Sensitized photodecomposition of organic bisphosphonates by singlet oxygen

J Am Chem Soc. 2012 Oct 17;134(41):16975-8. doi: 10.1021/ja307987g. Epub 2012 Oct 8.

Abstract

During efforts to stabilize metal oxide bound chromophores for photoelectrochemical applications, a novel photochemical reaction has been discovered. In the reaction, the bisphosphonate functional groups -C(PO(3)H(2))(2)(OH) in the metal complex [Ru(bpy)(2)(4,4'-(C(OH)(PO(3)H(2))(2)bpy)](2+) are converted into -COOH and H(3)PO(4). The reaction occurs by sensitized formation of (1)O(2) by the lowest metal-to-ligand charge transfer excited state(s) of [Ru(bpy)(2)(4,4'-(C(PO(3)H(2))(2)(OH))(2)(bpy))](2+)* followed by (1)O(2) oxidation of the bisphosphonate substituent. A related reaction occurs for the bisphosphonate-based drug, risedronic acid, in the presence of O(2), light, and a singlet oxygen sensitizer ([Ru(bpy)(3)](2+) or Rose Bengal).

Publication types

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

MeSH terms

  • Diphosphonates / chemical synthesis
  • Diphosphonates / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Phosphoric Acids / chemical synthesis
  • Phosphoric Acids / chemistry
  • Photochemical Processes
  • Singlet Oxygen / chemistry*

Substances

  • Diphosphonates
  • Organometallic Compounds
  • Phosphoric Acids
  • Singlet Oxygen