Evidence map›Paper›PMID 35438502›Full record

ArticleJournal of the American Chemical Society2022

Palladium-Mediated Incorporation of Carboranes into Small Molecules, Peptides, and Proteins.

Martin Gazvoda, Heemal H Dhanjee, Jacob Rodriguez, Joseph S Brown, Charlotte E Farquhar, Nicholas L Truex, Andrei Loas, Stephen L Buchwald, Bradley L Pentelute

Erratum issuedOpen access · greenAbstract read
In one paragraph

Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 11 papers.

0numbers the graph read from it
0cells of the map it votes in
11citing papers in PubMed
1.0field-weighted citation impact, top 26% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

11 citing papers in PubMed, 7 citations in OpenAlex.

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  10. Synthesis and Structural Characterization ofMolecules (Basel, Switzerland) · 2023
    Article
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4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

9 authors at 2 institutions in 1 country.

Martin GazvodaDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.ORCID 0000-0003-3421-0682
Heemal H DhanjeeDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.ORCID 0000-0002-3532-4430
Jacob RodriguezDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.ORCID 0000-0003-1202-5013
Joseph S BrownDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.ORCID 0000-0002-8145-800X
Charlotte E FarquharDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
Nicholas L TruexDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.ORCID 0000-0002-7369-685X
Andrei LoasDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.ORCID 0000-0001-5640-1645
Stephen L BuchwaldDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.ORCID 0000-0003-3875-4775
Bradley L PenteluteDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.ORCID 0000-0002-7242-801X
Massachusetts Institute of Technology · USBroad Institute · US

Funding

Cytosolic Delivery of Tumor Antigens into Dendritic CellsF32CA239362 · NCI · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI TRUEX, NICHOLAS L · 2020 to 2022
$179k
Chemo- and Regio- Selective Lysine Modification on the Surface of Native Proteins: Synthetic Methods for the Improvement of Cancer TherapeuticsF32GM131592 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI DHANJEE, HEEMAL · 2019 to 2022
$145k
NCI NIH HHS F32 CA239362NIGMS NIH HHS F32 GM131592
6 · The paper itself

Abstract

Carboranes represent a class of compounds with increasing therapeutic potential. However, few general approaches to readily embed carboranes into small molecules, peptides, and proteins are available. We report a strategy based on palladium-mediated C-X (X = C, S, and N) bond formation for the installation of carborane-containing moieties onto small molecules and peptides. We demonstrate the ability of Pd-based reagents with appropriate ligands to overcome the high hydrophobicity of the carborane group and enable chemoselective conjugation of cysteine residues at room temperature in aqueous buffer. Accordingly, carboranes can be efficiently installed on proteins by employing a combination of a bis-sulfonated biarylphosphine-ligated Pd reagent in an aqueous histidine buffer. This method is successfully employed on nanobodies, a fully synthetic affibody, and the antibody therapeutics trastuzumab and cetuximab. The conjugates of the affibody Z

Indexed as

BoranesPalladiumPeptidesProteinsTrastuzumabBoranesPalladiumPeptidesProteinsTrastuzumab

Identifiers

PMID35438502
PMCPMC9881053
OpenAlexW4224280977

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.