0000000001307342
AUTHOR
Elodie Gigot
Direct subphthalocyanine conjugation to bombesin vs. indirect conjugation to its lipidic nanocarrier
International audience; Bombesin (BBN) was covalently bound to graftable subphthalocyanine (SubPc) or to a cholesterol derivative, a component of a liposome that encapsulates non-graftable SubPc. The latter bioconjugation approach was suitable to address the stability of SubPc and was achieved by copper-free click-chemistry on the outer-face of the liposome. Liposomes were purified (FPLC) and then analyzed in size (outer diameter about 60 nm measured by DLS). In vitro binding studies allowed to determine the IC50 13.9 nM for one component of the liposome, cholesterol, conjugated to BBN. Hence, azido- (or alkynyl-) liposomes give fluorophores with no reactive functional group available on th…
Ortho -Functionalized Aryltetrazines by Direct Palladium-Catalyzed C−H Halogenation: Application to Fast Electrophilic Fluorination Reactions
International audience; A general catalyzed direct C-H functionalization of s-tetrazines is reported. Under mild reaction conditions, N-directed ortho-C-H activation of tetrazines allows the introduction of various functional groups, thus forming carbon-heteroatom bonds: C-X (X=I, Br, Cl) and C-O. Based on this methodology, we developed electrophilic mono- and poly-ortho-fluorination of tetrazines. Microwave irradiation was optimized to afford fluorinated s-aryltetrazines, with satisfactory selectivity, within only ten minutes. This work provides an efficient and practical entry for further accessing highly substituted tetrazine derivatives (iodo, bromo, chloro, fluoro, and acetate precurso…
Subphthalocyanines: addressing water-solubility, nano-encapsulation, and activation for optical imaging of B16 melanoma cells
Water-soluble disulfonato-subphthalocyanines (SubPcs) or hydrophobic nano-encapsulated SubPcs are efficient probes for the fluorescence imaging of cells. 20 nm large liposomes (TEM and DLS) incorporated about 13% SubPc. Moreover, some of these fluorophores were found to be pH activatable.
Préparation de liposomes fonctionnels pour l’encapsulation de composés bioactifs ou de sondes moléculaires fluorescentes pour l’imagerie cellulaire
At ICMUB Institute, SUV liposomes have been used to achieve fluorophore encapsulation (subphtalocyanine) for cellular imaging [1] and have been bioconjugated to a peptide (bombesin) to achieve site-specificity, thanks to the structural modification of cholesterol, a component of the liposome, upon introduction of a reactive function. Hence, such liposomes fonctionnalised on the outer face may react with the terminal function of the peptide. Upon purification of the liposome by FPLC a 15 % encapsulation rate was measured by UV/Vis and attempted by ICP. The (outer) diameter of the liposomes (dDLS and dMET) ranged between 20 and 60 nm depending on the type of function or substituents on the ou…
ChemInform Abstract: ortho-Functionalized Aryltetrazines by Direct Palladium-Catalyzed C-H Halogenation: Application to Fast Electrophilic Fluorination Reactions.
A general catalyzed direct C-H functionalization of s-tetrazines is reported. Under mild reaction conditions, N-directed ortho-C-H activation of tetrazines allows the introduction of various functional groups, thus forming carbon-heteroatom bonds: C-X (X=I, Br, Cl) and C-O. Based on this methodology, we developed electrophilic mono- and poly-ortho-fluorination of tetrazines. Microwave irradiation was optimized to afford fluorinated s-aryltetrazines, with satisfactory selectivity, within only ten minutes. This work provides an efficient and practical entry for further accessing highly substituted tetrazine derivatives (iodo, bromo, chloro, fluoro, and acetate precursors). It gives access to …
CCDC 1456530: Experimental Crystal Structure Determination
Related Article: Yann Bernhard, Elodie Gigot, Victor Goncalves, Mathieu Moreau, Nicolas Sok, Philippe Richard, Richard A. Decréau|2016|Org.Biomol.Chem.|14|4511|doi:10.1039/C6OB00530F