Evidence map›Paper›PMID 23092278›Full record

ReviewCurrent pharmaceutical design2013

From the chemistry of epoxy-sugar nucleosides to the discovery of anti-HIV agent 4'-ethynylstavudine-Festinavir.

Kazuhiro Haraguchi, Shingo Takeda, Yutaka Kubota, Hiroki Kumamoto, Hiromichi Tanaka, Takayuki Hamasaki, Masanori Baba, Elijah Paintsil, Yung-Chi Cheng

Abstract readReview
In one paragraph

Review in Current pharmaceutical design, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing papers in PubMed
–field-weighted citation impact
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

5 citing papers in PubMed.

  1. Article
  2. From in silico hit to long-acting late-stage preclinical candidate to combat HIV-1 infection.Proceedings of the National Academy of Sciences of the United States of America · 2018
    Article
  3. Review
  4. Review
  5. 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

9 authors.

Kazuhiro HaraguchiSchool of Pharmacy, Showa University, Japan. harakazu@pharm.showa-u.ac.jp
Shingo Takeda
Yutaka Kubota
Hiroki Kumamoto
Hiromichi Tanaka
Takayuki Hamasaki
Masanori Baba
Elijah Paintsil
Yung-Chi Cheng

Funding

BIOCHEMICAL PHARMACOLOGY OF ANTIHIV COMPOUNDSR01AI038204 · NIAID · YALE UNIVERSITY · PI CHENG, YUNG-CHI · 1995 to 2014
$5.2M
HIV Nucleoside Analogs Translational Studies: Resistance and MetabolismK08AI074404 · NIAID · YALE UNIVERSITY · PI PAINTSIL, ELIJAH · 2008 to 2012
$629k
NIAID NIH HHS AI-38204NIAID NIH HHS K08 AI074404NIAID NIH HHS K08AI074404NIAID NIH HHS R01 AI038204NIAID NIH HHS R56 AI038204
6 · The paper itself

Abstract

Branched sugar nucleosides have attracted much attention due to their biological activities. We have demonstrated that epoxysugar nucleosides serve as versatile precursor for the stereo-defined synthesis of these nucleoside derivatives on the basis of its ring opening with organoaluminum or organosilicon reagents. In this review article, novel methods for the synthesis of nucleoside analogues branched at the 1' and 4'-position will be described. During this study, we could discover an anti-HIV agent, 4'-ethynylstavudine (Festinavir). Festinavir showed more potent anti-HIV activity than the parent compound stavudine (d4T). Other significant properties of Festinavir are as follows: 1) much less toxic to various cells and also to mitochondorial DNA synthesis than d4T, 2) better substrate for human thymidine kinase than d4T, 3) resistant not only to chemical glycosidic bond cleavage but also to catabolism by thymidine phosphorylase, 4) the activity improves in the presence of a major mutation, K103N, associated with resistance to non-nucleoside reverse transcriptase inhibitors. Detailed profile of the antiviral activities, biology and pharmacology of Festinavir are also described.

Indexed as

Drug DiscoveryAnti-HIV AgentsCell LineEpoxy CompoundsHIV-1HumansMagnetic Resonance SpectroscopyNucleosidesStavudine4'-ethynylstavudineAnti-HIV AgentsEpoxy CompoundsNucleosidesStavudine

Identifiers

PMID23092278
PMCPMC3711117

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.