72593-77-2Relevant articles and documents
The discovery and enhanced properties of trichain lipids in lipopolyplex gene delivery systems
Mohammadi, Atefeh,Kudsiova, Laila,Mustapa, M. Firouz Mohd,Campbell, Frederick,Vlaho, Danielle,Welser, Katharina,Story, Harriet,Tagalakis, Aristides D.,Hart, Stephen L.,Barlow, David J.,Tabor, Alethea B.,Lawrence, M. Jayne,Hailes, Helen C.
, p. 945 - 957 (2019)
The formation of a novel trichain (TC) lipid was discovered when a cationic lipid possessing a terminal hydroxyl group and the helper lipid dioleoyl l-α-phosphatidylethanolamine (DOPE) were formulated as vesicles and stored. Importantly, the transfection efficacies of lipopolyplexes comprised of the TC lipid, a targeting peptide and DNA (LPDs) were found to be higher than when the corresponding dichain (DC) lipid was used. To explore this interesting discovery and determine if this concept can be more generally applied to improve gene delivery efficiencies, the design and synthesis of a series of novel TC cationic lipids and the corresponding DC lipids was undertaken. Transfection efficacies of the LPDs were found to be higher when using the TC lipids compared to the DC analogues, so experiments were carried out to investigate the reasons for this enhancement. Sizing experiments and transmission electron microscopy indicated that there were no major differences in the size and shape of the LPDs prepared using the TC and DC lipids, while circular dichroism spectroscopy showed that the presence of the third acyl chain did not influence the conformation of the DNA within the LPD. In contrast, small angle neutron scattering studies showed a considerable re-arrangement of lipid conformation upon formulation as LPDs, particularly of the TC lipids, while gel electrophoresis studies revealed that the use of a TC lipid in the LPD formulation resulted in enhanced DNA protection properties. Thus, the major enhancement in transfection performance of these novel TC lipids can be attributed to their ability to protect and subsequently release DNA. Importantly, the TC lipids described here highlight a valuable structural template for the generation of gene delivery vectors, based on the use of lipids with three hydrophobic chains.
Surface-promoted aggregation of amphiphilic quadruplex ligands drives their selectivity for alternative DNA structures
Laguerre, Aurélien,Chang, Yi,Pirrotta, Marc,Desbois, Nicolas,Gros, Claude P.,Lesniewska, Eric,Monchaud, David
, p. 7034 - 7039 (2015)
Scientists are currently truly committed to enhance the specificity of chemotherapeutics that target DNA. To this end, sequence-specific drugs have progressively given way to structure-specific therapeutics. However, while numerous strategies have been implemented to design high-affinity candidates, strategies devoted to the design of high-selectivity ligands are still rare. Here we report on such an approach via the study of an amphiphilic compound, TEGPy, that self-assembles at a liquid/solid interface to provide nanosized objects that are stable in water. The resulting aggregates, identified through atomic force microscopy measurements, were found to disassemble upon interaction with DNA in a structure-specific manner (quadruplex- versus duplex-DNA). Our results provide a fertile ground for devising new strategies aiming at concomitantly enhancing DNA structural specificity and the water-solubility of aggregation-prone ligands. This journal is
triAZOLOtriAZINE DERIVATIVES AS A2A RECEPTOR ANTAGONISTS
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, (2020/01/24)
The present invention provides triazolotriazine derivatives of formula (1) as A2A receptor antagonists. Compounds of formula (1) and pharmaceutical compositions including the compounds can be used for the treatment of disorders related to A2A receptor hyperfunctioning, such as certain types cancers. Compounds of formula (1) and methods of preparing the compounds are disclosed in the invention.
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.
