Design and Catalyzed Activation of Mycophenolic Acid Prodrugs.
Journal
ACS medicinal chemistry letters
ISSN: 1948-5875
Titre abrégé: ACS Med Chem Lett
Pays: United States
ID NLM: 101521073
Informations de publication
Date de publication:
13 May 2021
13 May 2021
Historique:
received:
03
02
2021
accepted:
05
04
2021
entrez:
31
5
2021
pubmed:
1
6
2021
medline:
1
6
2021
Statut:
epublish
Résumé
Mycophenolic acid (MPA) and its morpholino ester prodrug mycophenolate mofetil (MMF) are widely used in solid organ transplantation. These drugs prevent rejection due to their potent inhibition of inosine-5'-monophosphate dehydrogenase (IMPDH), an enzyme vital for lymphocyte proliferation. As a strategy to provide localized immunosuppression in cell transplantation, four mycophenolic acid prodrugs designed to release MPA by two distinct mechanisms were synthesized and characterized. A nitrobenzyl ether prodrug was effectively converted to MPA upon exposure to bacterial nitroreductase, while a propargyl ether was converted to the active drug by immobilized Pd
Identifiants
pubmed: 34055230
doi: 10.1021/acsmedchemlett.1c00079
pmc: PMC8155237
doi:
Types de publication
Journal Article
Langues
eng
Pagination
812-816Subventions
Organisme : NIDDK NIH HHS
ID : R15 DK127340
Pays : United States
Informations de copyright
© 2021 American Chemical Society.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
Références
Biomaterials. 2018 Mar;159:13-24
pubmed: 29309990
Angew Chem Int Ed Engl. 2017 Oct 2;56(41):12548-12552
pubmed: 28699691
Analyst. 2017 May 2;142(9):1545-1553
pubmed: 28374881
ACS Med Chem Lett. 2020 Jan 03;11(2):141-146
pubmed: 32071680
Chemistry. 2018 Nov 13;24(63):16783-16790
pubmed: 30187973
Bioorg Med Chem Lett. 2012 Nov 1;22(21):6583-6
pubmed: 23031595
J Med Chem. 2014 Jun 26;57(12):5395-404
pubmed: 24867590
J Med Chem. 2003 Sep 11;46(19):4009-20
pubmed: 12954054
Chem Commun (Camb). 2015 Aug 18;51(64):12787-90
pubmed: 26165999
Chem Sci. 2018 Jul 17;9(37):7354-7361
pubmed: 30542538
Mol Pharmacol. 2006 Apr;69(4):1288-95
pubmed: 16373689
Mol Pharm. 2009 May-Jun;6(3):801-12
pubmed: 19265397
Biomater Sci. 2020 Jan 1;8(1):266-277
pubmed: 31690897
Nat Protoc. 2012 May 31;7(6):1207-18
pubmed: 22653159
Chembiochem. 2009 Jun 15;10(9):1453-6
pubmed: 19444829
Cancer Lett. 2017 Nov 1;408:1-9
pubmed: 28838843
J Med Chem. 2016 Nov 10;59(21):9974-9980
pubmed: 27786474
Immunopharmacology. 2000 May;47(2-3):85-118
pubmed: 10878285
Nat Commun. 2014;5:3277
pubmed: 24522696
Diabetologia. 1993 Nov;36(11):1139-45
pubmed: 8270128
Bioorg Med Chem Lett. 2000 Sep 18;10(18):2083-6
pubmed: 10999476
Br J Cancer. 2003 Mar 24;88(6):937-9
pubmed: 12644833
J Invest Surg. 2014 Aug;27(4):205-13
pubmed: 24564245
Adv Drug Deliv Rev. 2017 Sep 1;118:65-77
pubmed: 28676386
Immunopharmacology. 2000 May;47(2-3):215-45
pubmed: 10878291
Pharm Res. 1990 Feb;7(2):161-6
pubmed: 2308896
Nat Chem. 2011 Mar;3(3):239-43
pubmed: 21336331
Lancet. 1996 Nov 16;348(9038):1357-9
pubmed: 8918281
J Med Chem. 2005 Nov 17;48(23):7457-67
pubmed: 16279805