Evidence map›Paper›PMID 28218845›Full record

ArticleJournal of medicinal chemistry2017

Phosphinophosphonates and Their Tris-pivaloyloxymethyl Prodrugs Reveal a Negatively Cooperative Butyrophilin Activation Mechanism.

Rebekah R Shippy, Xiaochen Lin, Sherry S Agabiti, Jin Li, Brendan M Zangari, Benjamin J Foust, Michael M Poe, Chia-Hung Christine Hsiao, Olga Vinogradova, David F Wiemer and 1 more

Open access · greenAbstract read
In one paragraph

Article in Journal of medicinal chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.

0numbers the graph read from it
0cells of the map it votes in
26citing papers in PubMed
2.1field-weighted citation impact, top 12% 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

26 citing papers in PubMed, 32 citations in OpenAlex.

  1. Cell stress activates γ9δ2 T cells via endogenous phosphoantigens and butyrophilin complex dynamics.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2026
    Article
  2. γ9δ2 T cells detect mevalonate diphosphate via BTN3A3.Cellular and molecular life sciences : CMLS · 2025
    Article
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  12. Potent double prodrug forms of synthetic phosphoantigens.Bioorganic & medicinal chemistry · 2020
    Article
  13. Review
  14. Article
  15. Article
  16. Article
  17. Probing the Ligand-Binding Pocket of BTN3A1.Journal of medicinal chemistry · 2019
    Article
  18. Review
  19. Article
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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

11 authors at 2 institutions in 1 country.

Rebekah R ShippyDepartment of Chemistry, University of Iowa , Iowa City, Iowa 52242, United States.
Xiaochen LinDepartment of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
Sherry S AgabitiDepartment of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
Jin LiDepartment of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
Brendan M ZangariDepartment of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
Benjamin J FoustDepartment of Chemistry, University of Iowa , Iowa City, Iowa 52242, United States.
Michael M PoeDepartment of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
Chia-Hung Christine HsiaoDepartment of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
Olga VinogradovaDepartment of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
David F WiemerDepartment of Chemistry, University of Iowa , Iowa City, Iowa 52242, United States.
Andrew J WiemerDepartment of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.ORCID 0000-0002-3029-1780
University of Connecticut · USUniversity of Iowa · US

Funding

Regulation of gamma delta T cell immunoediting by novel phosphoantigensR01CA186935 · NCI · UNIVERSITY OF CONNECTICUT STORRS · PI WIEMER, ANDREW J · 2015 to 2018
$1.5M
NCI NIH HHS R01 CA186935
6 · The paper itself

Abstract

Butyrophilin 3A1 (BTN3A1) binds small phosphorus-containing molecules, which initiates transmembrane signaling and activates butyrophilin-responsive cells. We synthesized several phosphinophosphonates and their corresponding tris-pivaloyloxymethyl (tris-POM) prodrugs and examined their effects on BTN3A1. An analog of (E)-4-hydroxy-3-methyl-but-2-enyl diphosphate (HMBPP) bound to BTN3A1 with intermediate affinity, which was enthalpy-driven. Docking studies revealed binding to the basic surface pocket and interactions between the allylic hydroxyl group and the BTN3A1 backbone. The phosphinophosphonate stimulated proliferation of Vγ9Vδ2 T cells with moderate activity (EC

Indexed as

Antigens, CDButyrophilinsCell LineHumansK562 CellsLymphocyte ActivationMolecular Docking SimulationOrganophosphonatesPhosphinesProdrugsT-LymphocytesAntigens, CDBTN3A1 protein, humanButyrophilinsOrganophosphonatesPhosphinesProdrugs

Identifiers

PMID28218845
PMCPMC5754923
OpenAlexW2589993399

What OpenQuestion holds

Textmetadata
LicenceTDM
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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.