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Novel monosaccharides as potent inhibitors of cell proliferation
Author(s) -
Colquhoun Alison,
Alaluf Simon,
Bradley Adrian,
Gemmell Natasha,
Gibbs Gary,
Osborn Helen M. I.,
Harwood Laurence M.,
Newsholme Eric A.
Publication year - 1997
Publication title -
cell biochemistry and function
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.933
H-Index - 61
eISSN - 1099-0844
pISSN - 0263-6484
DOI - 10.1002/(sici)1099-0844(199712)15:4<243::aid-cbf747>3.0.co;2-1
Subject(s) - monosaccharide , cell growth , cell , chemistry , pharmacology , computational biology , biochemistry , biology
The effects of several novel monosaccharides upon thymidine incorporation into both normal and tumour cells were investigated. The monosaccharide 2‐deoxy‐3‐[1‐(R)‐(ethoxycarbonyl)ethyl]‐α‐ D ‐ allo ‐pyranose had the most inhibitory effect on proliferation, with the (S)‐enantiomer having less inhibitory effects. The chiral centre at carbon‐7 was found to be an important part of the molecule, as 2‐deoxy‐3‐[methoxycarbonyl methyl]‐α‐ D ‐ allo ‐pyranose had greatly decreased anti‐proliferative properties in comparison with the parent compound. In addition, the 2‐deoxy structure at carbon‐2 was also found to be important, as 3‐[1‐(S)‐(ethoxycarbonyl)ethyl]‐α‐ D ‐ allo ‐hexopyranose had greatly decreased inhibitory properties in comparison with the parent compound. The results indicate that these novel monosaccharides possess potent anti‐proliferative properties, related to their chiral carbon‐7 and 2‐deoxy carbon‐2 structure and suggest that further substitutions of the functional group at carbon‐7 may improve these properties and possibly produce inhibitor selectivity for tumour cells in preference to normal cells. © 1997 John Wiley & Sons, Ltd.