Substituted phosphonate fluorescent sensors and use thereof

Abstract

The invention relates to new compounds of formula (1) wherein R is hydrogen or a linear or branched Calkyl; where X is O, S, or NRwhere Ris a hydrogen, a linear or branched Calkyl, Calkenyl or Calkynyl group, an aryl, a heteroaryl or Calkylaryl or alkylheteroaryl group and where one or both of C and D is OR, SR, NRRwhere R, Rand Rare each independently hydrogen, a linear or branched Calkyl, Calkenyl or Calkynyl group, an aryl or Calkylaryl group or a linear or branched Calkyl NRRchain where Rand Rare each independently hydrogen, a linear or branched Calkyl; or an optionally complex metal ion M/n wherein n is an integer from 1 to 8; or where one or both of C and D are amino acids or nucleic acids attached via either N, O or S; and wherein m is an integer from 1 to 8; and wherein either: I) A is a known aryl or heteroaryl fluorescent group and B is hydrogen, a linear or branched Calkyl, Calkenyl or Calkynyl group, an aryl, a heteroaryl or Calkylaryl or alkylheteroaryl group or phosphonate P(O)(OR); II) B is a known aryl or heteroaryl fluorescent group and A is hydrogen, a linear or branched Calkyl, Calkenyl or Calkynyl group, an aryl, a heteroaryl or Calkylaryl or alkylheteroaryl group or a linear or branched Calkyl NRRchain, or a linear or branched Cmono or di ester Calkylphosphonate or a linear or branched Calkylphosphonic acid; III) Both A and B are known aryl or heteroaryl fluorescent groups. The compounds are useful as fluorescent sensors for metal cations and have the advantages of excellent water solubility, selectivity and sensitivity to a variety of metal cations even in the presence of high concentrations of CaNaand K, good cell permeability, flexible and simple syntheses, ease of attachment to polymers and bio-polymers to aid the identification of both chemical and biological processes as well as for assaying physiological samples and for the attachment to surfaces such as glasses, ceramics and apatites.