Guanidine modification improves functions of natural RNA-targeting alkaloids

Tamaki Endoh; Sagar Satpathi; Yutong Chen; Saki Matsumoto; Tatsuya Ohyama; Peter Podbevšek; Janez Plavec; Kazumitsu Onizuka; Fumi Nagatsugi; Naoki Sugimoto

doi:10.1039/D3NJ05833F

Guanidine modification improves functions of natural RNA-targeting alkaloids†

Tamaki Endoh,

*^a Sagar Satpathi,

^a Yutong Chen,^b Saki Matsumoto,^a Tatsuya Ohyama,^a Peter Podbevšek,^c Janez Plavec,

^cde Kazumitsu Onizuka,

^b Fumi Nagatsugi

^b and Naoki Sugimoto

*^af

Author affiliations

* Corresponding authors

^a Frontier Institute for Biomolecular Engineering Research (FIBER), Konan University, 7-1-20 Minatojima-minamimachi, Kobe, Japan
E-mail: t-endoh@konan-u.ac.jp, sugimoto@konan-u.ac.jp
Fax: +81-78-303-1495
Tel: +81-78-303-1416

^b Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai, Miyagi 980-8577, Japan

^c Slovenian NMR Centre, National Institute of Chemistry, Hajdrihova 19, Ljubljana, Slovenia

^d EN → FIST Centre of Excellence, Trg OF 13, SI-1000 Ljubljana, Slovenia

^e Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, p. p. 537, SI-1000 Ljubljana, Slovenia

^f Graduate School of Frontiers of Innovative Research in Science and Technology (FIRST), Konan University, 7-1-20 Minatojima-minamimachi, Kobe, Japan

Abstract

One of the important issues for RNA-targeting drugs is to improve their binding properties. Herein, we modified berberine, which interacts with structured RNAs, with the guanidine moiety. Protein expression from target mRNA was efficiently reduced by the modification, suggesting a simple strategy to improve the therapeutic activity.

New Journal of Chemistry

Guanidine modification improves functions of natural RNA-targeting alkaloids†

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