Diamidinium and iminium aromatics as new aggregators of the bacterial signaling molecule, c-di-GMP

Bioorg Med Chem Lett. 2012 Jan 15;22(2):881-5. doi: 10.1016/j.bmcl.2011.12.039. Epub 2011 Dec 16.

Abstract

C-di-GMP has emerged as an important bacterial signaling molecule that is involved in biofilm formation. Small molecules that can form biologically inactive complexes with c-di-GMP have the potential to be used as anti-biofilm agents. Herein, we report that water-soluble diamidinium/iminium aromatics (such as berenil), which are traditionally considered as minor groove binders of nucleic acids, are capable of aggregating c-di-GMP into G-quadruplexes via π-stacking interactions.

Publication types

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

MeSH terms

  • Amidines / chemistry*
  • Cyclic GMP / analogs & derivatives*
  • Cyclic GMP / chemistry
  • G-Quadruplexes
  • Imines / chemistry*
  • Molecular Structure
  • Solubility
  • Stereoisomerism
  • Water / chemistry

Substances

  • Amidines
  • Imines
  • Water
  • bis(3',5')-cyclic diguanylic acid
  • Cyclic GMP