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

Content Provider	Springer Nature Link
Author	Moreira, Lizabeth Giménez Orella, Elsie A. Rosado, Karolyna Guido, Rafael V. C. Andricopulo, Adria D. Soto, Gabriela Ortiz Rodríguez, José W. Sanabria Ríos, David J. Carballeira, Néstor M.
Copyright Year	2015
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 IC$_{50’s}$ (24–38 µM) against the HIV-1 reverse transcriptase (RT) enzyme, comparable to nervonic acid (IC$_{50}$ = 12 µM). The ∆$^{9}$ acids were not as effective towards HIV-RT with the (9Z)-9-pentacosenoic acid displaying an IC$_{50}$ = 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 (IC$_{50}$ > 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.
Starting Page	1043
Ending Page	1050
Page Count	8
File Format	PDF
ISSN	00244201
Journal	Lipids
Volume Number	50
Issue Number	10
e-ISSN	15589307
Language	English
Publisher	Springer Berlin Heidelberg
Publisher Date	2015-09-07
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Fatty acids Human immunodeficiency virus Pentacosenoic acid Reverse transcriptase Synthesis Lipidology Neurochemistry Medical Biochemistry Nutrition Medicinal Chemistry Microbial Genetics and Genomics
Content Type	Text
Resource Type	Article
Subject	Cell Biology Organic Chemistry Biochemistry

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

Reduced Maternal Erythrocyte Long Chain Polyunsaturated Fatty Acids Exist in Early Pregnancy in Preeclampsia

Total Synthesis and Antileishmanial Activity of the Natural Occurring Acetylenic Fatty Acids 6-Heptadecynoic Acid and 6-Icosynoic Acid

Sources and Bioactive Properties of Conjugated Dietary Fatty Acids

Mechanisms of regulation of gene expression by fatty acids

Impact of Administered Bifidobacterium on Murine Host Fatty Acid Composition

Essential Fatty Acid Assimilation and Synthesis in Larvae of the Bivalve Crassostrea gigas

Structure and function of animal fatty acid synthase

The Complex and Important Cellular and Metabolic Functions of Saturated Fatty Acids

Aberrations in Plasma Phospholipid Fatty Acids in Lung Cancer Patients

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

Similar Documents

Reduced Maternal Erythrocyte Long Chain Polyunsaturated Fatty Acids Exist in Early Pregnancy in Preeclampsia

Total Synthesis and Antileishmanial Activity of the Natural Occurring Acetylenic Fatty Acids 6-Heptadecynoic Acid and 6-Icosynoic Acid

Sources and Bioactive Properties of Conjugated Dietary Fatty Acids

Mechanisms of regulation of gene expression by fatty acids

Impact of Administered Bifidobacterium on Murine Host Fatty Acid Composition

Essential Fatty Acid Assimilation and Synthesis in Larvae of the Bivalve Crassostrea gigas

Structure and function of animal fatty acid synthase

The Complex and Important Cellular and Metabolic Functions of Saturated Fatty Acids

Aberrations in Plasma Phospholipid Fatty Acids in Lung Cancer Patients

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