N-iodoacetyltyramine: Preparation and use in sup 125 I labeling by alkylation of sulfhydryl groups

Journal Article · Thu Jun 01 00:00:00 EDT 1989 · Analytical Biochemistry; (USA)

DOI:https://doi.org/10.1016/0003-2697(89)90150-4· OSTI ID:5482110

Lin, C M; Mihal, K A; Krueger, R J ^[1]

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1. Univ. of Nebraska, Lincoln (USA)

Preparation and use of N-iodoacetyltyramine in generation of {sup 125}I-labeled compounds is described. The kinetics of alkylation of N-acetylcysteine by N-iodoacetyltyramine (k2 = 3.0 M-1 s-1) and N-chloroacetyltyramine (k2 = 0.12 M-1 s-1) indicate that N-iodoacetyltyramine is more useful for labeling sulfhydryl-containing compounds to high specific activity with {sup 125}I. Conditions for preparation of carrier-free {sup 125}I-labeled N-iodoacetyl-3-monoiodotyramine in 50% yield based on starting iodide are described. The high degree of group specificity of N-iodoacetyl-3-monoiodotyramine reaction with sulfhydryl groups is demonstrated by the high reactivity toward sulfhydryl-containing bovine serum albumin and low reactivity toward N-ethylmaleimide-blocked bovine serum albumin and IgG. {sup 125}I-labeled N-iodoacetyl-3-monoiodotyramine was also used to prepare an {sup 125}I-labeled ACTH derivative that retains full biological activity, further demonstrating the selectivity toward reactions with sulfhydryl groups.

• OSTI ID: 5482110
• Journal Information: Analytical Biochemistry; (USA), Vol. 179:2; ISSN 0003-2697
• Country of Publication: United States
• Language: English

Related Subjects

59 BASIC BIOLOGICAL SCIENCES
THIOLS
LABELLING
TYRAMINE
CHEMICAL PREPARATION
ALBUMINS
ALKYLATION
CATTLE
IMMUNOGLOBULINS
IODINE 125
LABELLED COMPOUNDS
RATS
TRACER TECHNIQUES
AMINES
ANIMALS
AROMATICS
AUTONOMIC NERVOUS SYSTEM AGENTS
BETA DECAY RADIOISOTOPES
CHEMICAL REACTIONS
DAYS LIVING RADIOISOTOPES
DOMESTIC ANIMALS
DRUGS
ELECTRON CAPTURE RADIOISOTOPES
GLOBULINS
HYDROXY COMPOUNDS
INTERMEDIATE MASS NUCLEI
IODINE ISOTOPES
ISOTOPE APPLICATIONS
ISOTOPES
MAMMALS
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PHENOLS
PROTEINS
RADIOISOTOPES
RODENTS
RUMINANTS
SYMPATHOMIMETICS
SYNTHESIS
VERTEBRATES
550201* - Biochemistry- Tracer Techniques