Fluorodeoxyglycosylamine

Fluorodeoxyglycosylamine is a product of fluorodeoxyglucose and biological amines.^[1] The Maillard reaction of sugars and amines results in the formation of glycosylamines and Amadori products that are of biological significance, for drug delivery, role in central nervous system, and other potential applications.

This approach has also been used to prepare oximes of fluorodeoxyglucose using peptides,^[2] folic acid^[3] and rhodamine.^[4]

Fluorodeoxyglycosylamine in the form of fluorodeoxyglycosylamines (¹⁸F) may be reduced to provide fluorodeoxyglucamine (¹⁸F)^[5] as a positron emission tomography (PET) radiotracer.

References

^ Baranwal, A; Patel, H. H.; Mukherjee, J (2014). "18F-Fluorodeoxyglycosylamines: Maillard reaction of 18F-fluorodeoxyglucose with biological amines". Journal of Labelled Compounds and Radiopharmaceuticals. 57 (2): 86–91. doi:10.1002/jlcr.3168. PMC 5569313. PMID 24327460.
^ Namavari, M; Cheng, Z; Zhang, R; De, A; Levi, J; Hoerner, J. K.; Yaghoubi, S. S.; Syud, F. A.; Gambhir, S. S. (2009). "A novel method for direct site-specific radiolabeling of peptides using 18FFDG". Bioconjugate Chemistry. 20 (3): 432–6. doi:10.1021/bc800422b. PMC 2765576. PMID 19226160.
^ Al Jammaz, I; Al-Otaibi, B; Amer, S; Al-Hokbany, N; Okarvi, S (2012). "Novel synthesis and preclinical evaluation of folic acid derivatives labeled with (18)F-FDG for PET imaging of folate receptor-positive tumors". Nuclear Medicine and Biology. 39 (6): 864–70. doi:10.1016/j.nucmedbio.2012.02.005. PMID 22445744.
^ Aljammaz, Ibrahim; Al-Otaibi, Basim; Alhindas, Hussein; Okarvi, Subhani M. (2015). "Novel synthesis and initial preclinical evaluation of 18F-[FDG] labeled rhodamine: A potential PET myocardial perfusion imaging agent". Nuclear Medicine and Biology. 42 (10): 804–808. doi:10.1016/j.nucmedbio.2015.06.009. PMID 26160144.
^ Baranwal, Aparna; Mukherjee, Jogeshwar (2015). "18F-Fluorodeoxyglucamines: Reductive amination of hydrophilic 18F-fluoro-2-deoxyglucose with lipophilic amines for development of potential PET imaging agents". Bioorganic & Medicinal Chemistry Letters. 25 (15): 2902–2906. doi:10.1016/j.bmcl.2015.05.053. PMC 4469266. PMID 26048782.

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[1] Baranwal, A; Patel, H. H.; Mukherjee, J (2014). "18F-Fluorodeoxyglycosylamines: Maillard reaction of 18F-fluorodeoxyglucose with biological amines". Journal of Labelled Compounds and Radiopharmaceuticals. 57 (2): 86–91. doi:10.1002/jlcr.3168. PMC 5569313. PMID 24327460.

[2] Namavari, M; Cheng, Z; Zhang, R; De, A; Levi, J; Hoerner, J. K.; Yaghoubi, S. S.; Syud, F. A.; Gambhir, S. S. (2009). "A novel method for direct site-specific radiolabeling of peptides using 18FFDG". Bioconjugate Chemistry. 20 (3): 432–6. doi:10.1021/bc800422b. PMC 2765576. PMID 19226160.

[3] Al Jammaz, I; Al-Otaibi, B; Amer, S; Al-Hokbany, N; Okarvi, S (2012). "Novel synthesis and preclinical evaluation of folic acid derivatives labeled with (18)F-FDG for PET imaging of folate receptor-positive tumors". Nuclear Medicine and Biology. 39 (6): 864–70. doi:10.1016/j.nucmedbio.2012.02.005. PMID 22445744.

[4] Aljammaz, Ibrahim; Al-Otaibi, Basim; Alhindas, Hussein; Okarvi, Subhani M. (2015). "Novel synthesis and initial preclinical evaluation of 18F-[FDG] labeled rhodamine: A potential PET myocardial perfusion imaging agent". Nuclear Medicine and Biology. 42 (10): 804–808. doi:10.1016/j.nucmedbio.2015.06.009. PMID 26160144.

[5] Baranwal, Aparna; Mukherjee, Jogeshwar (2015). "18F-Fluorodeoxyglucamines: Reductive amination of hydrophilic 18F-fluoro-2-deoxyglucose with lipophilic amines for development of potential PET imaging agents". Bioorganic & Medicinal Chemistry Letters. 25 (15): 2902–2906. doi:10.1016/j.bmcl.2015.05.053. PMC 4469266. PMID 26048782.

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