Direct Intracellular Delivery of Benzene Diazonium Ions As Observed by Increased Tyrosine Phosphorylation.

Benzene Ions Phosphorylation Protein Tyrosine Phosphatase, Non-Receptor Type 1 / metabolism Proteins / chemistry Tyrosine / metabolism

Journal

Biochemistry
ISSN: 1520-4995
Titre abrégé: Biochemistry
Pays: United States
ID NLM: 0370623

Informations de publication

Date de publication:
19 04 2022
Historique:
pubmed: 19 3 2022
medline: 21 4 2022
entrez: 18 3 2022
Statut: ppublish

Résumé

A challenge within the field of bioconjugation is developing probes to uncover novel information on proteins and other biomolecules. Intracellular delivery of these probes offers the promise of giving relevant context to this information, and these probes can serve as hypothesis-generating tools within complex systems. Leveraging the utility of triazabutadiene chemistry, herein, we discuss the development of a probe that undergoes reduction-mediated deprotection to rapidly deliver a benzene diazonium ion (BDI) into cells. The intracellular BDI resulted in an increase in global tyrosine phosphorylation levels. Seeing phosphatase dysregulation as a potential source of this increase, a tyrosine phosphatase (PTP1B) was tested and shown to be both inhibited and covalently modified by the BDI. In addition to the expected azobenzene formation at tyrosine side chains, key reactive histidine residues were also modified.

Identifiants

DOI: 10.1021/acs.biochem.1c00820 PMID: 35302352 PMC: PMC9203130
pubmed: 35302352
doi: 10.1021/acs.biochem.1c00820
pmc: PMC9203130
mid: NIHMS1813139
doi:

Substances chimiques

Ions 0
Proteins 0
Tyrosine 42HK56048U
Protein Tyrosine Phosphatase, Non-Receptor Type 1 EC 3.1.3.48
Benzene J64922108F

Types de publication

Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.

Langues

eng

Sous-ensembles de citation

IM

Pagination

656-664

Subventions

Organisme : NIGMS NIH HHS
ID : R01 GM115595
Pays : United States
Organisme : Howard Hughes Medical Institute
ID : GT11435
Pays : United States

Commentaires et corrections

Type : ErratumIn

Références

Cell. 2018 May 3;173(4):815-817
pubmed: 29727668
Chem Commun (Camb). 2005 Oct 21;(39):4958-60
pubmed: 16205813
J Am Chem Soc. 2011 Feb 9;133(5):1534-44
pubmed: 21207964
Chem Soc Rev. 2015 Aug 7;44(15):5495-551
pubmed: 26000775
Trends Biochem Sci. 2010 Aug;35(8):442-9
pubmed: 20381358
Mol Cell. 2017 Feb 16;65(4):644-658.e5
pubmed: 28212750
Mol Cell Proteomics. 2019 Jul;18(7):1363-1381
pubmed: 31018989
Chem Res Toxicol. 1997 Dec;10(12):1378-86
pubmed: 9437529
Biochim Biophys Acta. 2013 Jan;1834(1):404-14
pubmed: 22842194
J Med Chem. 2018 Dec 27;61(24):11144-11157
pubmed: 30525586
J Agric Food Chem. 1982 May-Jun;30(3):521-5
pubmed: 7201479
Annu Rev Biochem. 2008;77:383-414
pubmed: 18366325
J Biol Chem. 1997 Jan 17;272(3):1639-45
pubmed: 8999839
J Am Chem Soc. 2005 Mar 23;127(11):3718-23
pubmed: 15771505
Chem Res Toxicol. 2000 Oct;13(10):1020-7
pubmed: 11080051
ACS Chem Biol. 2009 May 15;4(5):325-34
pubmed: 19298050
Biochim Biophys Acta. 2008 Nov;1780(11):1273-90
pubmed: 18267127
Nat Chem Biol. 2011 Nov 15;7(12):876-84
pubmed: 22086289
Nat Chem. 2017 Dec;9(12):1181-1190
pubmed: 29168484
Chem Rev. 2006 Nov;106(11):4622-43
pubmed: 17091930
Mutat Res. 1992 Jul;268(1):105-14
pubmed: 1378176
J Am Chem Soc. 2019 Aug 14;141(32):12634-12647
pubmed: 31339043
Anal Chem. 2021 Jul 27;93(29):10334-10342
pubmed: 34251175
Biochem J. 1915 Sep;9(3):385-92
pubmed: 16742386
J Am Chem Soc. 2004 Dec 15;126(49):15942-3
pubmed: 15584710
Chembiochem. 2016 Dec 2;17(23):2220-2222
pubmed: 27662242
Nature. 2016 Jun 15;534(7608):570-4
pubmed: 27309814
Biochemistry. 2017 Jan 10;56(1):96-106
pubmed: 27959494
Biochim Biophys Acta. 1962 Sep 10;63:212-4
pubmed: 13930038
Biochemistry. 2005 May 31;44(21):7704-12
pubmed: 15909985
Bioorg Khim. 2008 Jul-Aug;34(4):546-57
pubmed: 18695729
Nat Chem Biol. 2020 Feb;16(2):150-159
pubmed: 31768034
Biochemistry. 2017 Aug 1;56(30):3863-3873
pubmed: 28653834
Biochem J. 1997 Oct 1;327 ( Pt 1):139-45
pubmed: 9355745
Rapid Commun Mass Spectrom. 2007;21(5):817-8
pubmed: 17279478
Protein Sci. 2001 Aug;10(8):1596-605
pubmed: 11468356
Carcinogenesis. 1997 Aug;18(8):1603-8
pubmed: 9276636
Angew Chem Int Ed Engl. 2015 Mar 23;54(13):4051-4
pubmed: 25663253
J Am Chem Soc. 2017 Aug 30;139(34):11670-11673
pubmed: 28787141
Synlett. 2020;31(5):450-454
pubmed: 34349356
Chem Biol Interact. 1995 Jan;94(1):21-36
pubmed: 7820878
Sci Rep. 2019 Dec 13;9(1):19118
pubmed: 31836830
Bioconjug Chem. 2012 Dec 19;23(12):2321-8
pubmed: 23181702
Proc Natl Acad Sci U S A. 1997 Mar 4;94(5):1680-5
pubmed: 9050838
Anal Chem. 2014 Feb 4;86(3):1459-67
pubmed: 24410597
Biochemistry. 2017 Apr 11;56(14):2051-2060
pubmed: 28345882
Bioconjug Chem. 2021 Feb 17;32(2):254-258
pubmed: 33492934
J Am Chem Soc. 2004 Mar 31;126(12):3718-9
pubmed: 15038717
Nature. 2010 Dec 9;468(7325):790-5
pubmed: 21085121

