One-electron reduction of 2- and 6-methyl-1,4-naphthoquinone bioreductive alkylating agents.
One-electron reduction of 2- and 6-methyl-1,4-naphthoquinone bioreductive alkylating agents.
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2-和6-甲基-1,4-萘醌生物还原烷基化剂的单电子还原。
DOI：
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发表时间：
1986
影响因子：
7.3
通讯作者：
A. Sartorelli
中科院分区：
文献类型：
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作者：
I. Wilson;P. Wardman;T. Lin;A. Sartorelli
半醌，Q. -，2-和6-甲基-1，4-萘醌的衍生物，其中一些含有带有取代基的离去基团，如CH_2Br或CH_2OCONHCH_3，已通过（CH_3）_2COH自由基辐射还原Q而制得。Q. -的吸收光谱和衰减动力学都与2-甲基-1，4-萘醌产生的非常相似，没有证据表明半醌形式的离去基团被单分子消除，但在Q被双电子还原为氢醌时离去基团立即损失。Q/Q之间的氧化还原平衡O2/O2的特点，和还原电位的夫妇Q/Q. -在pH 7.6的水中的pH值。使用这些化合物作为生物还原性烷化剂或作为对缺氧细胞具有潜在选择性活性的放射增敏剂，这些观察的影响进行了讨论。
The semiquinones, Q.-, of derivatives of 2- and 6-methyl-1,4-naphthoquinones, some incorporating leaving groups with substituents such as CH2Br or CH2OCONHCH3, have been produced by radiolytic reduction of Q by (CH3)2COH radicals. The absorption spectra and decay kinetics of Q.- were all closely similar to that produced from 2-methyl-1,4-naphthoquinone, with no evidence for unimolecular elimination of a leaving group in the semiquinone form, but immediate loss of leaving group upon two-electron reduction of Q to the hydroquinone. The redox equilibria between Q/Q.- and O2/O2.- were characterized, and reduction potentials of the couples Q/Q.- in water at pH 7.6 were calculated. The implications of these observations for the use of these compounds as bioreductive alkylating agents or as radiosensitizers with potential selective activity toward hypoxic cells are discussed.