RESUMO
Cationic lipids have long been known to serve as antibacterial and antifungal agents. Prior efforts with attachment of cationic lipids to carbohydrate-based surfaces have suggested the possibility that carbohydrate-attached cationic lipids might serve as antibacterial and antifungal pharmaceutical agents. Toward the understanding of this possibility, we have synthesized several series of cationic lipids attached to a variety of glycosides with the intent of generating antimicrobial agents that would meet the requirement for serving as a pharmaceutical agent, specifically that the agent be effective at a very low concentration as well as being biodegradable within the organism being treated. The initial results of our approach to this goal are presented.
Assuntos
Glicosídeos/química , Lipídeos/química , Poliaminas/química , Antibacterianos/síntese química , Antibacterianos/química , Antifúngicos/síntese química , Antifúngicos/química , Configuração de Carboidratos , Glicosídeos/síntese química , Humanos , Lipídeos/síntese química , Testes de Sensibilidade Microbiana , Estrutura Molecular , Poliaminas/síntese química , Polieletrólitos , Sais/químicaRESUMO
Herein is reported the preparation of several series of symmetrical polyammonium salts that serve as cationic lipids or precursors thereof, and are structurally based on several series of parent diamines where dimethylazonia functionalities are present, separated by a central structural unit, and pendant terminal chains. The resultant materials are of significant interest for a variety of purposes, such as serving as antihydrophobic species and as transfectins, the details of which are provided in separate reports. Attempts to effect selective alkylation to provide the corresponding unsymmetrical cationic lipids were without success, always leading to relatively useless mixtures of products.
Assuntos
Lipídeos/síntese química , Poliaminas/síntese química , Compostos de Amônio Quaternário/química , Diaminas/química , Interações Hidrofóbicas e Hidrofílicas , Lipídeos/química , Poliaminas/química , Polieletrólitos , Compostos de Amônio Quaternário/síntese química , EstereoisomerismoRESUMO
In our continuing investigation of polycationic salts for purposes of antimicrobial action, ion-channel blocking, and construction of ionic liquids, we have prepared several series of polycationic salts derived from carbohydrate precursors. These salts are currently being investigated for optimal efficacy as antibacterials and antifungals, as well as for other applications. The syntheses of such series of salts are described here along with preliminary antibacterial testing results and a discussion of their properties indicating their potential utility for several purposes.
Assuntos
Carboidratos/química , Carboidratos/síntese química , Antibacterianos/síntese química , Antibacterianos/química , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Sequência de Carboidratos , Carboidratos/farmacologia , Géis , Glucosídeos/química , Testes de Sensibilidade Microbiana , Estrutura Molecular , Álcoois Açúcares/químicaRESUMO
Herein is reported the preparation of several series of polyammonium salts that serve as cationic lipids or precursors thereof, and are structurally based on the parent diamine 1,4-diazabicyclo[2.2.2]octane (dabco). Through selective alkylation of dabco a variety of di- and tetracationic lipid species and precursors thereof have been prepared. The resultant materials are of significant interest for a variety of purposes, including serving as antimicrobial agents and antihydrophobic species, the details of which are provided in separate reports.