Objectives: In this work, 9 lipophilic-acid chelating FQs (fluoroquinolones) comprising chelating groups have been prepared, characterized and screened for in vitro cytotoxicity, radical scavenging and antiinflammation propensities. Methods: Using sulforhodamine B colorimetric bioassay vs. cisplatin; FQs-inflicted reductions' of viability against breast T47D and MCF7, Pancreatic PANC-1, colorectal HT29, HCT116, SW620, CACO2, SW480 and Leukaemia K562 cancer cell lines were examined in quadruplicates/dose/cell line. Parameters including potency, toxicity, and selectivity (potency/toxicity) have been reported along with DPPH-and NO-radicals' scavenging capacities -as their molecular action mechanism-in comparison to ascorbic acid and indomethacin respectively. Using Griess assay in Lipopolysaccharide (LPS) prompted RAW264.7 macrophages; mitigation of inflammation was investigated. Results: nitroFQ 3b, unlike the rest of FQs in PANC1 and MCF7 cells, exhibited remarkably superior NO-radical scavenging/ antiinflammation capacity to indomethacin with respective antiproliferative IC 50 values (<50µM) 49 vs. cisplatin's 122 and 6 vs. cisplatin's 28 (p<0.01-0.001; n=4). Reduced FQ 4b of significantly dual DPPH-NO scavenging propensities exerted exceptionally substantial micromolar antiproliferation in colorectal cancer cells with respective antiproliferative IC 50 values (<50µM) of HCT116 0.84< HT29 1.6