A route for preparing new neamine derivatives targeting HIV-1 TAR RNA

Add time:08/19/2019    Source:sciencedirect.com

In the search for molecules possessing antibiotic or antiviral properties and ribonuclease like activity, that is, able to induce the cleavage of bacterial or viral RNA targets, we report a new route for preparing selectively neamine derivatives modified at their 4′- and/or 5-hydroxyl functions. Using trityl protective groups for the amino functions and 4-methoxybenzyl groups for the hydroxyl functions, new neamine derivatives, such as histidine, phenanthroline, flavin, adenine conjugates were efficiently obtained after a single deprotection step under acid conditions. For the first time, 4′-modified neamine derivatives were prepared. Most of the 4′-derivatives showed affinity and selectivity for TAR RNA close to those of the corresponding 5-derivatives. The most potent compound is the 4′-histidine derivative 31 which binds more tightly to TAR RNA compared to its 5-isomer and neamine and recognizes selectively TAR oligonucleotides having a bulge.

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