Evidence map›Paper›PMID 31310712›Full record

ArticleACS chemical biology2019

Expanding the Scope of RNA Metabolic Labeling with Vinyl Nucleosides and Inverse Electron-Demand Diels-Alder Chemistry.

Miles Kubota, Sarah Nainar, Shane M Parker, Whitney England, Filipp Furche, Robert C Spitale

Abstract read
In one paragraph

Article in ACS chemical biology, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.

0numbers the graph read from it
0cells of the map it votes in
20citing papers in PubMed
–field-weighted citation impact
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

20 citing papers in PubMed.

  1. Fluorogenic Sydnones for Bioorthogonal Labeling of DNA.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026
    Article
  2. Article
  3. Live-Cell RNA Imaging via Clickable TriPPPro Nucleotide Reporters.Angewandte Chemie (International ed. in English) · 2026
    Article
  4. Review
  5. Article
  6. Click Chemistry for Visualization of Newly Synthesized RNA and Antibody Labeling on Ultrathin Tissue Sections.Microscopy and microanalysis : the official journal of Microscopy Society of America, Microbeam Analysis Society, Microscopical Society of Canada · 2023
    Article
  7. Article
  8. Cycloaddition enabled mutational profiling of 5-vinyluridine in RNA.Chemical communications (Cambridge, England) · 2023
    Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Article
  14. Review
  15. Article
  16. Covalent labeling of nucleic acids.Chemical Society reviews · 2020
    Review
  17. Article
  18. Review
  19. Article
  20. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

6 authors.

Miles Kubota
Sarah Nainar
Whitney England

Funding

University of California Health Participation in the National COVID Cohort Collaborative (N3C)UL1TR001414 · NCATS · UNIVERSITY OF CALIFORNIA-IRVINE · PI COOPER, DAN M, VILAIN, ERIC J. · 2015 to 2023
$35.1M
Cracking the RNA Localization CodeDP2GM119164 · NIGMS · UNIVERSITY OF CALIFORNIA-IRVINE · PI SPITALE, ROBERT C · 2015 to 2015
$2.2M
Multicellular simultaneous chemotranscriptomic profiling of nascent transcription during learningR21MH113062 · NIMH · UNIVERSITY OF CALIFORNIA-IRVINE · PI SPITALE, ROBERT C · 2017 to 2018
$425k
NCATS NIH HHS UL1 TR001414NIGMS NIH HHS DP2 GM119164NIMH NIH HHS R21 MH113062
6 · The paper itself

Abstract

Optimized and stringent chemical methods to profile nascent RNA expression are still in demand. Herein, we expand the toolkit for metabolic labeling of RNA through application of inverse electron demand Diels-Alder (IEDDA) chemistry. Structural examination of metabolic enzymes guided the design and synthesis of vinyl-modified nucleosides, which we systematically tested for their ability to be installed through cellular machinery. Further, we tested these nucleosides against a panel of tetrazines to identify those which are able to react with a terminal alkene, but are stable enough for selective conjugation. The selected pairings then facilitated RNA functionalization with biotin and fluorophores. We found that this chemistry not only is amenable to preserving RNA integrity but also endows the ability to both tag and image RNA in cells. These key findings represent a significant advancement in methods to profile the nascent transcriptome using chemical approaches.

Indexed as

Cycloaddition ReactionHEK293 CellsHeterocyclic Compounds, 1-RingHumansKineticsMicroscopy, ConfocalMicroscopy, FluorescenceNucleosidesQuantum TheoryRNAVinyl CompoundsHeterocyclic Compounds, 1-RingNucleosidesRNAVinyl Compounds

Identifiers

PMID31310712
PMCPMC8061575

What OpenQuestion holds

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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.