Easy-to-Implement Hydrogen Isotope Exchange for the Labeling of


Journal

JACS Au
ISSN: 2691-3704
Titre abrégé: JACS Au
Pays: United States
ID NLM: 101775714

Informations de publication

Date de publication:
25 Apr 2022
Historique:
received: 08 11 2021
entrez: 13 5 2022
pubmed: 14 5 2022
medline: 14 5 2022
Statut: epublish

Résumé

Facilitating access to deuterated and tritiated complex molecules is of paramount importance due to the fundamental role of isotopically labeled compounds in drug discovery and development. Deuterated analogues of drugs are extensively used as internal standards for quantification purposes or as active pharmaceutical ingredients, whereas tritiated drugs are essential for preclinical ADME studies. In this report, we describe the labeling of prevalent substructures in FDA-approved drugs such as azines, indoles, alkylamine moieties, or benzylic carbons by the in situ generation of Rh nanoparticles able to catalyze both C(sp

Identifiants

pubmed: 35557763
doi: 10.1021/jacsau.1c00503
pmc: PMC9088292
doi:

Types de publication

Journal Article

Langues

eng

Pagination

801-808

Informations de copyright

© 2022 The Authors. Published by American Chemical Society.

Déclaration de conflit d'intérêts

The authors declare no competing financial interest.

Références

Angew Chem Int Ed Engl. 2015 Sep 1;54(36):10474-7
pubmed: 26371960
Chemistry. 2008;14(2):664-73
pubmed: 17910018
Science. 2017 Dec 1;358(6367):1182-1187
pubmed: 29123019
J Am Chem Soc. 2012 Jul 25;134(29):12239-44
pubmed: 22702889
Chemistry. 2020 Apr 16;26(22):4988-4996
pubmed: 31841248
Org Biomol Chem. 2017 Mar 22;15(12):2507-2511
pubmed: 28266672
Bioorg Khim. 2014 Jan-Feb;40(1):31-41
pubmed: 25898721
JACS Au. 2021 May 24;1(5):690-696
pubmed: 34056637
Chem Commun (Camb). 2014 Dec 7;50(94):14870-2
pubmed: 25325237
J Labelled Comp Radiopharm. 2020 May 30;63(6):266-280
pubmed: 31278771
Angew Chem Int Ed Engl. 2020 Nov 16;59(47):20879-20884
pubmed: 32721061
Angew Chem Int Ed Engl. 2018 Mar 12;57(12):3022-3047
pubmed: 29024330
Chem Rev. 2010 Sep 8;110(9):5425-46
pubmed: 20536148
Angew Chem Int Ed Engl. 2021 Mar 15;60(12):6357-6361
pubmed: 33332703
Br J Surg. 2021 Sep 27;108(9):1056-1063
pubmed: 33761533
J Med Chem. 2009 Jan 22;52(2):329-35
pubmed: 19108654
Nucleic Acids Symp Ser (Oxf). 2009;(53):105-6
pubmed: 19749282
Angew Chem Int Ed Engl. 2018 Feb 12;57(7):1758-1784
pubmed: 28815899
J Am Chem Soc. 2016 Oct 19;138(41):13489-13492
pubmed: 27709928
Med Res Rev. 2001 Sep;21(5):412-49
pubmed: 11579441
Sci Adv. 2018 Aug 22;4(8):eaat7314
pubmed: 30140744
J Labelled Comp Radiopharm. 2020 May 30;63(6):247-265
pubmed: 31410875
Angew Chem Int Ed Engl. 2020 Nov 16;59(47):21114-21120
pubmed: 33463019
Chem Sci. 2020 Aug 5;11(33):8912-8918
pubmed: 34123145
J Med Chem. 2019 Jun 13;62(11):5276-5297
pubmed: 30640460
Nat Commun. 2019 Oct 25;10(1):4867
pubmed: 31653853
J Am Chem Soc. 2019 Sep 18;141(37):14570-14575
pubmed: 31480842
Adv Mater. 2020 Dec;32(48):e2004421
pubmed: 33119173
Acc Chem Res. 2021 Mar 16;54(6):1465-1480
pubmed: 33622033
Angew Chem Int Ed Engl. 2014 Jan 3;53(1):230-4
pubmed: 24254536
J Am Chem Soc. 2021 Jul 28;143(29):10895-10901
pubmed: 34279928
Nature. 2021 Jan;589(7843):542-547
pubmed: 33238289
ACS Catal. 2017;7(9):5674-5678
pubmed: 29456876
Angew Chem Int Ed Engl. 2021 Aug 16;60(34):18645-18650
pubmed: 34114304
Org Lett. 2004 Apr 29;6(9):1485-7
pubmed: 15101773
Org Lett. 2016 Nov 18;18(22):5892-5895
pubmed: 27805814
Angew Chem Int Ed Engl. 2021 Dec 13;60(51):26671-26676
pubmed: 34424591
Chemistry. 2020 Oct 6;26(56):12738-12742
pubmed: 32716576

Auteurs

Etienne Levernier (E)

Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Université Paris-Saclay, CEA, INRAE, 91191 Gif-sur-Yvette, France.

Kevin Tatoueix (K)

Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Université Paris-Saclay, CEA, INRAE, 91191 Gif-sur-Yvette, France.

Sébastien Garcia-Argote (S)

Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Université Paris-Saclay, CEA, INRAE, 91191 Gif-sur-Yvette, France.

Viktor Pfeifer (V)

Boehringer Ingelheim Pharma GmbH & Co. KG, Birkendorfer Straße 65, 88397 Biberach an der Riß, Germany.

Ralf Kiesling (R)

Boehringer Ingelheim Pharma GmbH & Co. KG, Birkendorfer Straße 65, 88397 Biberach an der Riß, Germany.

Edmond Gravel (E)

Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Université Paris-Saclay, CEA, INRAE, 91191 Gif-sur-Yvette, France.

Sophie Feuillastre (S)

Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Université Paris-Saclay, CEA, INRAE, 91191 Gif-sur-Yvette, France.

Grégory Pieters (G)

Département Médicaments et Technologies pour la Santé (DMTS), SCBM, Université Paris-Saclay, CEA, INRAE, 91191 Gif-sur-Yvette, France.

Classifications MeSH