F-18-Fluorodeoxyglycosylamines: Maillard reaction of F-18-fluorodeoxyglucose with biological amines

The Maillard reaction of sugars and amines resulting in the formation of glycosylamines and Amadori products is of biological significance, for drug delivery, role in central nervous system, and other potential applications. We have examined the interaction of F-18-fluorodeoxyglucose (F-18-FDG) with...

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Bibliographic Details
Published inJournal of labelled compounds & radiopharmaceuticals Vol. 57; no. 2; pp. 86 - 91
Main Authors Baranwal, Aparna, Patel, Himika H., Mukherjee, Jogeshwar
Format Journal Article
LanguageEnglish
Published HOBOKEN Wiley 01.02.2014
Subjects
Biochemical Research Methods
Biochemistry & Molecular Biology
Chemistry
Chemistry, Analytical
Chemistry, Medicinal
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
GLUCOSE
F-18-FDG
Maillard reaction
quasi-Amadori product
SEROTONIN
PET
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Summary:The Maillard reaction of sugars and amines resulting in the formation of glycosylamines and Amadori products is of biological significance, for drug delivery, role in central nervous system, and other potential applications. We have examined the interaction of F-18-fluorodeoxyglucose (F-18-FDG) with biological amines to study the formation of F-18-fluorodeoxyglycosylamines (F-18-FDGly). Respective amines N-allyl-2-aminomethylpyrrolidine (NAP) and 2-(4-aminophenyl)-6-hydroxybenzothiazole (PIB precursor) were mixed with FDG to provide glycosylamines, FDGNAP and FDGBTA. Radiosynthesis using F-18-FDG (2-5mCi) was carried out to provide F-18-FDGNAP and F-18-FDGBTA. Binding of FDGBTA and F-18-FDGBTA was evaluated in human brain sections of Alzheimer's disease (AD) patients and control subjects using autoradiography. Both FDGNAP and FDGBTA were isolated as stable products. Kinetics of F-18-FDGNAP reaction indicated a significant product at 4h (63% radiochemical yield). F-18-FDGBTA was prepared in 57% yield. Preliminary studies of FDGBTA showed displacement of H-3-PIB (reduced by 80%), and F-18-FDGBTA indicated selective binding to A-amyloid plaques present in postmortem AD human brain, with a gray matter ratio of 3 between the AD patients and control subjects. We have demonstrated that F-18-FDG couples with amines under mild conditions to form F-18-FDGly in a manner similar to click chemistry. Although these amine derivatives are stable in vitro, stability in vivo and selective binding is under investigation. Copyright (c) 2013 John Wiley & Sons, Ltd.
Bibliography:NIH RePORTER
ISSN:0362-4803
1099-1344
DOI:10.1002/jlcr.3168