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To be dinuclear or not: Z-DNA induction by nickel complexes


Spingler, Bernhard; Antoni, Philipp M (2007). To be dinuclear or not: Z-DNA induction by nickel complexes. Chemistry - A European Journal, 13(23):6617-6622.

Abstract

The left-handed Z-DNA has been identified as a gene regulating element. Therefore the generation of Z-DNA through metal complexes might be an innovative way for the regulation of gene expression. Use of the new dinuclear complex N,N,N',N'-tetrakis-2(3,5-dimethylpyrazol-1-yl)ethyl]-1,3- propylenediamine-bis(nickel(II) dinitrate) (2) reversibly induced Z-DNA formation. However, when a 1:1 ratio of metal/dinucleating ligand was used as a control, the midpoint of the B- to Z-DNA transition was at the same nickel concentration as in case of the dinuclear complex. The novel mononuclear analogue, N-methyl-N,N-bis-2(3,5-dimethylpyrazol-1-yl)ethyl]amine- nickel (II)-dinitrate (3) was inducing the Z-DNA at a similar ratio versus nucleotides as free nickel(II) itself. For the first time, proton and nickel binding constants for the bis-2-(pyrazol-1-yl)ethyl]amine ligand system are reported and discussed. Both nickel complexes 2 and 3 were structurally characterized by single crystal analysis. Furthermore, the synthesis of the two new ligands, N,N,N',N'-tetrakis-2-(3,5-dimethylpyrazol -1-yl)ethyl]-1,2-propylenediamine (4) and N-methyl-N,N-bis-2(3,5-dimethylpyrazol-1-yl)ethyl]amine (5) is described. The two major synthetic pathways leading to polypyrazoyl amines in general are critically discussed with respect to yield, reproducibility and handling of the intermediates.

Abstract

The left-handed Z-DNA has been identified as a gene regulating element. Therefore the generation of Z-DNA through metal complexes might be an innovative way for the regulation of gene expression. Use of the new dinuclear complex N,N,N',N'-tetrakis-2(3,5-dimethylpyrazol-1-yl)ethyl]-1,3- propylenediamine-bis(nickel(II) dinitrate) (2) reversibly induced Z-DNA formation. However, when a 1:1 ratio of metal/dinucleating ligand was used as a control, the midpoint of the B- to Z-DNA transition was at the same nickel concentration as in case of the dinuclear complex. The novel mononuclear analogue, N-methyl-N,N-bis-2(3,5-dimethylpyrazol-1-yl)ethyl]amine- nickel (II)-dinitrate (3) was inducing the Z-DNA at a similar ratio versus nucleotides as free nickel(II) itself. For the first time, proton and nickel binding constants for the bis-2-(pyrazol-1-yl)ethyl]amine ligand system are reported and discussed. Both nickel complexes 2 and 3 were structurally characterized by single crystal analysis. Furthermore, the synthesis of the two new ligands, N,N,N',N'-tetrakis-2-(3,5-dimethylpyrazol -1-yl)ethyl]-1,2-propylenediamine (4) and N-methyl-N,N-bis-2(3,5-dimethylpyrazol-1-yl)ethyl]amine (5) is described. The two major synthetic pathways leading to polypyrazoyl amines in general are critically discussed with respect to yield, reproducibility and handling of the intermediates.

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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:2007
Deposited On:23 Oct 2012 13:24
Last Modified:05 Apr 2016 16:01
Publisher:Wiley-Blackwell
ISSN:0947-6539
Publisher DOI:https://doi.org/10.1002/chem.200600737
Other Identification Number:ISI:000248710700010

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