Synergetic DNA-Cleaving Activities of the Metal Complexes of a Polyether-Tethered Pyrrole-polyamide Dimer

A simple polyether‐tethered pyrrole‐polyamide dimer 1 was synthesized in 50% yield from the reaction of 2,2,2‐trichloro‐1‐(1‐methyl‐4‐nitro‐1H‐pyrrol‐2‐yl)ethanone with 2,2′‐[1,2‐ethanediylbis(oxy)]bisethanamine, and fully characterized on the basis of 1H‐ and 13C‐NMR, MS, HR‐MS, and IR data. Agaros...

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Bibliographic Details
Published in:Chemistry & biodiversity 2012-06, Vol.9 (6), p.1125-1132
Main Authors: Zhou, Chun-Qiong, Lin, Yan-Ling, Chen, Jin-Xiang, Chen, Wen-Hua
Format: Article
Language:English
Subjects:
Animals
Cattle
Coordination Complexes - chemistry
Copper - chemistry
Copper complexes
Dimerization
DNA
DNA - metabolism
DNA Cleavage
Hydrogen-Ion Concentration
Nylons - chemistry
Plasmids - metabolism
Polyesters - chemistry
Pyrroles - chemistry
Pyrrolepolyamide dimers
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Summary:A simple polyether‐tethered pyrrole‐polyamide dimer 1 was synthesized in 50% yield from the reaction of 2,2,2‐trichloro‐1‐(1‐methyl‐4‐nitro‐1H‐pyrrol‐2‐yl)ethanone with 2,2′‐[1,2‐ethanediylbis(oxy)]bisethanamine, and fully characterized on the basis of 1H‐ and 13C‐NMR, MS, HR‐MS, and IR data. Agarose gel‐electrophoresis study of the cleavage of plasmid pBR322 DNA by the complexes of compound 1 with seven metal ions indicated that most of the metal complexes were capable of efficiently cleaving DNA at pH 7.0 and 37°. Among them, the CuII complex exhibited the highest activity, with the maximal catalytic rate constant kmax and Michaelis constant KM being 5.61 h−1 and 7.30 mM, respectively. Spectroscopic, ESI‐MS, ethidium‐bromide (EB) displacement, and viscosity experiments indicated that compound 1 could form a 1 : 1 complex with CuII ion, and that this complex showed moderate binding affinity toward calf‐thymus DNA.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.201100183