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The biological study of 18F-Fluoroacetate as a PET probe
References
1.Pirotte B, Goldman S, Massager N, Philippe D, Wikler D,
Vandesteene A, Salmon I, Brotchi J, Levivier M.
Volumetric analysis of 18F-FDG PET in glioblastoma
multiforme: prognostic information and possible role in
definition of target volumes in radiation dose
escalation. J Nucl Med 2002; 43:1667-1673
2.Mathews, Van Holde, Ahern ‘BIOCHEMISTRY’ third edition;
Addison Wesley Longman published. ISBN 0-8053-3066-6.
3.Fricke E, Machtens S, Hofmann M, van den Hoff J, Bergh
S,Brunkhorst T, Meyer GJ, Karstens JH, Knapp WH, Boerner
AR. Positron emission tomography with 11C-acetate and 18F-
FDG in prostate cancer patients; Eur J Nucl Med Mol
Imaging 2003; 30:607-611
4.Ho CL, Yu SC, Yeung DW, 11C-Acetate PET imaging in
hepatocellular carcinoma and other liver masses. J Nucl
Med 2003; 44:213–221
5.Liu RS, Chang CP, Chu LS, Chu YK, Wu LC, Chou KL, Chang
CW, and Yeh SH. [C-11]Acetate positron emission
tomgraphy in the detection of brain tumors: comparison
with [F-18]Fluorodeoxyglucose. J Nucl Med 1997;38:240
6.Porenta G, Cherry S, Czernin J, Brunken R, Kuhle W,
Hashimoto T, Schelbert HR. Non-invasive determination of
myocardial blood flow, oxygen consumption and efficiency
in normal humans by carbon-11 acetate positron emission
tomography imaging. European J Nucl Med 1999; 26(11):1465-
74
7.Van den Hoff J, Burchert W, Wolpers HG., Meyer GJ and
Hundeshagen H. A kinetic model for cardiac PET with 1-11C-
acetate. J Nucl Med 1996; 37(3):521-9
8.Rubin PJ, Lee DS, Davila-Roman VG., Geltman EM,
Schechtman KB, Bergmann SR and Gropler RJ. Superiority of
C-11 acetate compared with F-18 fluorodeoxyglucose in
predicting myocardial functional recovery by positron
emission tomography in patients with acute myocardial
infarction. Am J Cardiology 1996;78(11):1230-5
9.Yeh SH, Liu RS, Wu LC, Yen SH, Chang CW and Chen KY. 11C-
Acetate clearance in nasopharyngeal carcinoma. Nucl Med
Comm 1999; 20(2):131-4
10.Pouteau E, Dumon H, Biourge V, Krempf M and Nguyen P. A
kinetic study of acetate metabolism in dogs using 1-13C-
acetate. J Nutrition 1998; 128(12 Suppl):2651S-2653S
11.Yoshimoto M, Waki A, Yonekura Y, Sadato N, Murata T,
Omata N, Takahashi, Michael J. Welch and Fujibayashi Y.
Characterization of acetate metabolism in tumor cells in
relation to cell proliferation: Acetate metabolism in
tumor cells. Nucl Med Biol 2001; 28:117–122
12.Nikolay V. Goncharov, Richard O. Jenkins and Andrey S.
Radilov. Toxicology of fluoroacetate: a review, with
possible directions for therapy research. Journal of
Applied Toxicity 2006; 26:148–161
13.R.A. Peter. Lethal synthesis. Proc. R. Soc. (Lond.)
1952; 139:143–175
14.R. A. Peters and T. H. Wilson. A further study of the
inhibition of aconitase by inhibitor fraction’ isolated
from tissues poisoned with fluoroacetate. Biochimica Et
Biophysica Acta 1952; 9:310–315
15.K. Hamacher, H.H Coenen. Efficient routine production of
the 18F-labeled amino acid O-(2-[18F]fluoroethyl)-L-
tyrosine. Applied Rad and iso 2002;57:853–856
16.Sykes, T. R., T. J. Ruth, M.J. Adam. Synthesis and
murine tissue uptake of sodium [18F]fluoroacetate. Int J
Rad Appl Instrum B 1986;13:497–500
17.Tjuvajev JG, Stockhammer G, Desai, et al. Imaging the
expression of transfected genes in vivo. Cancer Res
1995; 55:6126–6132
18.Sasajima T, Miyagawa T, Oku T, et al. Proliferation-
dependent changes in amino acid transport and glucose
metabolism in glioma cell lines. Eur J Nucl Med Mol
Imaging 2004;31:1244–1256
19.Chang, C. H., H. E. Wang, S.Y. Wu, K.H. Fan, T.H. Tsai,
T.W. Lee, S.R. Chang, R.S. Liu, C.F. Chen, C.H. Chen,
Y.K. Fu. Comparative evaluation of FET and FDG for
differentiating lung carcinoma from inflammation in
mice. Anticancer Res 2006; 26(2):917–925
20.Yamada, S., K. Kubota, R. Kubota, T. Ido, N. Tamahashi.
