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Synthesis, characterization, spectrophotometric and electrochemistry studies, and DNA cleavage of copper(II) complexes of a new azacrown bis-macrocycle and its mono-cyclic analogue


Khoramdareh, Zahra Kalantari; Hosseini-Yazdi, Seyed Abolfazl; Spingler, Bernhard; Khandar, Ali Akbar (2014). Synthesis, characterization, spectrophotometric and electrochemistry studies, and DNA cleavage of copper(II) complexes of a new azacrown bis-macrocycle and its mono-cyclic analogue. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 80(3-4):391-399.

Abstract

A new azacrown bis-macrocycle (5) and its mono–cyclic analogue (7) were synthesized and characterized by FT-IR, 1H NMR, 13C NMR, DEPT 13C NMR, MS, and elemental analysis. The reaction with copper(II) nitrate yielded the corresponding complexes, formulated as Cu(5)(NO3)2·3H2O (8), and Cu(7)(NO3)2·2.5H2O (9). Also the stoichiometries of the complexes were determined in alcoholic solution and the results show that for both complexes the ratio of ligand to metal was 1:1 in methanol. The redox behavior of both complexes has been studied by cyclic voltammetry in DMF. Cyclic voltamogram of 8 shows quasi-reversible CuII/CuI redox couple whereas 9 shows a reversible CuII/CuI redox couple. Mono- and bis-macrocycle copper(II) complexes (8 and 9 respectively) cleaved plasmid pGS2 DNA by using an oxidative mechanism with 3- mercaptopropionic acid (MPA) as the reductant under aerobic conditions. The bis-macrocycle copper(II) complex 8 showed higher cleavage efficiency than their mono-macrocycle analogue 9 at the same Cu2+ concentration.

Abstract

A new azacrown bis-macrocycle (5) and its mono–cyclic analogue (7) were synthesized and characterized by FT-IR, 1H NMR, 13C NMR, DEPT 13C NMR, MS, and elemental analysis. The reaction with copper(II) nitrate yielded the corresponding complexes, formulated as Cu(5)(NO3)2·3H2O (8), and Cu(7)(NO3)2·2.5H2O (9). Also the stoichiometries of the complexes were determined in alcoholic solution and the results show that for both complexes the ratio of ligand to metal was 1:1 in methanol. The redox behavior of both complexes has been studied by cyclic voltammetry in DMF. Cyclic voltamogram of 8 shows quasi-reversible CuII/CuI redox couple whereas 9 shows a reversible CuII/CuI redox couple. Mono- and bis-macrocycle copper(II) complexes (8 and 9 respectively) cleaved plasmid pGS2 DNA by using an oxidative mechanism with 3- mercaptopropionic acid (MPA) as the reductant under aerobic conditions. The bis-macrocycle copper(II) complex 8 showed higher cleavage efficiency than their mono-macrocycle analogue 9 at the same Cu2+ concentration.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:December 2014
Deposited On:01 Apr 2015 12:47
Last Modified:05 Apr 2016 19:11
Publisher:Springer
ISSN:1388-3127
Publisher DOI:https://doi.org/10.1007/s10847-014-0425-3

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