sup 18 F-labeled insulin: A prosthetic group methodology for incorporation of a positron emitter into peptides and proteins

In the present study we synthesize {sup 18}F-labeled insulin of high specific radioactivity. A new prosthetic group methodology, in which ({sup 18}F)fluoride displaces a bromide group of 4-(bromomethyl)-benzoylamine intermediates, was used. The 4-(fluoromethyl)benzoyl product was chemically stable....

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Bibliographic Details
Published in:Biochemistry (Easton) 1989-05, Vol.28:11
Main Authors: Shai, Y., Kirk, K.L., Channing, M.A., Dunn, B.B., Lesniak, M.A., Eastman, R.C., Finn, R.D., Roth, J., Jacobson, K.A.
Format: Article
Language:English
Subjects:
550201 - Biochemistry- Tracer Techniques
ADIPOSE TISSUE
ALDEHYDES
ANIMAL TISSUES
ANIMALS
BASIC BIOLOGICAL SCIENCES
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
BODY
CARBOHYDRATES
CHEMICAL PROPERTIES
CONNECTIVE TISSUE
FLUORINE 18
FLUORINE ISOTOPES
GLUCOSE
HEXOSES
HORMONES
HOURS LIVING RADIOISOTOPES
INSULIN
ISOMERIC TRANSITION ISOTOPES
ISOTOPE APPLICATIONS
ISOTOPES
LABELLING
LIGHT NUCLEI
MAMMALS
MEMBRANE PROTEINS
METABOLISM
MONOSACCHARIDES
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
PEPTIDE HORMONES
PEPTIDES
PROTEINS
RADIOISOTOPES
RATS
RECEPTORS
RODENTS
SACCHARIDES
TISSUES
TRACER TECHNIQUES
VERTEBRATES
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Summary:In the present study we synthesize {sup 18}F-labeled insulin of high specific radioactivity. A new prosthetic group methodology, in which ({sup 18}F)fluoride displaces a bromide group of 4-(bromomethyl)-benzoylamine intermediates, was used. The 4-(fluoromethyl)benzoyl product was chemically stable. {sup 18}F-Labeled insulin retains the essential biological properties of native insulin, as measured in vitro by binding to insulin receptors on human cells and stimulation of glucose metabolism in rat adipocytes. The overall process can be carried out speedily to yield a product of sufficient purity to permit in vivo studies. The method appears to be applicable to a wide variety of peptides.
ISSN:0006-2960
1520-4995
DOI:10.1021/bi00437a042