Synthesis and Pharmacological Properties of Linear Poly(Ethylene Glycol)s Conjugated to Interferon α-2b by Azo Coupling

Sheremet’ev, S. V.; Lonshakov, Dmitry V.; Коровкин, С А; Belosludtseva, E. M.; Катлинский, Антон Викентьевич; Семченко, А. В.; Борисова, О. В.

doi:10.1007/s11094-017-1532-4

Cited by 3 publications

(4 citation statements)

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“…A significant heart uptake and slow blood clearance, as well as radioactivity accumulation in the liver over time, are typical for proteins such as HSA (Figure S21). The results are comparable to the recent literature describing PET imaging with 18 F-labeled rat serum albumin (RSA) and 64 Cu-labeled HSA. 26,27 In a 2015 study conducted by Jagoda et al, PET imaging with 18 F-labeled RSA showed uptake in the heart and peripheral vasculature, with retention up to 2.5 h postinjection.…”

Section: ■ Discussionsupporting

confidence: 86%

“…The chemoselectivity of azo coupling reactions with diazonium salts toward tyrosine and histidine residues was recently studied. − Results are varying greatly, but several studies that described a high degree of tyrosine site-specificity in azo coupling reactions were reported even in the presence of competing amino acid targets such as histidine . Other studies demonstrated more selectivity for tyrosine at pH 8.5 but increased selectivity for histidine at pH 9.1 and higher…”

Section: Discussionmentioning

confidence: 99%

“…Popular strategies involve radiolabeling of chelator-decorated peptides and proteins, including antibodies and other immunoconjugates, with radiometals for PET and SPECT imaging such as 68 Ga, 64 Cu, and 111 In or those for radiotherapy such as 177 Lu and 225 Ac. Preconjugation labeling strategies are especially popular in 18 F chemistry as demonstrated with numerous prosthetic groups used for the labeling of peptides with 18 F. Chemoselective incorporation of radionuclides via metal chelators or prosthetic groups into peptides and proteins mainly exploits bioconjugation chemistry with nucleophilic groups such as amine and thiol as present in lysine and cysteine residues. A rather underutilized amino acid for peptide and protein conjugation is tyrosine.…”

Section: ■ Discussionmentioning

confidence: 99%

“…In this line, we tested the effect of radiolabeled diazo conjugates of NT(8−13) on the binding to neurotensin receptor NTR1. Recently, we have measured several multimeric neurotensin(8−13) analogues for their binding to the NTR1 to identify suitable candidates for radiolabeling with 18 F. 15,16 All tested NT(8−13) were modified at the N-terminal end of the peptide. Most peptides displayed rather low inhibitory potency compared to parent compound NT (8−13).…”

Section: ■ Discussionmentioning

confidence: 99%

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Radiometal-Containing Aryl Diazonium Salts for Chemoselective Bioconjugation of Tyrosine Residues

Leier¹,

Richter²,

Bergmann

et al. 2019

ACS Omega

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Tyrosine is an attractive target for chemo- and site-selective protein modification. The particular chemical nature of tyrosine residues allows bioconjugation chemistry with reactive aryl diazonium salts via electrophilic aromatic substitution to produce diazo compounds. In this work, we describe the preparation of 64Cu- and 68Ga-labeled 1,4,7-triazacyclononane-1,4,7-triacetic acid (NOTA)-diazonium salts as building blocks for azo coupling chemistry with tyrosine and tyrosine-containing peptides and proteins under mild conditions. 2-S-(4-aminobenzyl)-1,4,7-triazacyclononane-1,4,7-triacetic acid (p-NH2-Bn-NOTA) was used to form the corresponding 64Cu- and 68Ga-labeled complexes, followed by diazotization with NaNO2 in the presence of HCl. 64Cu- and 68Ga-labeled NOTA complexes were prepared in high radiochemical yields >80% starting from 20 μg of p-NH2-Bn-NOTA. Conversion of p-NH2-Bn-NOTA complexes into diazonium salts followed by azo coupling with l-tyrosine afforded 64Cu- and 68Ga-labeled tyrosine in radiochemical yields of 80 and 56%, respectively. Azo coupling with tyrosine-containing hexapeptide neurotensin NT(8–13) afforded 64Cu- and 68Ga-labeled NT(8–13) in radiochemical yields of 45 and 11%, respectively. Azo coupling of 64Cu-labeled NOTA-diazonium salt with human serum albumin (HSA) gave 64Cu-labeled HSA in radiochemical yields of 20%. The described azo coupling chemistry represents an innovative and versatile bioconjugation strategy for selective targeting of tyrosine residues in peptides and proteins.

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Section: ■ Discussionsupporting

confidence: 86%