New mannose derivatives: The tetrazole analogue of mannose-6-phosphate as angiogenesis inhibitor

Cătălina Ionescu (1) , Simona Sippelli (2, 1) , Loic Toupet (3, 4) , Véronique Barragan-Montero (1)

1 ICGM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
2 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
3 IPR - Institut de Physique de Rennes
4 GMCM - Groupe matière condensée et matériaux

Two novel compounds with mannose-derived structure, bearing a tetrazole (compound 3) and a sulfone group (compound 4) in terminal position, have been prepared from methyl α-D-mannopyranoside in reduced number of steps. The angiogenic activity of 3 and 4 has been screened using the chick chorioallantoic membrane (CAM) method. Tetrazole 3 has been identified to possess a promising bioactivity, being identified as angiogenesis inhibitor, with 68% of neovascular vessels when compared to control (PBS).

Keywords: Carboxylic acid; Iodination; mannose-6-phosphate analogues; Sulfone; Tetrazole

Domains: Physics [physics]; Chemical Sciences

Cătălina Ionescu, Simona Sippelli, Loic Toupet, Véronique Barragan-Montero. New mannose derivatives: The tetrazole analogue of mannose-6-phosphate as angiogenesis inhibitor. Bioorganic and Medicinal Chemistry Letters, 2016, 26 (2), pp.636-639. ⟨10.1016/j.bmcl.2015.11.059⟩. ⟨hal-01259520⟩