16724-63-3Relevant academic research and scientific papers
Preparation and characterization of a novel organic-inorganic nanohybrid "cerasome" formed with a liposomal membrane and silicate surface
Katagiri, Kiyofumi,Hashizume, Mineo,Ariga, Katsuhiko,Terashima, Takashi,Kikuchi, Jun-Ichi
, p. 5272 - 5281 (2007)
A novel class of organic-inorganic hybrids, the so-called cerasomes, which have a bilayer vesicular structure and a silicate surface, has been synthesized by combination of sol-gel reaction and self-assembly of organoalkoxysilanes with a molecular structure analogous to lipids. We have synthesized two cerasome-forming organoalkoxysilanes, N-[N-(3-triethoxysilyl)propylsuccinamoyl] dihexadecylamine (1) and N,N-dihexadecyl-;N"-[6-[(3-triethoxysilyl) propyldimethylammonio]hexanoyl]glycinamide bromide (2), and investigated the synthetic conditions of the cerasomes and their structural characteristics. For the proamphi philic 1, the cerasome was obtained under restricted pH conditions where acid-catalyzed hydrolysis of the triethoxysilyl moiety proceeded without disturbing the vesicle formation. In contrast, the amphiphilic 2, additionally having a hydrophilic quaternary ammonium group, formed stable dispersions of the cerasome in a wide pH range. The hydrolysis behavior of the triethoxysilyl groups was monitored by 1H NMR spectroscopy. Morphology of the cerasomes having the liposomal vesicular structure was confirmed by TEM observations. Extent of the development of siloxane networks through condensation among the silanol groups on the cerasome surface was evaluated by using MALDI-TOF-MS spectrometry. Formation of oligomers of the cerasome-forming lipids in the vesicle was clearly confirmed. Due to the siloxane network formation, the cerasome showed remarkably high morphological stability compared with a reference liposome, as evaluated by surfactant dissolution measurements.
Design of Ionizable Lipids to Overcome the Limiting Step of Endosomal Escape: Application in the Intracellular Delivery of mRNA, DNA, and siRNA
Habrant, Damien,Peuziat, Pauline,Colombani, Thibault,Dallet, Laurence,Gehin, Johan,Goudeau, Emilie,Evrard, Bérangère,Lambert, Olivier,Haudebourg, Thomas,Pitard, Bruno
, p. 3046 - 3062 (2016)
The intracellular delivery of nucleic acid molecules is a complex process involving several distinct steps; among these the endosomal escape appeared to be of particular importance for an efficient protein production (or inhibition) into host cells. In the present study, a new series of ionizable vectors, derived from naturally occurring aminoglycoside tobramycin, was prepared using improved synthetic procedures that allow structural variations on the linker and hydrophobic domain levels. Complexes formed between the new ionizable lipids and mRNA, DNA, or siRNA were characterized by cryo-TEM experiments and their transfection potency was evaluated using different cell types. We demonstrated that lead molecule 30, bearing a biodegradable diester linker, formed small complexes with nucleic acids and provided very high transfection efficiency with all nucleic acids and cell types tested. The obtained results suggested that the improved and "universal" delivery properties of 30 resulted from an optimized endosomal escape, through the lipid-mixing mechanism.
Gadolinium DO3A derivatives mimicking phospholipids; preparation and in vitro evaluation as pH responsive MRI contrast agents
Hovland,Gl?ga?rd,Aasen,Klaveness
, p. 929 - 933 (2001)
A series of Gd-DO3A derivatives (8a-d) mimicking phospholipids have been prepared. Two of the complexes, Gd-HADB-DO3A (8a) and Gd-HADO-DO3A (8b), have been evaluated as pH responsive MRI contrast agents in vitro. The T1-relaxivity (r1/sub
Liposomal nanohybrid cerasomes for mitochondria-targeted drug delivery
Wang, Yanfang,Wang, Beibei,Liao, Han,Song, Xiaojie,Wu, Hao,Wang, Huihui,Shen, Hujun,Ma, Xiaojun,Tan, Mingqian
, p. 7291 - 7299 (2015)
Mitochondrial dysfunctions cause numerous human disorders and the development of mitochondria-targeted nanocarriers for drug delivery has aroused great attention. Herein, we report the synthesis of a liposomal nanohybrid cerasome modified with triphosphonium (TPP) for drug delivery to the mitochondrial matrix. The cerasomes were observed to possess an average size of about 38 nm in diameter, and the theoretical simulation of GBEMP mapping demonstrated that the amphiphilic organotrialkoxysilanes were stable as a bilayer equilibrium conformation after self-assembly. The cerasomes showed good stability, excellent biocompatibility and sustainable drug release behavior. Moreover, the TPP-targeted cerasomes resulted in greater drug accumulation in mitochondria, thus leading to a greater antitumor effect as compared to non-targeted cerasomes by using doxorubicin as a modal drug. The specific accumulation of TPP-targeted cerasomes within mitochondria was also confirmed by using JC-1 as the fluorescent probe to analyze the mitochondrial transmembrane potential change.