high accumulation of fluorine-18-fluorodeoxyglucose in
turpentine-induced inflammatory tissue. J Nucl Med
1995;36:1301–1306
21.Clarke DD. Fluoroacetate and fluorocitrate: mechanism of
action. Neurochem. Res 1991; 16:1055–1058
22.Lauble H, Kennedy M, Emptage M, Stout C. The reaction of
fluorocitrate with aconitase and the crystal structure
of the enzymeinhibitor complex. Proc. Natl Acad 1996;
93:13699–13703
23.Y.F. Chen. Characterizing Metabolic Fate of 级C-14纳
acetate in F98 glioma cells: The Comparison of 1-级14C纳
acetate and 2-14C-acetate. Institute of Nuclear
Science, National Yang-Ming University Master Thesis 2004
24.Ponde DE, Oyama N, Dence CS, Welch MJ. [18F]
fluoroacetate, an analog of C-11 acetate for tumor
imaging. J Nucl Med. 2003; 44:295.
25.Oyama N, Ponde DE, Dence CS, Yokoyama O, Siegel BA,
Welch MJ. J Nucl Med. 2004; 45:331
26.Matthies A. Ezziddin S, Ulrich EM, Palmedo H, Biersack
HJ, Bender H, Stefan G. Imaging of prostate cancer
metastases with 18F-fluoroacetate using PET/CT. Eur J
Nucl Med Mol Imaging. 2004; 31:797.
The radiochemical synthesis of radiolabeled fluorinated nucleoside analogues and study as gene imaging probes
References
1.Greco O, Dachs GU. Gene directed enzyme/prodrug therapy
of cancer: historical appraisal and future prospective.
J. cell Physiol. 2001; 187:22–36.
2.Anders Björklund and Olle Lindvall. Parkinson disease
gene therapy moves toward the clinic. Nat Med. 2000; 6
(11): 1207–1208.
3.Liya Wang and Staffan Eriksson. Cloning and
characterization of full-length mouse thymidine kinase 2:
the N-terminal sequence directs import of the precursor
protein into mitochondria. Biochem. J. 2000; 351:469–476.
4.S. S. Gambhir, J. R. Barrio, H. R. Herschman and M. E.
Phelps. Assays for noninvasive imaging of reporter gene
expression. Nucl. Med. Biol. 1999; 26:481–490.
5.Moolten FL. Tumor chemosensitivity conferred by inserted
herpes thymidine kinase genes: paradigm for a prospective
cancer control strategy. Cancer Res 1986; 46:5276–5281.
6.Cheng YC, Grill SP, Dutschman GE, Nakayma K, Bastow KF.
Metabolism of 9-(1,3-dihydroxy-2-propeymethyl)guanine, a
new anti-herpes virus compound, in herpes simplex virus-
infected cells. J. Biol. Chem. 1983;258:12460–12464.
7.Freeman SM, Abboud CN, Whartenby KA, Packman CH, Koeplin
DS, Moolten FL, Abraham GN. The "bystander effect": tumor
regression when a fraction of the tumor mass is
genetically modified. Cancer Res 1993; 53:5274–5283.
8.Culver KW, Ram Z, Wallbridge, Ishii H, Oldfield EH,
Blaese RM. In vivo gene transfer with retroviral vector-
producer cells for treatment of experimental brain
tumors. Science 1992;256: 1550–1552.
9.Freeman SM, Abboud CN, Whartenby KA, Packman CH, Koeplin
DS, Moolten FL, Abraham GN. The “bystander effect”:
tumor regression when a fraction of the tumor mass is
genetically modified. Cancer Res. 1993;:5274–5283.
10.Van Dillen IJ, Mulder NH, Vaalburg W, de Vries EFJ,
Hospers GAP. Influence of the bystander effent on HSV-
tk/GCV gene ttherapy. A review, Curr. Gene Ther.
2002;2:307–322.
11.Oldfield EH, Ram Z, Culver K, Blease RM, DeVroom HL,
Anderson WF. Clinical protocols: gene therapy for the
treatment of brain tumors using intratumoral
transduction with the thymidine kinase gene and
intravenous ganciclovir. Hum Gene Ther. 1993; 4:39–69.
