial and antitumor dual action. The most active compounds exhibit antimicrobial activity at a micromolar level against Gram-positive bacteria Sa (ATCC 209p and clinical isolates), Bc (1–2 μM) and fungi Tm and Ca, and induced no notable hemolysis at MIC. The change in nature of substituents of the same length led to a drastic change of biological activity. Self-assembly behavior of the octadecyl and oleyl derivatives was studied. QPS demonstrated self-assembly within the micromolar range with the formation of nanosized aggregates capable of the solubilizing hydrophobic probe. The synthesized phosphonium salts were tested for cytotoxicity. The most potent salt was active against on M?Hela cell line with IC50 on the level of doxorubicin and good selectivity. According to the cytofluorimetry analysis, the salts induced mitochondria-dependent apoptosis.
Designing pH-sensitive gemini nanoparticles for non-viral gene delivery into keratinocytes
Donkuru, McDonald,Wettig, Shawn D.,Verrall, Ronald E.,Badea, Ildiko,Foldvari, Marianna
, p. 6232 - 6244 (2012)
This study aimed to develop a more effective non-viral gene delivery system for keratinocyte transfection. To this end, gemini nanoparticles were formulated from plasmid DNA, the lipid DOPE (dioleoylphosphatidylethanolamine) and surfactants, where the sur
Water-soluble lipophilic MR contrast agents for cell membrane labeling
Carney, Christiane E.,MacRenaris, Keith W.,Meade, Thomas J.
, p. 971 - 977 (2015)
Long-term cell tracking using MR imaging necessitates the development of contrast agents that both label and are retained by cells. One promising strategy for long-term cell labeling is the development of lipophilic Gd(III)-based contrast agents that anch
O,O-Silyl Group Migrations in Quinic Acid Derivatives: An Opportunity for Divergent Synthesis
Holmstedt, Suvi,Efimov, Alexander,Candeias, Nuno R.
, p. 3083 - 3087 (2021)
The O,O-silyl group migrations on a quinic acid-derived cyclitol have been studied, and the ease of migration was observed to be dependent on the silicon substituents and reaction conditions. Conditions were found to improve the formation of a main isomer during the O,O-silyl group migrations that could be integrated into the formal synthesis of vitamin D receptor modulator VS-105 and in the first total synthesis of a metabolite from the African ant Crematogaster nigriceps.
Quantitative Treatment of the Rotational Dynamics of Flexible-Chain Molecules. 13C NMR Relaxation Study of Hydrocarbon Chains Attached to the Fluorene Anchor
Pissas, D.,Dais, Photis,Mikros, E.
, p. 263 - 275 (1994)
13C spin-lattice relaxation times (T1) and nuclear Overhauser enhancements (NOEs) were measured for individual carbons in flexible-chain molecules consisting of a hydrocarbon chain attached to fluorene moiety at position 3 through an ester bond.Quantitative treatment of the relaxation data of the ring carbons revealed an anisotropic motion for all the molecules studied.The relaxation times of the chain carbons were analysed in terms of a correlation function describing multiple internal rotations about successive C-C bonds.The results (rotational diffusion constants) were used to discuss features of the chain mobility as a function of chain length and chain unsaturation.The assumptions involved in the quantitative treatment were examined and the values were compared with those of n-alkanes and lipid bilayers. - Keywords: 13C NMR spin-lattice relaxation times Rotational diffusion constants Rotational dynamics Overall and internal motions Hydrocarbon-chain esters of fluorene-3-carboxylic acid
Synthesis and solution properties of gemini surfactants containing oleyl chains
Li, Xingfu,Wettig, Shawn D.,Wang, Chuanzhong,Foldvari, Marianna,Verrall, Ronald E.
