SUBSTITUTED PHOSPHONATE FLUORESCENT SENSORS AND USE THEREOF

摘要

The invention relates to new compounds of formula (1) wherein R is hydrogen or a linear or branched C1-40alkyl; where X is O, S, or NR1 where R1 is a hydrogen, a linear or branched C1-40 alkyl, C2-40 alkenyl or C2-40 alkynyl group, an aryl, a heteroaryl or C1-40 alkylaryl or alkylheteroaryl group and where one or both of C and D is OR2, SR2, NR3R4 where R2, R3 and R4 are each independently hydrogen, a linear or branched C1-40 alkyl, C2-40 alkenyl or C2-40 alkynyl group, an aryl or C1-40 alkylaryl group or a linear or branched C1-40 alkyl NR5R6 chain where R5 and R6 are each independently hydrogen, a linear or branched C1-40 alkyl; or an optionally complex metal ion Mn+/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 C1-40 alkyl, C2-40 alkenyl or C2- 40 alkynyl group, an aryl, a heteroaryl or C1-40 alkylaryl or alkylheteroaryl group or phosphonate P(O)(OR2)2; II) B is a known aryl or heteroaryl fluorescent group and A is hydrogen, a linear or branched C1-40 alkyl, C2-40 alkenyl or C2-40 alkynyl group, an aryl, a heteroaryl or C1-40 alkylaryl or alkylheteroaryl group or a linear or branched C1-40 alkyl NR5R6 chain, or a linear or branched C1-40 alkyl mono or di ester C1-40 alkylphosphonate or a linear or branched C1-40 alkylphosphonic 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 Ca+2 Na+ and 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.