Functionalized pyrrolidine inhibitors of human type II alpha-mannosidases as anti-cancer agents: optimizing the fit to the active site

Bioorg Med Chem. 2008 Aug 1;16(15):7337-46. doi: 10.1016/j.bmc.2008.06.021. Epub 2008 Jun 14.

Abstract

Refining the chemical structure of functionalized pyrrolidine-based inhibitors of Golgi alpha-mannosidase II (GMII) to optimize binding affinity provided a lead molecule that demonstrated nanomolar competitive inhibition of alpha-mannosidases II and an optimal fit in the active site of Drosophila GMII by X-ray crystallography. Esters of this lead compound also inhibited the growth of human glioblastoma and brain-derived endothelial cells more than the growth of non-tumoral human fibroblasts, suggesting their potential for anti-cancer therapy.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Binding Sites
  • Cell Line, Tumor
  • Drosophila / enzymology
  • Endothelial Cells / drug effects
  • Fabaceae / enzymology
  • Glioblastoma
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Pyrrolidines / chemistry*
  • Pyrrolidines / pharmacology*
  • Structure-Activity Relationship
  • alpha-Mannosidase / antagonists & inhibitors*
  • alpha-Mannosidase / classification*

Substances

  • Antineoplastic Agents
  • Pyrrolidines
  • alpha-Mannosidase