Selective Transformations of Triglycerides into Fatty Amines, Amides, and Nitriles by using Heterogeneous Catalysis
Jamil, Md. A. R.,Siddiki, S. M. A. Hakim,Touchy, Abeda Sultana,Rashed, Md. Nurnobi,Poly, Sharmin Sultana,Jing, Yuan,Ting, Kah Wei,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-ichi
, p. 3115 - 3125 (2019/04/26)
The use of triglycerides as an important class of biomass is an effective strategy to realize a more sustainable society. Herein, three heterogeneous catalytic methods are reported for the selective one-pot transformation of triglycerides into value-added chemicals: i) the reductive amination of triglycerides into fatty amines with aqueous NH3 under H2 promoted by ZrO2-supported Pt clusters; ii) the amidation of triglycerides under gaseous NH3 catalyzed by high-silica H-beta (Hβ) zeolite at 180 °C; iii) the Hβ-promoted synthesis of nitriles from triglycerides and gaseous NH3 at 220 °C. These methods are widely applicable to the transformation of various triglycerides (C4–C18 skeletons) into the corresponding amines, amides, and nitriles.
A medicine silicon lipid ultrasound contrast agents in the preparation method and application of
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Paragraph 0046; 0049, (2018/07/30)
The invention provides a preparation method of a drug-loaded silicone grease ultrasonic contrast agent. The preparation method comprises fully dissolving silicone grease, polyethylene glycol phosphate derivatives and a fat-soluble anticancer drug in an organic solvent, adding water into the solution, carrying out whirling, removing the organic solvent, supplying water with a volume 3 times that of the solution into the solution, carrying out ultrasonic disintegration by an ultrasonic disintegrator, simultaneously and fast adding liquid fluorocarbon into the solution to obtain a pre-emulsion, and carrying out dialysis on the pre-emulsion in PBS for 1h to obtain a product. The preparation method has simple processes. The product has the average particle size of about 100nm and is conducive to aggregation at a tumor position by internal EPR effects. Siloxane silicone grease network distribution substantially improves structure stability and prolongs internal blood circulation time. Through HIFU, the drug-loaded silicone grease ultrasonic contrast agent release drugs at a local part of tumor tissue, drug treatment targeting is improved, HIFU treatment effects are substantially improved and HIFU-chemotherapy combined treatment is realized.
Conversion of Primary Amines to Symmetrical Secondary and Tertiary Amines using a Co-Rh Heterobimetallic Nanocatalyst
Chung, Hyunho,Han, Seulgi,Chung, Young Keun,Park, Ji Hoon
supporting information, p. 1267 - 1272 (2018/02/12)
Symmetrical tertiary amines have been efficiently realized from amine and secondary amines via deaminated homocoupling with heterogeneous bimetallic Co2Rh2/C as catalyst (molar ratio Co:Rh=2:2). Unsymmetric secondary anilines were produced from the reaction of anilines with symmetric tertiary amines. The Co2Rh2/C catalyst exhibited very high catalytic activity towards a wide range of amines and could be conveniently recycled ten times without considerable leaching. (Figure presented.).
Preparation method of silica body precursor-organosilane
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Paragraph 0030-0031, (2017/06/02)
The invention discloses a preparation method of a silica body precursor-organosilane. The preparation method comprises the following steps that cetyl alcohol reacts with cetane amine to obtain biscetylamine; biscetylamine reacts with succinic anhydride and then reacts with aminopropyltriethoxysilane to obtain the silica body precursor-organosilane. The preparation method is simple in process, high in product yield and low in production cost and has an important application value.
NOVEL LIPIDS AND LIPID NANOPARTICLE FORMULATIONS FOR DELIVERY OF NUCLEIC ACIDS
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, (2016/05/02)
Compounds are provided having the following structure: (I) or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5, R6, R7, R8, R9, L1, L2, a, b, c, d and e are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.
The C-and N-terminal residues of synthetic heptapeptide ion channels influence transport efficacy through phospholipid bilayers
Djedovic, Natasha,Ferdani, Riccardo,Harder, Egan,Pajewska, Jolanta,Pajewski, Robert,Weber, Michelle E.,Schlesinger, Paul H.,Gokel, George W.
, p. 291 - 305 (2007/10/03)
The synthetic peptide, R2N-COCH2OCH 2CO-Gly-Gly-Gly-PrO-Gly-Gly-Gly-OR′, was shown to be selective for Cl- over K+ when R is n-octadecyl and R′ is benzyl. Nineteen heptapeptides have now been prepared in which the N-terminal and C-terminal residues have been varied. All of the N-terminal residues are dialkyl but the C-terminal chains are esters, 2° amides, or 3° amides. The compounds having varied N-terminal anchors and C-terminal benzyl groups are as follows: 1, R = n-propyl; 2, R = n-hexyl; 3, R = n-octyl; 4, R = n-decyl; 5, R = n-dodecyl; 6, R = n-tetradecyl; 7, R = n-hexadecyl; 8, R = n-octadecyl. Compounds 9-19 have R = n-octadecyl and C-terminal residues as follows: 9, OR′ = OCH2CH3; 10, OR′ = OCH(CH 3)2; 11, OR′ = O(CH2)6CH 3; 12, OR′ = OCH2-c-C6H11; 13, OR′ = O(CH2)9CH3; 14, OR′ = O(CH2)17CH3; 15, NR′2 = N[(CH2)6CH3]2; 16, NHR′ = NH(CH2)9CH3; 17, NR′2 = N[(CH2)9CH3]2; 18, NHR′ = NH(CH2)17CH3; 19, NR′2 = N[(CH2)17CH3]2. The highest anion transport activities were observed as follows. For the benzyl esters whose N-terminal residues were varied, i.e. 1-8, compound 3 was most active. For the C18 anchored esters 10-14, n-heptyl ester 11 was most active. For the C18 anchored, C-terminal amides 15-19, di-n-decylamide 17 was most active. It was concluded that both the C-and N-terminal anchors were important for channel function in the bilayer but that activity was lost unless only one of the two anchoring groups was dominant. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