Quaternary ammonium salt functionalized spherical conjugated polymer nanoparticle and antibacterial application thereof
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, (2018/11/26)
The invention discloses a quaternary ammonium salt functionalized spherical conjugated polymer nanoparticle and antibacterial application thereof. The nanoparticle takes hydrophobic conjugated polymeras an inner core; a quaternary ammonium salt functional group molecule forms a housing on the surface through the hydrophobic effect, so that the spherical conjugated polymer nanoparticle is finallyobtained; the structural formula of the hydrophobic conjugated polymer is FORMULA as shown in the description; and the structural formula of the quaternary ammonium salt functional group molecule is FORMULA as shown in the description. Under a light-shielding condition, the conjugated polymer nanoparticle can realize broad-spectrum efficient bacteria resistance without a light source or other energy, has an antibacterial rate which is far higher than that of functional group molecule of the same concentration, is not liable to generate drug resistance, and provides a novel idea for developingan antibacterial nano material in the future.
Glycol-functionalized ionic liquids for high-temperature enzymatic ring-opening polymerization
Zhao, Hua,Afriyie, Lennox O.,Larm, Nathaniel E.,Baker, Gary A.
, p. 36025 - 36033 (2018/11/20)
Enzymatic ring-opening polymerization (ROP) is a benign method for preparing polyesters, such as polylactides and other polylactones. These reactions are typically carried out at relatively high temperatures (60-130 °C), however, there is a deficiency of enzyme-compatible solvents for such thermally-demanding biocatalytic processes. In this study, we have prepared a series of short-chained glycol-grafted ionic liquids (ILs) based on a phosphonium, imidazolium, pyridinium, ammonium, or piperidinium cationic headgroup. Most of these glycol-grafted ILs exhibit relatively low dynamic viscosities (33-123 mPa s at 30 °C), coupled with excellent short-term thermal stabilities with decomposition temperatures (Tdcp) in the 318-403 °C range. Significantly, the long-term thermal stability under conditions matching those for enzymatic ROP synthesis (130 °C for 7 days) is excellent for several of these task-specific ILs. Using Novozym 435-catalyzed ROP, these ILs are demonstrated to be viable solvents for the enzymatic production of reasonable yields (30-48%) of high molecular mass (Mw ～20 kDa) poly(l-lactide) and poly(?-caprolactone) compared to solventless conditions (12-14 kDa).
Polyethylene glycol derivatization of the non-active ion in active pharmaceutical ingredient ionic liquids enhances transdermal delivery
Zavgorodnya, Oleksandra,Shamshina, Julia L.,Mittenthal, Max,McCrary, Parker D.,Rachiero, Giovanni P.,Titi, Hatem M.,Rogers, Robin D.
, p. 1499 - 1508 (2017/02/23)
We report the synthesis of four salts composed of the salicylate anion ([Sal]?) paired with tributylammonium ([HN444]+), choline ([Cho]+), 1-methylpyrrolidinium ([HMPyrr]+), and triethylene glycol monomethyl ether tributylammonium ([mPEG3N444]+) cations. Three of the synthesized salts (room temperature liquids [mPEG3N444][Sal] and [Cho][Sal], and a supercooled liquid [HN444][Sal]) belong to the category of ionic liquids (ILs), and one salt (solid [HMPyrr][Sal]) was a crystalline solid. ILs in their neat form were studied for membrane transport through a silicon membrane, and exhibited higher transport compared to a control experiment with sodium salicylate dissolved in mPEG3OH as solvent, but lower membrane transport compared to salicylic acid dissolved in mPEG3OH. The ‘PEGylated’ IL, [mPEG3N444][Sal], crossed the membrane with an ca. ～2.5-fold faster rate than that of any of the non-PEGylated ILs. This work demonstrates not only that API-ILs can eliminate the use of a solvent vehicle during application and notably transport through a membrane as opposed to a higher melting crystalline salt, but also that the membrane transport can be further enhanced by PEGylation of the counter ions.
