Synthesis, Antibacterial and Cytotoxicity Assessment of Modified Uridine Molecules | Chapter 11 | Current Advances in Chemistry and Biochemistry Vol. 6

 Nucleoside derivatives continue to play an important role in the treatment of various diseases; therefore, in light of the importance of nucleoside analogues, we synthesized a series of nucleoside molecules, namely, uridine derivatives. The direct acylation of uridine molecules with N-acetylsulfanilyl chloride produced the corresponding 5-O-N-acetylsulfanilyluridine with ribose sugar moiety. The 5 -O-N-acetylsulfanilyluridine derivative was further transformed into a series of 2,3 -di-O-acyl derivatives containing a wide range of functionalities in a single molecular framework to produce newer products. The purity and structure of the products obtained have been confirmed. All uridine derivatives were tested in vitro for antibacterial activity against six human pathogenic bacterial strains. The study found that the selectively acylated derivatives 5 -O-Nacetylsulfanilyl-2,3 -di-O-lauroyluridine (7) and 5 -O-Nacetylsulfanilyl-2,3 -di-O-pivaloyluridine (10) inhibited Staphylococcus aureus and Bacillus cereus the best. Another interesting finding was that uridine derivatives were found to be more effective against Gram-positive bacteria than Gram-negative bacteria. Furthermore, the test compounds were tested for cytotoxicity using a brine shrimp lethality bioassay, and the compounds demonstrated varying rates of mortality at different concentrations. As a result, these synthesized derivatives have the potential to be used as antibacterial agents and are promising drug candidates for future therapeutic applications.

Author (s) Details

Asraful Alam
Laboratory of Carbohydrate and Nucleoside Chemistry (LCNC), Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong-4331, Bangladesh.

Md Anowar Hosen
Laboratory of Carbohydrate and Nucleoside Chemistry (LCNC), Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong-4331, Bangladesh.

Mariam Islam
Laboratory of Carbohydrate and Nucleoside Chemistry (LCNC), Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong-4331, Bangladesh.

Jannatul Ferdous
Laboratory of Carbohydrate and Nucleoside Chemistry (LCNC), Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong-4331, Bangladesh.

Yuki Fujii
Laboratory of Functional Morphology, Graduate School of Pharmaceutical Sciences, Nagasaki International University, Nagasaki 859-3298, Japan.

Yuki Fujii
Laboratory of Functional Morphology, Graduate School of Pharmaceutical Sciences, Nagasaki International University, Nagasaki 859-3298, Japan.

Sarkar M. A. Kawsar
Laboratory of Carbohydrate and Nucleoside Chemistry (LCNC), Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong-4331, Bangladesh

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