Preferred stereoselective transport of the D-isomer of cis-4-[ 18F]fluoro-proline at the blood-brain barrier

Journal of Cerebral Blood Flow and Metabolism

Volumn 25, Issue 5, 2005, Pages 607-616

  Langen, Karl Josef ^a,d   Hamacher, Kurt ^a,d   Bauer, Dagmar ^a,d   Bröer, Stefan ^b   Pauleit, Dirk ^a,d   Herzog, Hans ^a,d   Floeth, Frank ^c   Zilles, Karl ^a,d   Coenen, Heinz H ^a,d  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

^b AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^c UNIVERSITY HOSPITAL DÜSSELDORF   (Germany)

^d Brain Imaging Center West   (Germany)

Author keywords

Amino acid transport; Blood brain barrier; D L cis 4 18F fluoroproline; D L proline; PET

Indexed keywords

4 FLUOROPROLINE; AMINO ACID; FLUORINE 18; PROLINE; UNCLASSIFIED DRUG;

AMINO ACID TRANSPORT; ANIMAL CELL; ARTICLE; BLOOD BRAIN BARRIER; BRAIN CORTEX; CIS TRANS ISOMERISM; DRUG UPTAKE; ENANTIOMER; ISOMER; MALE; NEUROTRANSMITTER RELEASE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; PROTEIN ANALYSIS; RADIOACTIVITY; RAT; STEREOCHEMISTRY;

ANIMALS; AUTORADIOGRAPHY; BIOLOGICAL TRANSPORT; BLOOD-BRAIN BARRIER; BRAIN; FEMALE; HUMANS; MALE; MIDDLE AGED; POSITRON-EMISSION TOMOGRAPHY; PROLINE; RADIOPHARMACEUTICALS; RATS; STEREOISOMERISM; TISSUE DISTRIBUTION;

EID: 17644381964     PISSN: 0271678X     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.jcbfm.9600065     Document Type: Article

References (44)

