p-[18F]Fluoroethoxyphenyl BCNA for VZV-tk imaging
Journal of Medicinal Chemistry, 2007, Vol. 50, No. 26 6637
(2) Gambhir, S. S.; Bauer, E.; Black, M. E.; Liang, Q.; Kokoris, M. S.;
Barrio, J. R.; Iyer, M.; Namavari, M.; Phelps, M. E.; Herschman, H. R.
A mutant herpes simplex virus type 1 thymidine kinase reporter gene
shows improved sensitivity for imaging reporter gene expression with
positron emission tomography. Proc. Natl. Acad. Sci. U.S.A. 2000,
97, 2785–2790.
(16) Zhang, M. R.; Tsuchiyama, A.; Haradahira, T.; Yoshida, Y.; Furutsuka,
K.; Suzuki, K. Development of an automated system for synthesizing
18F-labeled compounds using [18F]fluoroethyl bromide as a synthetic
precursor. Appl. Radiat. Isot. 2002, 57, 335–342.
(17) Larsen, P.; Ulin, J.; Dahlstrom, K.; Jensen, M. Synthesis of
[
11C]iodomethane by iodination of [11C]methane. Appl. Radiat. Isot.
(3) Tjuvajev, J. G.; Doubrovin, M.; Akhurst, T.; Cai, S. D.; Balatoni, J.;
Alauddin, M. M.; Finn, R.; Bornmann, W.; Thaler, H.; Conti, P. S.;
Blasberg, R. G. Comparison of radiolabeled nucleoside probes (FIAU,
FHBG, and FHPG) for PET imaging of HSV1-tk gene expression.
J. Nucl. Med. 2002, 43, 1072–1083.
(4) Alauddin, M. M.; Shahinian, A.; Park, R.; Tohme, M.; Fissekis, J. D.;
Conti, P. S. Synthesis and evaluation of 2′-deoxy-2′-F-18-fluoro-5-
fluoro-1-beta-D-arabinofuranosyluracil as a potential PET imaging
agent for suicide gene expression. J. Nucl. Med. 2004, 45, 2063–2069.
(5) Yaghoubi, S. S.; Couto, M. A.; Chen, C. C.; Polavaram, L.; Cui, G. G.;
Sen, L. Y.; Gambhir, S. S. Preclinical safety evaluation of F-18-FHBG:
a PET reporter probe for imaging herpes simplex virus type 1
thymidine kinase (HSV1-tk) or mutant HSV1-sr39tk’s expression.
J. Nucl. Med. 2006, 47, 706–715.
(6) Herschman, H. R. PET reporter genes for noninvasive imaging of gene
therapy, cell tracking and transgenic analysis. Crit. ReV. Oncol.
Hematol. 2004, 51, 191–204.
(7) Serganova, I.; Blasberg, R. Reporter gene imaging: potential impact
on therapy. Nucl. Med. Biol. 2005, 32, 763–780.
(8) Wiebe, L. I.; Knaus, E. E. Enzyme-targeted, nucleoside-based radio-
pharmaceuticals for scintigraphic monitoring of gene transfer and
expression. Curr. Pharm. Des. 2001, 7, 1893–1906.
(9) McGuigan, C.; Yarnold, C. J.; Jones, G.; Velazquez, S.; Barucki, H.;
Brancale, A.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Potent
and selective inhibition of varicella-zoster virus (VZV) by nucleoside
analogues with an unusual bicyclic base. J. Med. Chem. 1999, 42,
4479–4484.
(10) McGuigan, C.; Barucki, H.; Blewett, S.; Carangio, A.; Erichsen, J. T.;
Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Highly potent
and selective inhibition of varicella-zoster virus by bicyclic furopy-
rimidine nucleosides bearing an aryl side chain. J. Med. Chem. 2000,
43, 4993–4997.
(11) Chitneni, S. K.; Deroose, C. M.; Balzarini, J.; Gijsbers, R.; Celen,
S. J. L.; de Groot, T. J.; Debyser, Z.; Mortelmans, L.; Verbruggen,
A. M.; Bormans, G. M. Synthesis and preliminary evaluation of 18F
or 11C labeled bicyclic nucleoside analogues as potential probes for
imaging varicella-zoster virus thymidine kinase gene expression using
positron emission tomography. J. Med. Chem. 2007, 50, 1041–1049.
(12) Wilson, A. A.; Dasilva, J. N.; Houle, S. Synthesis of two radioflu-
orinated cocaine analogues using distilled 2-[18F]fluoroethyl bromide.
Appl. Radiat. Isot. 1995, 46, 765–770.
(13) Luoni, G.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.;
Balzarini, J. Bicyclic nucleoside inhibitors of varicella-zoster virus:
the effect of branching in the p-alkylphenyl side chain. Bioorg. Med.
