Metal-Mediated, Autolytic Amide Bond Cleavage: A Strategy for the Selective, Metal Complexation-Catalyzed, Controlled Release of Metallodrugs.
Journal
Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056
Informations de publication
Date de publication:
26 07 2023
26 07 2023
Historique:
medline:
27
7
2023
pubmed:
12
7
2023
entrez:
12
7
2023
Statut:
ppublish
Résumé
Activation of metalloprodrugs or prodrug activation using transition metal catalysts represents emerging strategies for drug development; however, they are frequently hampered by poor spatiotemporal control and limited catalytic turnover. Here, we demonstrate that metal complex-mediated, autolytic release of active metallodrugs can be successfully employed to prepare clinical grade (radio-)pharmaceuticals. Optimization of the Lewis-acidic metal ion, chelate, amino acid linker, and biological targeting vector provides means to release peptide-based (radio-)metallopharmaceuticals in solution and from the solid phase using metal-mediated, autolytic amide bond cleavage (MMAAC). Our findings indicate that coordinative polarization of an amide bond by strong, trivalent Lewis acids such as Ga
Identifiants
pubmed: 37434328
doi: 10.1021/jacs.3c05492
pmc: PMC10530410
mid: NIHMS1920752
doi:
Substances chimiques
Amides
0
Gallium-67
4LJK511Z86
Gallium Radioisotopes
0
Delayed-Action Preparations
0
Metals
0
Coordination Complexes
0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
16261-16270Subventions
Organisme : NIBIB NIH HHS
ID : R01 EB032349
Pays : United States
Références
J Am Chem Soc. 2019 Nov 20;141(46):18444-18454
pubmed: 31625740
J Am Chem Soc. 2014 Feb 12;136(6):2178-91
pubmed: 24456115
Chem Commun (Camb). 2015 May 21;51(41):8626-9
pubmed: 25898264
J Am Chem Soc. 2021 Dec 8;143(48):20224-20240
pubmed: 34808054
J Am Chem Soc. 2010 Mar 17;132(10):3355-66
pubmed: 20166730
J Nucl Med. 2017 Nov;58(11):1786-1792
pubmed: 28546332
Adv Drug Deliv Rev. 2012 Aug;64(11):993-1004
pubmed: 22289471
J Am Chem Soc. 2020 Apr 8;142(14):6477-6482
pubmed: 32175731
J Am Chem Soc. 2020 May 6;142(18):8203-8210
pubmed: 32290655
J Inorg Biochem. 2011 Feb;105(2):313-20
pubmed: 21194633
Dalton Trans. 2016 Jun 21;45(25):10289-96
pubmed: 27241864
Chem Sci. 2018 Jul 17;9(37):7354-7361
pubmed: 30542538
Angew Chem Int Ed Engl. 2021 May 25;60(22):12446-12454
pubmed: 33719151
Bioconjug Chem. 2016 Feb 17;27(2):376-82
pubmed: 26367192
J Phys Chem Lett. 2022 Sep 15;13(36):8558-8563
pubmed: 36067512
J Am Chem Soc. 2006 Mar 15;128(10):3156-7
pubmed: 16522091
J Am Chem Soc. 2018 Jan 10;140(1):30-33
pubmed: 29211467
J Am Chem Soc. 2022 Jun 8;144(22):9543-9547
pubmed: 34882381
Science. 2012 Feb 10;335(6069):694-8
pubmed: 22267579
J Am Chem Soc. 2022 May 11;144(18):8317-8336
pubmed: 35482975
Sci Adv. 2020 Jul 15;6(29):eabb1421
pubmed: 32832637
Chem Soc Rev. 2020 Nov 7;49(21):7710-7729
pubmed: 33026001
J Pept Res. 1997 Sep;50(3):193-8
pubmed: 9309583
Circ Res. 2000 Oct 13;87(8):670-6
pubmed: 11029402
Theranostics. 2020 Jan 1;10(4):1678-1693
pubmed: 32042329
Nature. 2020 Apr;580(7802):220-226
pubmed: 32066140
J Am Chem Soc. 2019 Sep 18;141(37):14650-14660
pubmed: 31466441
Inorg Chem. 2010 Jul 19;49(14):6636-45
pubmed: 20550138
Pharmaceuticals (Basel). 2014 Jun 30;7(7):779-96
pubmed: 24983957
J Chem Phys. 2022 Nov 7;157(17):174301
pubmed: 36347691
Angew Chem Int Ed Engl. 2012 Jun 4;51(23):5723-6
pubmed: 22522567
Inorg Chem. 2011 Dec 5;50(23):12025-33
pubmed: 22040112
J Am Chem Soc. 2019 Oct 30;141(43):17048-17052
pubmed: 31503474
Chem Rev. 2022 Jun 8;122(11):10266-10318
pubmed: 35549242
Chem Sci. 2017 Jun 1;8(6):4619-4625
pubmed: 28626570
Metallomics. 2020 May 27;12(5):649-653
pubmed: 32393924
J Am Chem Soc. 2010 Apr 14;132(14):4994-5
pubmed: 20297791
Chem Sci. 2018 Jul 12;9(36):7198-7203
pubmed: 30288239
J Nutr. 2000 May;130(5S Suppl):1437S-46S
pubmed: 10801957
J Med Chem. 2013 Feb 28;56(4):1782-6
pubmed: 23391162
J Am Chem Soc. 2009 Jul 15;131(27):9475-7
pubmed: 19534521
Inorg Chem. 2012 Aug 20;51(16):8848-59
pubmed: 22845736
Bioconjug Chem. 2021 Jul 21;32(7):1232-1241
pubmed: 33284001
J Am Chem Soc. 2020 Jun 17;142(24):10869-10880
pubmed: 32456416
Phys Chem Chem Phys. 2019 Dec 18;22(1):107-113
pubmed: 31807746
Chem Rev. 2019 Jan 23;119(2):1138-1192
pubmed: 30299085
J Am Chem Soc. 2019 Oct 30;141(43):17133-17141
pubmed: 31580665
Mol Pharm. 2022 Sep 5;19(9):3217-3227
pubmed: 35895995
J Am Chem Soc. 2022 Mar 23;144(11):4966-4976
pubmed: 35258952
Angew Chem Int Ed Engl. 2022 Jun 27;61(26):e202202855
pubmed: 35419921
Angew Chem Int Ed Engl. 2022 Aug 22;61(34):e202205014
pubmed: 35733240