, p. 3172 - 3178 (2005)
Gemini surfactants 18:1-s-18:1, where s = 2, 3, and 6 methylene groups and 18:1 refers to oleyl carbon chains, have been synthesized, characterized and a number of micelle solution properties measured by using electrical conductance, fluorescence probe em
A Facile and Efficient Method for the Synthesis of Labeled and Unlabeled Very Long Chain Polyunsaturated Fatty Acids
Hamberg, Mats
, p. 489 - 494 (2021/04/19)
Several methods are available for elongation of fatty acid acyl chains. The present paper describes adaptation to the fatty acid field of a previously published protocol for manganese-based Wurtz type coupling of alkyl bromides. 22-Bromo-3(Z),6(Z),9(Z),12(Z),15(Z),18(Z)-docosahexaene, easily prepared from 4(Z),7(Z),10(Z),13(Z),16(Z),19(Z)-docosahexaenoic acid, was coupled to homologous ω-bromoesters by stirring for 4 hours at 40°C in the presence of manganese powder, a nickel catalyst and terpyridine. This afforded in yields of 70–75% a series of ω3-hexaenoates of chain lengths of 32–40 carbons. The corresponding fatty acids of >98% purity were obtained following saponification and final purification. By using methyl [2,2,3,3,4,4-2H6]10-bromodecanoate as coupling partner it was possible to prepare a very long chain fatty acid in isotopically labeled form, i.e., [2,2,3,3,4,4-2H6]14(Z),17(Z),20(Z),23(Z),26(Z),29(Z)-dotriacontahexaenoic acid. Also prepared were the monounsaturated long chain fatty acids 15(Z)-octadecenoic acid and 15(Z)-tetracosenoic acid. Very long chain fatty acids have been isolated from retina and other tissues and are of biological relevance. The methodology described will assist in further analytical and biological studies in this field.
OLEIC ACID DERIVATIVES, PHARMACEUTICAL COMPOSITION OR FOOD COMPOSITION COMPRISING SAID OLEIC ACID DERIVATIVES, AND THEIR USES
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Page/Page column 36-37, (2019/12/25)
This invention relates to oleic acid derivative comprising a hydrophobic part C17H33 linked to a particular polar head part "A", especially for use as a medicament, for instance, for the treatment of a disorder caused by the GPR120 receptor and/or the CD36 receptor, comprising administering to a subject in need thereof a therapeutically effective amount of said oleic acid derivative or of said pharmaceutical composition. The invention also relates to the use of said oleic acid derivative as a food composition.
At Long Last: Olefin Metathesis Macrocyclization at High Concentration
Sytniczuk, Adrian,Dabrowski, Micha?,Banach, ?ukasz,Urban, Mateusz,Czarnocka-?niada?a, Sylwia,Milewski, Mariusz,Kajetanowicz, Anna,Grela, Karol
supporting information, p. 8895 - 8901 (2018/07/05)
Macrocyclic lactones, ketones, and ethers can be obtained in the High-Concentration Ring-Closing Metathesis (HC-RCM) reaction in high yield and selectivity at concentrations 40 to 380 times higher than those typically used by organic chemists for similar macrocyclizations. The new method consists of using tailored ruthenium catalysts together with applying vacuum to distill off the macrocyclic product as it is formed by the metathetical backbiting of oligomers. Unlike classical RCM, no large quantities of organic solvents are used, but rather inexpensive nonvolatile diluents, such as natural or synthetic paraffin oils. Moreover, use of a protecting atmosphere or a glovebox is not needed, as the new catalysts are perfectly moisture and air stable. In addition, some other cyclic compounds previously reported as unobtainable by RCM in neat conditions, or in high dilutions even, can be formed with the help of the HC-RCM method.
Synthesis of Phosphonic Acid Ligands for Nanocrystal Surface Functionalization and Solution Processed Memristors
De Roo, Jonathan,Zhou, Zimu,Wang, Jiaying,Deblock, Loren,Crosby, Alfred J.,Owen, Jonathan S.,Nonnenmann, Stephen S.
, p. 8034 - 8039 (2018/10/25)
Here, we synthesized 2-ethylhexyl, 2-hexyldecyl, 2-[2-(2-methoxyethoxy)ethoxy]ethyl, oleyl, and n-octadecyl phosphonic acid and used them to functionalize CdSe and HfO2 nanocrystals. In contrast to branched carboxylic acids, postsynthetic surface functionalization of CdSe and HfO2 nanocrystals was readily achieved with branched phosphonic acids. Phosphonic acid capped HfO2 nanocrystals were subsequently evaluated as memristors using conductive atomic force microscopy. We found that 2-ethylhexyl phosphonic acid is a superior ligand, combining a high colloidal stability with a compact ligand shell that results in a record-low operating voltage that is promising for application in flexible electronics.
