Rapid Electrophilic 211 At-Astatination of Trimethylgermyl Arenes

A set of At-astatoarenes were synthesized from corresponding trimethylgermyl arenes with an average radiochemical conversion (RCC) of ca. 50 % for electron-rich and approx. 70 % in case of electron-deficient arenes. Both electron rich and electron poor substrates were successfully radiolabeled at ro...

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Published inChemPlusChem (Weinheim, Germany) Vol. 89; no. 9; p. e202400254
Main Authors Müller, Marius, Battisti, Umberto Maria, Zabrocki, Merlin, Hansson, Ellinor, Jensen, Holger, Aneheim, Emma, Lindegren, Sture, Herth, Matthias Manfred
Format Journal Article
LanguageEnglish
Published Germany 05.09.2024
Subjects
Electrophilic Aromatic Substitution
Trifluoro Acetic Acid
Astatine-211
Radiopharmaceuticals
Trimethylgermyl Arenes
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Abstract A set of At-astatoarenes were synthesized from corresponding trimethylgermyl arenes with an average radiochemical conversion (RCC) of ca. 50 % for electron-rich and approx. 70 % in case of electron-deficient arenes. Both electron rich and electron poor substrates were successfully radiolabeled at room temperature (RT) using relatively low precursor amounts (0.15 μmol/0.02 mL solvent (7.5 mM)). Ready access to ortho-, para- and meta- astatinated arenes was achievable. Optimized reaction conditions were successfully applied to label a poly (ADP-ribose) polymerase (PARP) inhibitor with a RCC of approx. 50 %. We believe that trimethylgermyl derivatives are a viable addition to the astatination precursor toolbox and facilitate astatination of arenes. The developed labeling method should easily be applicable for productions under good manufacturing practice (GMP).
AbstractList A set of 211 At‐astatoarenes were synthesized from corresponding trimethylgermyl arenes with an average radiochemical conversion (RCC) of ca. 50 % for electron‐rich and approx. 70 % in case of electron‐deficient arenes. Both electron rich and electron poor substrates were successfully radiolabeled at room temperature (RT) using relatively low precursor amounts (0.15 μmol/0.02 mL solvent (7.5 mM)). Ready access to ortho‐, para‐ and meta‐ astatinated arenes was achievable. Optimized reaction conditions were successfully applied to label a poly (ADP‐ribose) polymerase (PARP) inhibitor with a RCC of approx. 50 %. We believe that trimethylgermyl derivatives are a viable addition to the astatination precursor toolbox and facilitate astatination of arenes. The developed labeling method should easily be applicable for productions under good manufacturing practice (GMP).
A set of At-astatoarenes were synthesized from corresponding trimethylgermyl arenes with an average radiochemical conversion (RCC) of ca. 50 % for electron-rich and approx. 70 % in case of electron-deficient arenes. Both electron rich and electron poor substrates were successfully radiolabeled at room temperature (RT) using relatively low precursor amounts (0.15 μmol/0.02 mL solvent (7.5 mM)). Ready access to ortho-, para- and meta- astatinated arenes was achievable. Optimized reaction conditions were successfully applied to label a poly (ADP-ribose) polymerase (PARP) inhibitor with a RCC of approx. 50 %. We believe that trimethylgermyl derivatives are a viable addition to the astatination precursor toolbox and facilitate astatination of arenes. The developed labeling method should easily be applicable for productions under good manufacturing practice (GMP).
