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1 Supporting Information Synthesis and in vivo Biological Evaluation of 68 Ga Labelled Carbonic Anhydrase IX Targeting Small Molecules for Positron Emission Tomography Deborah Sneddon 1#, Raymon Niemans 2#, Matthias Bauwens 3, Ala Yaromina 2, Simon J.A. van Kuijk 2, Natasja G. Lieuwes 2, Rianne Biemans 2, Ivo Pooters 3, Paul A. Pellegrini 4, Nigel A. Lengkeek 4, Ivan Greguric 4, Kathryn F. Tonissen 1, Claudiu Supuran 5, Philippe Lambin 2, Ludwig Dubois 2,* and Sally-Ann Poulsen 1, * *Corresponding authors. Compound 3 1 H NMR and 13 C NMR S3 Compound 4 1 H NMR and 13 C NMR S4 Compound 5 1 H NMR and 13 C NMR S5 Compound 6 1 H NMR and 13 C NMR S6 Compound 7 1 H NMR and 13 C NMR S7 Compound 8 1 H NMR and 13 C NMR S8 Compound 9 1 H NMR and 13 C NMR S9 Compound 10 1 H NMR and 13 C NMR S10 Compound 11 1 H NMR and 13 C NMR S11 S1
2 Compound 12 1 H NMR and 13 C NMR S12 Compound 13 1 H NMR and 13 C NMR S13 Compound 14 1 H NMR and 13 C NMR S14 Compounds nat Ga-1 and nat Ga-2 1 H NMR S15 HRMS for compound nat Ga-2 showing characteristic splitting pattern S16 Variable temperature 1 H NMR of compound 13 S17 Additional 67 Ga radiolabelling data S20 [ 67 Ga] radiochemical traces (10 nmol compound 9 or 14) S21 [ 67 Ga]-1 radiochemical trace (25 nmol) S21 [ 67 Ga]-2 RP-HPLC trace co-injection of [ 67 Ga]-2 and nat Ga-2 S22 Example 68 Ga radiochemical trace S23 S2
3 Compound MHz 1 H NMR (CD 3 ) 2 SO Compound 3 125MHz 13 C NMR (CD 3 ) 2 SO S3
4 Compound MHz 1 H NMR CDCl 3 Compound MHz 13 C NMR CDCl 3 S4
5 Compound MHz 1 H NMR (CD 3 ) 2 SO Compound 5 125MHz 13 C NMR (CD 3 ) 2 SO S5
6 Compound MHz 1 H NMR (CD 3 ) 2 SO Compound MHz 13 C NMR (CD 3 ) 2 SO S6
7 Compound MHz 1 H NMR DMSO d 6 Compound 7 125MHz 13 C NMR (CD 3 ) 2 SO S7
8 Compound MHz 1 H NMR (CD 3 ) 2 SO Compound MHz 13 C NMR (CD 3 ) 2 SO 358 K S8
9 Compound MHz 1 H NMR (CD 3 ) 2 SO Compound MHz 13 C NMR (CD 3 ) 2 SO S9
10 Compound MHz 1 H NMR CDCl 3 Compound MHz 13 C NMR CDCl 3 S10
11 Compound MHz 1 H NMR CDCl 3 Compound MHz 13 C NMR CDCl 3 S11
12 Compound MHz 1 H NMR (CD 3 ) 2 SO Compound MHz 13 C NMR (CD 3 ) 2 SO S12
13 Compound MHz 1 H NMR (CD 3 ) 2 SO Compound MHz 13 C NMR (CD 3 ) 2 SO S13
14 Compound MHz 1 H NMR (CD 3 ) 2 SO Compound MHz 13 C NMR (CD 3 ) 2 SO S14
15 Compound [ nat Ga] MHz 1 H NMR (CD 3 ) 2 SO Compound [ nat Ga] MHz 1 H NMR (CD 3 ) 2 SO S15
16 HRMS for compound [natga]-2 showing characteristic splitting pattern S16
17 VT experimental data for compound 8 Compound MHz 1 H NMR (CD 3 ) 2 SO 298K S17
