Van Duuren B L, Segal A, Tseng S S, Rusch G M, Loewengart G, Maté U, Roth D, Smith A, Melchionne S, Seidman I
J Med Chem. 1978 Jan;21(1):26-31. doi: 10.1021/jm00199a005.
Seventeen analogues of the tumor-promoting agent anthralin were tested for the same biological property by repeated skin application on mouse skin using female ICR/Ha Swiss mice, after a single application of a subcarcinogenic dose of 7,12-dimethylbenz[a]anthracene. Seven of the compounds tested are new compounds. They are 1,8-diacetoxy-9-anthrone, 1,8-dimyristoyloxy-9-anthrone, 1,8-dihydroxy-10-acetyl-9-anthrone, 1,8-dihydroxy-10-myristoyl-9-anthrone, 1,8,10-trihydroxy-9-anthrone, 1,8-dihydroxy-9,10-dihydroanthracene, and myristoyljuglone. All compounds were used in pure form for the bioassays. Of the 17 test compounds four showed notable tumor-promoting activity. They are 1,8-dihydroxy-10-acetyl-9-anthrone, 1,8-dihydroxy-10-myristoyl-9-anthrone, 1-hydroxy-9-anthrone, and juglone. In order to determine whether there is any relationship between tumor-promoting activity and metal chelation in this series, the chelating abilities of anthralin and of its inactive analogue 1,8-dihydroxyanthraquinone were examined using the bivalent metal ions Cu(II), Zn(II), Mn(II), Mg(II), and Ca(II). No relationship between chelation and tumor-promoting ability was found.
在对雌性 ICR/Ha Swiss 小鼠单次涂抹亚致癌剂量的 7,12-二甲基苯并[a]蒽后，通过在小鼠皮肤上反复涂抹，对 17 种促肿瘤剂蒽林的类似物进行了相同生物学特性的测试。所测试的化合物中有 7 种是新化合物。它们是 1,8-二乙酰氧基-9-蒽酮、1,8-二肉豆蔻酰氧基-9-蒽酮、1,8-二羟基-10-乙酰基-9-蒽酮、1,8-二羟基-10-肉豆蔻酰基-9-蒽酮、1,8,10-三羟基-9-蒽酮、1,8-二羟基-9,10-二氢蒽以及肉豆蔻酰胡桃醌。所有化合物均以纯形式用于生物测定。在这 17 种测试化合物中，有 4 种表现出显著的促肿瘤活性。它们是 1,8-二羟基-10-乙酰基-9-蒽酮、1,8-二羟基-10-肉豆蔻酰基-9-蒽酮、1-羟基-9-蒽酮以及胡桃醌。为了确定该系列中促肿瘤活性与金属螯合之间是否存在任何关系，使用二价金属离子 Cu(II)、Zn(II)、Mn(II)、Mg(II) 和 Ca(II) 检测了蒽林及其无活性类似物 1,8-二羟基蒽醌的螯合能力。未发现螯合与促肿瘤能力之间存在关系。
