Two New Retigerane-Type Sesterterpenoids from the Lichen Leprocaulon microscopicum

International audienceTwo new sesterterpenes, 1 and 2, have been isolated from the lichen Leprocaulon microscopicum. In addition to classic chromatographic methods, a liquid-liquid chromatography technique, namely centrifugal partition chromatography (CPC) was applied for the purification of compound 2. The structures were determined by analyses of mass spectrometry and 1D- and 2D-NMR data. The relative configuration of the isolated compounds was assigned on the basis of 2D-NOESY experiments. The two compounds possess a rare pentacyclic carbon skeleton typical for lichen metabolism, and quite unusual in the vegetal kingdom

Design and synthesis of triphenylphosphonium-porphyrin@xylan nanoparticles for anticancer photodynamic therapy

Most photosensitizers (PS) suffer from a lack of water solubility and from a low selectivity toward tumor cells. Delivery systems using nanoparticles make it possible to improve PS water solubility, and also tumor targeting via the enhanced permeability and retention (EPR) effect. Among the organelles, mitochondria are attractive target sites for drug-delivery strategies since they perform a variety of key cellular processes. Our study was aimed at synthesizing nanoparticles consisting of xylan-carrying porphyrins attached to a triphenylphosphonium moiety, in order to enhance the PDT effect through mitochondrial targeting. Hybrid nanoparticles were designed that consisted of a silica core coated with xylan substituted with porphyrin derivatives carrying a triphenylphosphonium moiety. These hybrid nanoparticles have been constructed, along with their counterparts devoid of silica core, taking into consideration the controversy surrounding the use of silica nanoparticles. Phototoxicity experiments, conducted against the HCT-116 and HT-29 colorectal cancer cell lines, showed that nanoparticles with porphyrins bearing a triphenylphosphonium moiety exhibited an enhanced photocytotoxic effect in comparison with free porphyrin or nanoparticles with porphyrins without the triphenylphosphonium moiety

Design and synthesis of triphenylphosphonium-porphyrin@xylan nanoparticles for anticancer photodynamic therapy

Most photosensitizers (PS) suffer from a lack of water solubility and from a low selectivity toward tumor cells. Delivery systems using nanoparticles make it possible to improve PS water solubility, and also tumor targeting via the enhanced permeability and retention (EPR) effect. Among the organelles, mitochondria are attractive target sites for drug-delivery strategies since they perform a variety of key cellular processes. Our study was aimed at synthesizing nanoparticles consisting of xylan-carrying porphyrins attached to a triphenylphosphonium moiety, in order to enhance the PDT effect through mitochondrial targeting. Hybrid nanoparticles were designed that consisted of a silica core coated with xylan substituted with porphyrin derivatives carrying a triphenylphosphonium moiety. These hybrid nanoparticles have been constructed, along with their counterparts devoid of silica core, taking into consideration the controversy surrounding the use of silica nanoparticles. Phototoxicity experiments, conducted against the HCT-116 and HT-29 colorectal cancer cell lines, showed that nanoparticles with porphyrins bearing a triphenylphosphonium moiety exhibited an enhanced photocytotoxic effect in comparison with free porphyrin or nanoparticles with porphyrins without the triphenylphosphonium moiety

A rapid efficient microwave-assisted synthesis of a 3',5'-pentathymidine by copper(I)-catalyzed [3+2] cycloaddition.

International audienceStarting from 5?-O-tosylthymidine, sequential azidation and Cu-catalyzed [3+2] azide?alkyne 1,3-dipolar cycloaddition led to the formation of a 3?,5?-pentathymidine in high yield. The whole process needed only work-up/precipitation steps and was completed within just 18min, thanks to microwave activation

Chelation-controlled regioselective alkylation of pyrimidine 2'-deoxynucleosides.

International audienceProtection-deprotection steps, which are usually needed for regioselective alkylation of pyrimidine deoxynucleosides, can be avoided by choosing the appropriate solvent. The combined effects of low dielectric constant and possible sodium chelation by pyrimidine nucleosides may account for the unexpected regioselectivity observed in THF

Design of a new oligotriazole peptide nucleic acid analogue (oT-PNA)

International audienceWe describe in this Letter the synthesis of an original thymine azido-heterotrimer generated by Click Chemistry. This trimer has been obtained from an azido-thymidine and a new chloroethyl-propargylated PNA monomer analogue, after two azidation/click-reaction cycles. Conformational preferences of a rotameric intermediate have also been studied

Glycosyl bis-porphyrin conjugates: synthesis and potential application in PDT.

International audienceSyntheses of new glycosylated neutral and cationic porphyrin dimers linked at the meso-position via a flexible hydrocarbon chain are described. A detailed 1H and 13C NMR study allows their complete structural elucidation. The UV-visible, fluorescence and MALDI mass spectra are also presented. Photocytotoxicities of these compounds against K562 leukaemia cell line are compared to those of Photofrin II

Processing of in situ synthesized polycarbosilane-derived porous SiC using kraft pulp fibers

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Synthesis and photocytotoxic activity of new chlorin-polyamine conjugates

International audienceThis paper reports the synthesis of newchlorin-polyamineconjugates designed to improve the targeting of cancer cells. Photocytotoxicactivity of these photosensitizers was tested against human chronic myelogenous leukemia cells (K562) and compared to the effects of Photofrin II® and chlorin e6