Friday, April 11, 2014

Friday Fun: Insane in the Membrane

...CARBORANES in the Brain!*

Source: ACS Chemical Neuroscience | Sydney University 

From the pages of the (relatively new) journal ACS Chemical Neuroscience, comes this report about development of new antidepressants with rather...interesting appendages. The adamantyl (1) and Cookson's diketone (3) molecules shouldn't surprise, but the rest? You're not imagining things - those are blood-brain barrier-penetrant lead molecules based on cubane (2) and closo- and nido-carboranes (4,5). At 20 mg/kg, compounds 2 and 5 restore significant function to mice following stress tests. The authors indicate that, although the caged compounds look pretty huge, they're actually fairly isosteric (similar size) to a phenyl group, yet possess rugged metabolic stability.

*With apologies to Cypress Hill


  1. Looks like antidepressants for the nanoputians -

  2. pentaborane and decaborane have a very nasty neurotoxicity that carboranes fortunately lack, probably due to their high stability, so there is no surprise that acarborane-containing greasy molecule can cross blood-brain barier. Carboranes are interesting but there are only niche applications and the preparation from decaborane is unpleasant, so they are expensive