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美兰厚朴酚B二聚体对血液学和实体瘤细胞具有强大的抗癌活性。

Dimers of Melampomagnolide B Exhibit Potent Anticancer Activity against Hematological and Solid Tumor Cells.

作者信息

Janganati Venumadhav, Ponder Jessica, Jordan Craig T, Borrelli Michael J, Penthala Narsimha Reddy, Crooks Peter A

机构信息

Department of Pharmaceutical Sciences, College of Pharmacy and ‡Department of Radiology and Neurology, University of Arkansas for Medical Sciences , Little Rock, Arkansas 72205, United States.

Division of Hematology and §Department of Toxicology, University of Colorado , Aurora, Colorado 80045, United States.

出版信息

J Med Chem. 2015 Nov 25;58(22):8896-906. doi: 10.1021/acs.jmedchem.5b01187. Epub 2015 Nov 16.

DOI:10.1021/acs.jmedchem.5b01187
PMID:26540463
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4959447/
Abstract

Novel carbamate (7a-7h) and carbonate (7i, 7j, and 8) dimers of melampomagnolide B have been synthesized by reaction of the melampomagnolide-B-triazole carbamate synthon 6 with various terminal diamino- and dihydroxyalkanes. Dimeric carbamate products 7b, 7c, and 7f exhibited potent growth inhibition (GI50 = 0.16-0.99 μM) against the majority of cell lines in the NCI panel of 60 human hematological and solid tumor cell lines. Compound 7f and 8 exhibited anticancer activity that was 300-fold and 1 × 10(6)-fold more cytotoxic than DMAPT, respectively, at a concentration of 10 μM against rat 9L-SF gliosarcoma cells. Compounds 7a-7j and 8 were also screened against M9-ENL1 and acute myelogenous leukemia (AML) primary cell lines and exhibited 2- to 10-fold more potent antileukemic activity against M9-ENL1 cells (EC50 = 0.57-2.90 μM) when compared to parthenolide (EC50 = 6.0) and showed potent antileukemic activity against five primary AML cell lines (EC50 = 0.76-7.3 μM).

摘要

通过使美兰厚朴内酯 -B-三唑氨基甲酸酯合成子6与各种末端二氨基和二羟基烷烃反应，合成了新型的美兰厚朴内酯B的氨基甲酸酯（7a - 7h）和碳酸酯（7i、7j和8）二聚体。氨基甲酸酯二聚体产物7b、7c和7f对美国国立癌症研究所（NCI）的60种人类血液学和实体瘤细胞系组成的细胞系面板中的大多数细胞系表现出强效的生长抑制作用（GI50 = 0.16 - 0.99 μM）。在浓度为10 μM时，化合物7f和8对大鼠9L - SF胶质肉瘤细胞的抗癌活性分别比二甲基烯丙基三硫（DMAPT）的细胞毒性高300倍和1×10⁶倍。还针对M9 - ENL1和急性髓性白血病（AML）原代细胞系对化合物7a - 7j和8进行了筛选，与小白菊内酯（EC50 = 6.0）相比，它们对M9 - ENL1细胞表现出强2至10倍的抗白血病活性（EC50 = 0.57 - 2.90 μM），并且对五种AML原代细胞系表现出强效的抗白血病活性（EC50 = 0.76 - 7.3 μM）。

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本文引用的文献

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Melampomagnolide B: a new antileukemic sesquiterpene.美拉蒽酮 B：一种新型抗白血病倍半萜。
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The NF (Nuclear factor)-κB inhibitor parthenolide interacts with histone deacetylase inhibitors to induce MKK7/JNK1-dependent apoptosis in human acute myeloid leukaemia cells.NF（核因子）-κB 抑制剂小白菊内酯与组蛋白去乙酰化酶抑制剂相互作用，诱导人急性髓系白血病细胞中 MKK7/JNK1 依赖性凋亡。
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