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Bolton-Hunter radioiodination

Figure 12.7 The Bolton-Hunter reagent may be radioiodinated at its phenolic ring structure prior to reaction with an amine-containing molecule to form an amide bond modification. Figure 12.7 The Bolton-Hunter reagent may be radioiodinated at its phenolic ring structure prior to reaction with an amine-containing molecule to form an amide bond modification.
Several applications of photoreactive peptides require the presence of a radionuclide to allow specific and sensitive detection of the photo-cross-linked conjugates. In several cases, radioiodination of tyrosyl moieties and radiolabeled Bolton-Hunter reagents have been used. However, the presence of a radiolabel within the benzophenone photophore is desirable, particularly when the objective is to identify the site of photo-insertion of benzophenone. To this end some radiolabeled, benzophenone-based compounds have been developed and used in peptide synthesis, in particular tritiated Phe(4-Bz) (Scheme 24)J2161 [1-14C-carboxy]-4-benzoylbenzoic acid,1221 and 4-benzoyl-(2,3-3H2)-dihydrocinnamic acid.[154l In addition, 4-(4-hydroxybenzoyl)phenylalanine (Scheme 25) has been directly radioiodinated with Na125I and Chloramine-T)151 ... [Pg.125]

Other prelabeled small molecules have been synthesized and used to prepare radioiodinated protein derivatives under conditions that circumvent exposure of the protein to oxidizing conditions. One of these compounds, I-labeled methyl p-hydroxybenzimidate, reportedly is more selective for amino groups than the Bolton-Hunter reagent - (Fig. 1). [Pg.244]

Figure 76.6 Bolton-Hunter reagent. It is the prominent prosthetic group in radioiodination of peptides. Figure 76.6 Bolton-Hunter reagent. It is the prominent prosthetic group in radioiodination of peptides.
Cytokines, hormone-like proteins, enable cells of the immune system to communicate. Signore et al. (1992) have shown the feasibility of imaging infectious foci with radioiodinated cytokines. I-IL-1 has been studied to image inflammation in patients with rheumatoid arthritis. It allowed visualization of inflamed joints, but without speciflc flxation (Barrera et al., 2000). I-IL-8, radioiodinated by the Bolton-Hunter method, shows a hyperfixation in the rabbit, localized in the infectious foci, obtained by injection of Escherichia coli in the muscle (Van der Laken et al, 2000). [Pg.755]

Figure 5.12 Mechanism of Bolton—Hunter reagent in radioiodination of free amines of proteins. Figure 5.12 Mechanism of Bolton—Hunter reagent in radioiodination of free amines of proteins.
Bolton AE (1985) Radioiodination techniques (Amersham Review 18), 2nd ed., Amersham International pic, Amersham Bolton AE, Hunter WM (1973) Biochem J 133 529 Hermanson GT (1996) Bioconjugate techniques. Academic Press, New York,p 414... [Pg.188]

The most common method of radiolabeling employs Chloramine-T, the sodium salt of the N-monochloro derivative of p-toluenesulfonamide (Fig. 17). It breaks down slowly in aqueous solution to hypochlorous acid and is used as a mild oxidizing agent in radioiodination reactions. Other oxidation reagents used in radioiodination include l,3,4,6-tetrachloro-3a,6a-diphenylglycoluril (known commercially as lodo-gen. Fig. 17) or Bolton and Hunter reagent (104). [Pg.393]

Due to the ease of handling and efficiency, the Chloramine-T method is still the most widely used radioiodination procedure and represents an effective way to label a variety of proteins and peptides such as albumins, globulins, neuropeptides, and chemokines. Several other methods, such as the enzymatically catalyzed iodination with lactoperoxidase, have been developed. These methods allow the labeling with mild reaction conditions. In the case of extreme oxidation, sensitive proteins such as pituitary hormones and reactive pre-iodinated compounds such as the Bolton and Hunter reagent can be used to incorporate radioiodine. [Pg.2132]

Chemical structures of representative heterobifunctional reagents for the radioiodination of proteins, (a) Bolton and Hunter reagent, (b) water-soluble Bolton and Hunter reagent,... [Pg.2135]


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Bolton-Hunter

Hunter

Radioiodination

Radioiodine

Radioiodines

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