High Affinity and Specific Binding of HIV-1 TAR RNA by a Tat-Derived Oligourea

Molecular Transporters: Synthesis of Oligoguanidinium Transporters and Their Application to Drug Delivery and Real‐Time Imaging

“…[30,31] Furthermore, racemization, frequently encountered in peptide synthesis, is not a problem in peptoid synthesis, and the "submonomer" [31] approach to peptoid synthesis allows for facile modification of side-chain spacers. A C H T U N G T R E N N U N G Although the preparation of an oligourea [32] and peptoidpeptide hybrid [33] derivatives of Tat [49][50][51][52][53][54][55][56][57] have been previously A C H T U N G T R E N N U N G reported, their cellular uptake was not explicitly studied.…”

“…The desired peptoids were prepared by using the "submonomer" [32] approach followed by attachment of fluorescein through an aminohexanoic acid spacer onto the amine terminus. After cleavage from the solid-phase resin, the fluorescently labeled oligoamine peptoids thus obtained were converted in good yields (60-70 %) into oligoguanidine peptoids by treatment with excess pyrazole-1-carboxamidine [34] and sodium carbonate (Scheme 1).…”

Biological Applications of Foldamers

“…8.6) [161]. The oligourea bound the TAR RNA with submicromolar affinity (K D ¼ 111 nM), similar to a Tatderived peptide (K D ¼ 780 nM) as determined by electrophoretic mobility shift assay [161]. Furthermore, mutant TAR RNA could not displace the oligourea from labeled TAR RNA, demonstrating the specificity of the oligourea for binding TAR RNA [161].…”

“…8.6) [161]. The oligourea bound the TAR RNA with submicromolar affinity (K D ¼ 111 nM), similar to a Tatderived peptide (K D ¼ 780 nM) as determined by electrophoretic mobility shift assay [161].…”

Design and Synthesis of Guanidinoglycosides Directed against the TAR RNA of HIV‐1

“…Tat-derived basic peptides as well as the oligocarbamates and oligoureas bind to TAR RNA specifically with high affinities in vitro [4] [5]. Tat-mimetic compounds ALX40-4C [6] and CGP64222 [7] that target TAR RNA, demonstrate pronounced antiviral activity.…”