1. Arundine M, Tymianski M (2004) Molecular mechanisms of glutamate-dependent neurodegeneration in ischemia and traumatic brain injury. Cell Mol Life Sci 61:657-68, (review)
2. Balcar VJ, Johnston GA, Stephanson AL (1976) Transport of L-proline by rat brain slices. Brain Res 102:143-51
3. Bennett Jr JP, Logan WJ, Snyder SH (1972) Amino acid neurotransmitter candidates: sodium-dependent high-affinity uptake by unique synaptosomal fractions. Science 178:997-9
4. Boll M, Foltz M, Rubio-Aliaga I, Kottra G, Daniel H (2002) Functional characterization of two novel mammalian electrogenic proton-dependent amino acid cotransporters. J Biol Chem 277:22966-73
5. Bruckner H, Hausch M (1993) Gas chromatographic characterization of free D-amino acids in the blood serum of patients with renal disorders and of healthy volunteers. J Chromatogr 614:7-17
6. Cohen SM, Nadler JV (1997) Proline-induced potentiation of glutamate transmission. Brain Res 761:271-82
7. Corrigan JJ (1969) D-amino acids in animals. Science 164:142-9
8. Crump FT, Fremeau RT, Craig AM (1999) Localization of the brain-specific high-affinity L-proline transporter in cultured hippocampal neurons: molecular heterogeneity of synaptic terminals. Mol Cell Neurosci 13:25-39
9. Doraiswamy PM (2003) Alzheimer's disease and the glutamate NMDA receptor. Psychopharmacol Bull 37:41-9 (review)
10. Friedman M (1999) Chemistry, nutrition, and microbiology of D-amino acids. J Agric Food Chem 47:3457-79
11. Fremeau Jr RT, Caron MG, Blakely RD (1992) Molecular cloning and expression of a high affinity L-proline transporter expressed in putative glutamatergic pathways of rat brain. Neuron 8:915-26
12. Fremeau Jr RT, Velaz-Faircloth M, Miller JW, Henzi VA, Cohen SM, Nadler JV, Shafqat S, Blakely RD, Domin B (1996) A novel nonopioid action of enkephalins: competitive inhibition of the mammalian brain high affinity L-proline transporter. Mol Pharmacol 49:1033-41
13. Garweg G, Dahnke HG (1972) Various use of D-proline and L-proline in the brain of the mouse. Verh Anat Ges 67:297-303
14. Garweg G, Dahnke HG (1973) Amino-acid racemase in the organism of mammals. Naturwissenschaften 60:201
15. Garweg G, Dahnke HG (1974) Is the conversion of D-proline into L-proline in the brain a prerequisite for the incorporation into nerve-cell proteins? Verh Anat Ges 68:375-9
16. Groom AJ, Smith T, Turski L (2003) Multiple sclerosis and glutamate. Ann NY Acad Sci 993:229-75
17. Hauptmann M, Wilson DF, Erecinska M (1983) High affinity proline uptake in rat brain synaptosomes. FEBS Lett 161:301-5
18. 18F]fluoro-L-proline, radiotracer for PET-investigation of disordered matrix protein synthesis. J Labelled Compd Radiopharm 42:1135-42
19. Hamase K, Morikawa A, Zaitsu K (2002) D-Amino acids in mammals and their diagnostic value. J Chromatogr B Analyt Technol Biomed Life Sci 781:73-91 (review)
20. Harrison PJ, Law AJ, Eastwood SL (2003) Glutamate receptors and transporters in the hippocampus in schizophrenia. Ann NY Acad Sci 1003:94-101 (review)
21. Hynd MR, Scott HL, Dodd PR (2004) Glutamate-mediated excitotoxicity and neurodegeneration in Alzheimer's disease. Neurochem Int 45:583-95
22. Ito H, Kanno I, Kato C, Sasaki T, Ishii K, Ouchi Y, Iida A, Okazawa H, Hayashida K, Tsuyuguchi N, Ishii K, Kuwabara Y, Senda M (2004) Database of normal human cerebral blood flow, cerebral blood volume, cerebral oxygen extraction fraction and cerebral metabolic rate of oxygen measured by positron emission tomography with 15O-labelled carbon dioxide or water, carbon monoxide and oxygen: a multicentre study in Japan. Eur J Nucl Med Mol Imaging 31:635-43
23. 18F]Fluoro-L-proline in F98 glioma cells. Nucl Med Biol 29:685-692
24. Langen KJ, Jarosch M, Mühlensiepen H, Hamacher K, Hess E, Bröer S, Jansen P, Zilles K, Coenen HH (2003) Comparison of fluorotyrosines and methionine uptake in F98 rat gliomas. Nucl Med Biol 30:501-8
25. 18F]fluoro-L-proline. Nucl Med Biol 31:67-75
26. Nadler JV (1987) Sodium-dependent proline uptake in the rat hippocampal formation: association with ipsilateral-commissural projections of CA3 pyramidal cells. J Neurochem 49:1155-60
27. Nagata Y, Masui R, Akino T (1992) The presence of free D-serine, D-alanine and D-proline in human plasma. Experientia 48:986-8
28. Oldendorf WH (1971) Brain uptake of radiolabeled amino acids, amines, and hexoses after arterial injection. Am J Physiol 221:1629-39
29. Patlak CS, Blasberg RG, Fenstermacher JD (1983) Graphical evaluation of blood to brain transfer constants from multiple time uptake data. J Cereb Blood Flow Metab 3:1-7
30. 123I]iodo-α-methyl-L-tyrosine (IMT) SPECT in brain tumors. J Nucl Med 45:374-81
31. Peterson NA, Raghupathy E (1972) Characteristics of amino acid accumulation by synaptosomal particles isolated from rat brain. J Neurochem 19:1423-38
32. Renick SE, Kleven DT, Chan J, Stenius K, Milner TA, Pickel VM, Fremeau Jr RT (1999) The mammalian brain high-affinity L-proline transporter is enriched preferentially in synaptic vesicles in a subpopulation of excitatory nerve terminals in rat forebrain. J Neurosci 19:21-33
33. Rubio-Aliaga I, Boll M, Vogt Weisenhorn DM, Foltz M, Kottra G, Daniel H (2004) The proton/amino acid cotransporter PAT2 is expressed in neurons with a different subcellular localization than its paralog PAT1. J Biol Chem 279:2754-60
34. Schieber A, Bruckner H, Rupp-Classen M, Specht W, Nowitzki-Grimm S, Classen HG (1997) Evaluation of D-amino acid levels in rat by gas chromatography-selected ion monitoring mass spectrometry: no evidence for subacute toxicity of orally fed D-proline and D-aspartic acid. J Chromatogr B Biomed Sci Appl 691:1-12
35. Sershen H, Lajtha A (1976) Capillary transport of amino acids in the developing brain. Exp Neurol 53:465-74
36. Shafqat S, Velaz-Faircloth M, Henzi VA, Whitney KD, Yang-Feng TL, Seldin MF, Fremeau Jr RT (1995) Human brain-specific L-proline transporter: molecular cloning, functional expression, and chromosomal localization of the gene in human and mouse genomes. Mol Pharmacol 48:219-29
37. Snyder SH, Kim PM (2000) D-amino acids as putative neurotransmitters: focus on D-serine. Neurochem Res 25:553-60 (review)
38. Takanaga H, Tokuda N, Ohtsuki S, Hosoya K, Terasaki T (2002) ATA2 is predominantly expressed as system A at the blood-brain barrier and acts as brain-to-blood efflux transport for L-proline. Mol Pharmacol 61:1289-1296
39. Takano T, Lin JH, Arcuino G, Gao Q, Yang J, Nedergaard M (2001) Glutamate release promotes growth of malignant gliomas. Nat Med 7:1010-5
40. Todd MM, Weeks JB, Warner DS (1993) Microwave fixation for the determination of cerebral blood volume in rats. J Cereb Blood Flow Metab 13:328-36
41. Wang H, Wolosker H, Pevsner J, Snyder SH, Selkoe DJ (2000) Regulation of rat magnocellular neurosecretory system by D-aspartate: evidence for biological role(s) of a naturally occurring free D-amino acid in mammals. J Endocrinol 167:247-52
42. 11C]-methionine uptake in brain tumors: initial results of a comparative study. Eur J Nucl Med 27:542-9
43. 18F] fluoroprolines: diastereomeric effect on metabolism and uptake in mice. Nucl Med Biol 3:259-65
44. 18F]fluoroethyl)-L-tyrosine for tumor imaging. J Nucl Med 40:205-12