Inclusion complexes of 2-[Arylidenamino]-1,3,4-thiadiazino[6,5b]indoles have been prepared with β-cyclodextrin so as to increase the solubility of these compounds in polar medium which may increase theirbioaccessibility. The formation of inclusion complexes is known from the study of changes in physical andspectral properties of the compounds. The stability of the inclusion complexes has been studied by thedetermination of the thermodynamic parameters like change in free energy, change in enthalpy and change inentropy. Finally compounds and their inclusion complexes are screened for antibacterial and antioxidantactivities. It is found that both antibacterial and antioxidant activity of the compounds increase significantlyafter the inclusion complex formation. In addition, the presence of activating groups on arylidene unit furtherfavours inclusion complex formation and also stabilizes the same. Manuscript profile