Synthesis and evaluation of 18F labeled alanine derivatives as potential tumor imaging agents

Nuclear Medicine and Biology

Volumn 39, Issue 7, 2012, Pages 933-943

  Wang, Limin ^a   Zha, Zhihao ^a   Qu, Wenchao ^a   Qiao, Hongwen ^a   Lieberman, Brian P ^a   Plössl, Karl ^a   Kung, Hank F ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

18F; Alanine derivatives; Alanine serine cysteine preferring amino acid transporter; Amino acids; ASC; PET; Tumor imaging

Indexed keywords

3 (1 FLUOROMETHYL) DEXTRO ALANINE F 18; 3 (1 FLUOROMETHYL) LEVO ALANINE F 18; 3 (2 FLUOROETHYL) LEVO ALANINE F 18; ALANINE; ALANINE DERIVATIVE; AMINO ACID TRANSPORTER; CYSTEINE; FLUORODEOXYGLUCOSE F 18; RADIOPHARMACEUTICAL AGENT; SERINE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; DIAGNOSTIC AGENT; DRUG DERIVATIVE; FLUORINE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BREAST ADENOCARCINOMA; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG PROTEIN BINDING; DRUG PURITY; DRUG SCREENING; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; ENANTIOMER; GLIOMA; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; KIDNEY; LIVER; MALE; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PROSTATE CANCER; RADIOCHEMISTRY; RAT; STRUCTURE ANALYSIS; TRANSGENIC MOUSE; TUMOR GROWTH; ANIMAL; EXPERIMENTAL NEOPLASM; FEMALE; HUMAN; METHODOLOGY; SCINTISCANNING; STEREOISOMERISM; SYNTHESIS; TRANSPORT AT THE CELLULAR LEVEL; TUMOR CELL LINE;

ALANINE; ANIMALS; BIOLOGICAL TRANSPORT; CELL LINE, TUMOR; CHEMISTRY TECHNIQUES, SYNTHETIC; FEMALE; FLUORINE RADIOISOTOPES; HUMANS; ISOTOPE LABELING; MALE; MAMMARY NEOPLASMS, EXPERIMENTAL; MICE; POSITRON-EMISSION TOMOGRAPHY; RATS; STEREOISOMERISM;

EID: 84866028265     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2012.03.007     Document Type: Article

References (38)

