Epigenetic Pyrimidine Nucleotides in Competition with Natural dNTPs as Substrates for Diverse DNA Polymerases.


Journal

ACS chemical biology
ISSN: 1554-8937
Titre abrégé: ACS Chem Biol
Pays: United States
ID NLM: 101282906

Informations de publication

Date de publication:
21 10 2022
Historique:
pubmed: 10 6 2022
medline: 25 10 2022
entrez: 9 6 2022
Statut: ppublish

Résumé

Five 2'-deoxyribonucleoside triphosphates (dNTPs) derived from epigenetic pyrimidines (5-methylcytosine, 5-hydroxymethylcytosine, 5-formylcytosine, 5-hydroxymethyluracil, and 5-formyluracil) were prepared and systematically studied as substrates for nine DNA polymerases in competition with natural dNTPs by primer extension experiments. The incorporation of these substrates was evaluated by a restriction endonucleases cleavage-based assay and by a kinetic study of single nucleotide extension. All of the modified pyrimidine dNTPs were good substrates for the studied DNA polymerases that incorporated a significant percentage of the modified nucleotides into DNA even in the presence of natural nucleotides. 5-Methylcytosine dNTP was an even better substrate for most polymerases than natural dCTP. On the other hand, 5-hydroxymethyl-2'-deoxyuridine triphosphate was not the best substrate for SPO1 DNA polymerase, which naturally synthesizes 5hmU-rich genomes of the SPO1 bacteriophage. The results shed light onto the possibility of gene silencing through recycling and random incorporation of epigenetic nucleotides and into the replication of modified bacteriophage genomes.

Identifiants

pubmed: 35679536
doi: 10.1021/acschembio.2c00342
pmc: PMC9594043
doi:

Substances chimiques

Pyrimidine Nucleotides 0
5-Methylcytosine 6R795CQT4H
DNA-Directed DNA Polymerase EC 2.7.7.7
Nucleotides 0
DNA 9007-49-2
DNA Restriction Enzymes EC 3.1.21.-
Pyrimidines 0
Deoxyribonucleosides 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

