Positron Emission Tomography Basics: Radiochemistry. N. Scott Mason, Ph.D. Radiochemist University of Pittsburgh PET Facility
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1 Positron Emission Tomography Basics: Radiochemistry. Scott Mason, Ph.D. Radiochemist PET Facility
2 What is PET? Positron Emission Tomography In-Vivo Imaging and Quantification of rgan/tissue Function Uses Positron-Emitting Radiolabeled Tracers
3 What is PET? Positron Emission Tomography In-Vivo Imaging and Quantification of rgan/tissue Function Uses Positron-Emitting Radiolabeled Tracers
4 PET Imaging 1. Cyclotron 2. Radionuclide 3. Radiosynthesis 4. PET Imaging 5. Image Reconstruction 6. Data Analysis
5 PET Imaging 1. Cyclotron 2. Radionuclide 3. Radiosynthesis 4. PET Imaging 5. Image Reconstruction 6. Data Analysis
6 Cyclotron
7 Positron Emitting Radionuclides Atoms that can be included in amino acids, carbohydrates, steroids, water, other small molecules, etc. (F is isostere for H) Short half-life: maximizes SR to subject radiation dose, but also means the isotope must be produced locally ( 18 F can be shipped) Half-life (min)" 18 F 109! 11 C 20! 13 10! 15!2!
8 Radionuclide Production Cyclotron! Stable uclide! 11 MeV protons! 18! Unstable Radionuclide! n! 18 F!
9 Radionuclide Production 15 2 p,n 15 2 H 2 16 p,α 13 H p,α 11 C2 H 2 18 p,n H 18 F
10
11 Potential C-11 Chemistry 11 CH 3 Tf 11 CH 3 Li 11 CH CH 3 I 11 CH 3 H H 11 CH 11 C 2 (CH 3 ) 2 11 C R 11 C 2 MgBr R 11 CH 2 H R 11 C 2 H R 11 CH 2 I R 11 CH R 11 CCl R 11 CH 2 R 11 CHR R 11 CR 2
12 C-11 Carboxylation Chemistry 11 CH 3 Tf 11 CH 3 Li 11 CH CH 3 I 11 CH 3 H H 11 CH 11 C 2 (CH 3 ) 2 11 C R 11 C 2 MgBr R 11 CH 2 H R 11 C 2 H R 11 CH 2 I R 11 CH R 11 CCl R 11 CH 2 R 11 CHR R 11 CR 2
13 [C-11]WAY * Me * Two potential labeling sites
14 [C-11]carbonyl WAY MgCl [C-11]C 2 * - * Cl + Me H Me * [C-11]carbonyl WAY100635
15 C-11 Methylation 11 CH 3 Tf 11 CH 3 Li 11 CH CH 3 I 11 CH 3 H H 11 CH 11 C 2 (CH 3 ) 2 11 C R 11 C 2 MgBr R 11 CH 2 H R 11 C 2 H R 11 CH 2 I R 11 CH R 11 CCl R 11 CH 2 R 11 CHR R 11 CR 2
16 [C-11]MeI System
17 [C-11]MeI System [ 11 C]Methyl Iodide System
18 [C-11]β-CFT chemistry H 3 11 C H CCH µl acetone [C-11]CH 3 Tf CCH 3 F 2 60 o C HPLC purification F
19 [C-11]β-CFT micropet Imaging of Simian Unilateral MPTP Lesion Model of Parkinson s Disease Lesioned Striatum MPTP associated toxicity resulted in ~90% loss of DAT sites in left striatum as determined by PET Intact Striatum
20 Dopamine D2/D3 Imaging: [C-11]FLB457 H H [ 11 C]CH 3 Tf ah H 11 CH 3 Br Me Acetone Br Me
21 Dopamine D2/D3 Imaging: [C-11]FLB457 Specific Activity Concerns Ratio of radioactivity to cold mass Expressed as Ci/mmole Theoretical 9.4 x 10 6 Routinely achieved 2 x 10 3 Minimize cold mass associated with radioactivity administration (0.6 µg) Atmospheric C 2 acts to decrease specific activity
22 [C-11]Pittsburgh Compound B [C-11]PIB H S H 2 [ 11 C]CH 3 Tf Methyl Ethyl Ketone H S 11 CH 3 H 6-H-BTA-0 [ 11 C]6-H-BTA-1
23 [C-11]PIB Images Examples of Pittsburgh Compound-B (PIB) Logan DVR images for a control, a control-like mild cognitive impairment (MCI-2), an AD-like MCI (MCI-4), and the AD (AD-1) subject with highest PIB retention.
24 F-18 Fluoride Alkyl nucleophilic substitution (S2) Aromatic nucleophilic substitution (S2Ar) Issues Cation exchange and relatively anhydrous conditions
25 [F-18]FDG chemistry Ac H Ac Tf Ac 1. K[ 18 F], K HCl H H Ac H 18 F
26 [F-18]FDG chemistry
27 [F-18]FLT chemistry DMTr 1. K[ 18 F], K222, DMS 2. HCl H H 18 F
28 [F-18]FLT uptake in mice bearing xenografted SCCH tumors brain tumors
29 Metabolite Contribution H S [F-18]Altanserin 18 F H S H H [F-18]Altanserinol 18 F H 18 F [F-18]4-(4-Fluorobenzoyl)piperidine
30
31 Radiosynthesis of F-18]Altanserinol H S 2 H S K 18 F DMS hv 18 F EtH abh 4 H S H H 18 F
32
33
34 3 -[F-18]F-6-H-BTA-1 Radiochemistry H 36.54% S 18 F 20.92% HCH 3 [F-18]3'F-PiB Pr 2 2 S Pr % 4.00% CH 3 Precursors
35 3 -[F-18]F-6-H-BTA-1 Semi-Preparative HPLC 36.54% 20.92% 12.03% 4.00% Prodigy DS-Prep 10 x 250 mm, 3/1/6 MeC/ MeH/ TEA Buffer, 1 ml/min 0-5min, 5 ml/min 5-10 min, then 8mL/min
36 3 -[F-18]F-6-H-BTA-1 Final Product QC 36.54% 20.92% 12.03% 4.00% Prodigy DS-3 5µ 4.6 x 250 mm, 40% MeC / 60% TEA Buffer, 2.0 ml/min
37 The Regional Distribution of [18F]3 F-PiB in AD Brain is Very Similar to that of [11C]PiB
38 Radiopharmacy Quality Control Visual ph T 1/2 determination Radiochemical Identity Radiochemical Purity Chemical Purity (Specific Activity) Residual Volatile rganic Solvent Endotoxin Testing Sterility
39 Acknowledgments Chester A. Mathis, Ph.D. - Director Chemists Scott Mason Steve Kendro icole DeBlasio April Radelet Guo-feng Huang Physicists Julie Price Brian Lopresti Chip Laymon Eoin Carney Technologists James Ruszkiewicz Denise Ratica Collaborators Raj arendran Clayton Wiley Bill Klunk Jerry Schatten Jennifer Grandis Funding: IA, IMH, CI, CRR, UPMC
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