Synthesis and antimicrobial activity of amphiphilic carbohydrate derivatives

Abstract

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...

Different Schiff Bases—Structure, Importance and Classification

“…New groups of organic compounds are still being described, the combinations of which may form a group of extremely desirable compounds with antibiotic properties, suitable for an attempt to challenge the problem of antimicrobial resistance. In the instance of the results described in the article by R. C. N. Reis et al from 2008 [ 147 ], in which the activity of the coupling products of D-ribonic acid hydrazide and long-chain aldehydes and the hydrazinolysis products of D-ribo-1,4-lactone with N , N -disubstituted hydrazines was tested against M. tuberculosis , S. aureus , E. coli and C. Albicans , versus i.o. rifampicin, penicillin-G, chloramphenicol and nystatin, the authors noted that the greater the activity of the coupling products against M. tuberculosis and S. aureus , the longer the attached hydrocarbon chain was.…”

Antileishmanial Activity of Aldonamides andN-Acyl-Diamine Derivatives

“…Preparation of aldonamides 9-16 was achieved by the nucleophilic addition of N-alkylamines 1-8 to Dribono-1,4-lactone (Scheme 1) [9,16,17]. N-Acylated diamines 22-31 were prepared by reaction of fatty esters 17-21 with either 1,2-ethanediamine or 1,4-butanediamine [18,19].…”

Fast and Efficient Mechanosynthesis of Aldonamides by Aminolysis of Unprotected Sugar Lactones

“…Foamability properties have also been observed for derivatives such as N-alkyl-N-(2-hydroxyethyl) and N-cycloalkylaldonamides [7,8]. Properties of some aldonamides are also interesting for biological applications: abilities to protect hematopoietic stem and progenitor cells against cryoinjury (i.e., ice recrystallization inhibitory properties) [9,10] or bacteriostatic properties on some gram-positive bacteria [11,12] were reported, among others. In addition, aldonamides have been described as intermediates for the synthesis of glycoconjugates, evaluated as glucose-sensing materials [13], or for the synthesis of neo-glycoconjugates [14][15][16][17].…”