Synthesis, Characterization and antitumor activity of ethyl 8-nitrociprofloxacin – 1,2,3-triazole conjugates against prostate cancer cell lines PC3, DU145

• Library of novel 8-nitrociprofloxacin −1,2,3-triazoles hybrides were synthesized via green synthesis. • The anticancer screening was investigated against two prostate cancer, PC3 and DU145 cell lines. The results revealed that the fluorinated compounds emerged as the most potent tested compounds. • The anticancer assessment methods included MTT assays for cell viability, comet assays to detect DNA damage, quantitative real-time PCR to analyze gene expression, and annexin V-FITC/PI staining coupled with flow cytometry to measure apoptotic cells. Five novel 8-nitrociprofloxacin-1,2,3-triazole conjugates( 9a-e ) were synthesized via 1,3-dipolar cycloaddition reaction, by reacting ethyl 1-cyclopropyl-6-fluoro-8-nitro-4-oxo-7-(4-(3-oxobutanoyl) piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate( 7 ) with various aryl azides. The new compounds were characterized using High-Resolution Mass Spectrometry(HRMS), 1 H NMR, and 13 C NMR. Conjugates( 9a-e ) were tested for their in vitro anticancer activity against two prostate cancer cell lines, namely, PC3, DU145. Conjugates 9d and 9e exhibited remarkable anti-proliferative activity against DU145 and PC3 cell-lines. The IC50 of 9d and 9e for PC3 cell line is 0.0496 ± 0.2372 μM and 0.145 ± 0.337 μM, respectively. All derivatives ( 9a-e ) significantly increased the amount of DNA damage. Two conjugates 9d and 9e, showed enhanced cytotoxic activity against both prostate cancer cell lines in comparison to the other conjugates. Derivatives 9e , 9c and 9d significantly enhanced the expression of p53, Caspases3 and p21 by 4-folds. The AnnexinV–FITC/PI test revealed a late apoptosis at the level of 9.1–13.5 % as performed with DU145 cells cultured with derivatives 9e and 9d .