PECET, Facultad de Medicina, Universidad de Antioquia, Calle 70 # 52-21, Medellín, Colombia; Grupo de Química Orgánica de Productos Naturales, Instituto de Química, Calle 70 # 52-21, Medellín, Colombia.
Grupo de Química Orgánica de Productos Naturales, Instituto de Química, Calle 70 # 52-21, Medellín, Colombia.
Int J Parasitol Drugs Drug Resist. 2020 Aug;13:94-106. doi: 10.1016/j.ijpddr.2020.06.004. Epub 2020 Jun 26.
Toxicity and poor adherence to treatment that favors the generation of resistance in the Leishmania parasites highlight the need to develop better alternatives. Here, we evaluated the in vitro effectiveness of hydrazone derived from chromanes 2-(2,3-dihydro-4H-1-benzothiopyran-4-ylidene) hydrazide (TC1) and 2-(2,3-dihydro-4H-1-benzopyran-4-ylidene) hydrazide (TC2) and the mixture of triterpene saponin hederagenin-3-O-(3,4-O-diacetyl-ß-D-xylopyranosyl-(1à3)-a-L- rhamnopyranosyl-(1à2)-a-L-arabinofuranoside, hederagenin-3-O-(3,4-O-diacetyl-a-L- arabinopyranosyl-(1à3)-a-L-rhamnopyranosyl-(1à2)-a-L-arabinofuranoside and, hederagenin-3-O-(4-O-acetyl-ß-D-xylopyranosyl-(1à3)-a-L-rhamnopyranosyl-(1à2)-a-L-arabinofuranoside from Sapindus saponaria (SS) on L. braziliensis and L. pifanoi. Mixtures of TC1 or TC2 with saponin were formulated for topical application and the therapeutic effectiveness was evaluated in the model for cutaneous leishmaniasis (CL) in golden hamster. The mode of action of these compounds was tested on various parasite processes and ultrastructural parasite modifications. TC1, TC2 and SS showed moderate cytotoxicity when tested independently but toxicity was improved when tested in combination. The compounds were more active against intracellular Leishmania amastigotes. In vivo studies showed that combinations of TC1 or TC2 with SS in 1:1 ratio (w/w) cured 100% of hamsters with no signs associated with toxicity. The compounds did cause changes in the mitochondrial activity of the parasite with a decrease in ATP levels and depolarization of membrane potential and overproduction of reactive oxygen species; nevertheless, these effects were not related to alterations in membrane permeability. The phagolysosome ultrastructure was also affected impacting the survival of Leishmania but the function of the lysosome nor the pH inside the phagolysosome did not change. Lastly, there was a protease inhibition which was directly related to the decrease in the ability of Leishmania to infect and multiply inside the macrophage. The results suggest that the combination of TC1 and TC2 with SS in a 1:1 ratio is capable of curing CL in hamsters. This effect may be due to the ability of these compounds to affect parasite survival and the ability to infect new cells.
毒性和对治疗的不良依从性有利于利什曼原虫寄生虫产生耐药性,这突出表明需要开发更好的替代方法。在这里,我们评估了色满衍生的腙 2-(2,3-二氢-4H-1-苯并硫代吡喃-4-亚基)酰肼(TC1)和 2-(2,3-二氢-4H-1-苯并吡喃-4-亚基)酰肼(TC2)以及三萜皂苷皂皮酸 3-O-(3,4-O-二乙酰基-β-D-吡喃木糖基-(1à3)-a-L-鼠李吡喃糖基-(1à2)-a-L-阿拉伯呋喃糖苷、皂皮酸 3-O-(3,4-O-二乙酰基-a-L-阿拉伯吡喃糖基-(1à3)-a-L-鼠李吡喃糖基-(1à2)-a-L-阿拉伯呋喃糖苷和皂皮酸 3-O-(4-O-乙酰基-β-D-吡喃木糖基-(1à3)-a-L-鼠李吡喃糖基-(1à2)-a-L-阿拉伯呋喃糖苷对 L. braziliensis 和 L. pifanoi 的体外有效性。TC1 或 TC2 与皂苷的混合物被配制成局部应用,并在金仓鼠皮肤利什曼病(CL)模型中评估了治疗效果。这些化合物的作用模式在各种寄生虫过程和寄生虫超微结构修饰中进行了测试。当单独测试时,TC1、TC2 和 SS 表现出中等的细胞毒性,但当联合测试时,毒性得到改善。这些化合物对细胞内利什曼无鞭毛体更有效。体内研究表明,TC1 或 TC2 与 SS 以 1:1(w/w)的比例组合可治愈 100%的仓鼠,且无与毒性相关的迹象。化合物确实导致寄生虫线粒体活性发生变化,导致 ATP 水平降低、膜电位去极化和活性氧过度产生;然而,这些影响与膜通透性的改变无关。吞噬溶酶体的超微结构也受到影响,影响利什曼原虫的存活,但溶酶体的功能和吞噬溶酶体内的 pH 值没有改变。最后,存在蛋白酶抑制,这与利什曼原虫感染和在巨噬细胞内繁殖能力的降低直接相关。结果表明,TC1 和 TC2 与 SS 以 1:1 的比例组合能够治愈仓鼠中的 CL。这种效果可能是由于这些化合物能够影响寄生虫的存活和感染新细胞的能力。