6609-64-9Relevant academic research and scientific papers
Self-assembled micelles from an amphiphilic hyperbranched copolymer with polyphosphate arms for drug delivery
Liu, Jinyao,Huang, Wei,Pang, Yan,Zhu, Xinyuan,Zhou, Yongfeng,Yan, Deyue
, p. 10585 - 10592 (2010)
A novel type of amphiphilic hyperbranched multiarm copolymer [H40-star-(PLA-b-PEP-OH)] was synthesized through a two-step ring-opening polymerization (ROP) procedure and applied to drug delivery. First, Boltorn H40 was used as macroinitiator for the ROP of l-lactide to form the intermediate (H40-star-PLA-OH). Then, the ROP of ethyl ethylene phosphate was further initiated to produce H40-star-(PLA-b-PEP-OH). The resulting hyperbranched multiarm copolymers were characterized by 1H, 13C, and 31P NMR, GPC, and FTIR spectra. Benefiting from the amphiphilic structure, H40-star-(PLA-b-PEP-OH) was able to self-assemble into micelles in water with an average diameter of 130 nm. In vitro evaluation of these micelles demonstrated their excellent biocompatibility and efficient cellular uptake by methyl tetrazolium assay, flow cytometry, and confocal laser scanning microscopy measurements. Doxorubicin-loaded micelles were investigated for the proliferation inhibition of a Hela human cervical carcinoma cell line, and the Doxorubicin dose required for 50% cellular growth inhibition was found to be 1 μg/mL. These results indicate that H40-star-(PLA-b-PEP-OH) micelles can be used as safe, promising drug-delivery systems.
Synthesis and ring-opening polymerization of glycidyl ethylene phosphate with a formation of linear and branched polyphosphates
Nifant'ev, Ilya E.,Shlyakhtin, Andrey V.,Bagrov, Vladimir V.,Komarov, Pavel D.,Kosarev, Maxim A.,Tavtorkin, Alexander N.,Minyaev, Mikhail E.,Roznyatovsky, Vitaly A.,Ivchenko, Pavel V.
, p. 155 - 157 (2018)
Newly obtained cyclic monomer, glycidyl ethylene phosphate, readily forms branched or linear polymers via ring-opening polymerization catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene or by [(BHT)Mg(OBn)(THF)]2, respectively. The polymers obtained are promising for biomedical applications.
Synthesis and micellization of amphiphilic biodegradable methoxypolyethylene glycol/poly(d,l-lactide)/polyphosphate block copolymer
Wu, Qiuhua,Wang, Chuang,Zhang, Dan,Song, Ximing,Verpoort, Francis,Zhang, Guolin
, p. 980 - 984 (2011)
A new amphiphilic biodegradable methoxypolyethylene glycol/poly(d,l- lactide)/poly(ethyl ethylene phosphate) (MPEG-b-PLA-b-PEEP) block copolymer was synthesized by ring-opening polymerization of ethyl ethylene phosphate (EEP) with methoxypolyethylene glycol/poly(d,l-lactide) (MPEG-b-PLA) as a macroinitiator, which was prepared by ring-opening polymerization of d,l-lactide (LA) initiated by methoxypolyethylene glycol (MPEG) using stannous octoate as catalyst. The structures of the block copolymers were confirmed by IR, 1H NMR and GPC analysis. Fluorescence measurements were applied to determine the critical micelle concentration (CMC) of the copolymer micelle solutions. The diameter and the distribution of micelles were characterized by dynamic light scattering (DLS) and the shape was perceived using transmission electron microscopy (TEM). The results prove that the copolymers can self-assemble into nano-micelles in aqueous solutions. The CMC of the copolymer solutions increased and the size of the micelles reduced with increasing of the proportion of PEEP segments. TEM images demonstrate that all micelles are spherical.
Breathing air as oxidant: Optimization of 2-chloro-2-oxo-1,3,2-dioxaphospholane synthesis as a precursor for phosphoryl choline derivatives and cyclic phosphate monomers
Becker, Greta,Wurm, Frederik R.
