New ruthenium complexes containing enantiopure 2,6-bis[4′(R)-phenyloxazolin-2′-il-pyridine] ((R,R)-Ph-pybox), 2,6-bis[4′(S)-isopropyloxazolin-2′-il-pyridine] ((S,S)-ⁱPr-pybox) or 2,6-bis[4′(R)-isopropyloxazolin-2′-il-pyridine] ((R,R)-ⁱPr-pybox) and water soluble 1,3,5-triaza-7-phosphaadamantane (PTA) or N-substituted PTA phosphanes have been synthesized in high yields and fully characterized. The interactions of these compounds with plasmidic DNA and their cytotoxic activity against the human cervical cancer HeLa cell line are reported, pointing out for the first time the different behaviour of ruthenium enantiomers affecting the cell cycle in HeLa tumor cells.