New 6-amino-6-deoxy-glycoglycerolipids derived from 2-O-¦Â-d-glucopyranosylglycerol: insights into the structure-activity relationship of glycoglycerolipids as anti-tumor promoters

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• 作者：Diego Colombo^a ; ^{diego.colombo@unimi.it} ; Clarissa Gagliardi^a ; Maria Vetro^a ; Fiamma Ronchetti^a ; Midori Takasaki^b ; Takao Konoshima^b ; Nobutaka Suzuki^c ; Harukuni Tokuda^c
• 关键词：Aminoglycoglycerolipids ; Cancer chemoprevention ; EBV-EA ; AGGL
• 刊名：Carbohydrate Research
• 出版年：2013
• 出版时间：24 May, 2013
• 年：2013
• 卷：373
• 期：Complete
• 页码：64-74
• 全文大小：894 K

文摘

As part of a project aimed at obtaining compounds capable of inhibiting tumor promotion, new 6-amino-6-deoxyglycoglycerolipids (AGGLs) derived from 2-O-¦Â-d-glucopyranosyl-sn-glycerol were synthesized and tested for their anti-tumor-promoting activity using a short-term in vitro assay of the inhibition of Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The corresponding 6-amino-6-deoxy-¦Â-d-octylglucosides were also prepared as simplified aminoglycolipid models and tested. Comparison with the activity of a series of previously studied glycoglycerolipids showed that replacing the 6-oxygen of the glucose moiety by a nitrogen atom greatly reduced the in vitro activity of the compounds. A two-stage mouse skin carcinogenesis test of two representative aminoglycoglycerolipids confirmed their reduced activity also in this in vivo model.