Phosphonic acid-containing inhibitors of tyrosyl-DNA phosphodiesterase 1.

3′-processed substrate imidazopyrazines imidazopyridines one-pot Groebke-Blackburn-Bienayme multicomponent reactions phosphonic acid tyrosyl-DNA phosphodiesterase 1

Journal

Frontiers in chemistry
ISSN: 2296-2646
Titre abrégé: Front Chem
Pays: Switzerland
ID NLM: 101627988

Informations de publication

Date de publication:
2022
Historique:
received: 01 04 2022
accepted: 11 07 2022
entrez: 2 9 2022
pubmed: 3 9 2022
medline: 3 9 2022
Statut: epublish

Résumé

Tyrosyl-DNA phosphodiesterase 1 (TDP1) repairs stalled type I topoisomerase (TOP1)-DNA complexes by hydrolyzing the phosphodiester bond between the TOP1 Y723 residue and the 3'-phosphate of its DNA substrate. Although TDP1 antagonists could potentially reduce the dose of TOP1 inhibitors needed to achieve effective anticancer effects, the development of validated TDP1 inhibitors has proven to be challenging. This may, in part, be due to the open and extended nature of the TOP1 substrate binding region. We have previously reported imidazopyrazines and imidazopyridines that can inhibit TDP1 catalytic function

Identifiants

pubmed: 36051621
doi: 10.3389/fchem.2022.910953
pii: 910953
pmc: PMC9424690
doi:

Types de publication

Journal Article

Langues

eng

Pagination

910953

Informations de copyright

Copyright © 2022 Zhao, Wang, Lountos, Tropea, Needle, Pommier and Burke.

Déclaration de conflit d'intérêts

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Références

Nat Rev Cancer. 2006 Oct;6(10):789-802
pubmed: 16990856
J Biol Chem. 2005 Oct 28;280(43):36518-28
pubmed: 16141202
J Med Chem. 2001 Feb 1;44(3):340-9
pubmed: 11462975
Acta Crystallogr D Biol Crystallogr. 2009 Oct;65(Pt 10):1074-80
pubmed: 19770504
Chem Sci. 2021 Jan 28;12(11):3876-3884
pubmed: 34163656
Chem Biol. 2003 Feb;10(2):139-47
pubmed: 12618186
Bioorg Med Chem. 2016 Nov 1;24(21):5017-5027
pubmed: 27687971
Acta Crystallogr D Struct Biol. 2019 Oct 1;75(Pt 10):861-877
pubmed: 31588918
Cancers (Basel). 2021 Aug 09;13(16):
pubmed: 34439157
J Mol Biol. 2002 Dec 13;324(5):917-32
pubmed: 12470949
Molecules. 2021 Dec 23;27(1):
pubmed: 35011303
Drug Metab Rev. 2014 Nov;46(4):494-507
pubmed: 25327705
J Med Chem. 2012 Apr 26;55(8):3837-51
pubmed: 22458568
Chem Rev. 2009 Jul;109(7):2894-902
pubmed: 19476377
Expert Opin Ther Pat. 2011 Sep;21(9):1285-92
pubmed: 21843105
Acta Crystallogr D Biol Crystallogr. 2010 Jan;66(Pt 1):12-21
pubmed: 20057044
Angew Chem Int Ed Engl. 1998 Sep 4;37(16):2234-2237
pubmed: 29711433
Nat Rev Cancer. 2009 May;9(5):338-50
pubmed: 19377506
Yao Xue Xue Bao. 2016 Feb;51(2):215-25
pubmed: 29856574
Proc Natl Acad Sci U S A. 1996 Oct 15;93(21):11534-9
pubmed: 8876170
Acta Crystallogr D Biol Crystallogr. 2010 Apr;66(Pt 4):486-501
pubmed: 20383002
Acta Crystallogr D Biol Crystallogr. 2012 Apr;68(Pt 4):352-67
pubmed: 22505256
Acta Crystallogr D Biol Crystallogr. 2006 Aug;62(Pt 8):859-66
pubmed: 16855301
DNA Repair (Amst). 2014 Jan;13:1-9
pubmed: 24355542
J Am Chem Soc. 2020 Dec 16;142(50):21178-21188
pubmed: 33263997
Nat Commun. 2018 Jan 2;9(1):24
pubmed: 29295983
Curr Med Chem. 2010;17(15):1500-8
pubmed: 20166932
Nucleic Acids Res. 2019 Nov 4;47(19):10134-10150
pubmed: 31199869
J Appl Crystallogr. 2007 Aug 1;40(Pt 4):658-674
pubmed: 19461840
J Mol Biol. 2004 May 14;338(5):895-906
pubmed: 15111055
Nat Rev Cancer. 2015 Mar;15(3):137-51
pubmed: 25693836
Mol Divers. 2016 Feb;20(1):233-54
pubmed: 26016721
Protein Sci. 2020 Jan;29(1):315-329
pubmed: 31724275
Biomolecules. 2021 Jul 01;11(7):
pubmed: 34356597
DNA Repair (Amst). 2014 Jul;19:114-29
pubmed: 24856239
Acc Chem Res. 2003 Jun;36(6):426-33
pubmed: 12809529
J Med Chem. 2004 Feb 12;47(4):829-37
pubmed: 14761185
Proc Natl Acad Sci U S A. 2001 Oct 9;98(21):12009-14
pubmed: 11572945

Auteurs

Xue Zhi Zhao (XZ)

Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, MD, United States.

Wenjie Wang (W)

Developmental Therapeutics Branch and Laboratory of Molecular Pharmacology, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Bethesda, MD, United States.

George T Lountos (GT)

Basic Science Program, Frederick National Laboratory for Cancer Research, Frederick, MD, United States.

Joseph E Tropea (JE)

Center for Structural Biology, Center for Cancer Research, National Cancer Institute, Frederick, MD, United States.

Danielle Needle (D)

Center for Structural Biology, Center for Cancer Research, National Cancer Institute, Frederick, MD, United States.

Yves Pommier (Y)

Developmental Therapeutics Branch and Laboratory of Molecular Pharmacology, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Bethesda, MD, United States.

Terrence R Burke (TR)

Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, MD, United States.

Classifications MeSH