Nucleotide-Bearing Benzylidene-Tetrahydroxanthylium Near-IR Fluorophore for Sensing DNA Replication, Secondary Structures and Interactions.
DNA
fluorescence
nucleotides
real-time PCR
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
16 Sep 2020
16 Sep 2020
Historique:
received:
06
07
2020
pubmed:
8
7
2020
medline:
25
2
2021
entrez:
8
7
2020
Statut:
ppublish
Résumé
Thymidine triphosphate bearing benzylidene-tetrahydroxanthylium near-IR fluorophore linked to the 5-methyl group via triazole was synthesized through the CuAAC reaction and was used for polymerase synthesis of labelled DNA probes. The fluorophore lights up upon incorporation to DNA (up to 348-times) presumably due to interactions in major groove and the fluorescence further increases in the single-stranded oligonucleotide. The labelled dsDNA senses binding of small molecules and proteins by a strong decrease of fluorescence. The nucleotide was used as a light-up building block in real-time PCR for detection of SARS-CoV-2 virus.
Identifiants
pubmed: 32633433
doi: 10.1002/chem.202003192
pmc: PMC7361531
doi:
Substances chimiques
DNA Probes
0
Nucleotides
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
11950-11954Subventions
Organisme : Grantová Agentura České Republiky
ID : 17-14791S
Organisme : Akademie Věd České Republiky
ID : Praemium academiae
Organisme : European Regional Development Fund
ID : CZ.02.1.01/0.0/0.0/16_019/0000729
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
J Biol Chem. 1967 Feb 25;242(4):679-86
pubmed: 6017737
Chem Commun (Camb). 2013 May 21;49(41):4652-4
pubmed: 23579777
Nature. 1992 Oct 29;359(6398):859-61
pubmed: 1436062
Angew Chem Int Ed Engl. 2019 Oct 28;58(44):15631-15635
pubmed: 31461206
J Am Chem Soc. 2004 Apr 21;126(15):4820-7
pubmed: 15080686
Bioorg Med Chem. 2001 Sep;9(9):2511-8
pubmed: 11553493
Angew Chem Int Ed Engl. 2016 Jan 4;55(1):174-8
pubmed: 26768820
Chembiochem. 2011 Mar 7;12(4):567-75
pubmed: 21322103
Nucleic Acids Res. 2000 Oct 1;28(19):3752-61
pubmed: 11000267
Biotech Histochem. 1995 Sep;70(5):220-33
pubmed: 8580206
Acc Chem Res. 2019 Jun 18;52(6):1730-1737
pubmed: 31181911
Org Biomol Chem. 2020 Feb 7;18(5):912-919
pubmed: 31919486
Nat Chem. 2017 Nov;9(11):1043-1055
pubmed: 29064490
Molecules. 2012 Nov 15;17(11):13569-91
pubmed: 23154273
FEBS Lett. 1993 Jan 2;315(1):61-4
pubmed: 8416812
Angew Chem Int Ed Engl. 2018 Jul 26;57(31):9891-9895
pubmed: 29578619
Bioorg Med Chem. 2014 May 1;22(9):2613-21
pubmed: 24726303
Euro Surveill. 2020 Jan;25(3):
pubmed: 31992387
Org Biomol Chem. 2019 Jun 28;17(24):5943-5950
pubmed: 31157811
J Am Chem Soc. 2017 Feb 1;139(4):1372-1375
pubmed: 28080035
Chem Rev. 2010 May 12;110(5):2579-619
pubmed: 20205430
Bioconjug Chem. 2018 Nov 21;29(11):3906-3912
pubmed: 30365300
Org Biomol Chem. 2017 Feb 1;15(5):1190-1197
pubmed: 28084483
Angew Chem Int Ed Engl. 2018 Nov 19;57(47):15405-15409
pubmed: 30240107
J Am Chem Soc. 2013 Dec 18;135(50):19025-32
pubmed: 24295172
Chem Commun (Camb). 2015 Mar 21;51(23):4880-2
pubmed: 25704490
Sci Rep. 2019 Apr 10;9(1):5891
pubmed: 30971720
J Org Chem. 2012 Sep 21;77(18):8287-93
pubmed: 22935023
Chemistry. 2016 Feb 12;22(7):2386-95
pubmed: 26773846
Nat Biotechnol. 1999 Aug;17(8):804-7
pubmed: 10429248
Chem Commun (Camb). 2019 Dec 5;55(98):14817-14820
pubmed: 31763632
PLoS One. 2013 Jul 24;8(7):e70510
pubmed: 23894663
Org Biomol Chem. 2018 Feb 28;16(9):1496-1507
pubmed: 29417128
Biotechniques. 2005 Jul;39(1):75-85
pubmed: 16060372
Org Biomol Chem. 2019 Feb 20;17(8):2077-2080
pubmed: 30681106
Chem Sci. 2016 Sep 1;7(9):5775-5785
pubmed: 30034716
Anal Chem. 2007 Feb 1;79(3):1022-9
pubmed: 17263330
Chemistry. 2017 Jun 27;23(36):8736-8740
pubmed: 28481024
Analyst. 2015 Apr 21;140(8):2671-8
pubmed: 25734317
Acc Chem Res. 2016 Mar 15;49(3):418-27
pubmed: 26947566
Int J Food Microbiol. 2005 Jul 15;102(2):161-71
pubmed: 15913820
Chem Commun (Camb). 2013 Jun 25;49(50):5684-6
pubmed: 23685520
Angew Chem Int Ed Engl. 2009;48(35):6480-4
pubmed: 19637175
Nucleic Acids Res. 2003 Nov 1;31(21):6227-34
pubmed: 14576310
Chembiochem. 2018 Sep 17;19(18):1939-1943
pubmed: 29953711
Acc Chem Res. 2016 Apr 19;49(4):714-23
pubmed: 26963493
Chem Asian J. 2008 Jun 2;3(6):958-68
pubmed: 18446920
Nucleic Acids Res. 2016 May 5;44(8):e79
pubmed: 26819406
Chemistry. 2020 Sep 16;26(52):11950-11954
pubmed: 32633433
ACS Chem Biol. 2013 May 17;8(5):890-4
pubmed: 23402653
Biosens Bioelectron. 2017 May 15;91:699-705
pubmed: 28126659
Front Chem. 2020 Feb 28;8:112
pubmed: 32181238
Chembiochem. 2014 Apr 14;15(6):789-93
pubmed: 24644275