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Title: Synthesis of Janus compounds for the recognition of G-U mismatched nucleobase pairs
Author: Artigas Solé, Gerard
Marchán Sancho, Vicente
Keywords: Bioquímica
Àcids nucleics
Espectrometria de masses
Dianes farmacològiques
Medicines alternatives
Nucleic acids
Mass spectrometry
Drug targeting
Alternative medicine
Issue Date: 2-Oct-2013
Publisher: American Chemical Society
Abstract: The design and synthesis of two Janus-type heterocycles with the 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 1H 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 Janus-containing ligands and their ability to stabilize this secondary structure upon complexation.
Note: Versió postprint del document publicat a:
It is part of: Journal of Organic Chemistry, 2013, vol. 78, num. 21, p. 10666-10677
Related resource:
ISSN: 0022-3263
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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