Novel monosaccharides as potent inhibitors of cell proliferation.

Abstract:

: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]- alpha-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]-alpha-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]-alpha-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.

journal_name

Cell Biochem Funct

authors

Colquhoun A,Alaluf S,Bradley A,Gemmell N,Gibbs G,Osborn HM,Harwood LM,Newsholme EA

doi

10.1002/(SICI)1099-0844(199712)15:4<243::AID-CBF74

subject

Has Abstract

pub_date

1997-12-01 00:00:00

pages

243-9

issue

4

eissn

0263-6484

issn

1099-0844

pii

10.1002/(SICI)1099-0844(199712)15:4<243::AID-CBF74

journal_volume

15

pub_type

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