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Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013.
| Chemical name: | 2'-Deoxy-2'-[18F]fluoro-1-β-D-arabinofuranosyl-adenine |
|
| Abbreviated name: | [18F]FAA | |
| Synonym: | ||
| Agent Category: | Compound | |
| Target: | Unknown | |
| Target Category: | Non-catabolized trapping inside cells | |
| Method of detection: | PET | |
| Source of signal: | 18F | |
| Activation: | No | |
| Studies: |
| Click on the above structure for additional information in PubChem. |
Rodents
Background
[PubMed]
Adenylates are important in cellular metabolism and functions (1). Adenosine is converted intracellularly to adenosine triphosphate (ATP), which is an important source of energy as well as a regulator of cellular functions. Adenosine stimulates the acetylcholine-sensitive K+ current in the heart. Many fluorinated analogs of adenosine nucleoside have been investigated as potential antitumor and antiviral agents (2-5). 2'-Deoxy-2'-fluoro-9-β-D-arabinofuranosyl-adenine (FAA) has been reported to exhibit antitumor activity (6). [18F]FAA has been synthesized and studied in tumor-bearing mice with positron emission tomography (PET) imaging (7).
Synthesis
[PubMed]
Alauddin et al. (7) synthesized [18F]FAA by reaction of the respective triflate (N3,3’,5’-tri-methoxytrityl-2’-trifluoromethanesulfonyl-9-β-D-arabinofuranosyl-adenine) with tetrabutylammonium [18F]fluoride, followed by acid hydrolysis to remove the methoxytrityl protecting groups. The desired product, [18F]FAA, was purified with high-performance liquid chromatography with a radiochemical yield of 10%–12% (decay-corrected) and a radiochemical purity >99%. The average specific activity for [18F]FAA was >74 GBq/µmol (2,000 mCi/µmol) at the end of the synthesis. Total synthesis time was 90–95 min from the end of bombardment.
Animal Studies
Rodents
[PubMed]
Alauddin et al. (7) performed biodistribution studies of [18F]FAA in nude mice (n = 5) bearing an HT-29 tumor in the left flank and a herpes simplex virus thymidine kinase (HSV-tk)–transduced HT-29 tumor in the right flank. [18F]FAA cleared rapidly from the blood within 20 min after injection with a plasma half-life of ~10 min. The spleen had the highest accumulation at 120 min (the only time point studied) with 11.65% injected dose (ID)/g, followed by the kidney (3.5% ID/g), liver (2.4% ID/g), intestine (1.9% ID/g), heart (1.55% ID/g), and lung (1.4% ID/g). The accumulation in the two tumors was 1.75% ID/g in the wild-type tumor and 1.55% ID/g in the HSV-tk-transduced tumor with tumor/blood ratios of 3.27 and 2.92, respectively. The similar tumor uptakes suggested that [18F]FAA is not a substrate for HSV-tk gene. Radioactivity in the blood and muscle was 0.53% ID/g and 0.75% ID/g, respectively. PET images were obtained at 30, 60, and 120 min after injection. The spleen exhibited the highest radioactivity. Both tumors were clearly visualized. No significant differences in images were observed at the three time points. No blocking experiment was performed. The authors suggested that further studies are necessary to understand the mechanism of tumor accumulation.
NIH Support
CA72896
References
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- 5.
- Secrist J.A. , Shortnacy A.T. , Montgomery J.A. Synthesis and biological evaluations of certain 2-halo-2'-substituted derivatives of 9-beta-D-arabinofuranosyladenine. J Med Chem. 1988; 31 (2):405–10. [PubMed: 3339610]
- 6.
- Takahashi T. , Kanazawa J. , Akinaga S. , Tamaoki T. , Okabe M. Antitumor activity of 2-chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) adenine, a novel deoxyadenosine analog, against human colon tumor xenografts by oral administration. Cancer Chemother Pharmacol. 1999; 43 (3):233–40. [PubMed: 9923554]
- 7.
- Alauddin M.M. , Shahinian A. , Park R. , Tohme M. , Fissekis J.D. , Conti P.S. Biodistribution and PET imaging of [(18)F]-fluoroadenosine derivatives. Nucl Med Biol. 2007; 34 (3):267–72. [PMC free article: PMC1905838] [PubMed: 17383576]
- PMCPubMed Central citations
- PubChem SubstanceRelated PubChem Substances
- PubMedLinks to PubMed
- Review 3'-Deoxy-3'-[(18)F]fluoro-1-β-D-xylofuranosyl-adenine.[Molecular Imaging and Contrast...]Review 3'-Deoxy-3'-[(18)F]fluoro-1-β-D-xylofuranosyl-adenine.Leung K. Molecular Imaging and Contrast Agent Database (MICAD). 2004
- Review 1-(2'-Deoxy-2'-[(18)F]fluoro-β-d-arabinofuranosyl)-5-iodocytosine.[Molecular Imaging and Contrast...]Review 1-(2'-Deoxy-2'-[(18)F]fluoro-β-d-arabinofuranosyl)-5-iodocytosine.Shan L. Molecular Imaging and Contrast Agent Database (MICAD). 2004
- Biodistribution and PET imaging of [(18)F]-fluoroadenosine derivatives.[Nucl Med Biol. 2007]Biodistribution and PET imaging of [(18)F]-fluoroadenosine derivatives.Alauddin MM, Shahinian A, Park R, Tohme M, Fissekis JD, Conti PS. Nucl Med Biol. 2007 Apr; 34(3):267-72. Epub 2007 Feb 22.
- Review 1-(2’-Deoxy-2’-[(18)F]-fluoro-β-D-arabinofuranosyl)thymine.[Molecular Imaging and Contrast...]Review 1-(2’-Deoxy-2’-[(18)F]-fluoro-β-D-arabinofuranosyl)thymine.Chopra A. Molecular Imaging and Contrast Agent Database (MICAD). 2004
- C(2')-substituted purine nucleoside analogs. Interactions with adenosine deaminase and purine nucleoside phosphorylase and formation of analog nucleotides.[Biochem Pharmacol. 1982]C(2')-substituted purine nucleoside analogs. Interactions with adenosine deaminase and purine nucleoside phosphorylase and formation of analog nucleotides.Stoeckler JD, Bell CA, Parks RE Jr, Chu CK, Fox JJ, Ikehara M. Biochem Pharmacol. 1982 May 1; 31(9):1723-8.
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