12.Ram Z, Culver KW, Oshireo EM, et al. Therapy of
malignant brain tumors by intratumoral implantation of
retroviral vector producing cells. Nat Med. 1997;3:
1353–1361.
13.Alauddin MM, Conti PS. 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. Nucl. Med.
Biol. 1998; 25: 175–180.
14.Alauddin MM, Conti PS, Mazza SM, Hamzeh FM, Lever JR.
Synthesis of 9-[(3-[18F]-fluoro-1-hydroxy-2-propoxy)
methyl]guanine ([18F]-FHPG): A potential imaging agent
of viral infection and gene therapy using PET. Nucl.
Med. Biol. 1996; 23: 787–792.
15.Balatoni J, FinnR, Tjuvajev JG, Larson S, Blasberg RG.
Synthesis and quality assurance of radioiodinated 2’-
fluoro-2’-deoxy-1-β-D-arabinofuranosyl-5-iodo-uracil.
J. Labelled Cmp. Radiopharm. 1997:103.
16.Namavari M, BarrioJR, Tokyokuni T, Gambhir SS, Cherry
SR, Herschman HR, Phelps ME, Satyamurthy N. Synthesis of
8-[18F]fluoroguanine derivatives: in vivo probes for
imaging gene expression with positron emission
tomography. Nucl. Med. Biol. 2000; 2000: 157–162.
17.Tjuvajev JG, Avril N, Oku T, Sasajima T, Miyagawa T,
Joshi R, Safer M, Beattie B, DiResta G, Daghighian F,
Augensen F, Koutcher J, Zweit J, Humm J, Jarson SM, Finn
R, Blasberg R. Imaging herpes virus thymidine kinase
gene transfer and expression by positron emission
tomography. Cancer Res. 1998;58: 4333–4341.
18.Mian M. Alauddin, Antranik Shahinian, Erlinda M. Gordon,
James R. Bading, and Peter S. Conti. Preclinical
Evaluation of the Penciclovir Analog 9-(4-[18F]Fluoro-3-
Hydroxymethylbutyl)Guanine for In Vivo Measurement of
Suicide Gene Expression with PET. J Nucl Med. 2001;
42:1682–1690.
19.Jacobs A, Voges J, Reszka R, Lercher M, Gossmann A,
Kracht L, Kaestle C, Wagner R, Wienhard K, Heiss WD.
Positron-emission tomography of vector-mediated gene
expression in gene therapy for gliomas. Lancet 2001;
358:727–729.
20.J. C. Tseng, P. B. Zanzonico, B. Levin, R. Finn, S. M.
Larson, and D. Meruelo. Tumor-specific in vivo
transfection with HSV-1 thymidine kinase gene using a
sindbis viral vector as a basis for prodrug ganciclovir
activation and PET. J Nucl Med. 2006; 47:1136–1143
21.Aren van Waarde, David C.P. Cobben, Albert J.H.
Suurmeijer, Bram Mass, Willem Vaalburg, Erik F.J. de
Vries, Peter L. Jager, Harald J. Hoekstra, Philip H.
Elsinga. Selectivity of 18F-FLT and 18F-FDG for
differentiating tumor from inflammation in a rodent
model. J Nucl Med. 2004; 45:695–700.
22.Janet F. Eary, David A. Mankoff, Alexander M. Spence,
Mitchel S. Berger, Adam Olshen, Jeanne M. Link, Finbarr
O’Sullivan, and Kenneth A. Krohn. 2-[C-11]Thymidine
Imaging of Malignant Brain Tumors. Cancer Res. 1999;
59:615–621.
23.Anthony F. Shields, David A. Mankoff, Jeanne M. Link,
Michael M. Graham, Janet F. Eary, Susie M. Kozawa, Minna
Zheng, Barbara Lewellen, Thomas K. Lewellen, John R.
Grierson, and Kenneth A. Krohn. Carbon-11-Thymidine and
FDG to Measure Therapy Response. J Nucl Med.
1998;39:1757–1762.
24.Francis DL, Visvikis D, Costa DC, Arulampalam TH,
Townsend C, Luthra SK, et al. Potential impact of [18F]3-
deoxy-3-fluorothymidine versus [18F]fluoro-2-deoxy-D-
glucose in positron emission tomography for colorectal
cancer. Eur J Nucl Med Mol Imaging 2003; 30:988–994.
