Journal of the Brazilian Chemical Society | |
Synthesis of novel naphthoquinone-spermidine conjugates and their effects on DNA-topoisomerases I and II-alpha | |
Andréa S. Cunha2  Edson L. S. Lima2  Angelo C. Pinto2  Andressa Esteves-souza2  Aurea Echevarria1  Celso A. Camara1  Maria D. Vargas1  José C. Torres1  | |
[1] ,Universidade Federal do Rio de Janeiro Instituto de Química Rio de Janeiro RJ ,Brazil | |
关键词: spermidine; lapachol; lawsone; nor-lapachol; DNA-topoisomerase II-alpha; | |
DOI : 10.1590/S0103-50532006000300002 | |
来源: SciELO | |
【 摘 要 】
Novel derivatives of lapachol 2, nor-lapachol 3 and lawsone 4 have been synthesized by nucleophilic displacement of the methoxynaphthoquinones 2a, 3a and 4a with the polyamine (PA) N¹-Boc-N5-Bn-spermidine 1a. The respective products 2b-4b were obtained in good yields and characterized by spectroscopic and analytical methods. The inhibitory action of these naphthoquinone-PA conjugates on DNA-topoisomerases (topo) I and II-alpha was evaluated by relaxation assay of supercoiled DNA plasmid. All compounds (1a 2b, 3b and 4b) presented significant inhibition of topo II-alpha catalytic activity at the 2 µM dose. Considering that only PA 1a did not inhibit the enzyme catalytic activity at the 0.2 µM dose, the appended naphthoquinone moiety acts as a "value added" fragment. Compounds 1a 2b, 3b and 4b did not inhibit the enzyme DNA-topo I at the 200 µM dose.
【 授权许可】
CC BY
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