Synthesis, structure, DNA-binding, and cytotoxic activities of N-(5-chloro-2-hydroxyphenyl)-N′-[3-(2-hydroxyethylamino)propyl]oxamide and its dicopper(II) complex

Abstract

A dissymmetrical N,N′-bis(substituted)oxamide, N-(5-chloro-2-hydroxyphenyl)-N′[3-(2-hydroxyethylamino)propyl]oxamide (H₃oxpep), and its dicopper(II) complex, [Cu₂(oxpep)(phen)]ClO₄ (1) (phen = 1,10-phenanthroline), were synthesized. The crystal structure of 1 was determined by single-crystal X-ray diffraction. In 1, Cu1 and Cu2 are bridged by cis-oxpep³⁻ with Cu ··· Cu separation of 5.2007(6) Å. Cu1 is in a distorted square-pyramidal environment, while Cu2 has a square-planar coordination geometry. The 3-D supramolecular structure of 1 is formed through π–π stackings and hydrogen bonds. The DNA-binding properties and cytotoxic activities of the two compounds were investigated. The results suggest that the two compounds can interact with HS-DNA by intercalation with binding affinities following the order 1 > H₃oxpep, which is consistent with their anticancer activities.

Keywords:

• Dissymmetrical N,N′-bis(substituted)oxamide
• Dicopper(II) complex
• Crystal structure
• DNA-binding property
• Cytotoxic activity

Acknowledgments

This project was supported by the National Natural Science Foundation of China (No. 21071133), the Natural Science Foundation of Qingdao City (No. 09-1-3-73-jch), and the Program for Changjiang Scholars and Innovative Research Team in University (IRT0944).