, p. 3536 - 3540 (2017)
Phosphoryl choline derivatives are important compounds for drug development. Also other phosphoesters have received increased demand in recent years. Many of such compounds rely 2-chloro-2-oxo-1,3,2-dioxaphospholane (COP) as an intermediate. COP is available in a two-step reaction from the cyclic adduct of phosphorus chloride and ethylene glycol after oxidation. Although commercially available, in-house synthesis of COP is often required due to pricing, purity, and delivery issues. Air is a convenient and economical oxidizing agent, yet not used for synthesis of COP. While slow consumption of the P(III)-precursor 2-chloro-1,3,2-dioxaphospholane with molecular oxygen from a gas bottle, high amounts of unreacted oxygen are lavished and even may cause an explosion. Oxygen from air is a reasonable and safer alternative. Additionally, catalytic amounts of cobalt(II)chloride increase the reaction kinetics remarkably. The results presented allow a controlled and fast access to a variety of phosphoesters by optimized reaction conditions of COP and its derivatives.
Biomimetic Honeycomb-Structured Surfaces Formed from Block Copolymers Incorporating Acryloyl Phosphorylcholine
Stenzel, Martina H.,Davis, Thomas P.
, p. 1035 - 1038 (2003)
We report the preparation of biomimetic honeycomb-structured porous films. These regular arrays were obtained by casting block copolymers composed of polystyrene and poly(acryloyl phosphorylcholine), so that they mimicked a cell membrane. The size of the pores and regularity of the hexagonal array is strongly dependent on the block length. The block copolymers were prepared via RAFT (reversible addition fragmentation transfer) polymerization leading to well-defined products with a good control over block sizes.
Interaction between zwitterionic surfactants and amphiphilic drug: A tensiometric study
Ansari, Wajid H.,Noori, Sahar,Naqvi, Andleeb Z.,Kabir-Ud-Din
, p. 441 - 458 (2013)
The physicochemical properties, viz, critical micelle concentration (cmc), surface excess concentration (Γmax), minimum area per head group (Amin) of zwitterionic surfactants (designated as n(-)-2-m(+); n = 8, 10, 12 and m = 12, 14, 16) and their mixtures with amphiphilic antidepressant drug amitriptyline hydrochloride (AMT) were determined by using surface tension measurements. The cmc and ideal cmc (cmcid) values along with interaction parameters, βm and β α (calculated using Rubingh's and Rosen's models), suggest attractive interactions among the components. The Krafft temperature measurements also indicate strong attractive interactions. Γmax (or Amin) increases (or decreases) with the addition of gemini surfactant; the values being closer to that of the drug. These values and micellar mole fraction (Xm-calculated from Rubingh's model and X 1Moto-calculated from Motomura's model) indicate larger contribution of gemini surfactants in mixed micelles and smaller contribution at air/solution interface (as mole fraction values at interface, X σ1, are slightly smaller than X1m). The standard Gibbs energy of micellization (ΔG°mic) and adsorption (ΔG°ad) as well as excess energy of mixing (ΔGexm) are all negative. All these results suggest higher stability of the mixed systems. UV absorbance results also suggest that the mixed micelles are stable for several days. by Oldenbourg Wissenschaftsverlag.