1. McConathy J., Yu W., Jarkas N., Seo W., Schuster D.M., Goodman M.M. Radiohalogenated nonnatural amino acids as PET and SPECT tumor imaging agents. Med Res Rev 2011, [published, online July 26]. 10.1002/med.20250.
2. McConathy J., Goodman M.M. Non-natural amino acids for tumor imaging using positron emission tomography and single photon emission computed tomography. Cancer Metastasis Rev 2008, 27:555-573.
3. Plathow C., Weber W.A. Tumor cell metabolism imaging. J Nucl Med 2008, 49(Suppl. 2):43S-63S.
4. Jager P.L., Vaalburg W., Pruim J., de Vries E.G., Langen K.J., Piers D.A. Radiolabeled amino acids: basic aspects and clinical applications in oncology. J Nucl Med 2001, 42:432-445.
5. Okudaira H., Shikano N., Nishii R., Miyagi T., Yoshimoto M., Kobayashi M., et al. Putative transport mechanism and intracellular fate of trans-1-amino-3-18F-fluorocyclobutanecarboxylic acid in human prostate cancer. J Nucl Med 2011, 52:822-829.
6. Asano Y., Inoue Y., Ikeda Y., Kikuchi K., Hara T., Taguchi C., et al. Phase I clinical study of NMK36: a new PET tracer with the synthetic amino acid analogue anti-[(18)F]FACBC. Ann Nucl Med 2011, 25:414-418.
7. Wang L., Qu W., Lieberman B., Ploessl K., Kung H. Synthesis and in vitro evaluation of 18F labeled tyrosine derivatives as potential positron emission tomography (PET) imaging agents. Bioorg Med Chem Lett 2010, 20:3482-3485.
8. Popperl G., Kreth F.W., Herms J., Koch W., Mehrkens J.H., Gildehaus F.J., et al. Analysis of 18F-FET PET for grading of recurrent gliomas: is evaluation of uptake kinetics superior to standard methods?. J Nucl Med 2006, 47:393-403.
9. Lee T.S., Ahn S.H., Moon B.S., Chun K.S., Kang J.H., Cheon G.J., et al. Comparison of 18F-FDG, 18F-FET and 18F-FLT for differentiation between tumor and inflammation in rats. Nucl Med Biol 2009, 36:681-686.
10. Langen K.J., Hamacher K., Weckesser M., Floeth F., Stoffels G., Bauer D., et al. O-(2-[18F]fluoroethyl)-L-tyrosine: uptake mechanisms and clinical applications. Nucl Med Biol 2006, 33:287-294.
11. Ganapathy V., Thangaraju M., Prasad P. Nutrient transporters in cancer: relevance to Warburg hypothesis and beyond. Pharmacol Ther 2009, 121:29-40.
12. Hyde R., Taylor P.M., Hundal H.S. Amino acid transporters: roles in amino acid sensing and signalling in animal cells. Biochem J 2003, 373:1-18.
13. Fuchs B.C., Bode B.P. Amino acid transporters ASCT2 and LAT1 in cancer: partners in crime?. Semin Cancer Biol 2005, 15:254-266.
14. Fan X., Ross D.D., Arakawa H., Ganapathy V., Tamai I., Nakanishi T. Impact of system L amino acid transporter 1 (LAT1) on proliferation of human ovarian cancer cells: a possible target for combination therapy with anti-proliferative aminopeptidase inhibitors. Biochem Pharmacol 2010, 80:811-818.
15. Sakata T., Ferdous G., Tsuruta T., Satoh T., Baba S., Muto T., et al. L-type amino-acid transporter 1 as a novel biomarker for high-grade malignancy in prostate cancer. Pathol Int 2009, 59:7-18.
16. Singhal T., Narayanan T.K., Jain V., Mukherjee J., Mantil J. 11C-L-methionine positron emission tomography in the clinical management of cerebral gliomas. Mol Imaging Biol 2008, 10:1-18.
17. Langen K.J., Muhlensiepen H., Holschbach M., Hautzel H., Jansen P., Coenen H.H. Transport mechanisms of 3-[123I]iodo-a-methyl-L-tyrosine in a human glioma cell line: comparison with [3H-methyl]-L-methionine. J Nucl Med 2000, 41:1250-1255.
18. Fueger B.J., Czernin J., Cloughesy T., Silverman D.H., Geist C.L., Walter M.A., et al. Correlation of 6-18F-fluoro-L-dopa PET uptake with proliferation and tumor grade in newly diagnosed and recurrent gliomas. J Nucl Med 2010, 51:1532-1538.
19. Minn H., Kauhanen S., Seppanen M., Nuutila P. 18F-FDOPA: a multiple-target molecule. J Nucl Med 2009, 50:1915-1918.
20. Tolvanen T., Nagren K., Yu M., Sutinen E., Havu-Auren K., Jyrkkio S., et al. Human radiation dosimetry of [11C]MeAIB, a new tracer for imaging of system A amino acid transport. Eur J Nucl Med Mol Imaging 2006, 33:1178-1184.
