engleski

Synthesis and biological activity of 3-aminothymoquinone

Thymoquinone (TQ) is a natural benzoquinone with various biological and medicinal activities. The main disadvantage of TQ is its low aqueous solubility. In the present work we report the synthesis and biological activities of TQ derivative, 3-aminothymoquinone (ATQ). ATQ was prepared according to published literature reports, with slight modifications. The structure was identified by elemental analysis and characterized in solution by mass spectrometry and NMR spectroscopy. Antimicrobial activity was determined against four Gram-positive and four Gram-negative bacteria strains and three fungi using diffusion and micro-dilution methods. It was observed that antibacterial activity is diminished in case of ATQ when compared to TQ. On the other hand, ATQ showed strong antifungal activity in all tested fungi (Candida albicans ATCC 10231, Saccharomyces cerevisiae ATCC 9763 and Aspergillus brasiliensis ATCC 16404) with minimal inhibitory concentration (MIC) values significantly lower when compared to TQ and Nystatin which was used as the reference drug. Antiproliferative activity of TQ and ATQ was evaluated in five different cell lines: SW620 (metastatic human colon adenocarcinoma), CFPAC (ductal pancreatic adenocarcinoma), HepG2 (hepatocellular carcinoma), HeLa (cervical adenocarcinoma) and WI38 (human lung fibroblasts). ATQ had stronger effects in all tested cell lines when compared to TQ. In conclusion, ATQ, which is the C-3 amino derivative of TQ, exerts significantly higher antifungal and antitumor activity, when compared to parent compound.

Thymoquinone ; 3-aminothymoquinone ; Antibacterial activity ; Antifungal activity ; Antiproliferative activity

nije evidentirano