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Synthesis and Telomeric G-Quadruplex-Stabilizing Ability of Macrocyclic Hexaoxazoles Bearing Three Side Chains.


ABSTRACT: G-quadruplexes (G4s), which are structures formed in guanine-rich regions of DNA, are involved in a variety of significant biological functions, and therefore "sequence-dependent" selective G4-stabilizing agents are required as tools to investigate and modulate these functions. Here, we describe the synthesis of a new series of macrocyclic hexaoxazole-type G4 ligand (6OTD) bearing three side chains. One of these ligands, 5b, stabilizes telomeric G4 preferentially over the G4-forming DNA sequences of c-kit and K-ras, due to the interaction of its piperazinylalkyl side chain with the groove of telomeric G4.

SUBMITTER: Ma Y 

PROVIDER: S-EPMC6358838 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Synthesis and Telomeric G-Quadruplex-Stabilizing Ability of Macrocyclic Hexaoxazoles Bearing Three Side Chains.

Ma Yue Y   Iida Keisuke K   Sasaki Shogo S   Hirokawa Takatsugu T   Heddi Brahim B   Phan Anh Tuân AT   Nagasawa Kazuo K  

Molecules (Basel, Switzerland) 20190111 2


G-quadruplexes (G4s), which are structures formed in guanine-rich regions of DNA, are involved in a variety of significant biological functions, and therefore "sequence-dependent" selective G4-stabilizing agents are required as tools to investigate and modulate these functions. Here, we describe the synthesis of a new series of macrocyclic hexaoxazole-type G4 ligand (6OTD) bearing three side chains. One of these ligands, <b>5b</b>, stabilizes telomeric G4 preferentially over the G4-forming DNA s  ...[more]

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