Synthesis and preliminary evaluation of 9-(4-[18F]-fluoro-3- hydroxymethylbutyl)guanine ([18F]FHBG): A new potential imaging agent for viral infection and gene therapy using PET

Nuclear Medicine and Biology

Volumn 25, Issue 3, 1998, Pages 175-180

  Alauddin, Mian M ^b   Conti, Peter S ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b NONE

Author keywords

18F FHBG; Gene therapy; Penciclovir; PET; Thymidine kinase; Viral infection

Indexed keywords

9 (4 FLUORO 3 HYDROXYMETHYLBUTYL)GUANINE F 18; ANTIVIRUS AGENT; GANCICLOVIR; PENCICLOVIR; RADIOPHARMACEUTICAL AGENT; THYMIDINE KINASE; UNCLASSIFIED DRUG; VIRUS VECTOR;

ARTICLE; CANCER CELL CULTURE; CANCER THERAPY; COLON CANCER; DRUG SYNTHESIS; GENE THERAPY; GENETIC TRANSDUCTION; HUMAN; HUMAN CELL; ISOTOPE LABELING; RETROVIRUS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; VIRUS INFECTION;

ACYCLOVIR; ANTIVIRAL AGENTS; BIOLOGICAL TRANSPORT; COLONIC NEOPLASMS; FLUORINE RADIOISOTOPES; GENE THERAPY; GUANINE; HUMANS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; TUMOR CELLS, CULTURED; VIRUS DISEASES;

EID: 18244428952     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(97)00160-1     Document Type: Article

References (26)

