Evidence map›Paper›PMID 26345647›Full record

ArticleLipids2015

The (5Z)-5-Pentacosenoic and 5-Pentacosynoic Acids Inhibit the HIV-1 Reverse Transcriptase.

Lizabeth Giménez Moreira, Elsie A Orellano, Karolyna Rosado, Rafael V C Guido, Adriano D Andricopulo, Gabriela Ortiz Soto, José W Rodríguez, David J Sanabria-Ríos, Néstor M Carballeira

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

Article in Lipids, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
–field-weighted citation impact, top 97% 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

2 citing papers in PubMed, 3 citations in OpenAlex.

  1. Article
  2. 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 at 5 institutions in 3 countries.

Lizabeth Giménez MoreiraDepartment of Chemistry, University of Puerto Rico, Rio Piedras Campus, PO Box 23346, San Juan, PR, 00931-3346, USA.
Elsie A OrellanoDepartment of Chemistry, University of Puerto Rico, Rio Piedras Campus, PO Box 23346, San Juan, PR, 00931-3346, USA.
Karolyna RosadoDepartment of Chemistry, University of Puerto Rico, Rio Piedras Campus, PO Box 23346, San Juan, PR, 00931-3346, USA.
Rafael V C GuidoLaboratório de Química Medicinal e Computacional, Centro de Pesquisa e Inovação em Biodiversidade e Fármacos, Instituto de Física de São Carlos, Universidade de São Paulo, Avenida João Dagnone 1100, Jardim Santa Angelina, São Carlos, SP, 13563-120, Brazil.
Adriano D AndricopuloLaboratório de Química Medicinal e Computacional, Centro de Pesquisa e Inovação em Biodiversidade e Fármacos, Instituto de Física de São Carlos, Universidade de São Paulo, Avenida João Dagnone 1100, Jardim Santa Angelina, São Carlos, SP, 13563-120, Brazil.
Gabriela Ortiz SotoDepartment of Microbiology and Immunology, Universidad Central del Caribe School of Medicine, PO Box 60327, Bayamón, PR, 00960, USA.
José W RodríguezDepartment of Microbiology and Immunology, Universidad Central del Caribe School of Medicine, PO Box 60327, Bayamón, PR, 00960, USA.
David J Sanabria-RíosFaculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR, 00919, USA.
Néstor M CarballeiraDepartment of Chemistry, University of Puerto Rico, Rio Piedras Campus, PO Box 23346, San Juan, PR, 00931-3346, USA. nestor.carballeira1@upr.edu.
University of Puerto Rico at Río Piedras · PRCentral University of the Caribbean · PRUniversidade de São Paulo · BRInterAmerican University of Puerto Rico · PRWeatherford College · US

Funding

SCIENCE AND TECHNOLOGY COMPETENCY & EDUCATION CORE (STCE)P20GM103475 · NIGMS · UNIVERSITY OF PUERTO RICO MED SCIENCES · PI Humberto Guillermo Ortiz-Zuazaga · 2012 to 2026
$52.9M
Upgrade Laboratories Facilities at UPR-Rio PiedrasR25GM061151 · NIGMS · UNIVERSITY OF PUERTO RICO RIO PIEDRAS · PI CARBALLEIRA, NESTOR MANUEL · 2001 to 2023
$32.5M
TECHNOLOGIES AND RESOURCES FOR CORE LABORATORIESU54MD007587 · NIMHD · UNIVERSITY OF PUERTO RICO MED SCIENCES · PI LUCIANO, CARLOS A., NOBOA, CARIAMARIE · 2012 to 2018
$23.2M
UNIVERSIDAD CENTRAL DEL CARIBE BIOMEDICAL RESEARCH CENTERSG12MD007583 · NIMHD · UNIVERSIDAD CENTRAL DEL CARIBE · PI RODRIGUEZ, JOSE GINEL · 2012 to 2016
$8.4M
TRCLU54RR026139 · NCRR · UNIVERSITY OF PUERTO RICO MED SCIENCES · PI FRONTERA, WALTER R. · 2010 to 2011
$8.4M
Marine Fatty Acids as New Antifungal, Antimycobacterial, and Topo-l AgentsSC1GM084708 · NIGMS · UNIVERSITY OF PUERTO RICO RIO PIEDRAS · PI CARBALLEIRA, NESTOR MANUEL · 2008 to 2011
$986k
NCRR NIH HHS U54 RR026139NIGMS NIH HHS 5P20 GM 103475-13NIGMS NIH HHS R25 GM061151NIGMS NIH HHS SC1 GM084708NIGMS NIH HHS SC1GM084708NIMHD NIH HHS 8G12MD007583-28NIMHD NIH HHS 8U54MD007587-03NIMHD NIH HHS G12 MD007583NIMHD NIH HHS U54 MD007587
6 · The paper itself

Abstract

The natural fatty acids (5Z)-5-pentacosenoic and (9Z)-9-pentacosenoic acids were synthesized for the first time in eight steps starting from either 4-bromo-1-butanol or 8-bromo-1-butanol and in 20-58% overall yields, while the novel fatty acids 5-pentacosynoic and 9-pentacosynoic acids were also synthesized in six steps and in 34-43% overall yields. The ∆(5) acids displayed the best IC50's (24-38 µM) against the HIV-1 reverse transcriptase (RT) enzyme, comparable to nervonic acid (IC50 = 12 µM). The ∆(9) acids were not as effective towards HIV-RT with the (9Z)-9-pentacosenoic acid displaying an IC50 = 54 µM and the 9-pentacosynoic acid not inhibiting the enzyme at all. Fatty acid chain length and position of the unsaturation was important for the observed inhibition. None of the synthesized fatty acids were toxic (IC50 > 500 µM) towards peripheral blood mononuclear cells. Molecular modeling studies indicated the structural determinants underlying the biological activity of the most potent compounds. These results provide new insights into the structural requirements that must be present in fatty acids so as to enhance their inhibitory potential towards HIV-RT.

Indexed as

Cells, CulturedEnzyme InhibitorsFatty AcidsFatty Acids, UnsaturatedHIV Reverse TranscriptaseHumansLeukocytes, MononuclearModels, MolecularStructure-Activity Relationship5-pentacosenoic acid5-pentacosynoic acidEnzyme InhibitorsFatty AcidsFatty Acids, UnsaturatedHIV Reverse Transcriptasereverse transcriptase, Human immunodeficiency virus 1Fatty acidsHuman immunodeficiency virusPentacosenoic acidReverse transcriptaseSynthesis

Identifiers

PMID26345647
PMCPMC4841444
OpenAlexW1629184763

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Registered trials

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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.