25.Seitz U, Wagner M, Neumaier B, Wawra E, Glatting G,
Leder G, et al. Evaluation of pyrimidine metabolising
enzymes and in vitro uptake of 3-[18F]fluoro-3-
deoxythymidine ([18F]FLT) in pancreatic cancer cell
lines. Eur J Nucl Med Mol Imaging 2002;29: 1174–81.
26.Vesselle H, Grierson J, Muzi M, Pugsley JM, Schmidt RA,
Rabinowitz P, et al. In vivo validation of 3deoxy-3-[18F]
fluorothymidine ([18F]FLT) as a proliferation imaging
tracer in humans: correlation of [18F]FLT uptake by
positron emission tomography with Ki-67
immunohistochemistry and flow cytometry in human lung
tumors. Clin Cancer Res. 2002;8:3315–3323.
27.Buck AK, Schirrmeister H, Hetzel M, Von Der Heide M,
Halter G, Glatting G, et al. 3-deoxy-3-[18F]
fluorothymidine-positron emission tomography for
noninvasive assessment of proliferation in pulmonary
nodules. Cancer Res 2002;62:3331–3334.
28.Dittmann H, Dohmen BM, Kehlbach R, Bartusek G, Pritzkow
M, Sarbia M, et al. Early changes in [18F]FLT uptake
after chemotherapy: an experimental study. Eur J Nucl
Med Mol Imaging 2002; 29:1462–1469.
29.Vijayalakshmi D, Belt JA. Sodium-dependent nucleoside
transport in mouse intestinal epithelial cells. Two
transport systems with differing substrate
specificities. J Biol Chem 1988;263:19419–19423.
30.Jeffrey L. Schwartz, Yasuko Tamura, Robert Jordan, John
R. Grierson, and Kenneth A. Krohn. Monitoring tumor cell
proliferation by targeting DNA synthetic processes with
thymidine and thymidine analogs. J Nucl Med
2003;44:2027–2032.
31.Lewis W, Levine ES, Griniuviene B, et al. Fialuridine
and its metabolites inhibit DNA polymerase gamma at
sites of multiple adjacent analog incorporation,
decrease mtDNA abundance, and cause mitochondrial
structural defects in cultured hepatoblasts. Proc Natl
Acad Sci USA. 1996;93:3592–3597.
32.Lu L, Samuelsson L, Bergstrom M, Sato K, Fasth KJ,
Langstrom B. Rat studies comparing 11C-FMAU, 18F-FLT,
and 76Br-BFU as proliferation markers. J Nucl Med.2002;
43:1688 –1698.
33.Wang H, Oliver P, Nan L, et al. Radiolabeled 2’-
fluorodeoxyuracil-β-D-arabinofuranoside (FAU) and 2’-
fluoro-5-methyldeoxyuracil-β-D-arabinofuranoside (FMAU)
as tumor-imaging agents in mice. Cancer Chemother
Pharmacol. 2002; 49:419–424.
34.Mangner T, Klecker R, Anderson L, Shields A. Synthesis
of 2’-[18F]fluoro-2’-deoxy-β-D-arabinofuranosyl
nucleotides, [18F]FAU, [18F]FMAU, [18F]FBAU and [18F]
FIAU, as potential PET agents for imaging cellular
proliferation. Nucl Med Biol. 2003:215–224.
35.Conti P, Alauddin M, Fissekis J, Schmall B, Watanabe K.
Synthesis of 2’-fluoro-5-[11C]-methyl-1-beta-D-
arabinofuranosyluracil (11C-FMAU): a potential
nucleoside analog for in vivo study of cellular
proliferation with PET. Nucl Med Biol. 1995;22:783–789.
36.Sun HH, Thomas J, Jerry M, Muzik O, Douglas K and
Anthony F. Imaging DNA synthesis in vivo with 18F-FMAU
and PET. J Nucl Med 2005;46:292–296.
37.Haihao Sun, Andrew Sloan, Thomas J. Mangner, Ulka
Vaishampayan, Otto Muzik, Jerry M. Collins, Kirk
Douglas, Anthony F. Shields. Imaging DNA synthesis with
[18F]FMAU and positron emission tomography in patients
with cancer. Eur J Nucl Med Mol Imaging 2005;32:15–22.
38.Mian M. Alauddin, Peter S. Conti and John D. Fissekis.
Synthesis of [18F]-labeled-2’-deoxy-2’-fluoro-5-methyl-
1-β-D-arabinofuranosyluracil ([18F]-FMAU). J Label
Compd Radiopharm 2002;45:583–590.
