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Medicinal Chemistry


ISSN (Print): 1573-4064
ISSN (Online): 1875-6638

Anti-Proliferative Effects of Novel Glyco-Lipid-Arsenicals (III) on MCF-7 Human Breast Cancer Cells

Author(s): Norbert Wimmer, Jodie A. Robinson, Nagaraj Gopisetty-Venkata, Sarah J. Roberts-Thomson, Gregory R. Monteith and Istvan Toth

Volume 2 , Issue 1 , 2006

Page: [79 - 87] Pages: 9

DOI: 10.2174/157340606775197714

Price: $65


Arsenic trioxide appears to be effective in the treatment of pro-myelocytic leukaemia. The substituted phenylarsen(III)oxides are highly polar, they have a high tendency to undergo oxidation to As (V) and to form oligomers, to prevent this we protected the As-(OH)2 group as cyclic dithiaarsanes. To increase the compounds biological stability and passive diffusion we conjugated the compound of interest with lipoamino acids (Laas). Alternatively, we further conjugated the dithiaarsane derivative with a carbohydrate to utilize active transport systems and to target compound. We investigated two novel glyco-lipid arsenicals (III) (compounds 9 and 11) for their ability to initiate MCF-7 breast cancer cell death and characterized the mechanism by which death was initiated. A significant decrease in MCF-7 cell proliferation was observed using 1 μM and 10 μM compound (11) and 10 μM of compound (9). Treatment with compound (11) triggered apoptosis of MFC-7 cells while compound (9) induced inhibition of cellular proliferation was not via rapid induction of apoptosis and more likely reflected necrosis and/or alterations in the cell cycle. Differences in the anti-proliferative potency of the two compounds indicate that structural modifications influence effectiveness.

Keywords: Arsenicals, trivalent, trivalent organoarsenicals, Lipoaminoacid (Laa), chemotherapeutics

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