Interstrand DNA Cross-Links Derived from Reaction of a 2-Aminopurine Residue with an Abasic Site.
Journal
ACS chemical biology
ISSN: 1554-8937
Titre abrégé: ACS Chem Biol
Pays: United States
ID NLM: 101282906
Informations de publication
Date de publication:
19 07 2019
19 07 2019
Historique:
pubmed:
2
7
2019
medline:
31
12
2019
entrez:
2
7
2019
Statut:
ppublish
Résumé
Efficient methods for the site-specific installation of structurally defined interstrand cross-links in duplex DNA may be useful in a wide variety of fields. The work described here developed a high-yield synthesis of chemically stable interstrand cross-links resulting from a reductive amination reaction between an abasic site and the noncanonical nucleobase 2-aminopurine in duplex DNA. Results from footprinting, liquid chromatography-mass spectrometry, and stability studies support the formation of an
Identifiants
pubmed: 31259519
doi: 10.1021/acschembio.9b00208
pmc: PMC8667195
mid: NIHMS1760719
doi:
Substances chimiques
Cross-Linking Reagents
0
2-Aminopurine
452-06-2
DNA
9007-49-2
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Langues
eng
Sous-ensembles de citation
IM
Pagination
1481-1489Subventions
Organisme : NIEHS NIH HHS
ID : R01 ES021007
Pays : United States
Organisme : NIEHS NIH HHS
ID : T32 ES018827
Pays : United States
Références
Nucleic Acids Res. 2017 Jun 20;45(11):6486-6493
pubmed: 28431012
Bioconjug Chem. 2018 Nov 21;29(11):3810-3816
pubmed: 30350578
Biochemistry. 2002 Jun 4;41(22):7054-64
pubmed: 12033939
Methods Enzymol. 1980;65(1):499-560
pubmed: 6246368
Cell Rep. 2017 Oct 31;21(5):1375-1385
pubmed: 29091773
Angew Chem Int Ed Engl. 2010 Aug 9;49(34):5989-92
pubmed: 20632340
J Am Chem Soc. 2011 Sep 21;133(37):14488-91
pubmed: 21859143
Methods Enzymol. 2001;340:396-412
pubmed: 11494861
Anal Chem. 2008 Nov 15;80(22):8790-8
pubmed: 18947205
Biochemistry. 2015 Mar 10;54(9):1849-57
pubmed: 25679877
J Am Chem Soc. 2013 Jan 23;135(3):1015-25
pubmed: 23215239
Biochemistry. 2016 Dec 20;55(50):7033-7041
pubmed: 27992994
Angew Chem Int Ed Engl. 2014 Jul 1;53(27):7001-5
pubmed: 24840115
J Am Chem Soc. 2014 Mar 5;136(9):3483-90
pubmed: 24506784
Cell. 2016 Oct 6;167(2):498-511.e14
pubmed: 27693351
Q Rev Biophys. 2015 May;48(2):244-79
pubmed: 25881643
Nucleic Acids Res. 2008 Jan;36(1):253-62
pubmed: 18025040
Nucleic Acids Res. 1987 Sep 25;15(18):7451-62
pubmed: 3658699
Nucleic Acids Res. 2015 Apr 20;43(7):3434-41
pubmed: 25779045
Angew Chem Int Ed Engl. 2015 Jan 12;54(3):796-800
pubmed: 25446281
Curr Protoc Nucleic Acid Chem. 2016 Jun 01;65:5.16.1-5.16.15
pubmed: 27248783
Chem Res Toxicol. 2004 Jul;17(7):839-56
pubmed: 15257608
Chem Res Toxicol. 2009 Nov;22(11):1747-60
pubmed: 19757819
Nucleic Acids Res. 2014 Jun;42(11):7429-35
pubmed: 24782532
Proc Natl Acad Sci U S A. 1988 Sep;85(17):6242-6
pubmed: 3413094
J Biol Chem. 1987 Jul 25;262(21):10171-9
pubmed: 2440861
Angew Chem Int Ed Engl. 2015 Jun 22;54(26):7666-9
pubmed: 25967397
Bioorg Med Chem Lett. 2005 Apr 15;15(8):2111-3
pubmed: 15808479
Methods Mol Biol. 2012;920:203-19
pubmed: 22941606
Biochemistry. 1991 Apr 23;30(16):4055-61
pubmed: 2018771
Chem Commun (Camb). 2016 Jun 28;52(51):8014-7
pubmed: 27265774
J Am Chem Soc. 2013 Oct 30;135(43):16161-7
pubmed: 24087918
J Am Chem Soc. 2007 Feb 21;129(7):1852-3
pubmed: 17253689
Bioorg Med Chem. 2011 Oct 1;19(19):5788-93
pubmed: 21903404
Biochemistry. 1996 Sep 24;35(38):12329-37
pubmed: 8823167
J Org Chem. 2014 May 16;79(10):4423-37
pubmed: 24693949
Biopolymers. 1999;52(2):65-83
pubmed: 10898853
Biochemistry. 2015 Jul 14;54(27):4259-66
pubmed: 26103998
Chembiochem. 2017 Jul 18;18(14):1383-1386
pubmed: 28422400
Nucleic Acids Res. 2009 Apr;37(5):1555-65
pubmed: 19151089
J Am Chem Soc. 2015 Mar 25;137(11):3933-45
pubmed: 25710271
Nucleic Acids Res. 2016 Sep 6;44(15):7281-91
pubmed: 27257072
J Org Chem. 2000 May 19;65(10):2959-64
pubmed: 10814184
Anal Chem. 2008 Apr 15;80(8):2932-8
pubmed: 18324836
Chem Res Toxicol. 2000 Sep;13(9):907-12
pubmed: 10995264
Electrophoresis. 1990 May;11(5):355-60
pubmed: 2194789
Biochemistry. 1996 Apr 2;35(13):4026-33
pubmed: 8672436
J Am Chem Soc. 2009 Aug 12;131(31):11132-9
pubmed: 19722676
Anal Chem. 2003 Nov 15;75(22):6306-13
pubmed: 14616015