Azetidines-Containing Fluorescent Purine Analogs: Synthesis and Photophysical Properties.
RNA
fluorescence
heterocycles
modified nucleosides
nucleosides
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
25 May 2022
25 May 2022
Historique:
received:
10
03
2022
pubmed:
19
3
2022
medline:
27
5
2022
entrez:
18
3
2022
Statut:
ppublish
Résumé
Analogues of N,N-dimethyladenine exploiting both thieno-and isothiazolo-pyrimidine cores were modified with 3-subsituted azetidines to yield visibly emissive and responsive fluorophores. The emission quantum yields, among the highest seen for purine analogues (0.64 and 0.77 in water and dioxane respectively), correlated with the Hammett inductive constants of the substituents on the azetidine ring. Ribosylation of the difluoroazetidino-modified nucleobase yielded an emissive nucleoside that displayed a substantially lower emission quantum yield in water, compared to the precursor nucleobase. Importantly, high emission quantum yield was restored in deuterium oxide, which highlights the potential impact of the sugar moiety on the photophysical features of fluorescent nucleosides, a functionality usually considered non-chromophoric and photophysically benign.
Identifiants
pubmed: 35303392
doi: 10.1002/chem.202200765
pmc: PMC9133108
mid: NIHMS1791037
doi:
Substances chimiques
Antimetabolites
0
Azetidines
0
Fluorescent Dyes
0
Nucleosides
0
Purines
0
Water
059QF0KO0R
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200765Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM139407
Pays : United States
Organisme : NIGMS NIH HHS
ID : GM139407
Pays : United States
Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
RNA. 2010 Dec;16(12):2319-24
pubmed: 20962038
Chem Rev. 2003 Oct;103(10):3899-4032
pubmed: 14531716
Nat Methods. 2015 Mar;12(3):244-50, 3 p following 250
pubmed: 25599551
ACS Chem Biol. 2021 Jul 16;16(7):1208-1214
pubmed: 34190533
JACS Au. 2021 May 24;1(5):690-696
pubmed: 34056637
Gene. 2000 Oct 17;257(1):33-43
pubmed: 11054566
Bioorg Med Chem. 2014 Dec 15;22(24):6989-95
pubmed: 25457127
Chembiochem. 2020 Sep 14;21(18):2595-2598
pubmed: 32346955
Chem Sci. 2017 Apr 1;8(4):2983-2993
pubmed: 28451365
Eur Biophys J. 1988;16(3):131-42
pubmed: 2847910
RNA. 2017 Dec;23(12):1754-1769
pubmed: 28855326
Chem Rev. 2010 May 12;110(5):2579-619
pubmed: 20205430
J Am Chem Soc. 2011 Sep 28;133(38):14912-5
pubmed: 21866967
Chem Sci. 2020 Nov 19;12(4):1352-1362
pubmed: 34163898
Nucleic Acids Res. 2017 Feb 28;45(4):2007-2015
pubmed: 28204608
Molecules. 2011 Jun 21;16(6):5168-81
pubmed: 21694680
Nat Methods. 2017 Oct;14(10):987-994
pubmed: 28869757
J Am Chem Soc. 2015 Nov 25;137(46):14602-5
pubmed: 26523462
Angew Chem Int Ed Engl. 2018 Jan 22;57(4):1087-1090
pubmed: 29228460
Chemistry. 2020 May 12;26(27):6076-6084
pubmed: 32157755
Wiley Interdiscip Rev RNA. 2020 Sep;11(5):e1595
pubmed: 32301288
Nat Chem Biol. 2021 Apr;17(4):412-420
pubmed: 33462493