- Rational design 2-hydroxypropylphosphonium salts as cancer cell mitochondria-targeted vectors: Synthesis, structure, and biological properties
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It has been shown for a wide range of epoxy compounds that their interaction with triphenylphosphonium triflate occurs with a high chemoselectivity and leads to the formation of (2-hydroxypropyl)triphenylphosphonium triflates 3 substituted in the 3-position with an alkoxy, alkylcarboxyl group, or halogen, which were isolated in a high yield. Using the methodology for the disclosure of epichlorohydrin with alcohols in the presence of boron trifluoride ether-ate, followed by the substitution of iodine for chlorine and treatment with triphenylphosphine, 2-hydroxypropyltriphenylphosphonium iodides 4 were also obtained. The molecular and supramolec-ular structure of the obtained phosphonium salts was established, and their high antitumor activity was revealed in relation to duodenal adenocarcinoma. The formation of liposomal systems based on phosphonium salt 3 and L-α-phosphatidylcholine (PC) was employed for improving the bioavailabil-ity and reducing the toxicity. They were produced by the thin film rehydration method and exhibited cytotoxic properties. This rational design of phosphonium salts 3 and 4 has promising potential of new vectors for targeted delivery into mitochondria of tumor cells.
- Amerhanova, Syumbelya K.,Dimukhametov, Mudaris N.,Gubaidullin, Aidar T.,Islamov, Daut R.,Litvinov, Igor A.,Lyubina, Anna P.,Mironov, Vladimir F.,Nemtarev, Andrey V.,Pashirova, Tatiana N.,Titov, Eugenii A.,Tsepaeva, Olga V.,Voloshina, Alexandra D.
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- Synthesis, surface active and thermodynamic parameters of novel quaternary ammonium salts
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Reactions of octanol, nonanol, decanol, and dodecanol with epichlorohydrin were carried out in the presence of sodium hydroxide as a catalyst. The synthesized non-ionic surfactants were modified with triethanolamine. Surface activity at the water-air interface and electrical conductivity of the resulting surfactants at 10, 20, 30 and 40 °C were determined and thermodynamic parameters of micellization and adsorption were calculated. It was established that the synthesized quaternary ammonium salts have the ability to localize thin crude oil films on the water surface formed due to spill. AOCS 2012.
- Asadov, Ziyafaddin H.,Rahimov, Ravan A.,Ahmadova, Gulnara A.,Mammadova, Khuraman A.
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p. 721 - 727
(2013/02/23)
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- Preparation and properties of phosphate surfactants containing ether and hydroxy groups
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Phosphate surfactants containing ether and hydroxyl groups were prepared by a simple reaction between the corresponding epoxide and the diethyl phosphate. The relationships between the structure and colloidal properties were evaluated in terms of the critical micelle concentration (CMC), γCMC, foaming ability, and water absorbing and holding abilities. Based on these results, it was concluded that the ether and hydroxy groups synergistically worked together to decrease the CMC and increase the foaming ability. The degree of neutralization remarkably affected the colloidal properties. The highly neutralized states showed a more positive effect on water holding power but an opposite effect on the foaming ability. Copyright
- Osanai, Shuichi,Yamada, Go,Hidano, Ruri,Beppu, Koji,Namiwa, Kimiyoshi
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supporting information; experimental part
p. 41 - 49
(2011/12/05)
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- Synthesis and characterization of nonconventional surfactants of aromatic amino acid-glycerol ethers: Effect of the amino acid moiety on the orientation and surface properties of these soap-type amphiphiles
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The synthesis, characterization, and surface properties of soaptype amphiphiles comprising alkyl chains of 10-16 carbon atoms linked through an ether group to a glycerolamino acid hydrophilic head group is described. The surface properties of members of this series derived from histidine and tyrosine were compared with those of phenylalanine and tryptophan derivatives described previously and with those of conventional soaps. In all cases, the amino acid derivatives showed superior surface properties, and an interesting differentiation was discovered regarding the orientation of tryptophan derivatives.
- Varka, Evdoxia-Maria A.,Heli, Maria G.,Coutouli-Argyropoulou, Evdoxia,Pegiadou, Sofia A.
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p. 8305 - 8311
(2007/10/03)
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- The kinetics of chloromethyloxirane reaction with alcohols and their adducts in the presence of stannic chloride
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Rate constants of the reaction of chloromethyloxirane (epichlorohydrin) with methyl, n-propyl, isopropyl, n-, sec-, tert-butyl, n-hexyl, n-octyl, and n-decyl alcohols in the presence of stannic chloride were studied at 30, 40, and 50°C. Reaction is not first order in respect to epichlorohydrine and is particularly fast at the beginning and its rate constants are proportional to the concentration of the catalyst. The rate constants increase in the homologous series of C1-C10 alcohols. The reaction rates of 2-chloromethyloxirane with 1-chloromethyl-2-alkoxyethanols are ca. 2.5-times larger than that with corresponding alcohols.
- Chlebicki,Pozniak
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- Liquid-Liquid-Extraction of Metal Ions with Lariat Ethers
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Lariat ethers of various ring size and substitution are synthesized and characterized by physical data and chemical analysis.The extraction behaviour of the crown compounds towards Na+, K+, Cs+ and Ag+ in a picric acid solution has been investigated.The extraction constants for 1:1 and 1:2 complexes are determined using the equilibrium distribution data.The results show that the flexible side chain in the investigated compounds has in no case a positive effect on the metal picrate extraction.
- Gloe, K.,Muehl, P.,Beger, J.,Poeschmann, C.,Petrich, M.,Beyer, L.
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p. 413 - 421
(2007/10/02)
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- Substituted ammonium carbamates and method for preparing same
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Compounds corresponding to the formula: STR1 in which R is a saturated or unsaturated straight chain C5 -C18 aliphatic radical and X represents --O--, --S--, --NH-- or --CH2 -- are provided by reacting compounds corresponding to the formula: STR2 in which R and X are as defined above and R1 and R2 together represent an epoxy radical with ammonium carbamate. These compounds may be used as intermediates in the preparation of the hydrohalide salts, particularly the hydrochloride and hydrobromide salts, and acetates of hydroxylated primary amines corresponding to the formula: in which R and X are as defined above which are useful as medicaments, antiseptics, sterilizing agents and preservatives.
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- Hydroxylated amines with bacteriostatic activity
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The invention relates to new chemical compounds and to processes for their preparation. The compounds according to the invention correspond to the formula in which R is a saturated or unsaturated straight-chain C5 to C18 aliphatic radical and X represents --O--, --S--, --NH-- or --CH2 --, the salts, esters and quaternary alkyl ammonium salts of these compounds. These compounds may be used in particular as medicaments, as antiseptics, sterilizing agents and preservatives.
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