Dangate Milind, Franchini Laura, Ronchetti Fiamma, Arai Takanari, Iida Akira, Tokuda Harukuni, Colombo Diego
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Italy.
Bioorg Med Chem. 2009 Aug 15;17(16):5968-73. doi: 10.1016/j.bmc.2009.06.064. Epub 2009 Jul 3.
New sulfoquinovosyldiacylglycerols derived from 2-O-beta-d-glucopyranosyl-sn-glycerol, carrying acyl chains of various length on the glycerol moiety, were prepared through a convenient synthetic procedure in which a sulfonate is introduced at the C-6 position of glucose by oxidation of a thioacetate in the presence of the unprotected secondary hydroxyl groups, and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. Our study has allowed to ascertain the role of the 6'-sulfonate group and the need of a free hydroxyl group on the glycerol moiety in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA).
通过一种简便的合成方法制备了新的磺基喹喔啉二酰基甘油，其由2-O-β-D-吡喃葡萄糖基-sn-甘油衍生而来，甘油部分带有不同长度的酰基链。该合成方法是在未保护的仲羟基存在下，通过硫代乙酸酯的氧化在葡萄糖的C-6位引入磺酸盐。并使用针对爱泼斯坦-巴尔病毒早期抗原（EBV-EA）激活的短期体外试验测试了它们的抗肿瘤促进活性。我们的研究已确定了6'-磺酸盐基团的作用以及甘油部分上自由羟基在抑制肿瘤促进剂12-O-十四烷酰佛波醇-13-乙酸酯（TPA）促进的EBV激活中的必要性。
