Oligonucleotide Bioconjugation with Bifunctional Palladium Reagents.

Cross-Linking Reagents / chemical synthesis Oligonucleotides / chemical synthesis Organometallic Compounds / chemical synthesis Palladium / chemistry Peptides / chemistry Trastuzumab / chemistry
bioconjugation oligonucleotides organometallic reagents palladium oxidative addition complexes proteins

Journal

Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543

Informations de publication

Date de publication:
17 05 2021
Historique:
received: 03 03 2021
pubmed: 18 3 2021
medline: 14 9 2021
entrez: 17 3 2021
Statut: ppublish

Résumé

Organometallic reagents enable practical strategies for bioconjugation. Innovations in the design of water-soluble ligands and the enhancement of reaction rates have allowed for chemoselective cross-coupling reactions of peptides and proteins to be carried out in water. There are currently no organometallic-based methods for oligonucleotide bioconjugation to other biomolecules. Here we report bifunctional palladium(II)-oxidative addition complexes (OACs) as reagents for high-yielding oligonucleotide bioconjugation reactions. These bifunctional OACs react chemoselectively with amine-modified oligonucleotides to generate the first isolable, bench stable oligonucleotide-palladium(II) OACs. These complexes undergo site-selective C-S arylation with a broad range of native thiol-containing biomolecules at low micromolar concentrations in under one hour. This approach provided oligonucleotide-peptide, oligonucleotide-protein, oligonucleotide-small molecule, and oligonucleotide-oligonucleotide conjugates in >80 % yield and afforded conjugation of multiple copies of oligonucleotides onto a monoclonal antibody.

Identifiants

DOI: 10.1002/anie.202103180 PMID: 33730425 PMC: PMC8143041
pubmed: 33730425
doi: 10.1002/anie.202103180
pmc: PMC8143041
mid: NIHMS1689676
doi:

Substances chimiques

Cross-Linking Reagents 0
Oligonucleotides 0
Organometallic Compounds 0
Peptides 0
Palladium 5TWQ1V240M
Trastuzumab P188ANX8CK

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

12109-12115

Subventions

Organisme : NIGMS NIH HHS
ID : F32 GM131592
Pays : United States
Organisme : NIEHS NIH HHS
ID : P30 ES002109
Pays : United States

Informations de copyright

© 2021 Wiley-VCH GmbH.

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Auteurs

Muhammad Jbara (M)

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA, 02139, USA.
ORCID: 0000-0002-4206-5908

Jacob Rodriguez (J)

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA, 02139, USA.

Heemal H Dhanjee (HH)

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA, 02139, USA.

Andrei Loas (A)

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA, 02139, USA.

Stephen L Buchwald (SL)

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA, 02139, USA.

Bradley L Pentelute (BL)

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA, 02139, USA.
The Koch Institute for Integrative Cancer Research, Massachusetts Institute of Technology, 500 Main Street, Cambridge, MA, 02142, USA.
Center for Environmental Health Sciences, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA, 02139, USA.
Broad Institute of MIT and Harvard, 415 Main Street, Cambridge, MA, 02142, USA.
ORCID: 0000-0002-7242-801X

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Classifications MeSH

questionsmedicales.fr › Actions chimiques et utilisations › Utilisations spécialisées de produits chimiques › Produits chimiques de laboratoire › Indicateurs et réactifs › Réactifs réticulants › Oligonucleotide Bioconjugation with...
questionsmedicales.fr › Acides nucléiques, nucléotides et nucléosides › Nucléotides › Polynucléotides › Oligonucléotides › Oligonucleotide Bioconjugation with...
questionsmedicales.fr › Composés chimiques organiques › Composés organométalliques › Oligonucleotide Bioconjugation with...
questionsmedicales.fr › Produits chimiques inorganiques › Métaux › Métaux lourds › Palladium › Oligonucleotide Bioconjugation with...
questionsmedicales.fr › Acides aminés, peptides et protéines › Peptides › Oligonucleotide Bioconjugation with...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Globulines › Sérum-globulines › Immunoglobulines › Anticorps › Anticorps monoclonaux › Anticorps monoclonaux humanisés › Trastuzumab › Oligonucleotide Bioconjugation with...