- A triphenylphosphonium-functionalized mitochondriotropic nanocarrier for efficient co-delivery of doxorubicin and chloroquine and enhanced antineoplastic activity
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Drug delivery systems that target subcellular organelles and, in particular, mitochondria are considered to have great potential in treating disorders that are associated with mitochondrial dysfunction, including cancer or neurodegenerative diseases. To t
- Panagiotaki, Katerina N.,Sideratou, Zili,Vlahopoulos, Spiros A.,Paravatou-Petsotas, Maria,Zachariadis, Michael,Khoury, Nikolas,Zoumpourlis, Vassilis,Tsiourvas, Dimitris
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- Triphenilphosphonium analogs of chloramphenicol as dual-acting antimicrobial and antiproliferating agents
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In the current work, in continuation of our recent research, we synthesized and studied new chimeric compounds, including the ribosome-targeting antibiotic chloramphenicol (CHL) and the membrane-penetrating cation triphenylphosphonium (TPP), which are lin
- Abad, Etna,Antonenko, Yuri N.,Bogdanov, Alexey A.,Kajiwara, Susumu,Khairullina, Zimfira Z.,Konevega, Andrey L.,Lukianov, Dmitrii A.,Lyakhovich, Alex,Makarov, Gennady I.,Murayama, Somay Y.,Nazarov, Pavel A.,Osterman, Ilya A.,Paleskava, Alena,Pavlova, Julia A.,Skvortsov, Dmitry A.,Sumbatyan, Natalia V.,Tereshchenkov, Andrey G.,Volynkina, Inna A.
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- Synthesis and chemiluminescent properties of amino-acylated luminol derivatives bearing phosphonium cations
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The monitoring of reactive oxygen species in living cells provides valuable information on cell function and performance. Lately, the development of chemiluminescence-based reactive oxygen species monitoring has gained increased attention due to the advantages posed by chemiluminescence, including its rapid measurement and high sensitivity. In this respect, specific organelle-targeting trackers with strong chemiluminescence performance are of high importance. We herein report the synthesis and chemiluminescence properties of eight novel phosphonium-functionalized amino-acylated luminol and isoluminol derivatives, designed as mitochondriotropic chemiluminescence reactive oxygen species trackers. Three different phosphonium cationic moieties were employed (phenyl, p-tolyl, and cyclohexyl), as well as two alkanoyl chains (hexanoyl and undecanoyl) as bridges/linkers. Synthesis is accomplished via the acylation of the corresponding phthalimides, as phthalhydrazide precursors, followed by hydrazinolysis. This method was chosen because the direct acylation of (iso)luminol was discouraging. The new derivatives’ chemiluminescence was evaluated and compared with that of the parent molecules. A relatively poor chemiluminescence performance was observed for all derivatives, with the isoluminol-based ones being the poorest. This result is mainly attributed to the low yield of the fluorescence species formation during the chemiluminescence oxidation reaction.
- Pantelia, Anna,Daskalaki, Ira,Consuelo Cuquerella,Rotas, Georgios,Miranda, Miguel A.,Vougioukalakis, Georgios C.
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- Tuning the Hydrophobicity of a Mitochondria-Targeted NO Photodonor
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A few compounds in which the nitric oxide (NO) photodonor N-[4-nitro-3-(trifluoromethyl)phenyl]propane-1,3-diamine is joined to the mitochondria-targeting alkyltriphenylphosphonium moiety via flexible spacers of variable length were synthesized. The lipop
- Sodano, Federica,Rolando, Barbara,Spyrakis, Francesca,Failla, Mariacristina,Lazzarato, Loretta,Gazzano, Elena,Riganti, Chiara,Fruttero, Roberta,Gasco, Alberto,Sortino, Salvatore
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p. 1238 - 1245
(2018/05/14)
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- From broad-spectrum biocides to quorum sensing disruptors and mussel repellents: Antifouling profile of alkyl triphenylphosphonium salts
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'Onium' compounds, including ammonium and phosphonium salts, have been employed as antiseptics and disinfectants. These cationic biocides have been incorporated into multiple materials, principally to avoid bacterial attachment. In this work, we selected
- Martín-Rodríguez, Alberto J.,Babarro, Jose M. F.,Lahoz, Fernando,Sansón, Marta,Martín, Víctor S.,Norte, Manuel,Fernández, José J.
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- PHARMACEUTICAL SUBSTANCES ON THE BASIS OF MITOCHONDRIALLY ADDRESSED ANTIOXIDANTS
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This invention relates to the fields of pharmaceutics and medicine, and, in particular, relates to the production and use of pharmaceutical substances on the basis of mitochondria-addressed compounds. The invention discloses methods for synthesis, purification and storage of mitochondria-addressed antioxidants, making it possible to produce said substances in a form and quality meeting the demands made on active ingredients of medicinal preparations - the pharmaceutical substances. The invention also discloses methods for design and selection of new mitochondria-addressed antioxidants having specified properties.