18 Compound MHz 1 H NMR (CD 3 ) 2 SO 313K Compound MHz 1 H NMR (CD 3 ) 2 SO 328K S18
19 Compound MHz 1 H NMR (CD 3 ) 2 SO 343K Compound MHz 1 H NMR (CD 3 ) 2 SO 358K S19
20 Radiolabelling with 67 Ga additional data Table 4: HPLC conditions for purification of 67 Ga DOTA complexes [ 67 Ga]-1 and [ 67 Ga]-2 at 25 1 nmole Sample Compound Column a Flow rate Mobile Retention (nmol) (ml/min) Phase b Time (min) [ 67 Ga]-1 25 Analytical 1.5 8: Analytical 1.5 8: Semi 3 12: Semi 3 12: [ 67 Ga]-2 25 Analytical : Analytical : Semi 3 16: Semi 3 16: Semi 3 16: a Where Analytical refers to the Atlantis T3, mm, 3 µm analytical column and Semi to the Atlantis T3, mm, 5 µm semi-preparatory column. Injection sizes adjusted appropriately for each column size. b Mobile phase expressed as a ratio of MeCN: Ammonium formate buffer (120 mm, ph 4.3) S20
21 Analytical radio-trace chromatograms of complexes [ 67 Ga]-1 and [ 67 Ga]-2 produced in high yield from ~20 MBq of 67 GaCl3 10 nmol Atlantis T mm, 3 µm, 1.5 ml/min flow rate (10 nmol of either compound 9 or compound 14), ~20 MBq 67 GaCl 3 in sodium acetate buffer (ph 4.3) Radioactivity Radioactivity UV UV S21
22 Analytical radio-trace chromatograms of compound [ 67 Ga]-1 25 nmol Atlantis T mm, 3 µm, 1.5 ml/min flow rate (25 nmole compound 9, ~20 MBq 67 GaCl 3 in sodium acetate buffer (ph 4.3) Radioactivity UV Analytical radio-trace chromatograms of compound [ 67 Ga]-2 co-injected with nat Ga-2 and compound 14. Atlantis T mm, 3 µm, 1.5 ml/min flow rate, 12:88 MeCN: NH 4 CO 2 H (120 mm, ph 4.3). Compound 14 elutes at 8.2 minutes, [ nat/67 Ga]-2 at 13.5 minutes. Radioactivity UV S22
23 [ 68 Ga]-2 example analytical data (Inertsil ODS C18, 5 µm, mm, 100:0 0:100 H 2 O + 0.1% TFA/ MeCN +0.1% TFA, 1 ml/min) Compound 14 Retention time minutes 2,00 1,00 0,00 0,00 5,00 10,00 15,00 min [ nat Ga]-2 mau *1000 Retention time minutes BKG1 BKG2 Reg #1 Reg #2 BKG3 Reg #3 Reg #4 Reg #5 BKG4 Reg #6 Reg #7 BKG5 Reg #8 BKG6 Reg #9 Reg #10 Reg #11 BKG7 Reg #12 Reg #13 Reg #14 BKG8 UV1 40 mau 20 0 BKG1 Reg #1 BKG2 BKG3 Reg #2 Reg #3 BKG4 UV1-20 0,00 5,00 10,00 15,00 min 4,0 [ 68 Ga]-2 2,0 Retention time minutes 200 mau UV1 0,0 0,00 5,00 10,00 15,00 min CPS ChA CPS 0,00 5,00 10,00 15,00 min 5 CPS *1000 ChB 0 10,0 0,00 5,00 10,00 15,00 min ChB 5,0 0,0 0,00 5,00 10,00 15,00 min 500 CPS ChA S23 KG1 BKG2 BKG3 Reg #3 BKG1 BKG4 Reg #1 Reg #2 Reg #3 BKG2 Reg #1 Reg #2 BKG3 Reg #4 BKG4 Reg #4
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