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. 1966 May;10(5):465–479.

Chemical and serological studies with an iodine-containing synthetic immunological determinant 4-hydroxy-3-iodo-5-nitrophenylacetic acid (NIP) and related compounds

A Brownstone, N A Mitchison, R Pitt-Rivers
PMCID: PMC1423692  PMID: 5939478

Abstract

The synthesis and properties of 4-hydroxy-3-iodo-5-nitrophenylacetic acid (NIP) and several related compounds are described. Conjugates of NIP with proteins are prepared from the azide, synthesized from commercial 4-hydroxy-phenylacetic acid. Sera from rabbits and mice immunized with NIP—ovalbumin or NIP—chicken serum globulin bind N131IP-containing compounds, as judged from precipitation of radioactivity by salting-out of immunoglobulins. Homogeneous binding is obtained with N131IP—polylysine, N131IP—ε-amino-n-caproic acid (N131IP—aminocap), and other structurally related haptens; non-homogeneous binding is obtained with N131IP—bovine serum albumin. Binding to salt-precipitated immunoglobulin of N131IP—aminocap, the hapten of choice for this purpose, provides an assay for antibody measurable at concentrations down to at least M-9 serum binding capacity (∼0.1 μg antibody/ml). Structurally related compounds and NIP—protein conjugates competitively inhibit binding of N131IP—aminocap. The inhibitions indicate that the iodine contained in NIP, but not the carrier protein, contributes significantly to the binding site.

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Selected References

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