Construction and luminescence property of a highly ordered 2D self-assembled amphiphilic bidentate organoplatinum(II) complex
Xiang, Yunjie,Li, Wenjing,Fang, Yuxi,Zhang, Dengqing,Li, Xianying,Jin, Wusong
, p. 27360 - 27369 (2016/03/30)
Rod-coil shaped amphiphilic bidentate dichloro(phenanthroline)platinum(ii) complexes, 1-Pt and 2-Pt, which possess different hydrophilic lateral chains on one side of an identical aromatic rod core, are synthesized. 1-Pt first forms dimers then arranges into well-defined two-dimensional (2D) films consisting of highly ordered molecular arrays both from methanol and on substrate. 2-Pt, as a building-block, yields micrometer-sized rigid 2D sheets without formation of an initial dimer. Red luminescence of the film is induced by self-assembly of nonemissive 1-Pt molecules, whereas sheets based on nonemissive 2-Pt gives weak yellow emission. These results indicate that the coil-rod ratio plays an important role in the structure and optical properties of these self-assemblies. Moreover, the film on the substrate at the macroscopic scale, exhibits multi-stimuli responsiveness, which predicts its application in smart chemosensing devices and probes.
Preparation method of non-ionic fullerene-containing amphiphilic molecule
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Paragraph 0052, (2017/02/02)
The invention relates to a preparation method of a non-ionic fullerene-containing amphiphilic molecule. According to the invention, oligomeric ethylene glycol monomethyl ether bromo-derivative and hydroxy benzene (naphthalene, pyrene) formaldehyde are used as raw materials to synthesize an intermediate product oligomeric ethylene glycol monomethyl ether substituted benzene (naphthalene, pyrene) formaldehyde; and then, oligomeric ethylene glycol monomethyl ether substituted benzene (naphthalene, pyrene) formaldehyde is used as a donor unit and fullerene is used as a receptor so as to synthesize the non-ionic fullerene-containing amphiphilic molecule. The target product obtained has advantages of novel structure, high heat stability and adjustable solubility, can form a self-assembly structure in a solution and under the solvent-free condition, and is suitable for fields of surface chemistry, supramolecular self-assembly, photoelectronic device and the like.
Self-Organization and Vesicle Formation of Amphiphilic Fulleromonodendrons Bearing Oligo(poly(ethylene oxide)) Chains
Chen, Mengjun,Zhu, Hongxia,Zhou, Shengju,Xu, Wenlong,Dong, Shuli,Li, Hongguang,Hao, Jingcheng
, p. 2338 - 2347 (2016/03/26)
A new series of N-methylfulleropyrrolidines bearing oligo(poly(ethylene oxide))-appended Percec monodendrons (fulleromonodendrons, 4a-f) have been synthesized. The substituted position of the oligo(poly(ethylene oxide)) chain(s) on the phenyl group of the Percec monodendron for 4a-f was varied, which is at the 4-, 2,4-, 3,5-, 3,4,5-, 2,3,4- and 2,4,6- position, respectively. 4a-e are obtained as solids at 25°C and can self-organize into lamellar phases as revealed by X-ray diffraction (XRD) and small-angle X-ray scattering (SAXS) measurements, while 4f appears as a viscous liquid. The substitution patterns of the oligo(poly(ethylene oxide)) chain(s) also significantly influence the solubility of 4a-f, especially in ethanol and water. Formation of self-organized supramolecular structures of 4d and 4e in water as well as 4d in ethanol is evidenced from UV-vis and dynamic light scattering (DLS) measurements. Further studies in water using various imaging techniques including transmission electron microscopy (TEM), freeze-fracture TEM (FF-TEM), cryo-TEM and atomic force microscopy (AFM) observations revealed the formation of well-defined vesicles for 4d and plate-like aggregates for 4e, indicating that the aggregation behavior of the fulleromonodendrons is highly dependent on their molecular structures. For 4d in ethanol, only irregular aggregates were noticed, indicating the solvent also plays a role on regulating the aggregation behavior. After functionalization with the Percec monodendrons, 4a-f can preserve the intriguing electrochemical properties of pristine C60 as revealed by cyclic voltammetries. The thermotropic properties of 4a-f have also been investigated. It was found that all of them show good thermal stability, but no mesophases were detected within the investigated temperature ranges. (Figure Presented).
