Vincent Chaleix

Porphyrin-functionalized mesoporous organosilica nanoparticles for two-photon imaging of cancer cells and drug delivery

The synthesis of a zinc porphyrin derivative possessing eight triethoxysilyl groups was performed through a CuAAC-click reaction. This porphyrin was covalently entrapped in ethenylene-bridged mesoporous organosilica nanoparticles which efficiently allowed performing doxorubicin delivery and two-photon imaging of breast cancer cells.

Synthesis and photobiocidal properties of cationic porphyrin-grafted paper.

We report on the synthesis of cellulose paper bearing a cationic porphyrin, designed for antimicrobial applications. Tricationic porphyrin has been covalently grafted on paper, without previous chemical modification of the cellulosic support, using 1,3,5-triazine derivative as linker. The obtained porphyrin-grafted paper was characterized by infrared (ATR-FTIR), UV-visible and diffuse reflectance UV-vis (DRUV) spectroscopies to confirm the triazine linkage. Thermogravimetric analysis (TGA) was used to investigate thermal properties of grafted paper. Antimicrobial activity of porphyrin-cellulose material was tested under visible light irradiation against Staphylococcus aureus and Escherichia coli. The two bacterial strains deposited on the resulting photosensitizing filter paper are efficiently killed after illumination.

Development of curcumin–cyclodextrin/cellulose nanocrystals complexes: New anticancer drug delivery systems

The synthesis of curcumin-cyclodextrin/cellulose nanocrystals (CNCx) nano complexes was performed. CNCx were functionalized by ionic association with cationic β-cyclodextrin (CD) and CD/CNCx complexes were used to encapsulate curcumin. Preliminary in vitro results showed that the resulting curcumin-CD/CNCx complexes exerted antiproliferative effect on colorectal and prostatic cancer cell lines, with IC50s lower than that of curcumin alone.

Delivery of tanshinone IIA and α-mangostin from gold/PEI/cyclodextrin nanoparticle platform designed for prostate cancer chemotherapy

A new anti-cancer drug delivery system, based on gold nanoparticles, has been designed for hydrophobic active compounds. The system is a conjugate of gold/polyethyleneimine (AuNPs/PEI) nanoparticles and sulphated β-cyclodextrin (CD). Anionic cyclodextrin was attached to the positively charged AuNPs/PEI nanoparticles by ionic bonds. Tanshinone IIA and α-mangostin were extracted, purified and encapsulated into the AuNPs/PEI/CD nanoparticles. In vitro preliminary cell viability assays against prostate cancer cell lines PC-3 and DU145 showed that encapsulation resulted in increased cytotoxicity.

Uncommon chlorinated xanthone and other antibacterial compounds from the lichen Cladonia incrassata.

Bioassay-guided fractionation of an extract of the lichen Cladonia incrassata against Staphylococcus aureus led to a novel compound, 1,5-dihydroxy-2,4,6-trichloro-7-methylxanthone (1), along with six known compounds: (-)-usnic acid (2), didymic acid (3), condidymic acid (4), squamatic acid (5), thamnolic acid (6), and prasinic acid (7). Didymic, condidymic, and prasinic acids were isolated for the first time from C. incrassata. Didymic, condidymic, and (-)-usnic acids were active against S. aureus (a minimum inhibitory concentration of 7.5 µg/mL).

Efficient quantification of primary amine functions grafted onto apatite ceramics by using two UV-Vis spectrophotometric methods

Enhancement of osteogenic properties of bone substitutes is best achieved by the covalent attachment of appropriate biomolecules, e.g. proteins and peptides, on amino-functionalized implant materials. Measurement of the free amino surface density of these materials is mandatory before derivatization. Two photometric methods were developed to assay the free amino groups of organosilane molecules covalently grafted onto hydroxyapatite and silicon-substituted hydroxyapatite ceramic surfaces. Reaction of amino-derivatized apatites with ninhydrin led to the formation of Ruhemanns purple quantified by the absorbance at 586 nm. Alternatively, ceramics were reacted with Fmoc-derivatized amino acids in the presence of piperidine, leading to the dibenzofulvene–piperidine adduct measured at 301 nm. Both methods allow the detection of free amino groups down to 1.0 × 10−8 mol g−1 of apatite-ceramics and, since they are conducted under non-acid conditions, preserve the acid-sensitive structure of hydroxyapatite.

Synthesis and biological activity of mustard derivatives of thymine.

The synthesis and biological activity of a novel DNA cross-linking antitumor agent is presented. The new alkylating agent significantly inhibited cell proliferation, migration and invasion as tested in vitro on the A431 vulvar epidermal carcinoma cell line.

Partial structural characterization and antioxidant activity of a phenolic–xylan from Castanea sativa hardwood

4-O-Methylglucuronoxylans (MGX) were isolated from chestnut wood sawdust using two different procedures: chlorite delignification followed by the classical alkaline extraction step, and an unusual green chemistry process of delignification using phthalocyanine/H2O2 followed by a simple extraction with hot water. Antioxidant properties of both MGX were evaluated against the stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) by electronic spin resonance (ESR). IC50 of water-extracted MGX was found to be less than 225 μg mL(-1), in contrast with alkali-extracted MGX for which no radical scavenging was observed. Characterization of extracts by colorimetric assay, GC, LC-MS and NMR spectroscopy provided some clues to understanding structure-function relationships of MGX in connection with their antioxidant activity.

Optimization of Lead and Cadmium Binding by Oxidation of Biosorbent Polysaccharidic Moieties

The polysaccharidic moieties of three biosorbents (Douglas fir and argan tree barks and argan endocarp) were selectively oxidized, and the subsequent modified materials were tested for their ability to bind Pb(II) or Cd(II) from aqueous solutions. Chemical modifications consisted in two selective oxidations, alone or in combination, of the following groups: primary alcohols with NaOBr catalyzed by (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl, and vicinal diols with periodate/chlorite. The sodium chlorite oxidation step induced biosorbent degradation that led to a significant decrease of mass yield. Modified materials, characterized by FT-IR spectroscopy and measurement of surface acidity, were investigated for their adsorption capabilities of Cd(II) and Pb(II). Results were compared to the capabilities of crude materials using the Langmuir adsorption model in terms of affinity (b) and maximum binding capacity (qmax). Ion exchange properties were found better for lead than for cadmium before and after chemical modifications. Compared to crude barks, the best results were obtained for Douglas fir barks whose oxidation resulted in significant enhancements of qmax up to × 10 in the case of lead.

Microwave-assisted expeditious O-alkylation of meso-hydroxyphenylporphyrins

A mild method for O-alkylation of meso-hydroxyphenylporphyrin has been developed using microwave irradiation. This method is clean and efficient for many substrates and results in significant improvement in reaction yield and in a dramatic decrease in reaction time in comparison to thermal heating.