Author Battisti, Umberto Maria
Lindegren, Sture
Müller, Marius
Hansson, Ellinor
Herth, Matthias Manfred
Jensen, Holger
Aneheim, Emma
Zabrocki, Merlin
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  givenname: Ellinor
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  givenname: Sture
  surname: Lindegren
  fullname: Lindegren, Sture
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  givenname: Matthias Manfred
  orcidid: 0000-0002-7788-513X
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Cites_doi 10.1007/s00259-018-4167-0
10.1021/acs.orglett.6b02911
10.1002/chem.202104169
10.1021/cr00002a004
10.1016/B978-0-12-822960-6.00013-2
10.1021/acs.oprd.5b00201
10.1002/cplu.201900114
10.1002/anie.200906294
10.1002/jlcr.2580180606
10.2174/1874471010801030177
10.1039/C8OB02394H
10.1103/PhysRev.57.459
10.1016/j.bmc.2017.09.022
10.1002/anie.201804878
10.1289/ehp.761451
10.1089/cbr.2012.1292
10.1016/0969-8051(94)00077-W
10.1016/0020-708X(80)90033-2
10.1021/bc00018a006
10.1039/D1OB00789K
10.1016/j.nucmedbio.2020.11.003
10.1002/chem.202203366
10.1002/anie.202008372
10.2967/jnumed.117.203539
10.1021/ol501243g
10.1021/acs.orglett.8b00232
10.1021/acs.joc.7b02920
10.1016/0969-8043(95)00285-5
10.1007/BF02167979
10.1021/acs.jmedchem.1c01326
10.1002/jlcr.2580170508
10.1016/0020-708X(82)90155-7
10.1002/marc.202100655
10.1002/anie.201404436
10.1021/ja8001919
10.2174/1381612003399275
10.1007/BF02162464
10.3390/ph15060685
10.1016/0883-2889(87)90001-3
10.2967/jnumed.116.178673
10.1039/D1SC02789A
10.1007/BF02386681
10.1002/chem.201600922
10.1089/cbr.2020.3576
10.1021/acs.orglett.5b02875
10.2174/1874471011306020001
10.1088/1742-6596/41/1/009
10.1016/0883-2889(86)90274-1
10.2967/jnumed.123.267043
10.1002/1099-1344(20001030)43:12<1219::AID-JLCR409>3.0.CO;2-P
10.3390/ph16040595
10.1021/acs.bioconjchem.2c00042
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Issue 9
Keywords Electrophilic Aromatic Substitution
Trifluoro Acetic Acid
Astatine-211
Radiopharmaceuticals
Trimethylgermyl Arenes
Language English
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References e_1_2_9_52_1
e_1_2_9_33_2
e_1_2_9_10_1
e_1_2_9_56_1
e_1_2_9_12_2
e_1_2_9_31_2
e_1_2_9_54_1
e_1_2_9_14_1
e_1_2_9_16_2
e_1_2_9_35_2
e_1_2_9_58_2
e_1_2_9_37_1
e_1_2_9_18_1
e_1_2_9_39_2
e_1_2_9_41_1
e_1_2_9_62_2
e_1_2_9_60_2
e_1_2_9_22_1
e_1_2_9_45_1
e_1_2_9_20_2
e_1_2_9_66_1
e_1_2_9_43_2
e_1_2_9_64_2
e_1_2_9_6_1
e_1_2_9_4_2
e_1_2_9_2_2
Watanebe S. (e_1_2_9_50_2) 2019; 17
Denk C. (e_1_2_9_59_2) 2019; 84
e_1_2_9_8_2
García-Vázquez R. (e_1_2_9_63_2) 2022; 15
e_1_2_9_24_2
e_1_2_9_49_2
e_1_2_9_47_1
e_1_2_9_26_2
e_1_2_9_28_2
Fakiri M. E. (e_1_2_9_51_2) 2024; 65
e_1_2_9_53_1
e_1_2_9_30_2
e_1_2_9_11_1
e_1_2_9_34_1
e_1_2_9_57_1
e_1_2_9_55_1
e_1_2_9_32_2
e_1_2_9_13_2
e_1_2_9_38_2
e_1_2_9_17_1
e_1_2_9_15_2
e_1_2_9_36_2
e_1_2_9_19_2
e_1_2_9_42_1
e_1_2_9_61_2
e_1_2_9_40_1
Wilbur D. S. (e_1_2_9_21_2) 2010; 51
e_1_2_9_44_2
e_1_2_9_46_1
e_1_2_9_67_1
e_1_2_9_23_2
e_1_2_9_65_2
e_1_2_9_7_2
e_1_2_9_5_2
e_1_2_9_3_2
e_1_2_9_1_1
e_1_2_9_9_2
e_1_2_9_25_2
e_1_2_9_27_2
e_1_2_9_48_1
e_1_2_9_29_1
References_xml – ident: e_1_2_9_42_1
– ident: e_1_2_9_5_2
  doi: 10.1007/s00259-018-4167-0
– ident: e_1_2_9_31_2
  doi: 10.1021/acs.orglett.6b02911
– ident: e_1_2_9_38_2
  doi: 10.1002/chem.202104169
– ident: e_1_2_9_48_1
– ident: e_1_2_9_56_1
  doi: 10.1021/cr00002a004
– ident: e_1_2_9_17_1
  doi: 10.1016/B978-0-12-822960-6.00013-2
– ident: e_1_2_9_47_1
  doi: 10.1021/acs.oprd.5b00201
– volume: 84
  start-page: 775
  year: 2019
  ident: e_1_2_9_59_2
  publication-title: ChemPlusChem
  doi: 10.1002/cplu.201900114
  contributor:
    fullname: Denk C.
– ident: e_1_2_9_61_2
  doi: 10.1002/anie.200906294
– ident: e_1_2_9_26_2
  doi: 10.1002/jlcr.2580180606
– ident: e_1_2_9_44_2
  doi: 10.2174/1874471010801030177
– volume: 17
  start-page: 165
  year: 2019
  ident: e_1_2_9_50_2
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/C8OB02394H
  contributor:
    fullname: Watanebe S.
