Evidence map›Paper›PMID 27494208›Full record

ArticleThe Journal of organic chemistry2016

Synthesis and Biological Evaluation of Several Bryostatin Analogues Bearing a Diacylglycerol Lactone C-Ring.

David O Baumann, Kevin M McGowan, Noemi Kedei, Megan L Peach, Peter M Blumberg, Gary E Keck

Open access · greenAbstract read
In one paragraph

Article in The Journal of organic chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
0.9field-weighted citation impact, top 23% 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

2 citing papers in PubMed, 7 citations in OpenAlex.

  1. Synthesis and Biological Evaluation of Fluorescent Bryostatin Analogues.Chembiochem : a European journal of chemical biology · 2018
    Article
  2. 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 at 4 institutions in 1 country.

David O BaumannDepartment of Chemistry, University of Utah , 315 S 1300 E, RM 2020, Salt Lake City, Utah 84112, United States.
Kevin M McGowanDepartment of Chemistry, University of Utah , 315 S 1300 E, RM 2020, Salt Lake City, Utah 84112, United States.
Noemi KedeiLaboratory of Cancer Biology and Genetics, Center for Cancer Research, National Cancer Institute , Bethesda, Maryland 20892-4255, United States.
Megan L PeachBasic Science Program, Leidos Biomedical Research, Inc., Chemical Biology Laboratory, Frederick National Laboratory for Cancer Research , Frederick, Maryland 21702, United States.
Peter M BlumbergLaboratory of Cancer Biology and Genetics, Center for Cancer Research, National Cancer Institute , Bethesda, Maryland 20892-4255, United States.
Gary E KeckDepartment of Chemistry, University of Utah , 315 S 1300 E, RM 2020, Salt Lake City, Utah 84112, United States.
University of Utah · USCenter for Cancer Research · USLeidos (United States) · USNational Cancer Institute · US

Funding

Molecular Mechanism of Action of Phorbol EsterZIABC005270 · NCI · DIVISION OF BASIC SCIENCES - NCI · PI BLUMBERG, PETER · 2009 to 2018
$18.4M
CHIRAL APPROACHES TO NATURAL PRODUCT SYNTHESISR01GM028961 · NIGMS · UNIVERSITY OF UTAH · PI KECK, GARY E · 1985 to 2014
$5.5M
MOLECULAR MECHANISM OF ACTION OF PHORBOL ESTER TUMOR PROMOTERSZ01BC005270 · NCI · DIVISION OF BASIC SCIENCES - NCI · PI BLUMBERG, PETER · 1996 to 2008
$4.3M
CCR NIH HHS HHSN261200800001CIntramural NIH HHS Z01 BC005270NCI NIH HHS HHSN261200800001ENCI NIH HHS ZIA BC005270NIGMS NIH HHS R01 GM028961
6 · The paper itself

Abstract

As an initial step in designing a simplified bryostatin hybrid molecule, three bryostatin analogues bearing a diacylglycerol lactone-based C-ring, which possessed the requisite pharmacophores for binding to protein kinase C (PKC) together with a modified bryostatin-like A- and B-ring region, were synthesized and evaluated. Merle 46 and Merle 47 exhibited binding affinity to PKC alpha with Ki values of 7000 ± 990 and 4940 ± 470 nM, respectively. Reinstallation of the trans-olefin and gem-dimethyl group present in bryostatin 1 in Merle 48 resulted in improved binding affinity, 363 ± 42 nM. While Merle 46 and 47 were only marginally active biologically, Merle 48 showed sufficient activity on the U937 cells to confirm that it was PMA-like for growth and attachment, as predicted by the substitution pattern of its A- and B-rings.

Indexed as

BryostatinsCarbon-13 Magnetic Resonance SpectroscopyDiglyceridesLactonesProtein Kinase CProton Magnetic Resonance SpectroscopySpectrometry, Mass, Electrospray IonizationSubstrate SpecificityBryostatinsDiglyceridesLactonesProtein Kinase C

Identifiers

PMID27494208
PMCPMC6957265
OpenAlexW2492264016

What OpenQuestion holds

Textmetadata
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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.