Emulsion polymerization of 2-amino-4-(1-benzyl-1H-indol-3-yl) thiophene-3-carbonitrile (ABITC) using ammonium persulfate (APS) as an oxidizing agent afforded two isomers of poly (2-amino-4-(1-benzyl-1H-indol-3-yl) thiophene-3-carbonitrile) (PABITC) with high molecular weight 35673 and 28596 g/mol. Chemical structure and morphology of the newly synthesized polymers were investigated by IR, 1HNMR, SEM, and GPC. Nano capsulation of ABITC, PABITC, and PABITC/Doxorubicin by polyethylene glycol (PEG) was achieved by the nano-precipitation method. The anti-proliferative activity of the newly synthesized PABITC and nano-capsulation against HepG2, Huh7, and A549 cancer cell lines were investigated using MTT assay. The result obtained indicates that the encapsulation of ABITC inside PEG-NP led to an improvement in their anti-proliferative activity against cancer cell lines compared to free ABITC. The free PABITC revealed moderate anti-proliferative activity against tested cells and their encapsulation form with PEG-NP revealed no significant change in the activity with the fold changed not exceed 1-time fold. Furthermore, the anti-proliferative activity of PABITC -NP was improved after Doxorubicin (DOX) encapsulation against tested cells compared to PABITC - PEG-NP. In addition, PABITC exhibited potent antibacterial activity against tested microbes comparing to monomer ABITC and the reference drug amikacin. Moreover, the binding mode of the monomer ABITC beside two repeated units of monomer inside the active site of the DNA gyrase B chain (PDB ID: 1KIJ) as promising bacterial target and CDK2 enzyme (PDB ID: 1PYE)] as promising cancer target was studied using molecular docking technique.