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Page/Page column 20
(2012/10/07)
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- PHARMACEUTICAL SUBSTANCES ON THE BASIS OF MITOCHONDRIA-ADDRESSED ANTIOXIDANTS
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This invention relates to the fields of pharmaceutics and medicine, and, in particular, relates to the production and use of pharmaceutical substances on the basis of mitochondria-addressed compounds. The invention discloses methods for synthesis, purification and storage of mitochondria-addressed antioxidants, making it possible to produce said substances in a form and quality meeting the demands made on active ingredients of medicinal preparations—the pharmaceutical substances. The invention also discloses methods for design and selection of new mitochondria-addressed antioxidants having specified properties.
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Page/Page column 17
(2012/10/18)
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- Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl- 4(1H)-quinolones
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A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships.
- Wube, Abraham A.,Hüfner, Antje,Thomaschitz, Christina,Blunder, Martina,Kollroser, Manfred,Bauer, Rudolf,Bucar, Franz
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experimental part
p. 567 - 579
(2011/03/17)
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- Synthesis of (S)-(+)-enantiomers of food-relevant (n-5)-monoenoic and saturated anteiso-fatty acids by a Wittig reaction
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We developed an enantioselective synthesis for the food-relevant anteiso-fatty acids a15:0, a16:0, and a17:0. Different (carboxyalkyl)triphenylphosphonium bromide salts were coupled with (S)-3-methylpentanal in a Wittig reaction. Mixtures of the obtained cis-/trans-isomers were separated by Ag+-HPLC to give the novel cis-isomers of (S)-(+)-a15:1n-5, (S)-(+)-a16:1n-5, and (S)-(+)-a17:1n-5. Hydrogenation of the monoenoic products led to (S)-(+)-a15:0, (S)-(+)-a16:0, and (S)-(+)-a17:0, which are essential for the assessment of the bioactivity of tests with standards of anteiso-fatty acids.
- Thurnhofer, Saskia,Vetter, Walter
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p. 1140 - 1145
(2007/10/03)
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- Development of an enzyme-linked immunosorbent assay for the determination of the linear alkylbenzene sulfonates and long-chain sulfophenyl carboxylates using antibodies generated by pseudoheterologous immunization
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ELISA methods have been developed for screening contamination of water resources by linear alkyl benzene sulfonates (LAS) or the most immediate degradation products, the long chain sulfophenyl carboxylates, SPCs. The assay uses antibodies raised through pseudoheterologous immunization strategies using an equimolar mixture of two immunogens (SFA-KLH and 13C13-SPC-KLH) prepared by coupling N-(4-alkylpnenyl)sulfonyl-3-aminopropanoic acid (SFA) andp-(1-carboxy-13-tridecyl)-phenylsulfonic acid (13C13-SPC) to keyhole limpet hemocyanin (KLH). The immunizing haptens have been designed to address recognition versus two different epitopes of the molecule. The SFA hapten maximizes recognition of the alkyl moiety while preserving the complexity of the different alkyl chains present in the LAS technical mixture. The 13C13-SPC hapten addresses recognition of the common and highly antigenic phenylsulfonic group. The antisera raised using this strategy have been shown to be superior to those obtained through homologous immunization procedures using a single substance. By using an indirect ELISA format, LAS and long-chain SPCs can be detected down to 1.8 and 0.2 μg L-1, respectively. Coefficients of variation of 6 and 12% within and between assays, respectively, demonstrate immunoassay reproducibility. The assay can be used in media with a wide range of pH and ionic strength values. Preliminary experiments performed to assess matrix effects have demonstrated the potential applicability of the method as a screening tool to assess contamination by these types of surfactants in natural water samples.
- Ramon-Azcon, Javier,Galve, Roger,Sanchez-Baeza, Francisco,Marco, M.-Pilar
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- Synthesis of trans-vaccenic acid and cis-9-trans-11-conjugated linoleic acid
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The preparation of the monounsaturated fatty acid, trans-vaccenic acid 4 (TVA), using both Wittig and one-pot Julia-Kocieński olefination protocol, was achieved in good yield. Similarly a Wittig approach was employed for the stereoselective synthesis of cis-9-trans-11-conjugated linoleic acid 2 from trans-2-nonenal and (8-carboxyoctyl)triphenylphosphonium bromide 12.
