Reiter Christoph, Fröhlich Tony, Zeino Maen, Marschall Manfred, Bahsi Hanife, Leidenberger Maria, Friedrich Oliver, Kappes Barbara, Hampel Frank, Efferth Thomas, Tsogoeva Svetlana B
Department of Chemistry and Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), University of Erlangen-Nuremberg, Henkestraße 42, 91054 Erlangen, Germany.
Department of Pharmaceutical Biology, Institute of Pharmacy and Biochemistry, University of Mainz, Staudinger Weg 5, 55128 Mainz, Germany.
Eur J Med Chem. 2015 Jun 5;97:164-72. doi: 10.1016/j.ejmech.2015.04.053. Epub 2015 Apr 28.
In our ongoing search for highly active hybrid molecules exceeding their parent compounds in anticancer, antimalaria as well as antiviral activity and being an alternative to the standard drugs, we present the synthesis and biological investigations of 2nd generation 1,2,4-trioxane-ferrocene hybrids. In vitro tests against the CCRF-CEM leukemia cell line revealed di-1,2,4-trioxane-ferrocene hybrid 7 as the most active compound (IC50 of 0.01 μM). Regarding the activity against the multidrug resistant subline CEM/ADR5000, 1,2,4-trioxane-ferrocene hybrid 5 showed a remarkable activity (IC50 of 0.53 μM). Contrary to the antimalaria activity of hybrids 4-8 against Plasmodium falciparum 3D7 strain with slightly higher IC50 values (between 7.2 and 30.2 nM) than that of their parent compound DHA, hybrids 5-7 possessed very promising activity (IC50 values lower than 0.5 μM) against human cytomegalovirus (HCMV). The application of 1,2,4-trioxane-ferrocene hybrids against HCMV is unprecedented and demonstrated here for the first time.
在我们持续寻找在抗癌、抗疟疾以及抗病毒活性方面超过其母体化合物且可作为标准药物替代品的高活性杂化分子的过程中,我们展示了第二代1,2,4 - 三氧杂环己烷 - 二茂铁杂化物的合成及生物学研究。针对CCRF - CEM白血病细胞系的体外测试表明,二 - 1,2,4 - 三氧杂环己烷 - 二茂铁杂化物7是最具活性的化合物(IC50为0.01 μM)。关于对多药耐药亚系CEM/ADR5000的活性,1,2,4 - 三氧杂环己烷 - 二茂铁杂化物5表现出显著活性(IC50为0.53 μM)。与杂化物4 - 8对恶性疟原虫3D7菌株的抗疟疾活性相反,其IC50值(在7.2至30.2 nM之间)略高于其母体化合物DHA,杂化物5 - 7对人巨细胞病毒(HCMV)具有非常有前景的活性(IC50值低于0.5 μM)。1,2,4 - 三氧杂环己烷 - 二茂铁杂化物对HCMV的应用是前所未有的,在此首次得到证明。