Biodistribution and catabolism of 18F-labeled N-ε-fructoselysine as a model of Amadori products
Abstract
Amadori products are formed in the early stage of the so-called Maillard reaction between reducing sugars and amino acids or proteins. Such nonenzymatic glycosylation may occur during the heating or storage of foods, but also under physiological conditions. N-epsilon-fructoselysine is formed via this reaction between the epsilon-amino group of peptide-bound lysine and glucose. Despite the fact that, in certain heated foods, up to 50% of lysyl moieties may be modified to such lysine derivatives, up to now, very little is known about the metabolic fate of alimentary administered Amadori compounds. In the present study, N-succinimidyl-4-[18F]fluorobenzoate was used to modify N-epsilon-fructoselysine at the alpha-amino group of the lysyl moiety. The in vitro stability of the resulting 4-[18F]fluorobenzoylated derivative was tested in different tissue homogenates. Furthermore, the 4-[18F]fluorobenzoylated N-epsilon-fructoselysine was used in positron emission tomography studies, as well as in studies concerning biodistribution and catabolism. The results show that the 4-[18F]fluorobenzoylated N-epsilon-fructoselysine is phosphorylated in vitro, as well as in vivo. This phosphorylation is caused by fructosamine 3-kinases and occurs in vivo, particularly in the kidneys. Despite the action of these enzymes, it was shown that a large part of the intravenously applied radiolabeled N-epsilon-fructoselysine was excreted nearly unchanged in the urine. Therefore, it was concluded that the predominant part of peptide-bound lysine that was fructosylated during food processing is not available for nutrition.
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- Authors
- Hultsch, C., Hellwig, M., Pawelke, B., Bergmann, R., Rode, K., Pietzsch, J., Krause, R., & Henle, T.
- Affiliations
- Helmholtz-Zentrum Dresden-Rossendorf (DE)
- Technische Universität Dresden (DE)
- Corresponding author
- Hultsch, Christina
- Venue
- Nuclear Medicine and Biology
- Publisher
- Elsevier BV
- Published
- 2006-10
- Volume
- 33
- Issue
- 7
- Pages
- 865-873
- ISSN
- 0969-8051 (ISSN-L)
- OpenAlex
- W2074142044
- Cited by
- 17
- References
- 27
- Citations by year
- 2024: 2 · 2023: 1 · 2022: 1 · 2019: 1 · 2017: 1 · 2016: 1 · 2015: 2 · 2014: 1 · 2013: 2
- FWCI
- 0.68
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Nuclear Medicine and Biology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Clinical Biochemistry › Advanced Glycation End Products research
- Health Sciences › Medicine › Radiology, Nuclear Medicine and Imaging › Radiopharmaceutical Chemistry and Applications
- Life Sciences › Agricultural and Biological Sciences › Food Science › Potato Plant Research
- Keywords
- Amadori products, Maillard reaction, glycation, tissue distribution, catabolism, phosphorylation, fructosamine-3-kinase, kidney, urinary excretion, food processing, positron emission tomography
- MeSH terms
- Animals, Fluorine Radioisotopes, Lysine, Male, Metabolic Clearance Rate, Metabolism, Organ Specificity, Tissue Distribution, Maillard Reaction, Rats, Wistar, Radiopharmaceuticals, Positron-Emission Tomography, Rats
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