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Reinvestigating Old Pharmacophores: Are 4‑Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?

Overview of attention for article published in Journal of Medicinal Chemistry, December 2015
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Title
Reinvestigating Old Pharmacophores: Are 4‑Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?
Published in
Journal of Medicinal Chemistry, December 2015
DOI 10.1021/acs.jmedchem.5b01374
Pubmed ID
Authors

Natasa Terzić, Jelena Konstantinović, Mikloš Tot, Jovana Burojević, Olgica Djurković-Djaković, Jelena Srbljanović, Tijana Štajner, Tatjana Verbić, Mario Zlatović, Marta Machado, Inês S. Albuquerque, Miguel Prudêncio, Richard J. Sciotti, Stevan Pecic, Sarah D’Alessandro, Donatella Taramelli, Bogdan A. Šolaja

Abstract

The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro, and in vivo activity against P. berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intra-hepatocytic parasite inhibitors, with compound 25 having an IC50 = 0.31 µM and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC50= 0.33 µM). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V P. falciparum gametocytes (IC50 = 1.16  0.37 µM). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors.

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Mendeley readers

Mendeley readers

The data shown below were compiled from readership statistics for 57 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Portugal 2 4%
Unknown 55 96%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 9 16%
Researcher 7 12%
Student > Master 7 12%
Professor > Associate Professor 5 9%
Professor 5 9%
Other 12 21%
Unknown 12 21%
Readers by discipline Count As %
Chemistry 22 39%
Agricultural and Biological Sciences 5 9%
Biochemistry, Genetics and Molecular Biology 3 5%
Immunology and Microbiology 2 4%
Pharmacology, Toxicology and Pharmaceutical Science 1 2%
Other 4 7%
Unknown 20 35%
Attention Score in Context

Attention Score in Context

This research output has an Altmetric Attention Score of 1. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 25 April 2016.
All research outputs
#18,432,465
of 22,835,198 outputs
Outputs from Journal of Medicinal Chemistry
#21,197
of 22,077 outputs
Outputs of similar age
#280,477
of 388,246 outputs
Outputs of similar age from Journal of Medicinal Chemistry
#124
of 142 outputs
Altmetric has tracked 22,835,198 research outputs across all sources so far. This one is in the 11th percentile – i.e., 11% of other outputs scored the same or lower than it.
So far Altmetric has tracked 22,077 research outputs from this source. They typically receive a little more attention than average, with a mean Attention Score of 6.7. This one is in the 2nd percentile – i.e., 2% of its peers scored the same or lower than it.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 388,246 tracked outputs that were published within six weeks on either side of this one in any source. This one is in the 16th percentile – i.e., 16% of its contemporaries scored the same or lower than it.
We're also able to compare this research output to 142 others from the same source and published within six weeks on either side of this one. This one is in the 9th percentile – i.e., 9% of its contemporaries scored the same or lower than it.