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J Med Chem. 2014 Oct 23;57(20):8293-306. doi: 10.1021/jm500522y. Epub 2014 Oct 10.

C-glycoside mimetics inhibit glioma stem cell proliferation, migration, and invasion.

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UMR 5253-ICG Montpellier, Equipe AM2N, ENSCM, 8, Rue de l'Ecole Normale, 34296 Montpellier CEDEX 5, France.


This paper reports the design and synthesis of C-glycoside mimetics (d-glycero-d-talo- and d-glycero-d-galactopyranose analogues), a subset of the recently published phostines, belonging to the [1,2]oxaphosphinane core. Eighteen new compounds were tested against 11 cancer cell types belonging to six categories of tumor tissues and three different species. The hit compound 5.3d inhibited invasion and migration of both GBM stem cells (Gli7 and Gli4) and GBM cancer cell lines (C6, SNB75) on fibronectin, vitronectin, and laminin. Ki values for Gli7 and Gli4 migration inhibition on fibronectin were 16 and 31 nM respectively. Ki values for invasion inhibition in a 3D system were 46 nM for Gli7 and 290 nM for Gli4. These activities were associated with an antiproliferative effect on Gli4 (EC50 = 5.20 μM) and Gli7 (EC50 = 2.33 μM). In conclusion, the heptopyranose mimetic 5.3d, devoid of toxicity on astrocyte and cortical neuron cultures at concentrations below 100 μM, opens new therapeutic perspectives against glioblastoma.

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