70 新規レキシトロプシン誘導体の合成、及び紫外線照射下におけるDNA切断活性(ポスター発表の部)

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Low molecular weight substances which possess both sequence specific DNA biding and cleaving activities are of considerable interest in the field of fundamental molecular biology. Among them, oligo-N-methylpyrrolecarboxamides such as Netropsin 1 and Distamycin 2 and their analogues have attracted attention because of their strong minor groove nonintercalative binding ability to double stranded B-DNA at specific AT rich region. Various oligo-N-methylpyrrolecarboxamides in Table 1 were synthesized by the way summarized in Scheme 1. Benzyl 1-methyl-4-nitropyrrole-2-carboxylate 9a was reduced using nickel boride and the resulting 4-amino compound was condensed with 8 to afford 9b. The reduction-condensation process was repeated, leading to the oligopeptides 9c and 9d. The 4-amino compounds obtained as above were formylated to give 10a〜10d, respectively. The carboxylic acids obtained by the hydrogenolysis of 10a〜10d were transformed into the N-succinimidyl esters 11a〜11d, respectively. The esters were condensed with various amines to afford the amides 4,5, and 6. Compounds 4〜6 exhibited DNA cleaving activities, depending on the drug concentrations. These activities were reduced in the presence of hydroxyl radical scavengers such as sodium benzoate. UV-A irradiation for the mixtures of compounds 4d〜6d and DMPO led to the generation of ESR signals due to spin adducts. (e.g. Fig 3) In these signals, the characteristic 1:2:2:1 quartet of DMPO-OH adduct, the triplet of triplet of DMPO-H adduct, and an unidentified six lines were observed.
天然有機化合物討論会の論文
1990-09-25

70 新規レキシトロプシン誘導体の合成、及び紫外線照射下におけるDNA切断活性(ポスター発表の部)

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