Auteurs

Natasha R Cornejo (NR)

Department of Chemistry and Biochemistry, University of Arizona, 1306 East University Boulevard, Tucson, Arizona 85721, United States.

Bismark Amofah (B)

Department of Chemistry and Biochemistry, University of Arizona, 1306 East University Boulevard, Tucson, Arizona 85721, United States.

Austin Lipinski (A)

Department of Medicine, Division of Endocrinology, University of Arizona College of Medicine, Tucson, Arizona 85721, United States.

Paul R Langlais (PR)

Department of Medicine, Division of Endocrinology, University of Arizona College of Medicine, Tucson, Arizona 85721, United States.

Indraneel Ghosh (I)

Department of Chemistry and Biochemistry, University of Arizona, 1306 East University Boulevard, Tucson, Arizona 85721, United States.

John C Jewett (JC)

Department of Chemistry and Biochemistry, University of Arizona, 1306 East University Boulevard, Tucson, Arizona 85721, United States.
ORCID: 0000-0001-5822-4080

Articles similaires

FBXO22 inhibits colitis and colorectal carcinogenesis by regulating the degradation of the S2448-phosphorylated form of mTOR.

Minle Li, Xuan Chen, Pengfei Qu et al.
1.00
Animals TOR Serine-Threonine Kinases Colorectal Neoplasms Colitis Mice

Exploring structural diversity across the protein universe with The Encyclopedia of Domains.

Andy M Lau, Nicola Bordin, Shaun M Kandathil et al.
1.00
Databases, Protein Protein Domains Protein Folding Proteins Deep Learning

Formin-like 1β phosphorylation at S1086 is necessary for secretory polarized traffic of exosomes at the immune synapse in Jurkat T lymphocytes.

Javier Ruiz-Navarro, Sara Fernández-Hermira, Irene Sanz-Fernández et al.
1.00
Humans Formins Phosphorylation Exosomes Jurkat Cells

Post-translational modifications of fibrinogen: implications for clotting, fibrin structure and degradation.

Francesca Nencini, Alessandra Bettiol, Flavia Rita Argento et al.
1.00
Protein Processing, Post-Translational Humans Blood Coagulation Fibrin Fibrinogen

Classifications MeSH

questionsmedicales.fr › Composés chimiques organiques › Hydrocarbures › Hydrocarbures cycliques › Hydrocarbures aromatiques › Dérivés du benzène › Benzène › Direct Intracellular Delivery of Benzene...
questionsmedicales.fr › Produits chimiques inorganiques › Électrolytes › Ions › Direct Intracellular Delivery of Benzene...
questionsmedicales.fr › Métabolisme › Phosphorylation › Direct Intracellular Delivery of Benzene...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Protéines et peptides de signalisation intracellulaire › Protein Tyrosine Phosphatases › Protein Tyrosine Phosphatases, Non-Receptor › Protein Tyrosine Phosphatase, Non-Receptor Type 1 › Direct Intracellular Delivery of Benzene...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Direct Intracellular Delivery of Benzene...
questionsmedicales.fr › Acides aminés, peptides et protéines › Acides aminés › Acides aminés cycliques › Acides aminés aromatiques › Tyrosine › Direct Intracellular Delivery of Benzene...