In this paper, 1-tosyl-3-hydroxyl-1,5,8-triazacyclodecane (2) was prepared in optimized conditions. The structure of title compound 2 was established on the basis of spectroscopic data. The binding of compounds 2, 3, 4 to DNA was investigated with melting temperature measurements and molecular-modeling calculations. The results showed that the introduction of hydroxyl and tosyl groups into triazacyclicamines may enhance the interaction between the compound 2 and DNA. The free macrocyclic ligand 2 could catalyze cleavage supercoiled pBR322 DNA to the nicked and the linear form at the same time at near neutral conditions and 37 degrees C without any metal ions aid. In addition, compound 2 showed selectively inhibition to lung cancer cells. Thus, this leading compound might be useful as artificial restriction enzymes and may be usefully applied in the development of anti-tumor drug.