Marie-Christiane Carré

COVALENT COUPLING OF A SHORT POLYETHER ON SODIUM ALGINATE : SYNTHESIS AND CHARACTERIZATION OF THE RESULTING AMPHIPHILIC DERIVATIVE

Abstract A covalent sodium alginate-polyoxyethylene model derivative was prepared by reductive amination of aldehydic sodium alginate, in order to obtain a polymer with amphiphilic properties. Characterization of this derivative was carried out by NMR spectroscopy, viscosity measurements and low-angle laser light scattering. The data obtained suggest a limited capacity of the polymer structure to expand, resulting from intramolecular self-aggregation and formation of hydrophobic microdomains.

Arynic condensation of ketone enolates 181: Efficient access to benzocyclenones and polycyclic indanone derivatives

Abstract It is shown that benzocyclobutenols 1 are excellent starting materials for the obtention of polycyclic aromatic ketones. Thus under basic conditions they lead to benzocyclenedione mono ketals which may be hydrolyzed into the corresponding benzocyclenediones. Under acidic conditions, a transposition takes place leading to indanone derivatives. The mechanism of this transposition is discussed.

SYNTHESIS AND CHARACTERIZATION OF SOME COVALENT DEXTRAN-POLYOXYETHYLENEGLYCOL DERIVATIVES

Abstract Covalent dextran-polyoxyethyleneglycol compounds were prepared in order to obtain amphiphilic polymers which may, possibly due to incompatible structures, undergo phase separation at the molecular level. Characterization of these derivatives was carried out by n.m.r. spectroscopy, gel permeation chromatography and low angle laser light scattering (LALLS) measurements.

Arynic condensation of ketone enolates 19. Synthesis of polycyclic phenylethanolamines

Abstract A series of new polycyclic phenylethanolamines is efficiently synthesized by arynic condensation of α-aminoketone enolates in the presence of the complex base NaNH 2 -Bu t ONa.

Arynic Condensation of Nitrile Anions in the Presence of the Complex Base NaNH2-CH3CH2(OCH2CH2)2ONa

Abstract Nitrite anions are easily condensed with aryl halides in the presence of the Complex Base NaNH2-CH3CH2(OCH2CH2)2ONa via the intermediate arynes.

Specific fluorescent tracers. Imaging and applications for photodynamic therapy

Our main objective is to enlarge the fluorescence use in biosciences, with especially the photodynamic therapy (PDT) used for cancer treatment as one of the target applications. Meta-tetra(hydroxyphenyl)chlorin (m-THPC) is a second-generation photosensitiser, applied in photodynamic therapy. The localisation of this sensitiser as well as its induced cell death mechanisms in human breast cancer cells (MCF-7 and its resistant subline MCF-7DXR, DXR: doxorubicin) were evaluated using fluorescence microscopy. In addition, we will present two additional routes, whose aims are to create new features to respond to the PDT questioning: firstly, the synthesis of fluorescent tracers, with a particular attention to the presence of hydrophilic groups (glucosamine ring) on the basic fluorophore structure to orientate the localisation of the probe and, secondly, the use of scanning near-field optical microscopy to reach a better resolution for the fluorescence microscopy analysis.

Fluorescence as a Characterization Tool to Study Amphiphilic Polymer Aggregation in Aqueous Media

Abstract Fluorescence spectroscopy based on pyrene and DMAC (i.e., 1,1-dicyano-4-(4′-(N,N-dimethylamino)phenyl)-1,3-butadiene) probes was used to investigate the aggregation of amphiphilic polymers in aqueous solution. The fluorescence data related to the cohesion of the microdomains formed were correlated to the polymer microstructure, either by taking into account the sequence distribution for poly(NVP-co-C16VIB) (i.e., poly(N-vinyl-2-pyrrolidinone)-co-(3-hexadecyl-1-vinylimidazolium bromide)) or the cryo-TEM images for poly(C1VPB-co-C16VPB) (i.e., poly(1-methyl-3-vinylpyridinium bromide)-co-(1-hexadecyl-3-vinylpyridinium bromide)).

New easy access to benzocyclobutenone derivatives

Abstract Benzocyclobutenone derivatives are easily obtained by oxidative transformation of functional polycyclic benzocyclobutenols synthetized by arynic condensations.

Synthetic photochemistry. Part 2. Generation of benzocyclobutenols by photocyclisation of benzocycloalkenones

The irradiation of benzocycloalkenones (2) was examined in t-butyl alcohol and cyclisation into benzocyclobutenols (1) was observed for n= 7–9. On irradiation, substituted benzocycloalkenones (4) cyclised by an external mechanism to tricyclic benzocyclobutenols (7) and/or by an internal mechanism to alcohols (5) and/or (6), the relative ratio of these products depending on the nature of the alkyl substituent and the ring size. The results are related to the mechanism of the photoenolisation reaction.

Arynic Condensation of Ketone Enolates XX. New Access To Polycyclic Phenylethanolamines

Abstract A new preparation of two kinds of potentially biologically active phenylethanolamines is described. The basic reaction of these syntheses is arynic condensation of ketone enolates in the presence of Complex Bases.