The studies on the synthesis and DNA intercalative properties of a new type of anthracene probes possessing crown ethers and uracyl groups

A new procedure for the synthesis of aminoanthracene DNA probe 1 was develo ped. The model studies on the influence of protective groups on the reactio n course towards formation of aminoanthracene 3a were performed. The result s of these studies were utilized in the synthesis of anthracene crown ether 10a. Binding studies of this compound show low affinity (K = 2.3x10(-1) M- 1) of this probe to CT-DNA. Smaller binding constant of this compound as co mpared to compound 3a is presumably caused by complexation of sodium cation from the buffer. The model studies towards incorporation of uracyl group i nto aminoanthracene 10a by formation of amide bonds were performed. The rea ction proceeds only in the presence of p-nitrophenyl leaving group.