Y. Qiao et al. / Bioorg. Med. Chem. Lett. 19 (2009) 4873–4877
4877
the cyclotron operator team of the PET Centre of Xuan Wu hospital,
for providing [18F]fluoride activity and technical assistance.
References and notes
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Figure 3. Comparison of tumor-to-brain uptake ratios of [18F]1 and [18F]2 with
those of [18F]FDG and
tumor.
L
-[18F]FET together in the same animal model bearing S 180
5. (a) Moon, B. S.; Lee, T. S.; Lee, K. C.; An, G. I.; Cheon, G. J.; Lim, S. M.; Choi, C. W.;
Chic, D. Y.; Chuna, K. S. Bioorg. Med. Chem. Lett. 2007, 17, 200; (b) Martarello, L.;
McConathy, J.; Camp, V. M.; Malveaux, E. J.; Simpson, N. E.; Simpson, C. P.;
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Wester, H. J.; Schwaiger, M.; Senekowitsch-Schmidtke, R. J. Nucl. Med. 1999, 40,
1367; (c) Weber, W. A.; Wester, H. J.; Grosu, A. L.; Herz, M.; Dzewas, B.;
Feldmann, H. J., et al Eur. J. Nucl. Med. 2000, 27, 542.
and T/M (tumor-to-muscle = 2.62) ratios appeared at the same time
point (30 min post-injection) and consequently acid [18F]1 can be
better than ester [18F]2 as the imaging agent. On one hand, [18F]1
and [18F]2 showed obvious advantages of biological properties in
biodistribution data when compared with [18F]FDG and -[18F]FET.
L
7. Wienhard, K.; Herholz, K.; Coenen, H. H.; Rudolf, J.; Kling, P.; Stocklin, G.; Heiss,
Besides, the two F-18 labeled fluoroarylvaline derivatives can be
easily and efficiently labeled with fluorine-18.Therefore, we expect
that the two tracers, especially the acid compound [18F]2, can have
potential application in tumor detection, particularly for brain tu-
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10. Structure analysis data. F-19 substituted ester 1: 1H NMR (500 MHz, CDCl3): d
8.28 (m, 1H, Ar-H), 8.15 (dd, J = 8.6, 1.8 Hz, 1H, Ar-H), 8.06 (dd, J = 11.0, 1.8 Hz,
1H, Ar-H), 7.22–7.19 (m, 1H, NH), 4.82–4.80 (m, 1H, CHCH(CH3)2), 3.82 (s, 1H,
OCH3), 2.35–2.33 (m, 1H, CH(CH3)2), 1.06–1.02 (s, 6H, CH(CH3)2); 13C NMR
(125 MHz, CDCl3): d 171.87, 161.15, 159.90 (d, 1C, JCF = 250.5 Hz), 150.31,
133.42, 126.58, 119.57, 112.26 (d, 1C, JCF = 30.0 Hz), 57.98, 52.45, 31.46, 19.01,
17.86; 19F NMR (400 MHz, CDCl3): d À109.37, À109.40, À109.42, À109.45; MS
(EI) m/z: 298.27, found: 299.13; Anal. Calcd for C13H15FN2O5: C, 52.35; H, 5.07;
N, 9.39. Found: C, 52.73; H, 4.79; N, 9.68. F-19 substituted acid 2: 1H NMR
(500 MHz, CDCl3): d 8.31 (m, 1H, Ar-H), 8.17 (dd, J = 8.5, 2.0 Hz, 1H, Ar-H), 8.07
(dd, J = 11.5, 2.0 Hz, 1H, Ar-H), 7.22–7.18 (m, 1H, NH), 4.87–4.84 (m, 1H,
CHCH(CH3)2), 2.46–2.39 (m, 1H, CH(CH3)2), 1.11–1.07 (m, 6H, CH(CH3)2); 13C
NMR (100 MHz, CDCl3): d 172.91, 163.42, 158.95 (d, 1C, JCF = 251.1 Hz), 149.49
(d, 1C, JCF = 9.0 Hz), 131.52 (d, 1C, JCF = 3.6 Hz), 131.07 (d, 1C, JCF = 16.6 Hz),
119.99 (d, 1C, JCF = 3.3 Hz), 112.38 (d, 1C, JCF = 27.5 Hz), 58.44, 30.18, 19.61,
18.49; 19F NMR (400 MHz, CDCl3): d À109.39, À109.42, À109.44, À109.47; MS
(EI) m/z: 284.24, found: 284.19; Anal. Calcd for C12H13FN2O: C, 50.71; H, 4.61;
N, 9.86. Found: C, 51.05; H, 4.34; N, 10.13.
mor imaging. In conclusion,
[
18F]FNBMBA ([18F]1) and
[
18F]MFNBMB ([18F]2) designed and synthesized in this study, par-
ticularly the acidic F-18 labeled product ([18F]2), demonstrate po-
tential value as more useful PET radiotracers for tumor imaging
than [18F]FDG and -[18F]FET. As an elementary study of [18F]1 and
L
[
18F]2 to be the potential PET radiotracers, however, our research
on such [18F]fluoroarylvaline derivatives still needs more investiga-
tion and further evaluation of them with PET to be better.
Acknowledgments
We acknowledged with thanks for financial supports from the
National Natural Science foundation of China (No. 20371009 and
20671014) and Beijing Key Subject Program. We also wish to thank