Diaminas N-monoalquiladas foram sintetizadas e tratadas com D-ribonolactona ou D-gliconolactona. As aldonamidas resultantes foram avaliadas para atividade antimicrobiana contra S. aureus, E. coli, M. tuberculosis and C. albicans. Duas hidrazidas foram também preparadas a partir da ribonoidrazida e suas atividades biológicas comparadas com aquelas de análogos amida. Todos os derivados da ribonolactona mostraram ter atividade antitubercular moderada, alguns foram ativos também contra S. aureus. N-monoalkylated diamines were synthesised and treated with D-ribonolactone or D-gluconolactone. The resulting aldonamides were evaluated for their antimicrobial activity against S. aureus, E. coli, M. tuberculosis and C. albicans. Two hydrazides were also prepared from ribonohydrazide and their biological activity was compared to their amide analogues. All the ribono-derivatives displayed moderated antitubercular activity, and some of them were also active against S. aureus.
Keywords: antimicrobial, M. tuberculosis, amphiphilic, aldonamide
IntroductionSurfactants are amphiphilic molecules which are widely used in many industries. Although conventional nonionic surfactants can be produced in large scale from petrochemical raw materials, the increasing need for biodegradable and less toxic products has led to numerous studies of new sugar-based surfactants, which can be prepared from natural raw materials. [1][2][3][4][5][6][7][8][9][10][11] These compounds possess a carbohydrate hydrophilic head (mono-or oligosaccharide), and a hydrophobic tail, usually derived from a fatty acid. The two moieties can be directly linked via a functional group (ester, ether, hydrazine, amine, etc) or separated by a spacer (gemini surfactants). Carbohydrate surfactants are of great interest because they are not noxious for the environment. 12,13 Due to their functional properties they can be used in several areas, such as food industry (emulsion stabilization, foaming), 14,15 biology (extraction membrane proteins), 16 glycobiology, 17,18 immunology, 19 detergents, and cosmetology (non-alergic compounds).Carbohydrate-derivated amphiphilic compounds have also been studied for their antimicrobial action. [20][21][22][23][24] These compounds can display two mechanisms of action. They can act as nonionic surfactants: the hydrophilic moiety of surface active compounds binds to the hydrophilic portion of the membrane via hydrogen bonds. The hydrophobic moiety is then able to penetrate the lipid bilayer structure, provocating a disorder in the permeability and fluidity of the membrane. 25 They can also act as inhibitors of enzymes involved in the biosynthesis of the bacterial cell wall. Galactofuranosyl 1 26 and galactopyranosyl derivatives 2 27 and 3 28 (Figure 1) bearing long alkyl chains displayed antitubercular activity.In the last years the intensive use of antibiotic has lead to an increase of the emergence of resistant bacteria. 29,30 There is a growing need for new class of antibacterial compounds having different mechanism of action compar...