In 1920s and 1930s, K. Landsteiner et al. revealed that antibodies are raised against organic small molecules when an animal is injected with the biological protein combined with organic small molecules which are ordinarily non-antigenic.1) The antibodies produced independently of an antibody against the protein, show an antigen-antibody reaction with small molecules, but do not provoke an immune response. Aromatic compounds like dinitrophenol (1), and sugars are known as the small molecules called "haptens (incomplete antigens)".
N-Succinimidyl 6-(2,4-dinitroanilino)hexanoate (2) is a hapten-labeling reagent containing the 2,4-dinitrophenyl group (DNP). 2 can bind covalently to an amino group of peptides and proteins, etc. via the succinimidyl moiety. The combination of labeled compounds and an anti-DNP antibody is applied to radioimmunoassay, ELISA, and immunohistochemical staining.2) Furthermore, research has also been reported on drug delivery systems (DDS) by using synthetic macromolecules labeled with 2,3) and on cell-surface receptor models incorporating 2.4)
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