Elo H, Mutikainen I
Department of Chemistry, University of Helsinki, Finland.
Z Naturforsch C J Biosci. 1988 Jul-Aug;43(7-8):601-5. doi: 10.1515/znc-1988-7-819.
In order to study the structure-activity relationships of bis(guanylhydrazone) type polyamine antimetabolites, trifluoromethylglyoxal bis(guanylhydrazone) (CF3-GBG), a close analog of the antileukemic drug methylglyoxal bis(guanylhydrazone) (mitoguazone, MGBG) was synthesized according to a novel modification of previous methods, yielding single crystals. Single-crystal X-ray crystallography revealed the presence of an isomer different from the one detected in the case of MGBG and all other bis(guanylhydrazones) so far studied. In contrast to MGBG, CF3-GBG was shown to be a very weak inhibitor of yeast adenosylmethionine decarboxylase, being thus devoid of value as a polyamine antimetabolite. In addition, the compound did not have antiproliferative activity against mouse L1210 leukemia cells in vitro. As long as analogous isomers of the two compounds are not available, no conclusions can be drawn about the reasons lying behind the drastical differences between their biological properties.
为了研究双（胍腙）型多胺抗代谢物的构效关系，我们根据之前方法的一种新改进合成了三氟甲基乙二醛双（胍腙）（CF3 - GBG），它是抗白血病药物甲基乙二醛双（胍腙）（米托胍腙，MGBG）的一种紧密类似物，并得到了单晶。单晶X射线晶体学研究表明，存在一种异构体，它与在MGBG以及迄今为止研究的所有其他双（胍腙）中检测到的异构体不同。与MGBG相反，CF3 - GBG被证明是酵母腺苷甲硫氨酸脱羧酶的一种非常弱的抑制剂，因此作为一种多胺抗代谢物没有价值。此外，该化合物在体外对小鼠L1210白血病细胞没有抗增殖活性。只要这两种化合物的类似异构体不可得，就无法得出关于它们生物学性质存在巨大差异背后原因的结论。