Chem. Lett. 2005, 15, 3791–3796.
(14) Carpita, A.; Mannocci, L.; Rossi, R. Silver(I)-catalysed protiodesily-
lation of 1-(trimethylsilyl)-1-alkynes. Eur. J. Org. Chem. 2005, 1859–
1864.
1997, 48, 153–157.
(18) Hansch, C.; Steward, A. R.; Anderson, S. M.; Bentley, D. The parabolic
dependence of drug action upon lipophilic character as revealed by a
study of hypnotics. J. Med. Chem. 1968, 11, 1–11.
(19) Glave, W. R.; Hansch, C. Relationship between lipophilic character
and anesthetic activity. J. Pharm. Sci. 1972, 61, 589–591.
(20) Dischino, D. D.; Welch, M. J.; Kilbourn, M. R.; Raichle, M. E.
Relationship between lipophilicity and brain extraction of C-11-labeled
radiopharmaceuticals. J. Nucl. Med. 1983, 24, 1030–1038.
(21) Levin, V. A. Relationship of octanol/water partition coefficient and
molecular weight to rat brain capillary permeability. J. Med. Chem.
1980, 23, 682–684.
(22) Vanbilloen, H. P.; Kieffer, D. M.; Cleynhens, B. J.; Bormans, G. M.;
Mortelmans, L.; Verbruggen, A. M. Evaluation of 99mTc-labeled
tropanes with alkyl substituents on the 3ꢀ-phenyl ring as potential
dopamine transporter tracers. Nucl. Med. Biol. 2006, 33, 413–418.
(23) Elsinga, P. H.; Hendrikse, N. H.; Bart, J.; van Waarde, A.; Vaalburg,
W. Positron emission tomography studies on binding of central nervous
system drugs and P-glycoprotein function in the rodent brain. Mol.
Imaging Biol. 2005, 7, 37–44.
(24) Chitneni, S. K.; Balzarini, J.; Celen, S.; Dyubankova, N.; Verbruggen,
A. M.; Bormans, G. M. Relation between structure and brain uptake
of carbon-11 labeled acyclic and furo[2,3-d]pyrimidine-derivatives of
bicyclic nucleoside analogues (BCNAs). Unpublished data.
(25) Kida, T.; Noguchi, J.; Zhang, M. R.; Suhara, T.; Suzuki, K. Metabolite
analysis of [11C]Ro15-4513 in mice, rats, monkeys and humans. Nucl.
Med. Biol. 2003, 30, 779–784.
(26) Balzarini, J.; Sienaert, R.; Liekens, S.; Van Kuilenburg, A.; Carangio,
A.; Esnouf, R.; De Clercq, E.; McGuigan, C. Lack of susceptibility
of bicyclic nucleoside analogs, highly potent inhibitors of varicella-
zoster virus, to the catabolic action of thymidine phosphorylase and
dihydropyrimidine dehydrogenase. Mol. Pharmacol. 2002, 61, 1140–
1145.
(27) Alauddin, M. M.; Shahinian, A.; Gordon, E. M.; Bading, J. R.; Conti,
P. S. Preclinical evaluation of the penciclovir analog 9-(4-[F-18] fluoro-
3-hydroxymethylbutyl)guanine for in vivo measurement of suicide
gene expression with PET. J. Nucl. Med. 2001, 42, 1682–1690.
(28) Geraerts, M.; Michiels, M.; Baekelandt, V.; Debyser, Z.; Gijsbers, R.
Upscaling of lentiviral vector production by tangential flow filtration.
J. Gene Med. 2005, 7, 1299–1310.
(29) Sienaert, R.; Naesens, L.; Brancale, A.; De Clercq, E.; McGuigan,
C.; Balzarini, J. Specific recognition of the bicyclic pyrimidine
nucleoside analogs, a new class of highly potent and selective inhibitors
of varicella-zoster virus (VZV), by the VZV-encoded thymidine kinase.
Mol. Pharmacol. 2002, 61, 249–254.
(30) Bird, L. E.; Ren, J.; Wright, A.; Leslie, K. D.; Degreve, B.; Balzarini,
J.; Stammers, D. K. Crystal structure of varicella-zoster virus thymidine
kinase. J. Biol. Chem. 2003, 278, 24680–24687.
(15) Yoshida, Y.; Sakakura, Y.; Aso, N.; Okada, S.; Tanabe, Y. Practical
and efficient methods for sulfonylation of alcohols using Ts(Ms)Cl/
Et3N and catalytic Me3N·HCl as combined base: promising alternative
to traditional pyridine. Tetrahedron 1999, 55, 2183–2192.
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