Synthesis, Characterization, Antimicrobial and Antitumor Activities of Sucrose Octa(N-ethyl)carbamate.

Claudia D Raposo,Maria T Barros,Ricardo C Calhelha,Isabel C F R Ferreira,Krasimira T Petrova,Marina Sokovic

doi:10.2174/1573406410666150807111029

Claudia D Raposo, Maria T Barros + Show 4 more

Open Access

https://doi.org/10.2174/1573406410666150807111029

Copy DOI

Abstract

Sucrose octa(N-ethyl)carbamate was synthesized directly from sucrose and ethyl isocyanate, and its structure was confirmed by various analytical methods, such as (1)H and (13)C NMR, FTIR, m.p., MS, and optical rotation. Its antibacterial, antifungal and cytotoxic activities were investigated. It exhibited strong inhibition against all bacteria tested, namely S. aureus (MIC 0.18±0.006), B. cereus (MIC 0.094±0.000), M. flavus (MIC 0.28±0.01), L. monocytogenes (MIC 0.18±0.006), P. aeruginosa (MIC 0.094±0.002), S. typhimurium (MIC 0.094±0.002), E. coli (MIC 0.18±0.006) and E. cloacae (MIC 0.18±0.006) and strong antifungal activity towards T. viride (MIC 0.09 ± 0.006), A. versicolor (MIC 0.18 ± 0.01), A. ochraceus (MIC 0.375 ± 0.01) and P. ochrochloron (MIC 0.375 ± 0.04). Furthermore, it showed moderate antitumor potential against human breast (GI50 357.20±14.12), colon (GI50 332.43±11.19) and cervical (GI50 282.67±3.97) cell lines and, more important, without hepatotoxicity.

Highlights

The excessive or careless use of antibiotics has contributed to an increased number of drug resistant microorganisms
Various glycosides can be found in natural resources, mainly in the form of glycoconjugates, where the saccharide moiety plays an important role in modulating their biological activities [8]
A synthesis using a polar aprotic solvent such as pyridine was attempted, and the desired sucrose octa(N-ethyl)carbamate was formed in good yield (Scheme 1)

Summary

INTRODUCTION

The excessive or careless use of antibiotics has contributed to an increased number of drug resistant microorganisms. A growing number of compounds with carbamate linkages have shown strong antimicrobial and cytotoxic activities have been reported [4,5,6,7]. The wide variety of potent biological activities of natural and synthetic sugar derivatives encouraged us to develop novel biological active compounds based on sucrose [18, 19]. It is a biorenewable and biocompatible raw material and is a promising starting material for the synthesis of new compounds with biological activity [20]. The antimicrobial, antifungal and cytotoxic activities of the products were tested and compared with those of commercial agents – streptomycin and ampicillin (antimicrobial), bifonazole and ketoconazole (antifungal), and ellipticine (cytotoxic)

Chemistry

Antibacterial Activity

Antifungal Activity

Antitumor Activity and Hepatotoxicity

CONCLUSIONS

General Methods