Glycol and Phosphate Depot Forms of 4- and/or 5-Modified Nucleosides Exhibiting Antibacterial Activity

3′-Amino modifications enhance the antifungal properties of N4-alkyl-5-methylcytidines for potential biocides

“…The antibacterial effect of our synthesized compounds was studied in vitro by their ability to inhibit the microorganism growth. [34][35][36] The antibacterial assay was carried out against such Gram-positive bacteria, such as Bacillus subtilis, two strains of Staphylococcus aureus, streptococcus-like bacteria Leuconostoc mesenteroides and Micrococcus luteus, and two strains of Mycobacterium smegmatis, and Gram-negative bacteria including Escherichia coli and Pseudomonas aeruginosa. 3 0 -Modified N 4 -alkyl-5-methyl-2 0 ,3 0 -dideoxycytidines demonstrate activity against Gram-positive bacteria as well as mycobacteria (Table 1), and there is no activity against Gram-negative microorganisms (with the exception of N 4 -dodecyl-3 0 -amino-5-methyl-2 0 ,3 0 -dideoxycytidine 10b, which also showed high inhibitory activity against Gram-negative bacteria, E. coli (49 mM)).…”

Analogues of Pyrimidine Nucleosides as Mycobacteria Growth Inhibitors

“…In order to develop a new set of antibacterial nucleosides, a representative library [74][75][76] of 3′-and 5′-tri-or tetraethylene glycol prodrugs of 5-alkyloxymethyl-and 5-alkyltriazolylmethyl-2′-deoxyuridines with described anti-tuberculosis activity were synthesized (Figure 10) [44,45]. The compounds were two orders of magnitude more soluble compared to the parent nucleosides, had significant inhibitory activity against a number of bacteria, including drug-resistant strains of M. smegmatis (as well as S. aureus), and exhibited low cytotoxicity [74][75][76]. The replacement of the triethylene glycol residue in C-5′ position by tetraethylene glycol led to an increase in water solubility and a significant decrease in inhibitory activity.…”

“…In order to develop a new set of antibacterial nucleosides, a representative library [ 74 , 75 , 76 ] of 3′- and 5′-tri- or tetraethylene glycol prodrugs of 5-alkyloxymethyl- and 5-alkyltriazolylmethyl-2′-deoxyuridines with described anti-tuberculosis activity were synthesized ( Figure 10 ) [ 44 , 45 ].…”

“…The compounds were two orders of magnitude more soluble compared to the parent nucleosides, had significant inhibitory activity against a number of bacteria, including drug-resistant strains of M. smegmatis (as well as S. aureus ), and exhibited low cytotoxicity [ 74 , 75 , 76 ]. The replacement of the triethylene glycol residue in C-5′ position by tetraethylene glycol led to an increase in water solubility and a significant decrease in inhibitory activity.…”

Pyrimidine Nucleosides Analogues as Mycobacteria Growth Inhibitors

“…In order to develop a new set of antibacterial nucleosides, a representative library [72][73][74] of 3′-and 5′-trior tetraethylene glycol prodrugs of 5-alkyloxymethyl-and 5alkyltriazolylmethyl-2′-deoxyuridines with described antituberculosis activity were synthesized (Figure 10) [42,43]. The compounds were two orders of magnitude more soluble compared to the parent nucleosides, had significant inhibitory activity against a number of bacteria, including drug-resistant strains of M. smegmatis (as well as S. aureus), and exhibited low cytotoxicity [72][73][74]. The replacement of the triethylene glycol residue in C-5′ position by tetraethylene glycol led to an increase in water solubility and a significant decrease in inhibitory activity.…”