Facile and rapid access to linear and truncated microcystin analogues for the implementation of immunoassays

Org Biomol Chem. 2010 Feb 7;8(3):676-90. doi: 10.1039/b920193a. Epub 2009 Dec 8.

Abstract

A series of simplified microcystin-LR analogues based on Adda [(2S,3S,8S,9S,4E,6E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldecadienoic acid] or its corresponding aldol precursor linked to a polypeptide moiety have been synthesised and assessed for their binding affinity by the monoclonal antibody mAb MC159, an anti-microcystin-LR mAb recently selected by us for the detection of microcystins through various immunoassay formats. Some modifications have been brought to the enantiospecific synthesis of N-Boc-Adda developed by Pearson et al. (Org. Lett., 2000, 2, 2901) which enabled us to access in an economical and time-saving manner a small library of MC-LR linear analogues. Among which Adda was chosen to synthesise, as an illustrative example, a fluorescent probe derived from this beta-amino acid. This probe was subsequently solid-phase immobilised by means of oxime ligation in order to lead to biochips suitable for microcystin detection through the SPIT-FRI method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Amides / chemistry
  • Antibodies, Monoclonal / immunology
  • Cross Reactions
  • Decanoic Acids / chemistry
  • Fluorescent Dyes / chemistry
  • Glass / chemistry
  • Immobilized Proteins / chemical synthesis
  • Immobilized Proteins / chemistry
  • Immobilized Proteins / immunology
  • Immunoassay / methods*
  • Indicators and Reagents / chemistry
  • Kinetics
  • Microcystins / chemistry*
  • Peptide Fragments / chemical synthesis
  • Peptide Fragments / chemistry*
  • Peptide Fragments / immunology
  • Stereoisomerism

Substances

  • Aldehydes
  • Amides
  • Antibodies, Monoclonal
  • Decanoic Acids
  • Fluorescent Dyes
  • Immobilized Proteins
  • Indicators and Reagents
  • Microcystins
  • Peptide Fragments
  • phenyldecanoic acid
  • microcystin
  • 3-hydroxybutanal