RESUMO
A series of boron-containing lipids were prepared by reactions of cyclic oxonium derivatives of polyhedron boranes and metallacarboranes (closo-dodecaborate anion, cobalt and iron bis(dicarbollides)) with amine and carboxylic acids which are derived from cholesterol. Stable liposomal formulations, on the basis of synthesized boron-containing lipids, hydrogenated soybean l-α-phosphatidylcholine and (HSPC) 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethylene glycol)-2000] (DSPE-PEG) as excipients, were prepared and then characterized by dynamic light scattering (DLS) that revealed the formation of particles to be smaller than 200â nm in diameter. The resulting liposomal formulations showed moderate to excellent loading and entrapment efficiency, thus justifying the design of the compounds to fit in the lipid bilayer and ensuring ease of in vivo use for future application. The liposomal formulations based on cobalt and iron bis(dicarbollide)-based lipids were found to be nontoxic against both human breast normal epithelial cells MCF-10A and human breast cancer cells MCF-7.
Assuntos
Compostos de Boro , Boro , Colesterol , Lipídeos , Lipossomos , Boranos/química , Boro/química , Compostos de Boro/síntese química , Compostos de Boro/química , Colesterol/química , Humanos , Lipídeos/síntese química , Lipídeos/química , Lipídeos/farmacologia , Lipossomos/síntese química , Lipossomos/química , Lipossomos/farmacologia , Células MCF-7 , Compostos Organometálicos/química , Compostos Organometálicos/farmacologiaRESUMO
The synthesis of the acetonitrilium and propionitrilium derivatives of closo-dodecaborate [B12H12]2- was discussed. The nucleophilic addition reactions of water, alcohols and secondary amines to the activated triple bond of the nitrilium derivatives yielded the corresponding iminols, imidates and amidines. The obtained results were supported by X-ray diffraction studies and DFT calculations.
RESUMO
8-Tetrahydrofuronium and 8-tetrahydropyronium derivatives of iron bis(dicarbollide)(-I) were synthesized. Their reactions of ring cleavage by MeOH, N3(-), amines and 1,2-bis(diphenylphosphino)ethane were investigated. 8-Tetrahydrofuronium iron bis(dicarbollide)(-I) was found to be more active in these reactions in comparison with 8-tetrahydropyronium and 8-dioxonium species, respectively. The first conjugates of iron bis(1,2-dicarbollide)(-I) with 2'-deoxyadenosine modified via the C-8 position of the purine base were synthesized. Reactions of these oxonium compounds with 1,2-bis(diphenylphosphino)ethane (dppe) led to zwitter-ionic monophosphonium salts. One of these compounds has given rise to a novel ferracarborane/cobaltacarborane hybrid complex.
Assuntos
Complexos de Coordenação/química , Ferro/química , Cobalto/química , Desoxiadenosinas/química , Estrutura Molecular , Porfirinas/química , Difração de Raios XRESUMO
Cyclic oxonium derivatives of polyhedral boron hydrides are a relatively new class of boron compounds. They have great potential for the modification of various types of organic and bioorganic molecules and the synthesis of compounds that could be used in different fields from the treatment of nuclear wastes to the treatment of cancer. In the present Perspective we would like to present an overview of the results of the preparation and synthetic application of these compounds.