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Synthesis and DNA cleavage activity of 2-hydrazinyl-1,4,5,6-tetrahydropyrimidine containing hydroxy group.

Abstract：

:2-Hydrazinyl-1,4,5,6-tetrahydropyrimidin-5-ol dihydrochloride 2, as well as 2-hydrazinyl-4,5-dihydro-1H-imidazole dihydrochloride 1, was synthesized as metal-free DNA cleaving agent. Agarose gel electrophoresis was used to assess the plasmid pUC 19 DNA cleavage activities in the presence of 1 and 2. DNA cleavage efficiency of 2 exhibits remarkable increases compared with its corresponding non-hydroxy compound 1. Kinetic data of DNA cleavage promoted by 2 fit to the Michaelis-Menten-type equation with k(max) of 0.0378+/-0.0013 h(-1) giving 10(6)-fold rate acceleration over uncatalyzed DNA. The acceleration is driven by the spatial proximity of the nucleophilic hydroxy group and the electrophilic activation for the phosphodiester by the ammonium and/or guanidinium groups. In vitro cytotoxic activities toward Hela cells and human leukemia HL-60 cells were also examined, and 2 exhibits stronger cytotoxic activities than 1.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Shao Y,Ding Y,Jia ZL,Lu XM,Ke ZH,Xu WH,Lu GY

doi

10.1016/j.bmc.2009.05.044

subject

Has Abstract

pub_date

2009-07-01 00:00:00

pages

4274-9

issue

13

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(09)00497-0

journal_volume

17

pub_type

杂志文章

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