- Duffy, Patricia E.,Quinn, Sonia M.,Roche, Helen M.,Evans, Paul
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p. 4838 - 4843
(2007/10/03)
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- Synthesis of carboxyl-tethered symmetric conjugated polyenes as fluorescent transmembrane probes of lipid bilayers
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The synthesis of a new series of fluorescent transmembrane probes in which two hydrophilic methyl ester or carboxyl groups are connected by a polymethylene chain, with four, five or six conjugated double bonds in a central position, is reported. The length of the linear structures was designed to match the width of typical lipid bilayers. These bolaamphiphilic compounds result, with overall yields higher than 80%, from an easy PdII-catalyzed double cross-coupling between terminal acetylene esters and conjugated 1,ω-dihalopolyenes, followed by selective triple bond partial reduction with activated zinc, and iodine isomerization to the all-(E) isomer. An alternative approach, based on a Stille double cross-coupling between the appropriate all-(E)-ω-halopolyenes and (E)-bis(tributylstannyl)ethene, yielded mixtures that could not be resolved by standard chromatographic methods due to the presence of other simultaneous coupling reactions, which are also discussed in detail. Nevertheless, the Stille method can be of utility for the obtention of carbonyl-polyene conjugated analogs. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Quesada, Ernesto,Acuna, A. Ulises,Amat-Guerri, Francisco
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p. 1308 - 1318
(2007/10/03)
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- Absolute Configuration of a Ceramide with a Novel Branched-chain Fatty Acid Isolated from the Epiphytic Dinoflagellate, Coolia monotis
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The absolute configuration of the chiral center at the C15 position of a novel branched-chain fatty acid derived from a new ceramide isolated from the epiphytic dinoflagellate Coolia monotis was determined to be of R from by reversed-phase HPLC after clea
- Akasaka, Kazuaki,Shichijyukari, Seiya,Matsuoka, Shigeru,Murata, Michio,Meguro, Hiroshi,Ohrui, Hiroshi
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p. 1842 - 1846
(2007/10/03)
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- Alicyclic Claisen rearrangement with a two-atom ring contraction. A new synthetic approach to cembranoids
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Methylenation of certain olefinic lactones with dimethyl titanocene, followed by thermal or triisobutylaluminium-mediated Claisen rearrangement leads to cembrane-like 11-15-membered ring ketones bearing an isopropenyl side chain.
- Petasis,Bzowej
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p. 1721 - 1724
(2007/10/02)
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- Metabolites of pentanedioic acid derivatives
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The present invention relates to pentanedioic acid derivatives. The present invention further relates to pharmaceutical compositions containing such compounds and to the use of such compounds and compositions as hypolipidemic drugs.
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- Thromboxane Synthetase Inhibitors (TXSI). Design, Synthesis, and Evaluation of a Novel Series of ω-Pyridylalkenoic Acids
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A novel series of ω-pyridylalkenoic acids has been prepared by applying the Wittig reaction.Modifications were made in the ω-aryl moiety, the alkylene chain length, the α-methylene group adjacent to the carbonyl group, and the carboxyl group in the molecu
- Kato, Kaneyoshi,Ohkawa, Shigenori,Terao, Shinji,Terashita, Zen-ichi,Nishikawa, Kohei
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p. 287 - 294
(2007/10/02)
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- Novel Synthesis of ω-(Diphenylphosphinyl)alkylcarboxylic Acids from Triphenyl-ω-carboxyalkylphosphonium Salts
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A novel method for the synthesis of triphenylphosphonium salts of the type (C6H5)3P+(CH2)nCO2H,X- (1: n=2,3; X=Cl; n=5,10,11; X=Br) from the corresponding ω-haloalkylcarboxylic acids and triphenylphosphine has been described.When members of 1 were treated with NaH/Me2SO/THF at room temperature under N2, the corresponding ω-(diphenylphosphinyl)alkylcarboxylic acids 2 (n=3,5,10,11) were isolated.The yields were good (62-75percent) for compounds with longer side chains (n=10,11).In one case (n=3), (C6H5)3P was isolated as a side product (yield 20percent).Attempts to prepare the Wittig reagents from 1 and the subsequent reaction with aldehydes (benzaldehyde and 9-anthraldehyde) failed to yield the expected alkenes.However, members of 2 were produced, and it was possible to recover >90percent of the unreacted 9-anthraldehyde.The structures of the compounds in the series 1 and 2 have been established via the spectral properties and elemental analyses.The 31P and 13C chemical shifts as well as C-P coupling constants have been evaluated and analyzed.A tentative mechanism has been proposed for the formation of 2 from 1.
- Narayanan, Kolazi S.,Berlin, K. Darrell
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p. 2240 - 2243
(2007/10/02)
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