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Synthesis, Conformational Studies, Binding Assessment and Liposome Insertion of a Thioether-Bridged Mimetic of the Antigen GM3 Ganglioside Lactone

✍ Scribed by Lucio Toma; Emanuela Di Cola; Andrea Ienco; Laura Legnani; Carlotta Lunghi; Gloriano Moneti; Barbara Richichi; Sandra Ristori; Daniela Dell'Atti; Cristina Nativi


Book ID
101822151
Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
131 KB
Volume
8
Category
Article
ISSN
1439-4227

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✦ Synopsis


Oncogenic transformations are often associated with abnormal glycosylation in human tumours. [1] In recent years a variety of monoclonal antibodies have been developed to specifically recognize carbohydrate epitopes that result from these faulty glycosylation processes. These epitopes, known as tumourassociated antigens (TAAs), have been successfully used as markers of tumour progression, [2][3][4][5] and include catbohyrates expressed on normal tissues, but which are accumulated in high density on the surface of tumour cells. [2] GM3 Ganglioside, a glycosphingolipid found in essentially all types of cells and tissues, is over expressed in melanoma cells with metastatic potential. [6] The corresponding GM3 lactone (1 a, Scheme 1) has also been found in melanoma as a minor component; [7] its formation is likely promoted by the lower pH environment of tumour cells [8] and, possibly, by a different conformation of GM3 ganglioside induced on the tumour cell surface as a result of localised high density. [7b]