A comparative study of N.C.A. Fluorine-18 labeling of proteins via acylation and photochemical conjugation
Three methods for 18F-labeling of proteins were evaluated with respect to conjugation yields, suitability for remote-controlled routine synthesis, and in vivo stability of the conjugates— i.e., photochemical conjugation (PCC) using 4-azidophenacyl-[ 18F]fluoride ([ 18F]APF) as well as classical conj...
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Published in | Nuclear medicine and biology Vol. 23; no. 3; pp. 365 - 372 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
United States
Elsevier Inc
01.04.1996
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Subjects | |
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Abstract | Three methods for
18F-labeling of proteins were evaluated with respect to conjugation yields, suitability for remote-controlled routine synthesis, and
in vivo stability of the conjugates—
i.e., photochemical conjugation (PCC) using 4-azidophenacyl-[
18F]fluoride ([
18F]APF) as well as classical conjugation using 4-nitrophenyl 2-[
18F]fluoropropionate ([
18F]NPFP) and
N-succinimidyl 4-[18F]fluorobenzoate ([
18F]SFB). For this purpose, [
18F]APF was synthesized in one step with a radiochemical yield (RCY) of up to 70% within about 15 min. The
18F-labeling was performed by photogeneration of the corresponding [
18F]arylnitrene by irradiating [
18F]APF with UV light in presence of the protein in aqueous buffered solution. Using this procedure, human serum albumin (HSA), transferrin, IgG, and avidin were labeled. The [
18F]NPFP was synthesized according to a recently published method. Preparation of [
18F]SFB was achieved within 35 min with radiochemical yields of 55 ± 10% by an improved method using
O-(
N-succinimidyl)-
N-N,N′,N′-tetramethyluronium tetrafluoroborate (TSTU) as activating reagent. Compared to [
18F]APF, protein labeling with [
18F]NPFP and [
18F]SFB gave rise to considerably higher RCY, of up to 90%. Labeling studies showed that conjugation yields using [
18F]NPFP depend on the lysine, tyrosine, and histidine content of the proteins used, whereas conjugation with [
18F]APF and [
18F]SFB predominantly depends on the Lys content. Owing to competing
O-acylation of Tyr residues, [
18F]fluoropropionylated HSA was partially unstable under slightly basic conditions. Biodistribution studies with
18F-labeled HSA in NMRI mice revealed the highest
in vivo stability for the [
18F]SFB conjugate. Based on these results, [
18F]SFB seems to be the most suitable
18F-labeling agent for proteins, particularly for the labeling of antibodies. |
---|---|
AbstractList | Three methods for
18F-labeling of proteins were evaluated with respect to conjugation yields, suitability for remote-controlled routine synthesis, and
in vivo stability of the conjugates—
i.e., photochemical conjugation (PCC) using 4-azidophenacyl-[
18F]fluoride ([
18F]APF) as well as classical conjugation using 4-nitrophenyl 2-[
18F]fluoropropionate ([
18F]NPFP) and
N-succinimidyl 4-[18F]fluorobenzoate ([
18F]SFB). For this purpose, [
18F]APF was synthesized in one step with a radiochemical yield (RCY) of up to 70% within about 15 min. The
18F-labeling was performed by photogeneration of the corresponding [
18F]arylnitrene by irradiating [
18F]APF with UV light in presence of the protein in aqueous buffered solution. Using this procedure, human serum albumin (HSA), transferrin, IgG, and avidin were labeled. The [
18F]NPFP was synthesized according to a recently published method. Preparation of [
18F]SFB was achieved within 35 min with radiochemical yields of 55 ± 10% by an improved method using
O-(
N-succinimidyl)-
N-N,N′,N′-tetramethyluronium tetrafluoroborate (TSTU) as activating reagent. Compared to [
18F]APF, protein labeling with [
18F]NPFP and [
18F]SFB gave rise to considerably higher RCY, of up to 90%. Labeling studies showed that conjugation yields using [
18F]NPFP depend on the lysine, tyrosine, and histidine content of the proteins used, whereas conjugation with [