21. Sutinen E., Jyrkkio S., Alanen K., Nagren K., Minn H. Uptake of [N-methyl-11C]alpha-methylaminoisobutyric acid in untreated head and neck cancer studied by PET. Eur J Nucl Med Mol Imaging 2003, 30:72-77.
22. Schmall B., Conti P.S., Alauddin M.M. Synthesis of [11C-methyl]-alpha-aminoisobutyric acid (AIB). Nucl Med Biol 1996, 23:263-266.
23. Schuster D.M., Savir-Baruch B., Nieh P.T., Master V.A., Halkar R.K., Rossi P.J., et al. Detection of recurrent prostate carcinoma with anti-1-amino-3-18F-fluorocyclobutane-1-carboxylic acid PET/CT and 111In-capromab pendetide SPECT/CT. Radiology 2011, 259:852-861.
24. Yu W., Williams L., Camp V., Olson J., Goodman M. Synthesis and biological evaluation of anti-1-amino-2-[18F]fluoro-cyclobutyl-1-carboxylic acid (anti-2-[18F]FACBC) in rat 9L gliosarcoma. Bioorg Med Chem Lett 2010, 20:2140-2143.
25. Oka S., Okudaira H., Yoshida Y., Schuster D.M., Goodman M.M., Shirakami Y. Transport mechanisms of trans-1-amino-3-fluoro[1-(14)C]cyclobutanecarboxylic acid in prostate cancer cells. Nucl Med Biol 2011, 39:109-119.
26. Fuchs B.C., Finger R.E., Onan M.C., Bode B.P. ASCT2 silencing regulates mammalian target-of-rapamycin growth and survival signaling in human hepatoma cells. Am J Physiol Cell Physiol 2007, 293:C55-C63.
27. Nakanishi T., Tamai I. Solute carrier transporters as targets for drug delivery and pharmacological intervention for chemotherapy. J Pharm Sci 2011, 100:3731-3750.
28. Lee B.H., Gerfen G.J., Miller M.J. Alternate syntheses of delta-N-hydroxy-L-ornithine derivatives and applications to the synthesis of rhodotorulic acid. J Org Chem 1984, 49:2418-2423.
29. Qu W., Zha Z., Ploessl K., Lieberman B.P., Zhu L., Wise D.R., et al. Synthesis of optically pure 4-fluoro-glutamines as potential metabolic imaging agents for tumors. J Am Chem Soc 2011, 133:1122-1133.
30. Vaalburg W., Coenen H.H., Crouzel C., Elsinga P.H., Langstrom B., Lemaire C., et al. Amino acids for the measurement of protein synthesis in vivo by PET. Int J Rad Appl Instrum B 1992, 19:227-237.
31. Tsukada H., Sato K., Fukumoto D., Kakiuchi T. Evaluation of D-isomers of O-F-18-fluoromethyl, O-F-18-fluoroethyl and O-F-18-fluoropropyl tyrosine as tumour imaging agents in mice. Eur J Nucl Med Mol Imaging 2006, 33:1017-1024.
32. Bauwens M., Lahoutte T., Kersemans K., Gallez C., Bossuyt A., Meltens J. Comparison of the uptake of [I-123/125]-2-iodo-D-tyrosine and [I-123/125]-2-iodo-L-tyrosine in R1M rhabdomyosarcoma cells in vitro and in R1M tumor-bearing Wag/Rij rats in vivo. Nucl Med Biol 2006, 33:735-741.
33. Wang L., Lieberman B.P., Plossl K., Qu W., Kung H.F. Synthesis and comparative biological evaluation of L- and D-isomers of 18F-labeled fluoroalkyl phenylalanine derivatives as tumor imaging agents. Nucl Med Biol 2011, 38:301-312.
34. Utsunomiya-Tate N., Endou H., Kanai Y. Cloning and functional characterization of a system ASC-like Na+-dependent neutral amino acid transporter. J Biol Chem 1996, 271:14883-14890.
35. Esslinger C.S., Cybulski K.A., Rhoderick J.F. N-gamma-aryl glutamine analogues as probes of the ASCT2 neutral amino acid transporter binding site. Bioorg Med Chem 2005, 13:1111-1118.
36. Scharff R., Wool I.G. Effect of diabetes on the concentration of amino acids in plasma and heart muscle of rats. Biochem J 1966, 99:173-178.
37. Martarello L., McConathy J., Camp V.M., Malveaux E.J., Simpson N.E., Simpson C.P., et al. Synthesis of syn- and anti-1-amino-3-[18F]fluoromethyl-cyclobutane-1-carboxylic acid (FMACBC), potential PET ligands for tumor detection. J Med Chem 2002, 45:2250-2259.
38. Schoenherr R.M., Kelly-Spratt K.S., Lin C., Whiteaker J.R., Liu T., Holzman T., et al. Proteome and transcriptome profiles of a Her2/Neu-driven mouse model of breast cancer. Proteomics Clin Appl 2011, 5:179-188.