New electropolymerizable monomer, useful for detecting a target ligand in a biological sample, comprises an electropolymerizable unit e.g. acetylene and metallo-porphyrin substituted by ionized/ionizable entities

摘要

Electropolymerizable monomer, to be polymerized in aqueous solution, comprises an electropolymerizable unit such as acetylene, pyrroles, thiophenes, indoles, anilines, azines, p-phenylenevinylenes, p-phenylenes, pyrenes, furans, selenophenes, pyrridazines, carbazoles or (meth)acrylates or their derivatives and a metallo-porphyrin substituted by at least two entities that are ionized or ionizable in aqueous solution, is new. Independent claims are included for: (1) a metallo-porphyrin monomer of formula (I); (2) the preparation of (I); (3) electroactive probe either in the form of a conducting homopolymer susceptible to be obtained by electropolymerization of a monomer carrying a biological ligand, or in the form of a conducting copolymer susceptible to be obtained by copolymerization of at least two different monomers, where at least one of the monomers carrying a biological ligand such as (I); (4) detection of at least a target ligand in a biological sample, comprising contacting the sample with an electroactive probe carrying a ligand probe, for the ligand probe/target ligand interaction and recording and optionally quantifying the potential or current difference emitted by the probe before and contacting with the sample; (5) electrode comprising a conducting support of which whole or part of the surface is covered with the probe; (6) polymerization process comprising electropolymerization of (I) in aqueous phase; and (7) polymer susceptible to be obtained by the process. R 1-R 3H, a group i.e. ionized or ionizable in aqueous solution or a biological ligand; A 1-A 3spacer group e.g. -(CH 2) n1-, -(CH 2-CH 2-O) n2-, phenyl-diyl, phenyl moiety of formula (IIa) or phenoxy moiety of formula (IIb); n1 : 0-5; n2 : 1-5; R, R a-R hH or electron donor/attractor; X : a spacer e.g. -(CH 2) m1-, substituted phenyl moiety of formula (IIc), -(CH 2-CH 2-O) m4-, a polypeptide chain containing 1-3 amino acids or -(CH=CH) m5-; m1 : 1-6; m2-m5 : 1-3; R 11H or 1-4C alkyl; M : transition metal, Mg, Al, Sn or Ge; and R : R f, H, methyl, ethyl or O-CH 3. Provided that at least two groups of R 1-R 3are the groups i.e. ionized or ionizable in aqueous solution or a biological ligand. [Image] [Image].