Evidence map›Paper›PMID 28345343›Full record

ArticleThe Journal of organic chemistry2017

Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging.

Wen Chyan, Henry R Kilgore, Brian Gold, Ronald T Raines

Abstract read
In one paragraph

Article in The Journal of organic chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.

0numbers the graph read from it
0cells of the map it votes in
9citing papers in PubMed
1.1field-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

9 citing papers in PubMed, 29 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Enzyme-activated probes in optical imaging: a focus on atherosclerosis.Dalton transactions (Cambridge, England : 2003) · 2021
    Review
  5. Article
  6. Review
  7. Article
  8. Article
  9. The n→π* Interaction.Accounts of chemical research · 2017
    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

4 authors at 1 institution in 1 country.

Wen ChyanDepartment of Chemistry, ‡Graduate Program in Biophysics, and §Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
Henry R KilgoreDepartment of Chemistry, ‡Graduate Program in Biophysics, and §Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
Brian GoldDepartment of Chemistry, ‡Graduate Program in Biophysics, and §Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.
Ronald T RainesDepartment of Chemistry, ‡Graduate Program in Biophysics, and §Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.ORCID 0000-0001-7164-1719
University of Wisconsin–Madison · US

Funding

TR&D 3: TECHNOLOGY DEVELOPMENT FOR NMR STUDIES OF SMALL MOLECULES (METABOLOMICS, NATURAL PRODUCTS, METABOLITE-PROTEIN INTERACTIONS) pp.537-585 P41GM103399 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI MARKLEY, JOHN LUTE · 2012 to 2019
$9.4M
RIBONUCLEASES IN CANCER THERAPYR01CA073808 · NCI · UNIVERSITY OF WISCONSIN-MADISON · PI RAINES, RONALD T · 1997 to 2024
$7.3M
STRUCTURE--FUNCTION ANALYSIS OF RIBONUCLEASE AR01GM044783 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI RAINES, RONALD T · 1990 to 2021
$7.1M
QExactive (Orbitrap) mass spectrometerS10OD020022 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI VESTLING, MARTHA M · 2015 to 2015
$483k
NCI NIH HHS R01 CA073808NIGMS NIH HHS P41 GM103399NIGMS NIH HHS R01 GM044783NIH HHS S10 OD020022
6 · The paper itself

Abstract

Fluorogenic probes are invaluable tools for spatiotemporal investigations within live cells. In common fluorogenic probes, the intrinsic fluorescence of a small-molecule fluorophore is masked by esterification until entry into a cell, where endogenous esterases catalyze the hydrolysis of the masking groups, generating fluorescence. The susceptibility of masking groups to spontaneous hydrolysis is a major limitation of these probes. Previous attempts to address this problem have incorporated auto-immolative linkers at the cost of atom economy and synthetic adversity. Here, we report on a linker-free strategy that employs adventitious electronic and steric interactions in easy-to-synthesize probes. We find that X···C═O n→π* interactions and acyl group size are optimized in 2',7'-dichlorofluorescein diisobutyrate. This probe is relatively stable to spontaneous hydrolysis but is a highly reactive substrate for esterases both in vitro and in cellulo, yielding a bright, photostable fluorophore with utility in biomolecular imaging.

Indexed as

AnimalsCatalysisCell Culture TechniquesCulture MediaFluorescent DyesSpectrometry, FluorescenceCulture MediaFluorescent Dyes

Identifiers

PMID28345343
PMCPMC5519408
OpenAlexW2600173974

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.