– ident: e_1_2_9_16_2
  doi: 10.2174/1874471010801030177
– ident: e_1_2_9_7_2
  doi: 10.1103/PhysRev.57.459
– ident: e_1_2_9_36_2
  doi: 10.1016/j.bmc.2017.09.022
– ident: e_1_2_9_66_1
  doi: 10.1002/anie.201804878
– ident: e_1_2_9_46_1
  doi: 10.1289/ehp.761451
– ident: e_1_2_9_12_2
  doi: 10.1089/cbr.2012.1292
– ident: e_1_2_9_15_2
  doi: 10.1016/0969-8051(94)00077-W
– ident: e_1_2_9_27_2
  doi: 10.1016/0020-708X(80)90033-2
– ident: e_1_2_9_49_2
  doi: 10.1021/bc00018a006
– ident: e_1_2_9_39_2
  doi: 10.1039/D1OB00789K
– ident: e_1_2_9_57_1
– ident: e_1_2_9_45_1
  doi: 10.1016/j.nucmedbio.2020.11.003
– ident: e_1_2_9_54_1
  doi: 10.1002/chem.202203366
– ident: e_1_2_9_22_1
– ident: e_1_2_9_52_1
  doi: 10.1002/anie.202008372
– ident: e_1_2_9_3_2
  doi: 10.2967/jnumed.117.203539
– ident: e_1_2_9_30_2
  doi: 10.1021/ol501243g
– ident: e_1_2_9_40_1
  doi: 10.1021/acs.orglett.8b00232
– ident: e_1_2_9_11_1
– ident: e_1_2_9_55_1
  doi: 10.1021/acs.joc.7b02920
– ident: e_1_2_9_8_2
  doi: 10.1016/0969-8043(95)00285-5
– ident: e_1_2_9_23_2
  doi: 10.1007/BF02167979
– volume: 15
  year: 2022
  ident: e_1_2_9_63_2
  publication-title: Pharmaceuticals
  contributor:
    fullname: García-Vázquez R.
– ident: e_1_2_9_14_1
– ident: e_1_2_9_60_2
  doi: 10.1021/acs.jmedchem.1c01326
– ident: e_1_2_9_25_2
  doi: 10.1002/jlcr.2580170508
– ident: e_1_2_9_6_1
– ident: e_1_2_9_28_2
  doi: 10.1016/0020-708X(82)90155-7
– ident: e_1_2_9_65_2
  doi: 10.1002/marc.202100655
– volume: 51
  start-page: 1454
  year: 2010
  ident: e_1_2_9_21_2
  publication-title: J. Nucl. Med.
  contributor:
    fullname: Wilbur D. S.
– ident: e_1_2_9_33_2
  doi: 10.1002/anie.201404436
– ident: e_1_2_9_67_1
  doi: 10.1021/ja8001919
– ident: e_1_2_9_1_1
– ident: e_1_2_9_10_1
  doi: 10.2174/1381612003399275
– ident: e_1_2_9_19_2
  doi: 10.1007/BF02162464
– ident: e_1_2_9_62_2
  doi: 10.3390/ph15060685
– ident: e_1_2_9_53_1
  doi: 10.1016/0883-2889(87)90001-3
– ident: e_1_2_9_4_2
  doi: 10.2967/jnumed.116.178673
– ident: e_1_2_9_41_1
  doi: 10.1039/D1SC02789A
– ident: e_1_2_9_24_2
  doi: 10.1007/BF02386681
– ident: e_1_2_9_35_2
  doi: 10.1002/chem.201600922
– ident: e_1_2_9_2_2
  doi: 10.1089/cbr.2020.3576
– ident: e_1_2_9_32_2
  doi: 10.1021/acs.orglett.5b02875
– ident: e_1_2_9_13_2
  doi: 10.2174/1874471011306020001
– ident: e_1_2_9_9_2
  doi: 10.1088/1742-6596/41/1/009
– ident: e_1_2_9_43_2
  doi: 10.1016/0883-2889(86)90274-1
– volume: 65
  start-page: 123.267043
  year: 2024
  ident: e_1_2_9_51_2
  publication-title: J. Nucl. Med.
  doi: 10.2967/jnumed.123.267043
  contributor:
    fullname: Fakiri M. E.
– ident: e_1_2_9_18_1
– ident: e_1_2_9_20_2
  doi: 10.1002/1099-1344(20001030)43:12<1219::AID-JLCR409>3.0.CO;2-P
– ident: e_1_2_9_37_1
– ident: e_1_2_9_34_1
– ident: e_1_2_9_58_2
  doi: 10.3390/ph16040595
– ident: e_1_2_9_29_1
– ident: e_1_2_9_64_2
  doi: 10.1021/acs.bioconjchem.2c00042
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Snippet A set of At-astatoarenes were synthesized from corresponding trimethylgermyl arenes with an average radiochemical conversion (RCC) of ca. 50 % for...
A set of 211 At‐astatoarenes were synthesized from corresponding trimethylgermyl arenes with an average radiochemical conversion (RCC) of ca. 50 % for...
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