Synthesis of diglycosylated (di)sulfides and comparative evaluation of their antiproliferative effect against tumor cell lines: A focus on the nature of sugar-recognizing mediators involved

A mini-library of symmetrical and unsymmetrical diglycosyl (di)sulfides, containing d-galactose, l-fucose and N-acetyl glucosamine units, were synthesized and tested for the antiproliferative activity against cervix carcinoma (HeLa) and melanoma (A375) tumor cell lines as well as healthy fibroblasts...

Full description

Saved in:
Bibliographic Details
Published in:Carbohydrate research 2019-08, Vol.482, p.107740-107740, Article 107740
Main Authors: Di Gaetano, Sonia, Bedini, Emiliano, Landolfi, Alfredo, Pedone, Emilia, Pirone, Luciano, Saviano, Michele, Traboni, Serena, Capasso, Domenica, Iadonisi, Alfonso
Format: Article
Language:English
Subjects:
Anti-proliferative activity
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Cell Proliferation - drug effects
Chemistry Techniques, Synthetic
Drug Screening Assays, Antitumor
Galectins
Glycosyl disulfide
Glycosyl sulfide
Glycosylation
HeLa Cells
Humans
Sugars - chemistry
Sulfides - chemical synthesis
Sulfides - chemistry
Sulfides - pharmacology
Tumor cells
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A mini-library of symmetrical and unsymmetrical diglycosyl (di)sulfides, containing d-galactose, l-fucose and N-acetyl glucosamine units, were synthesized and tested for the antiproliferative activity against cervix carcinoma (HeLa) and melanoma (A375) tumor cell lines as well as healthy fibroblasts (HDF). Comparative analysis of results seems to indicate that the most relevant antiproliferative effect is not primarily influenced by interactions with galectins, as the most cytotoxic compound observed for HeLa and A375 is not a ligand for such receptors. The most active molecules against HeLa and A375 lines also exhibited a good selectivity, showing a low toxicity to HDF cells. Obtained results offer useful indications for future design of structurally simple antitumor molecules based on sugar moieties with bridging sulfur atoms. [Display omitted] •Rapid synthesis of a minilibrary of four representative diglycosyl (di)sulfides.•Comparative evaluation of anti-proliferative activity toward tumor cell lines.•Evidence of negligible role of galectins in the antiproliferative mechanism.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2019.107740