THE BINDING OF COPPER IONS TO DAUNOMYCIN AND ADRIAMYCIN
THE BINDING OF COPPER IONS TO DAUNOMYCIN AND ADRIAMYCIN
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DOI：
10.1016/s0162-0134(00)80218-4
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发表时间：
1982-01-01
影响因子：
3.9
通讯作者：
DABROWIAK, JC
中科院分区：
文献类型：
--
作者：
GREENAWAY, FT;DABROWIAK, JC
利用可见吸收，CD [圆二色性]，1H NMR和EPR光谱，Cu（II）的柔红霉素，阿霉素和N-三氟乙酰柔红霉素在水和乙醇中的结合特性进行了探讨。药物形成2种水溶性络合物，其Cu-药物化学计量比为1：1和1：2，并且形成的表观pKa分别为5.6和6.5。在pH值高于约8，药物与Cu（II）形成不溶性聚合物络合物。在乙醇中也观察到类似物质。的化合物的结构进行了解释，在结合的去质子化的羟基醌部分的药物的铜离子。未发现氨基与柔红霉素结合的证据。[讨论了本研究对柔红霉素和阿霉素作用机制的适用性。]
Using visible absorption, CD [circular dichroism], 1H NMR and EPR spectroscopy, the Cu(II) binding properties of daunomycin, adriamycin and N-trifluoroacetyl daunomycin in water and ethanol were explored. The drugs form 2 water soluble complexes having Cu-drug stoichiometries of 1:1 and 1:2, and with apparent pKa of formation of 5.6 and 6.5, respectively. At pH values above .apprx. 8, the drugs form insoluble polymeric complexes with Cu(II). Similar species are also observed in ethanol. The structure of the compounds were interpreted in terms of binding of the deprotonated hydroxyquinone portion of the drug to the Cu ion. No evidence for the binding of the amino group on daunosamine was found. [Applicability of this study to the mechanism of action of daunomycin and adriamycin is discussed.].