Evidence map›Paper›PMID 36848848›Full record

ArticleEuropean journal of medicinal chemistry2023

Investigating a new C2-symmetric testosterone dimer and its dihydrotestosterone analog: Synthesis, antiproliferative activity on prostate cancer cell lines and interaction with CYP3A4.

Alexis Paquin, Laurie Fortin, Julie Girouard, Carlos Reyes-Moreno, Irina F Sevrioukova, Gervais Bérubé

Open access · greenAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in European journal of medicinal chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
0.3field-weighted citation impact, top 50% 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

1 citing paper in PubMed, 2 citations in OpenAlex.

  1. 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 2 institutions in 2 countries.

Alexis PaquinLaboratoire de Recherche en Chimie Médicinale (LRCM) et Groupe de Recherche en Signalisation Cellulaire (GRSC), Département de Chimie, Biochimie et Physique, Université du Québec é Trois-Riviéres, C.P. 500, Trois-Riviéres, QC, G9A 5H7, Canada.
Laurie FortinLaboratoire de Recherche en Oncologie et Immunobiologie (LROI) et Groupe de Recherche en Signalisation Cellulaire (GRSC), Département de Biologie Médicale, Université du Québec à Trois-Rivières, C.P. 500, Trois-Rivières, QC, G9A 5H7, Canada.
Julie GirouardLaboratoire de Recherche en Oncologie et Immunobiologie (LROI) et Groupe de Recherche en Signalisation Cellulaire (GRSC), Département de Biologie Médicale, Université du Québec à Trois-Rivières, C.P. 500, Trois-Rivières, QC, G9A 5H7, Canada.
Carlos Reyes-MorenoLaboratoire de Recherche en Oncologie et Immunobiologie (LROI) et Groupe de Recherche en Signalisation Cellulaire (GRSC), Département de Biologie Médicale, Université du Québec à Trois-Rivières, C.P. 500, Trois-Rivières, QC, G9A 5H7, Canada.
Irina F SevrioukovaDepartment of Molecular Biology and Biochemistry, University of California, Irvine, CA, 92697, United States. Electronic address: sevrioui@uci.edu.
Gervais BérubéLaboratoire de Recherche en Chimie Médicinale (LRCM) et Groupe de Recherche en Signalisation Cellulaire (GRSC), Département de Chimie, Biochimie et Physique, Université du Québec é Trois-Riviéres, C.P. 500, Trois-Riviéres, QC, G9A 5H7, Canada. Electronic address: Gervais.Berube@uqtr.ca.
Université du Québec à Trois-Rivières · CAUniversity of California, Irvine · US

Funding

Toxicological importance of CYP3A4 catalysis and inhibitionR01ES025767 · NIEHS · UNIVERSITY OF CALIFORNIA-IRVINE · PI SEVRIOUKOVA, IRINA F · 2016 to 2025
$4.0M
NIEHS NIH HHS R01 ES025767
6 · The paper itself

Abstract

The synthesis of a 17α-linked C2-symmetric testosterone dimer and its dihydrotestosterone analog is reported. The dimers were synthesized using a short five-step reaction sequence with 28% and 38% overall yield for the testosterone and dihydrotestosterone dimer, respectively. The dimerization reaction was achieved by an olefin metathesis reaction with 2nd generation Hoveyda-Grubbs catalyst. The dimers and their corresponding 17α-allyl precursors were tested for the antiproliferative activity on androgen-dependent (LNCaP) and androgen-independent (PC3) prostate cancer cell lines. The effects on cells were compared with that of the antiandrogen cyproterone acetate (CPA). The results showed that the dimers were active on both cell lines, with an increased activity towards androgen-dependent LNCaP cells. However, the testosterone dimer (11) was fivefold more active than the dihydrotestosterone dimer (15), with an IC

Indexed as

Prostatic NeoplasmsTestosteroneAndrogensCell LineCell Line, TumorCytochrome P-450 CYP3ADihydrotestosteroneHumansMaleAndrogensCYP3A4 protein, humanCytochrome P-450 CYP3ADihydrotestosteroneTestosteroneAndrogen dimersCYP3A4DihydrotestosteroneProstate cancerTestosterone

Identifiers

PMID36848848
PMCPMC10246735
OpenAlexW4321487052

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.