Synthesis and Nucleic Acid-Binding Properties of Water-Soluble Porphyrins Appending Platinum(II) Complexes

We synthesized two water-soluble porphyrins appending platinum(II) complexes [α,β-(4a) and α,α-(4b) 5,15-bis(2-trans-[PtCl(NH3)2]N-2-aminoethylaminocarbonylphenyl) 2,3,7,8,12,13,17,18-octamethylporphyrin] and studied their reactions with a variety of nucleic acids [disodium adenosine-5'-monophosphate (AMP), disodium guanosine-5'-monophosphate (GMP), disodium thymidine-5'-monophosphate (TMP), disodium cytidine-5'-monophosphate (CMP), synthetic polymer poly(dG)-poly(dC), poly(dA)-poly(dT)] by 1H-NMR, UV-vis and FAB-MS spectroscopies. Based on the denaturation experiments of synthetic nucleic acid polymers, we conclude that the presence of the porphyrins (5.6 μM) does not cause significant changes in the melting temperature of poly(dA)-poly(dT) (28 μM) (ΔT=1 °C) and shows reannealing. On the other hand, gradual melting of poly(dG)-poly(dC) (28 μM) occurs at a low temperature (ΔT=−27 °C) in the presence of the porphyrins (5.6 μM), and the solutions do not show reannealing phenomena. The results of UV-vis and 1H-NMR experiments revealed that the porphyrins bind to guanine bases and that the porphyrins bind to GMP more strongly than to the other nucleotides. The binding modes between the porphyrins and synthetic nucleic acids are affected more by the coordination of the nucleobase [poly(dG)-poly(dC)] to the Pt(II) in the porphyrins than by Coulomb and hydrophobic interactions.