Ionization and divalent cation dissociation constants of nalidixic and oxolinic acids

Kim Timmers , Rolf Sternglanz
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引用次数: 89

Abstract

The ionization constants and some divalent cation dissociation constants of nalidixic and oxolinic acids, both specific inhibitors of bacterial DNA replication, have been determined. The carboxylic pKa′ values are 6.1 and 6.9 at 25° for nalidixic and oxolinic acids, respectively. These values indicate that intramolecular hydrogen-bonding stabilizes the un-ionized form of these compounds in aqueous solution. Both compounds bind divalent cations; the divalent cation dissociation constants for oxolinic acid are somewhat smaller that those for nalidixic acid. We suggest that both compounds may act by forming a complex in situ with a divalent cation in a metalloprotein involved in DNA replication. The evidence that both drugs inhibit at the same target site is briefly reviewed.

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钠二酸和草啉酸的电离和二价阳离子解离常数
测定了细菌DNA复制特异性抑制剂萘啶酸和草啉酸的电离常数和一些二价阳离子解离常数。在25°温度下,钠二酸和草啉酸的羧基pKa′值分别为6.1和6.9。这些数值表明,分子内氢键稳定了这些化合物在水溶液中的非离子化形式。这两种化合物都结合二价阳离子;氧喹啉酸的二价阳离子解离常数略小于萘啶酸。我们认为这两种化合物可能通过在参与DNA复制的金属蛋白中与二价阳离子原位形成复合物而起作用。简要回顾了两种药物在同一靶点抑制的证据。
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