As part of a project aimed at obtaining compounds capable of inhibiting tumor promotion, new 6-amino-6-deoxyglycoglycerolipids (AGGLs) derived from 2-O-β-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-β-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.

New 6-amino-6-deoxy-glycoglycerolipids derived from 2-O-beta-D-glucopyranosylglycerol: insights into the structure-activity relationship of glycoglycerolipids as anti-tumor promoters / D. Colombo, C. Gagliardi, M. Vetro, F. Ronchetti, M. Takasaki, T. Konoshima, N. Suzuki, H. Tokuda. - In: CARBOHYDRATE RESEARCH. - ISSN 0008-6215. - 373(2013), pp. 64-74. [10.1016/j.carres.2013.03.007]

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

D. Colombo
Primo
;
M. Vetro;F. Ronchetti;
2013

Abstract

As part of a project aimed at obtaining compounds capable of inhibiting tumor promotion, new 6-amino-6-deoxyglycoglycerolipids (AGGLs) derived from 2-O-β-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-β-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.
AGGL; Aminoglycoglycerolipids; Cancer chemoprevention; EBV-EA
Settore BIO/10 - Biochimica
2013
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/219397
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