Effect of Asymmetric Dimeric Zwitterionic Surfactants on Micellization Behavior of Amphiphilic Drugs
Noori, Sahar,Naqvi, Andleeb Z.,Ansari, Wajid H.,Kabir-Ud-Din
, p. 1292 - 1309 (2015)
Abstract The micellization process in mixtures of amphiphilic drugs and asymmetric dimeric zwitterionic surfactants have been investigated tensiometrically. The drugs used are from two families: imipramine hydrochloride (IMP) - a tricyclic antidepressant and ibuprofen (IBF) - a nonsteroidal antiinflammatory drug, whereas zwitterionic dimeric surfactants are heterogemini surfactants that contain quaternary ammonium and phosphate groups as heads. The results show that the cmc of drug-surfactant mixtures decreases with the increase in stoichiometric mole fraction of surfactants (α 1), suggesting attractive interaction among the two components. This is supported by the values of cmc id (critical micelle concentration values for ideal mixing) which are always greater than experimental cmc values. Also, the decrease in magnitude is more in IBF-dimeric surfactant mixed systems than in IMP-dimeric surfactant mixed systems. Micellar mole fraction values, obtained using Rubingh's (Formula presented.) and Motomura's (Formula presented.) models, are lower than the micellar mole fraction for ideal mixing (Formula presented.). The micellar interaction parameter (βm) follows the order: 8(-)-2-16(+) > 10(-)-2-16(+) > 10(-)-2-14(+) > 8(-)-2-14(+). The results are explained on the basis of difference in tail lengths. Interfacial mole fraction (Formula presented.) values, evaluated using Rosen's model, are higher than (Formula presented.) values for IMP-10(-)-2-16(+) and IMP-10(-)-2-14(+) systems while for all other systems (except 8(-)-2-14(+)) the values are smaller than (Formula presented.). The interaction parameter at the interface (βσ) is negative and (Formula presented.) values are greater than (Formula presented.) in magnitude. All the results indicate that the dimeric surfactants are mostly in cationic form.
Preparation method of cyclic chlorinated phosphate
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Paragraph 0025-0039, (2021/01/29)
The present invention relates to a cyclic chlorinated phosphate preparation method, wherein phosphorus oxychloride and alkyl siloxane are subjected to a cyclization reaction in the presence of an aprotic solvent to prepare cyclic chlorinated phosphate, the structural formula of alkyl siloxane is shown in the specification, the structural formula of the cyclic chlorinated phosphate is shown in thespecification, and n is a number between 1 and 5. According to the invention, synthesis is a one-step reaction, the reaction avoids an oxidation reaction (the oxidation reaction is a high-risk process), and the method is high in reaction selectivity and yield, few in reaction steps and suitable for industrial production.
Five-membered ring phosphate compound, and preparation method and application thereof
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Paragraph 0091-0095, (2020/06/17)
The invention belongs to the technical field of flame retardance, and especially relates to a five-membered ring phosphate compound. The structural general formula of the five-membered ring phosphatecompound is represented by formula 1 shown in the description; and in the formula, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R and R are independently selected from hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkynyloxy group, an enyloxy group, a silyl group, a siloxane group, aryl silicon, an arylsilyl group, an arylsiloxy group, a halogenated phenyl group, a halogenated biphenyl group, a phenolic group, an alkyl-containing phenolic group, an alkenyl-containing phenolic group, an alkynyl-containing phenolic group, a nitrile-containing phenolic group, a monohalogenated phenolic group and a polyhalogenated phenolic group. The five-membered ring phosphate compound provided by the invention has excellent flame retardancy, can effectively prevent electrolytes from being oxidized when being applied to the field of batteries, reduces oxygenolysis of the electrolytes on positive electrodes, and remarkably improves the comprehensive properties of high temperature, circulation, storage and the like of the batteries.
Flame-retardant additive, preparation method therefor and application of flame-retardant additive
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Paragraph 0053-0062, (2020/01/03)
The invention discloses a flame-retardant additive, a preparation method therefor and an application of the flame-retardant additive. In view of that phosphorus-containing flame retardants in the prior art have many performance disadvantages and the problem of high manufacturing and service costs, the invention provides a novel phosphorus-containing flame retardant. The flame retardant is used asa flame-retardant additive in an electrolyte of a non-aqueous electrolytte secondary battery. The invention simultaneously provides the preparation method for the flame retardant. The phosphorus-containing flame retardant prepared by the method not only can effectively improve safety of batteries, but also has a specific positive-negative pole membrane forming function, and thus, comprehensive properties such as high-/low-temperature, cycling and storage properties of the secondary battery can be remarkably improved. The preparation method for the flame retardant, provided by the invention, has the advantages that the raw material cost is low, the preparation process is simple in step, the operation is safe, the product purity is high, and the environmental pollution is light.