18F]APF and [
18F]SFB predominantly depends on the Lys content. Owing to competing
O-acylation of Tyr residues, [
18F]fluoropropionylated HSA was partially unstable under slightly basic conditions. Biodistribution studies with
18F-labeled HSA in NMRI mice revealed the highest
in vivo stability for the [
18F]SFB conjugate. Based on these results, [
18F]SFB seems to be the most suitable
18F-labeling agent for proteins, particularly for the labeling of antibodies. Three methods for 18F-labeling of proteins were evaluated with respect to conjugation yields, suitability for remote-controlled routine synthesis, and in vivo stability of the conjugates-i.e., photochemical conjugation (PCC) using 4-azidophenacyl-[18F]fluoride ([18F]APF) as well as classical conjugation using 4-nitrophenyl 2-[18F]fluoropropionate ([18F]NPFP) and N-succinimidyl 4-[18F]fluorobenzoate ([18F]SFB). For this purpose, [18F]APF was synthesized in one step with a radiochemical yield (RCY) of up to 70% within about 15 min. The 18F-labeling was performed by photogeneration of the corresponding [18F]arylnitrene by irradiating [18F]APF with UV light in presence of the protein in aqueous buffered solution. Using this procedure, human serum albumin (HSA), transferrin, IgG, and avidin were labeled. The [18F]NPFP was synthesized according to a recently published method. Preparation of [18F]SFB was achieved within 35 min with radiochemical yields of 55 +/- 10% by an improved method using O-(N-succinimidyl)-N-N,N',N'-tetramethyluronium tetrafluoroborate (TSTU) as activating reagent. Compared to [18F]APF, protein labeling with [18F]NPFP and [18F]SFB gave rise to considerably higher RCY, of up to 90%. Labeling studies showed that conjugation yields using [18F]NPFP depend on the lysine, tyrosine, and histidine content of the proteins used, whereas conjugation with [18F]APF and [18F]SFB predominantly depends on the Lys content. Owing to competing O-acylation of Tyr residues, [18F]fluoropropionylated HSA was partially unstable under slightly basic conditions. Biodistribution studies with 18F-labeled HSA in NMRI mice revealed the highest in vivo stability for the [18F]SFB conjugate. Based on these results, [18F]SFB seems to be the most suitable 18F-labeling agent for proteins, particularly for the labeling of antibodies. |
Author | Wester, Hans-Jürgen Hamacher, Kurt Stöcklin, Gerhard |
Author_xml | – sequence: 1 givenname: Hans-Jürgen surname: Wester fullname: Wester, Hans-Jürgen – sequence: 2 givenname: Kurt surname: Hamacher fullname: Hamacher, Kurt – sequence: 3 givenname: Gerhard surname: Stöcklin fullname: Stöcklin, Gerhard |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/8782249$$D View this record in MEDLINE/PubMed |
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Keywords | Proteins Fluorine-18 Conjugation In vivo stability Antibody labeling |
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Radiopharm. doi: 10.1002/jlcr.2580270711 contributor: fullname: Haka |
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18F-labeling of proteins were evaluated with respect to conjugation yields, suitability for remote-controlled routine synthesis, and
in vivo... Three methods for 18F-labeling of proteins were evaluated with respect to conjugation yields, suitability for remote-controlled routine synthesis, and in vivo... |
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SubjectTerms | Acylation Animals Antibody labeling Avidin Azides Benzoates Conjugation Fluorine Radioisotopes - pharmacokinetics Fluorine-18 Humans Immunoglobulin G In vivo stability Indicators and Reagents Isotope Labeling - methods Mice Mice, Inbred Strains Photochemistry Proteins Proteins - pharmacokinetics Serum Albumin Succinimides Tissue Distribution Transferrin |
Title | A comparative study of N.C.A. Fluorine-18 labeling of proteins via acylation and photochemical conjugation |
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