Synthesis, characterization, and bioactivities of copper complexes with N-substituted Di(picolyl)amines

• Published in: Transition metal chemistry (Weinheim) 2009-04, Vol.34 (3), p.337-345
• Main Authors: Wang, Lin-Yun, Chen, Qiu-Yun, Huang, Juan, Wang, Kun, Feng, Chang-Jian, Gen, Zhi-Rong
• Format: Article
• Language: English
• Subjects: Catalysis; Chemistry; Chemistry and Materials Science; Copper; Crystal structure; Deoxyribonucleic acid; DNA; Inorganic Chemistry; Organometallic Chemistry; Physical Chemistry
• ISSN: 0340-4285; 1572-901X
• DOI: 10.1007/s11243-009-9200-5

Three new Cu(II) complexes with ethyl bis(2-pyridylmethyl)amino-2-propionate (Etdpa), or bis(2-pyridylmethyl)amino-2-propionate (Adpa), were synthesized and characterized by physico-chemical and spectroscopic methods. The X-ray crystal structure of [(Adpa)CuCl] shows that the copper(II) atom is coordinated by three N atoms, one oxygen atom from the ligand (Adpa) and one chloride anion, forming a trigonal bipyramidal geometry. The spectrophotometric and fluorescence titration data indicate that the interaction of square pyramidal [(Etdpa)CuCl 2 ] with ct-DNA is weak, but the trigonal bipyramidal complexes [(Adpa)Cu(H 2 O)](ClO 4 ) and [(Adpa)CuCl] interact with ct-DNA with the mode of intercalation. The inhibition activities of the three new copper(II) complexes on the four cancer cells (Mcf-7, Eca-109, A549, and Hela) are in the order: [(Adpa)Cu(H 2 O)](ClO 4 ) > [(Adpa)CuCl] > [(Etdpa)CuCl 2 ], which correlates with their DNA-binding properties. The results show that the substituents introduced on the secondary amino nitrogen atom of dpa have great contribution to the antitumor activities of these copper(II) complexes. It is also found that the coordination of copper(II) ions with AdpaH can decrease the toxicity of AdpaH.