3497-06-1Relevant articles and documents
Rational design 2-hydroxypropylphosphonium salts as cancer cell mitochondria-targeted vectors: Synthesis, structure, and biological properties
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.
, (2021/11/01)
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.
Chemo-enzymatic synthesis and antimicrobial evaluation of alkyloxy propanol amine-based cationic ether lipids
Reddy,Rao,Karuna,Kumar,Murthy,Prasad
, p. 437 - 448 (2013/07/27)
The present study involved the synthesis and antimicrobial evaluation of alkyloxy propanol amine-based cationic lipids N,N-dimethyl-1-octadecylamino-3- alkyloxy-2-propanol (series A, 7a-e) and N-methyl-N,N-di-(2-hydroxy-3-alkyloxy-2 propyl) octadecylamine (series B, 9a-e) and their acetylated derivatives (8a-e and 10a-e). A simple three-step chemo-enzymatic approach was employed for the synthesis of 7a-e and 9a-e in 71-80 and 67-88 % yields, respectively. The first step involved the synthesis of a series of glycidyl ethers from a series of alcohols (C4, C8, C10, C12, C 14) which were opened in the second step with octadecylamine to obtain 1-octadecylamino-3-alkyloxy-2 propanol (5a-e) and N,N-di-(2-hydroxy-3- alkyloxypropyl) octadecylamine (6a-e). In the third step, alkyloxy propanolamines (5a-e, 6a-e) were quaternized using methyl iodide to yield quaternized ammonium salts. The quaternized ammonium salts were enzymatically acetylated using Candida antarctica lipase-B based immobilized enzyme Novozym 435 to obtain their acetylated derivatives. The quaternized salts as well as their acetylated derivatives were evaluated for antibacterial and antifungal properties. The title compounds were found to possess moderate to good antibacterial activities against all the studied bacterial strains namely, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Klebsiella aerogenes compared to streptomycin and cetyl trimethyl ammonium bromide (CTAB). The title compounds exhibited relatively good antifungal activities against Candida albicans and no significant activities against other fungal strains namely, Saccharomyces cerevisiae, Rhizopus oryzae and Aspergillus niger when compared to amphotericin B and CTAB.
Compositions containing lysophosphatidic acids which inhibit apoptosis and uses thereof
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Page/Page column 1, (2008/06/13)
The invention provides anti-apoptotic compositions lysophosphatidic acids and methods for making and using the compositions. Such compositions can also contain LPA potentiating agents, including proteins, lipid membrane structures and polymers such as polyethylene glycols. The compositions can additionally contain other pharmaceutically effective agents such as drugs, antibiotics, wound healing agents and antioxidants.