2781-2788

Références

Chem Sci. 2019 Mar 4;10(14):3937-3942
pubmed: 31015933
J Am Chem Soc. 2012 Jul 25;134(29):11840-3
pubmed: 22475415
Genome Biol. 2017 Jan 30;18(1):23
pubmed: 28137275
Proc Natl Acad Sci U S A. 1998 Jul 21;95(15):8727-32
pubmed: 9671746
Chem Sci. 2017 Jun 1;8(6):4505-4510
pubmed: 28660064
Science. 2012 May 18;336(6083):934-7
pubmed: 22539555
Nature. 2015 Nov 5;527(7576):118-22
pubmed: 26524525
Nucleic Acids Res. 1997 Apr 15;25(8):1570-7
pubmed: 9092664
EcoSal Plus. 2021 Dec 15;9(2):eESP00282019
pubmed: 34910575
J Org Chem. 1993;58(7):1664-1665
pubmed: 35859906
J Mol Biol. 2009 Apr 24;388(1):48-70
pubmed: 19285085
Nat Commun. 2015 Oct 27;6:8716
pubmed: 26503889
Nucleic Acids Res. 2009 Dec;37(22):7612-22
pubmed: 19820117
Somat Cell Mol Genet. 1995 Jul;21(4):285-8
pubmed: 8525434
Mutat Res. 1998 May 25;400(1-2):361-8
pubmed: 9685696
Acc Chem Res. 2019 Jun 18;52(6):1730-1737
pubmed: 31181911
Nat Chem Biol. 2014 Jul;10(7):574-81
pubmed: 24838012
J Am Chem Soc. 2013 Oct 2;135(39):14593-9
pubmed: 23980549
Nat Rev Genet. 2010 Mar;11(3):204-20
pubmed: 20142834
Angew Chem Int Ed Engl. 2018 Jul 26;57(31):9891-9895
pubmed: 29578619
Angew Chem Int Ed Engl. 2014 Jun 23;53(26):6734-7
pubmed: 24850380
FEBS Lett. 2002 May 22;519(1-3):128-34
pubmed: 12023031
Angew Chem Int Ed Engl. 2011 Sep 5;50(37):8727-30
pubmed: 21805545
Science. 2011 Sep 2;333(6047):1303-7
pubmed: 21817016
Chembiochem. 2011 Feb 11;12(3):431-8
pubmed: 21290545
Mutat Res Rev Mutat Res. 2016 Jan-Mar;767:59-66
pubmed: 27036066
Anal Chem. 2017 Apr 4;89(7):4153-4160
pubmed: 28271879
Nat Chem. 2018 Dec;10(12):1258-1266
pubmed: 30349137
Angew Chem Int Ed Engl. 2015 Oct 12;54(42):12511-4
pubmed: 26137924
Cell Chem Biol. 2016 Jan 21;23(1):74-85
pubmed: 26933737
Somat Cell Mol Genet. 1991 Nov;17(6):543-50
pubmed: 1722592
Org Lett. 2013 Jan 18;15(2):366-9
pubmed: 23286330
Nucleic Acids Res. 1998 Oct 15;26(20):4582-7
pubmed: 9753724
ACS Chem Biol. 2016 Nov 18;11(11):3165-3171
pubmed: 27668519
Chemistry. 2017 Feb 10;23(9):2109-2118
pubmed: 27901305
Biochemistry. 2004 May 18;43(19):5688-97
pubmed: 15134443
Front Microbiol. 2019 Mar 29;10:584
pubmed: 30984133
Chem Rev. 2015 Mar 25;115(6):2225-39
pubmed: 25675246
Mutat Res. 1993 Apr;286(2):217-20
pubmed: 7681533
Acc Chem Res. 2016 Mar 15;49(3):418-27
pubmed: 26947566
Angew Chem Int Ed Engl. 2018 Apr 9;57(16):4296-4312
pubmed: 28941008
Front Microbiol. 2020 Oct 27;11:604618
pubmed: 33193286
Gene. 1992 Sep 1;118(1):109-13
pubmed: 1324872
Angew Chem Int Ed Engl. 2014 Jul 14;53(29):7552-5
pubmed: 24890276
Chem Commun (Camb). 2017 Dec 12;53(99):13253-13255
pubmed: 29184924
Proc Natl Acad Sci U S A. 2018 Apr 03;115(14):E3116-E3125
pubmed: 29555775
Chem Rev. 2016 Oct 26;116(20):12655-12687
pubmed: 27319741
PLoS One. 2010 Dec 23;5(12):e15367
pubmed: 21203455
Cancer. 1996 Feb 15;77(4):691-6
pubmed: 8616761
Curr Opin Chem Biol. 2020 Aug;57:1-7
pubmed: 32145439

Auteurs

Šimon Pospíšil (Š)

Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nam. 2, CZ-16000 Prague 6, Czech Republic.
Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, CZ-12843 Prague 2, Czech Republic.

Alessandro Panattoni (A)

Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nam. 2, CZ-16000 Prague 6, Czech Republic.

Filip Gracias (F)

Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nam. 2, CZ-16000 Prague 6, Czech Republic.

Veronika Sýkorová (V)

Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nam. 2, CZ-16000 Prague 6, Czech Republic.

Viola Vaňková Hausnerová (VV)

Lab. of Microbial Genetics and Gene Expression, Institute of Microbiology, Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague 4, Czech Republic.

Dragana Vítovská (D)

Lab. of Microbial Genetics and Gene Expression, Institute of Microbiology, Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague 4, Czech Republic.

Hana Šanderová (H)

Lab. of Microbial Genetics and Gene Expression, Institute of Microbiology, Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague 4, Czech Republic.

Libor Krásný (L)

Lab. of Microbial Genetics and Gene Expression, Institute of Microbiology, Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague 4, Czech Republic.

Michal Hocek (M)

Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nam. 2, CZ-16000 Prague 6, Czech Republic.
Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, CZ-12843 Prague 2, Czech Republic.

Articles similaires

Animals Epigenesis, Genetic DNA Methylation Skates, Fish CpG Islands
Schizosaccharomyces Meiosis Schizosaccharomyces pombe Proteins Mitosis Epigenesis, Genetic
Tumor Microenvironment Nanoparticles Immunotherapy Cellular Senescence Animals

Classifications MeSH