39.K. Hamacher, H.H Coenen. Efficient routine production of
the 18F-labeled amino acid O-(2-[18F]fluoroethyl)-L-
tyrosine. Applied Rad and iso 2002;57:853–856.
40.Watanabe KA, Su T-L, Reichman U, Greenberg N, Lopez C,
Fox JJ. Nucleosides 129. Synthesis of antiviral
nucleosides: 5-Alkenyl 1-(2-deoxy-2-fluoro-β-D-
arabinofuranosyl)uracils. J Med Chem 1994; 27:91–4.
41.Tjuvajev JG, Stockhammer G, Desai, et al. Imaging the
expression of transfected genes in vivo. Cancer Res
1995;55:6126–6132
42.Sasajima T, Miyagawa T, Oku T, et al. Proliferation-
dependent changes in amino acid transport and glucose
metabolism in glioma cell lines. Eur J Nucl Med Mol
Imaging 2004;31:1244–1256
43.Kyoichi A. Watanabe, Uri Reichman, Kosaku Hirota, Carlos
Lopez and Jack J. Fox. Nucleoside 110. Synthesis and
antiherpes virus activity of some 2’-fluoro-2’-
deoxyarabinofuranosylpyrimidine nucleosides. J Med
Chem 1979;22:21-24
44.Martin J, Mansuri M, Ghazzouli I, Chen M, Howell H,
Brodfuehrer P and Benigni D. J Med Chem 1987;30:867-871
45.Chou T, Kong X, Scheck A, Price R, Vidal P, Fanucchi M,
Watanabe K and Fox J. Antiviral Res 1988;10:153-166
46.Fox J, Chou T, Kong X, Fanucchi M, Cheng Y, Takahashi K
and Watanabe K. Antimicrob. Agents Chemother
1987;31:1355-1358
47.Watanabe K, Pankiewicz K, Nawrot B, Gadler H and Price
R. Nucleosides. 146. 1-Methyl-5-(2’-deoxy-2’-fluoro-
beta-D-arabinofuranosyl)uracil, the C-nucleoside
isostere of the potent antiviral agent 1-(2’-deoxy-2’-
fluoro-beta-D-arabinofuranosyl)thymine (FMAU). Studies
directed toward the synthesis of 2'-deoxy-2'-substituted
arabino nucleosides. J Med Chem 1987;30:2314-2316
48.Mian M. Alauddin, Antranic Shahinian, Ryan Park, Micheal
Tohme, John D. Fissekis and Peter S. Conti. In vivo
evaluation of 2’-deoxy-2’-[18F]fluoro-5-iodo-1-刍-D-
arabinofuranosyluracil ([18F]FIAU) and 2’-deoxy-2’-
[18F]fluoro-5-ethyl-1-b-D-arabinofuranosyluracil ([18F]
FEAU) as markers for suicide gene expression. Eur J Nucl
Med Mol Imaging 2007;30:822-827
49.Klecker RW, Kakti AG and Collins JM. Toxicity,
metabolism, DNA incorporation with lack of repair, and
lactate production for 1-(2’-fluoro-2’-deoxy-刍-D-
arabinofuranosyl)-5-iodouracil in U937 and MOLT-4 cells.
Mol Pharmacol 1994;46:1204-1209
50.Juri Gelovani Tjuvajev, Mikhail Doubrovin, Timothy
Akhurst, Shangde Cai, Julius Balatoni, Mian M. Alauddin,
Ronald Finn, William Bornmann, Howard Thaler, Peter S.
Conti and Ronald G. Blasberg. Comparison of radiolabeled
nucleoside probes (FIAU, FHBG and FHPG) for PET imaging
of HSV1-tk gene expression J Nucl Med 2002;43:1072–1083.
51.James R. Bading, Antranik H. Shahinian, Amy Vail, Pravin
Bathija, G.W. Koszalka, Robert T. Koda, Mian M.
Alauddin, John D. Fissekis, Peter S. Conti.
Pharmacokinetics of the thymidine analog 2’-fluoro-5-
methyl-1-b-D-arabinofuranosyluracil (FMAU) in tumor-
bearing rats. Nucl Med Biol 2004;31:407-418
52.Haihao Sun, Andrew Sloan, Thomas J. Mangner1, Ulka
Vaishampayan, Otto Muzik, Jerry M. Collins, Kirk
Douglas, Anthony F. Shields. Imaging DNA synthesis with
[18F]FMAU and positron emission tomography in patients
with cancer. Eur J Nucl Med Mol Imaging 2005;32:15-22
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