Enzymatic Syntheses and Applications of Fluorescent Cyclic Dinucleotides.


Journal

Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783

Informations de publication

Date de publication:
12 May 2020
Historique:
received: 09 03 2020
pubmed: 12 3 2020
medline: 19 8 2020
entrez: 12 3 2020
Statut: ppublish

Résumé

Bacterial cyclic dinucleotides (CDNs) play important roles in regulating biofilm formation, motility and virulence. In eukaryotic cells, theses bacterial CDNs are recognized as pathogen-associated molecular patterns (PAMPs) and trigger an innate immune response. We report the photophysical analyses of a novel group of enzymatically synthesized emissive CDN analogues comprised of two families of isomorphic ribonucleotides. The highly favorable photophysical features of the CDN analogues, when compared to their non-emissive natural counterparts, are used to monitor in real time the dinucleotide cyclase-mediated synthesis and phosphodiesterase (PDE)-mediated hydrolysis of homodimeric and mixed CDNs, providing effective means to probe the activities of two classes of bacterial enzymes and insight into their biomolecular recognition and catalytic features.

Identifiants

pubmed: 32157755
doi: 10.1002/chem.202001194
pmc: PMC7220823
mid: NIHMS1574641
doi:

Substances chimiques

Bacterial Proteins 0
Dinucleoside Phosphates 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

6076-6084

Subventions

Organisme : NIGMS NIH HHS
ID : R01 GM069773
Pays : United States
Organisme : NIGMS NIH HHS
ID : GM 069773
Pays : United States

Informations de copyright

© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Références

Front Microbiol. 2019 Sep 13;10:2111
pubmed: 31572324
Cell. 2013 Aug 29;154(5):962-970
pubmed: 23993090
Chem Rev. 2013 Oct 9;113(10):7354-401
pubmed: 23767818
Org Biomol Chem. 2012 Dec 14;10(46):9113-29
pubmed: 23108253
Chem Sci. 2016 Sep 1;7(9):6238-6244
pubmed: 30034764
Genes (Basel). 2017 Aug 07;8(8):
pubmed: 28783096
J Am Chem Soc. 2017 Nov 8;139(44):15556-15559
pubmed: 29043790
J Bacteriol. 2005 Jul;187(14):4774-81
pubmed: 15995192
Nucleic Acids Res. 2018 Apr 6;46(6):2765-2776
pubmed: 29514227
J Am Chem Soc. 2015 Nov 25;137(46):14602-5
pubmed: 26523462
J Am Chem Soc. 2011 Oct 5;133(39):15578-92
pubmed: 21838307
Angew Chem Int Ed Engl. 2018 Jan 22;57(4):1087-1090
pubmed: 29228460
Mol Cell. 2013 Jul 25;51(2):226-35
pubmed: 23747010
Cell. 2014 Aug 28;158(5):1011-1021
pubmed: 25131990
Cell. 2012 Apr 13;149(2):358-70
pubmed: 22500802
J Biol Chem. 2009 May 8;284(19):13174-84
pubmed: 19244251
Mol Biosyst. 2012 Mar;8(3):772-8
pubmed: 22182995
Angew Chem Int Ed Engl. 2016 Jul 4;55(28):7974-7978
pubmed: 27273741
Chem Rev. 2010 May 12;110(5):2579-619
pubmed: 20205430
Cell Res. 2014 Oct;24(10):1270-3
pubmed: 25245040
J Am Chem Soc. 2011 Sep 28;133(38):14912-5
pubmed: 21866967
Immunity. 2017 Mar 21;46(3):433-445
pubmed: 28329705
Cell Rep. 2013 May 30;3(5):1355-61
pubmed: 23707065
J Am Chem Soc. 2012 Jan 18;134(2):1019-29
pubmed: 22142443
J Bacteriol. 2008 May;190(10):3622-31
pubmed: 18344366
Nature. 1987 Jan 15-21;325(6101):279-81
pubmed: 18990795
Nat Rev Microbiol. 2013 Aug;11(8):513-24
pubmed: 23812326
Microb Biotechnol. 2012 Mar;5(2):168-76
pubmed: 21958423
Cell. 2013 May 23;153(5):1094-107
pubmed: 23647843
Angew Chem Int Ed Engl. 2017 Jan 24;56(5):1303-1307
pubmed: 28000329
Microbiol Mol Biol Rev. 2013 Mar;77(1):1-52
pubmed: 23471616
J Bacteriol. 2012 Sep;194(18):4837-46
pubmed: 22753070
Nat Chem Biol. 2017 Mar 22;13(4):350-359
pubmed: 28328921
Chemistry. 2019 Mar 21;25(17):4379-4389
pubmed: 30648291
Chem Rev. 2018 Aug 8;118(15):7069-7163
pubmed: 29664617
Chem Soc Rev. 2013 Jan 7;42(1):305-41
pubmed: 23023210
J Am Chem Soc. 2017 Nov 15;139(45):16154-16160
pubmed: 29056046
Nat Rev Microbiol. 2017 May;15(5):271-284
pubmed: 28163311
Sci Rep. 2017 Aug 31;7(1):10281
pubmed: 28860517
Nat Immunol. 2016 Sep 20;17(10):1142-9
pubmed: 27648547
Mol Cell. 2014 Sep 18;55(6):931-937
pubmed: 25201413
J Am Chem Soc. 2014 Oct 29;136(43):15176-84
pubmed: 25255464
Nature. 2019 Mar;567(7747):194-199
pubmed: 30787435
Structure. 2015 May 5;23(5):843-850
pubmed: 25865248

Auteurs

Yao Li (Y)

Department of Chemistry and Biochemistry, University of California San Diego, 9500 Gilman Drive, La Jolla, CA, 92093-0358, USA.

Paul T Ludford (PT)

Department of Chemistry and Biochemistry, University of California San Diego, 9500 Gilman Drive, La Jolla, CA, 92093-0358, USA.

Andrea Fin (A)

Department of Chemistry and Biochemistry, University of California San Diego, 9500 Gilman Drive, La Jolla, CA, 92093-0358, USA.
Dipartimento di Scienza e Tecnologia del Farmaco, University of Turin, Via P. Giuria 9, 10125, Turin, Italy.

Alexander R Rovira (AR)

Department of Chemistry and Biochemistry, University of California San Diego, 9500 Gilman Drive, La Jolla, CA, 92093-0358, USA.

Yitzhak Tor (Y)

Department of Chemistry and Biochemistry, University of California San Diego, 9500 Gilman Drive, La Jolla, CA, 92093-0358, USA.

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Classifications MeSH