Design and synthesis of a novel peptidomimetic inhibitor of HIV-1 Tat–TAR interactions: Squaryldiamide as a new potential bioisostere of unsubstituted guanidine

By performing RNA-targeted structure–activity-relationship (SAR) studies, we discovered a novel peptidomimetic containing squaryldiamide as a potential bioisostere replacement for guanidine that binds TAR RNA with high affinity. By performing RNA-targeted structure–activity relationship studies, we...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2005-10, Vol.15 (19), p.4243-4246
Main Authors: Lee, Chi-Wan, Cao, Hong, Ichiyama, Kozi, Rana, Tariq M.
Format: Article
Language:English
Subjects:
Anti-HIV Agents - chemical synthesis
Anti-HIV Agents - pharmacology
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiviral agents
Biological and medical sciences
Cyclobutanes
Diamide - chemical synthesis
Diamide - pharmacology
Drug Design
Gene Products, tat - chemistry
Guanidine
HIV Long Terminal Repeat - drug effects
HIV-1 - chemistry
Medical sciences
Molecular Mimicry
Oligopeptides - chemical synthesis
Oligopeptides - metabolism
Oligopeptides - pharmacology
Pharmacology. Drug treatments
RNA-Binding Proteins - chemistry
RNA–protein interactions
Structure-Activity Relationship
tat Gene Products, Human Immunodeficiency Virus
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Summary:By performing RNA-targeted structure–activity-relationship (SAR) studies, we discovered a novel peptidomimetic containing squaryldiamide as a potential bioisostere replacement for guanidine that binds TAR RNA with high affinity. By performing RNA-targeted structure–activity relationship studies, we discovered a novel peptidomimetic containing squaryldiamide as a potential bioisostere replacement for guanidine that binds transactivation responsive RNA with high affinity.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2005.06.077