Methods for identifying and characterizing interactions involving RNA

Blakeley, Brett D.; DePorter, Sandra M.; Mohan, Utpal; Burai, Ritwik; Tolbert, Blanton S.; McNaughton, Brian R.

doi:10.1016/j.tet.2012.07.001

Cited by 23 publications

(19 citation statements)

References 146 publications

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“…As shown in Scheme 3, the guanidinylated ligands (24)(25)(26)(27) were prepared by direct guanidinylation of their precursors (20)(21)(22)(23) following previously reported procedures. n=2 JanusB-Nea2 (23) JanusB-Nea2G4 (27) Scheme 3.…”

Section: Hydrolysis Of the Intermediate With Lioh Afforded The Expectmentioning

confidence: 99%

“…n=2 JanusB-Nea2 (23) JanusB-Nea2G4 (27) Scheme 3. Synthesis of Janus-Neamine/Guanidinoneamine ligands.…”

Section: Hydrolysis Of the Intermediate With Lioh Afforded The Expectmentioning

confidence: 99%

“…Our next objective was to study the interaction of Janus-Neamine ligands (20)(21)(22)(23) and their guanidinylated derivatives, Janus-Guanidinoneamine (24)(25)(26)(27), with Tau RNA, and in particular to evaluate their ability to stabilize Tau RNA. Besides wt we choose two of the mutated sequences associated with the development of tauopathies, +3 and +16.…”

Section: Hydrolysis Of the Intermediate With Lioh Afforded The Expectmentioning

confidence: 99%

“…These results prompted us to evaluate the ability of Janus-Guanidinoneamine ligands (24)(25)(26)(27) to stabilize the +3 mutated sequence. As shown in Table 2, guanidinylation of the aminoglycoside moiety in Janus-Neamine ligands had always a positive effect on the thermal stability of the RNA upon complexation.…”

mentioning

confidence: 99%

“…26 As an alternative to fluorescein, we choose the fluorescent nucleotide analogue 2-aminopurine-2'-deoxyribonucleotide (2-AP), which has also been widely used to determine binding affinities for RNA. 27 In order to minimize alterations in the structure and stability of +3 Tau RNA, we decided to replace the adenine base of the loop with 2-AP. Again, changes in 2-AP fluorescence intensity upon excitation at 290 nm were measured as a function of the concentration of the ligands.…”

mentioning

confidence: 99%

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Synthesis of Janus Compounds for the Recognition of G-U Mismatched Nucleobase Pairs

Artigas

Marchán

2013

J. Org. Chem.

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The design and synthesis of two Janus-type heterocycles with capacity to simultaneously recognize guanine and uracyl in G-U mismatched pairs through complementary hydrogen bond pairing is described. Both compounds were conveniently functionalized with a carboxylic function and efficiently attached to a tripeptide sequence by using solid-phase methodologies. Ligands based on the derivatization of such Janus compounds with a small aminoglycoside, neamine, and its guanidinylated analogue have been synthesized, and their interaction with Tau RNA has been investigated by using several biophysical techniques, including UV-monitored melting curves, fluorescence titration experiments and 1 H NMR.The overall results indicated that Janus-neamine/guanidinoneamine showed some preference for the +3 mutated RNA sequence associated with the development of some tauopathies, although preliminary NMR studies have not confirmed binding to G-U pairs.Moreover, a good correlation has been found between the RNA binding affinity of such 2 Janus-containing ligands and their ability to stabilize this secondary structure upon complexation.

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