Vanden Bossche H, Willemsens G, Marichal P
Laboratory of Comparative Biochemistry, Janssen Pharmaceutica Research Laboratories, Beerse, Belgium.
Crit Rev Microbiol. 1987;15(1):57-72. doi: 10.3109/10408418709104448.
The past years have seen a continuous effort toward the synthesis of new antifungal agents. Most of them belong to the N-substituted imidazoles and triazoles. Another interesting series of antifungals are the allylamines. Biochemically, both the azole derivatives and the allylamines belong to the class of ergosterol biosynthesis inhibitors and thus differ from the polyene macrolide antibiotics. Indeed, it is now believed that the antifungal action of the polyenes, nystatin and amphotericin B, is due to a direct interaction with ergosterol itself. A more detailed analysis of the ergosterol biosynthesis inhibitors revealed that ergosterol depletion is the consequence of the interaction of the azole derivatives, e.g., miconazole, ketoconazole, and itraconazole, with the cytochrome P-450 involved in the 14 alpha-demethylation of lanosterol. Both the accumulation of 14 alpha-methylsterols and the concomitant decreased ergosterol content affect the membranes and membrane-bound enzymes of yeast and fungi. The allylamines seem to act by inhibition of the squalene epoxidase resulting in ergosterol depletion and accumulation of squalene. The target for the fluorinated pyrimidine, flucytosine, is completely different. Its antifungal properties may result from its conversion to 5-fluorouracil. The latter is then phosphorylated and incorporated into RNA, thus disrupting the protein synthesis in the yeast cell. These different biochemical targets for the antifungals of use in candidosis are discussed in this paper.
过去几年一直在不断努力合成新的抗真菌剂。其中大多数属于N-取代咪唑和三唑类。另一类有趣的抗真菌剂是烯丙胺类。从生物化学角度来看,唑类衍生物和烯丙胺类都属于麦角甾醇生物合成抑制剂类别,因此与多烯大环内酯类抗生素不同。事实上,现在人们认为多烯类药物制霉菌素和两性霉素B的抗真菌作用是由于它们与麦角甾醇本身直接相互作用。对麦角甾醇生物合成抑制剂的更详细分析表明,麦角甾醇耗竭是唑类衍生物(如咪康唑、酮康唑和伊曲康唑)与参与羊毛甾醇14α-去甲基化的细胞色素P-450相互作用的结果。14α-甲基甾醇的积累以及随之而来的麦角甾醇含量降低都会影响酵母和真菌的细胞膜及膜结合酶。烯丙胺类似乎是通过抑制角鲨烯环氧化酶起作用,导致麦角甾醇耗竭和角鲨烯积累。含氟嘧啶氟胞嘧啶的作用靶点则完全不同。其抗真菌特性可能源于它转化为5-氟尿嘧啶。后者随后被磷酸化并掺入RNA,从而破坏酵母细胞中的蛋白质合成。本文讨论了用于念珠菌病的抗真菌剂的这些不同生物化学靶点。