Evidence map›Paper›PMID 28802670›Full record

ArticleBioorganic & medicinal chemistry2017

Chemoselective fluorination and chemoinformatic analysis of griseofulvin: Natural vs fluorinated fungal metabolites.

Noemi D Paguigan, Mohammed H Al-Huniti, Huzefa A Raja, Austin Czarnecki, Joanna E Burdette, Mariana González-Medina, José L Medina-Franco, Stephen J Polyak, Cedric J Pearce, Mitchell P Croatt and 1 more

Open access · hybridAbstract read
In one paragraph

Article in Bioorganic & medicinal chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.

0numbers the graph read from it
0cells of the map it votes in
10citing papers in PubMed
1.7field-weighted citation impact, top 17% 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

10 citing papers in PubMed, 23 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Enzymatic synthesis of fluorinated compounds.Applied microbiology and biotechnology · 2021
    Review
  5. Article
  6. Review
  7. Article
  8. Review
  9. Mapping the Fungal Battlefield: UsingFrontiers in microbiology · 2019
    Article
  10. 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

11 authors at 5 institutions in 2 countries.

Noemi D PaguiganDepartment of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA.
Mohammed H Al-HunitiDepartment of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA.
Huzefa A RajaDepartment of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA.
Austin CzarneckiDepartment of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, IL 60612, USA.
Joanna E BurdetteDepartment of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, IL 60612, USA.
Mariana González-MedinaDepartment of Pharmacy, School of Chemistry, Universidad Nacional Autónoma de México, Avenida Universidad 3000, Mexico City 04510, Mexico.
José L Medina-FrancoDepartment of Pharmacy, School of Chemistry, Universidad Nacional Autónoma de México, Avenida Universidad 3000, Mexico City 04510, Mexico.
Stephen J PolyakDepartment of Laboratory Medicine, University of Washington, Seattle, WA 98195, USA; Department of Global Health, University of Washington, Seattle, WA 98104, USA; Department of Microbiology, University of Washington, Seattle, WA 98195, USA.
Cedric J PearceMycosynthetix Inc., 505 Meadowlands Drive, Suite 103, Hillsborough, NC 27278, USA.
Mitchell P CroattDepartment of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA.
Nicholas H OberliesDepartment of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, USA. Electronic address: nicholas_oberlies@uncg.edu.
University of North Carolina at Greensboro · USUniversidad Nacional Autónoma de México · MXUniversity of Illinois Chicago · USMycosynthetix (United States) · USUniversity of Washington · US

Funding

Project 3:Isolation Chemistry of Filamentous Fungi and Biological EvaluationP01CA125066 · NCI · OHIO STATE UNIVERSITY · PI JIMMY ORJALA · 2007 to 2026
$27.2M
NCI NIH HHS P01 CA125066
6 · The paper itself

Abstract

Griseofulvin is a fungal metabolite and antifungal drug used for the treatment of dermatophytosis in both humans and animals. Recently, griseofulvin and its analogues have attracted renewed attention due to reports of their potential anticancer effects. In this study griseofulvin (1) and related analogues (2-6, with 4 being new to literature) were isolated from Xylaria cubensis. Six fluorinated analogues (7-12) were synthesized, each in a single step using the isolated natural products and Selectflour, so as to examine the effects of fluorine incorporation on the bioactivities of this structural class. The isolated and synthesized compounds were screened for activity against a panel of cancer cell lines (MDA-MB-435, MDA-MB-231, OVCAR3, and Huh7.5.1) and for antifungal activity against Microsporum gypseum. A comparison of the chemical space occupied by the natural and fluorinated analogues was carried out by using principal component analysis, documenting that the isolated and fluorinated analogues occupy complementary regions of chemical space. However, the most active compounds, including two fluorinated derivatives, were centered around the chemical space that was occupied by the parent compound, griseofulvin, suggesting that modifications must preserve certain attributes of griseofulvin to conserve its activity.

Indexed as

Medical InformaticsAntifungal AgentsAntineoplastic AgentsCell ProliferationDose-Response Relationship, DrugDrug Screening Assays, AntitumorGriseofulvinHalogenationHumansMicrobial Sensitivity TestsMicrosporumMolecular StructurePrincipal Component AnalysisStructure-Activity RelationshipTumor Cells, CulturedXylarialesAntifungal AgentsAntineoplastic AgentsGriseofulvinAntifungalCytotoxicityFluorinationGriseofulvinSelectfluorXylaria cubensis

Identifiers

PMID28802670
PMCPMC5632135
OpenAlexW2742052884

What OpenQuestion holds

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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.