Deploying solid-phase synthesis to access thymine-containing nucleoside analogs that inhibit DNA repair nuclease SNM1A.


Journal

Organic & biomolecular chemistry
ISSN: 1477-0539
Titre abrégé: Org Biomol Chem
Pays: England
ID NLM: 101154995

Informations de publication

Date de publication:
19 07 2023
Historique:
medline: 21 7 2023
pubmed: 7 7 2023
entrez: 7 7 2023
Statut: epublish

Résumé

Nucleoside analogs show useful bioactive properties. A versatile solid-phase synthesis that readily enables the diversification of thymine-containing nucleoside analogs is presented. The utility of the approach is demonstrated with the preparation of a library of compounds for analysis with SNM1A, a DNA damage repair enzyme that contributes to cytotoxicity. This exploration provided the most promising nucleoside-derived inhibitor of SNM1A to date with an IC

Identifiants

pubmed: 37417819
doi: 10.1039/d3ob00836c
pmc: PMC10529636
mid: NIHMS1913070
doi:

Substances chimiques

Nucleosides 0
Thymine QR26YLT7LT
Exodeoxyribonucleases EC 3.1.-

Types de publication

Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

5873-5879

Subventions

Organisme : NIGMS NIH HHS
ID : F32 GM136023
Pays : United States
Organisme : NIGMS NIH HHS
ID : R01 GM131627
Pays : United States

Références

Future Oncol. 2010 Jun;6(6):1015-29
pubmed: 20528238
Chem Rev. 2021 Jul 14;121(13):7957-8094
pubmed: 34129337
ChemistrySelect. 2018 Dec 6;3(45):12824-12829
pubmed: 31414040
Bioorg Med Chem. 2021 Sep 15;46:116369
pubmed: 34482229
ChemMedChem. 2022 Mar 4;17(5):e202100603
pubmed: 34905656
Nucleic Acids Res. 2015 Jan;43(1):247-58
pubmed: 25505141
Cell. 2001 Apr 20;105(2):177-86
pubmed: 11336668
Org Lett. 2007 Sep 13;9(19):3797-800
pubmed: 17713918
Nat Protoc. 2006;1(2):550-3
pubmed: 17191086
Chem Commun (Camb). 2016 May 10;52(40):6727-30
pubmed: 27121860
Chem Rev. 2020 May 27;120(10):4301-4354
pubmed: 32356973
Heliyon. 2021 Jan 02;7(1):e05867
pubmed: 33426353
Nucleic Acids Res. 2007;35(18):6115-23
pubmed: 17804464
EMBO J. 2017 Jul 14;36(14):2047-2060
pubmed: 28607004
Cell. 2008 Sep 19;134(6):969-80
pubmed: 18805090
J Med Chem. 2016 Jun 9;59(11):5158-71
pubmed: 26599421
Genes Dev. 2011 Sep 1;25(17):1859-70
pubmed: 21896658
J Comb Chem. 2007 May-Jun;9(3):370-85
pubmed: 17417912
Chem Rev. 2021 Jun 23;121(12):7122-7154
pubmed: 33443411
Nucleic Acids Res. 2015 Dec 15;43(22):11047-60
pubmed: 26582912
Carbohydr Polym. 2020 Jan 15;228:115393
pubmed: 31635737
Cell Cycle. 2011 Dec 1;10(23):3999-4008
pubmed: 22101340
Org Biomol Chem. 2019 Sep 21;17(35):8094-8105
pubmed: 31380542
Molecules. 2021 Jan 09;26(2):
pubmed: 33435514
Drug Dev Res. 2022 Feb;83(1):3-15
pubmed: 34506652
Nat Rev Cancer. 2011 Jun 24;11(7):467-80
pubmed: 21701511
J Biol Chem. 2012 Jul 27;287(31):26254-67
pubmed: 22692201
Org Lett. 2022 Mar 25;24(11):2170-2174
pubmed: 35271284
Org Biomol Chem. 2008 Oct 21;6(20):3741-50
pubmed: 18843404

Auteurs

Christine A Arbour (CA)

Department of Biology and Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA. imper@mit.edu.

Ellen M Fay (EM)

School of Chemistry and Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St., Dublin 2, Ireland.

Joanna F McGouran (JF)

School of Chemistry and Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St., Dublin 2, Ireland.

Barbara Imperiali (B)

Department of Biology and Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA. imper@mit.edu.

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Classifications MeSH