1. 1. Alauddin M. M., Conti P. S., Mazza S. M., Hamzeh F. M. and Lever J. R. (1996) Synthesis of F-18 9-[3-fluoro-1-hydroxy-2-propoxy)methyl]guanine (FHPG) for in vivo imaging of viral infection and gene therapy with PET. J. Nucl. Med. 37, 193P.
2. 18F]FHPG): A potential imaging agent of viral infection and gene therapy using PET. Nucl. Med. Biol. 23, 787-792.
3. 18F]fluoro-1-hydroxy-2-propoxy)methyl]guanine (F-18 FHPG) in HT-29 cells. J. Nucl. Med. 38, 176P.
4. 4. Bading J. R., Alauddin M. M., Fissekis J. D., Kirkman E., Raman R. K. and Conti P. S. (1997) Pharmacokinetics of F-18 fluorohydroxypropoxymethylguanine. J. Nucl. Med. 38, 43P.
5. 5. Barrio J. R., Namavari M., Satyamurthy N., Srinivasan A., Herschman H., Gambhir S. et al. (1996) 8-[F-18]Fluoroacyclovir: An in vivo probe for gene expression with PET. J. Nucl. Med. 37, 193P.
6. 6. Becker E. D. (1980) High Resolution NMR, p. 99. Academic Press, New York.
7. 7. Boyd M. R., Bacon T. H., Sutton D. and Cole M. (1987) Antiherpesvirus activity of 9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine (BRL 39123) in cell culture. Antimicrob. Agents Chemother. 31, 1238-1242.
8. 8. Boyd M. R., Bacon T. H. and Sutton D. (1988) Anti-herpesvirus activity of 9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine (BRL 39123) in animals. Antimicrob. Agents Chemother. 32, 358-363.
9. 9. Cavalli L. (1976) Fluorine-19 NMR spectroscopy. In: Annual Report of NMR Spectroscopy (Edited by Mooney E. F.), Vol.6B, pp. 43-100. Academic Press, New York.
10. 10. Cheng Y-C., Grill S. P., Dutschman G. E., Nakayama K. and Bastow K. F. (1983) Metabolism of 9-(1,3-dihydroxy-2-propoxymethyl)guanine, a new anti-herpes virus compound in herpes simplex virus-infected cells. J. Biol. Chem. 258, 12460-12464.
11. 11C]-Citalopram. Int. J. Radiat. Appl. Instrum. Part A 4, 541-543.
12. 12. Earnshaw D. L., Bacon T. H., Darlison S. J., Edmonds K., Perkins R. M. and Vere Hodge R. A. (1992) Mode of antiviral action of penciclovir in MRC-5 cells infected with herpes simplex virus type 1 (HSV-1), HSV-2, and varicella-zoster virus. Antimicrob. Agents Chemother. 36, 2747-2757.
13. 13. Elion G. B., Rurman P. A., Fyfe J. A., De Miranda P., Beauchamp L. and Schaeffer H. J. (1977) Selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymathyl)guanine. Proc. Natl. Acad. Sci. USA 74, 5716-5720.
14. 14. Goldman S., Monclus M., Cool V., Damhout P., Luxen A., Levvier M. et al. (1996) A novel PET tracer for evaluation of gene therapy. J. Nucl. Med. 37, 53P.
15. 15. Harnden M. R., Jarvest R. L., Bacon T. H. and Boyd M. R. (1987) Synthesis and antiviral activity of 9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]purines. J. Med. Chem. 30, 1636-1642.
16. 16. Kelley J. L. and Beauchamp L. (1983) Antiviral agents. Annu. Rep. Med. Chem. 18, 139-148.
17. 17. Martin J. C., Dvorak C. A., Smee D. F., Matthews T. R. and Verheyden P. H. (1983) 9-[(1, 3-Dihydroxy-2-propoxy)-methyl]-guanine: A new selective antiherpes agent. J. Med. Chem. 26, 759-671.
18. 18. Martin J. C., McGee D., Jeffrey G., Hobbs D. W., Smee D. F., Mathews T. R. et al. (1986) Synthesis and anti-herpes-virus activity of acyclic 2′-deoxyguanosine analogues related to 9-[(1, 3-dihydroxy-2-propoxy) methyl]guanine. J. Med. Chem. 29, 1384-1389.
19. 18F-fluoro-3-hydroxy-2-propoxy)-methyl]-guanine. J. Label. Compd. Radiopharm. 37, 193-195.
20. 20. Schaeffer H. J., Bauchamp L., De Miranda P. and Elion G. (1978) 9-(2-Hydroxyethyloxymethyl)guanine activity against viruses of the herpes group. Nature 272, 583-585.
21. 21. Smee D. F., Martin J. C., Verheyden J. P. H. and Mathew T. R. (1983) Anti-herpesvirus activity of the acyclic nucleoside 9-(1, 3-dhydroxy-2-propoxymethyl)guanine. Antimicrob. Agents Chemother. 23, 676-682.
22. 22. Smee D. F., Boehme R., Chernow M., Binko B. P. and Mathew T. R. (1985) Intracellular metabolism and enzymatic phosphorylation of 9-(1, 3-dhydroxy-2-propoxymethyl)guanine and acyclovir in herpes simplex virus infected and uninfected cells. Biochem. Pharmacol. 34, 1049-1056.
23. 23. Smee D. F., Campbell N. L. and Mathew T. R. (1985) Comparative anti-herpesvirus activities of the 9-(1, 3-dhydroxy-2-propoxymethyl) guanine, acyclovir, and two 2′-fluoropyrimidine nucleosides. Antiviral Res. 5, 259-267.
24. 24. Smith K. O., Galloway K. S., Kennell W. L., Ogilvie K. K. and Radatus B. K. (1982) A new nucleoside analogue, 9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]-methyl]guanine, highly active in vitro against herpes simplex virus types 1 and 2. Antimicrob. Agents Chemother. 22, 55-61.
25. 25. Vere Hodge R. A. and Perkins R. M. (1989) Mode of action of 9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine (BRL 39123) against herpes simplex virus in MRC-5 cells. Antimicrob. Agents Chemother. 33, 223-229.
26. 11C]N-methyl acyclovir. J. Label. Compd. Radiopharm. 29, 765-766.