Recognition of Nucleic Acid Junctions Using Triptycene‐Based Molecules

Barros, Stephanie A.; Chenoweth, David M.

doi:10.1002/anie.201407061

Cited by 48 publications

(37 citation statements)

References 92 publications

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“…Chemical and enzymatic probing of the 5′‐end of the σ 32 mRNA secondary structure reveals that the regulatory regions (regions A and B) within the RNA structure form a perfectly paired three‐way junction (3WJ) . Recently, we developed a new class of nucleic acid junction binders based on the triptycene scaffold . Herein, we report the first triptycene‐based small molecules that are able to modulate the stability of the σ 32 mRNA.…”

Section: Figurementioning

confidence: 99%

Modulation of the E. coli rpoH Temperature Sensor with Triptycene‐Based Small Molecules

2016

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Regulation of the heat shock response (HSR) is essential in all living systems. In E. coli, the HSR is regulated by the alternative σ factor, σ32, which is encoded by the rpoH gene. The mRNA of rpoH adopts a complex secondary structure critical for proper translation of the σ32 protein. At low temperature the rpoH gene transcript forms a highly structured mRNA containing several three-way junctions, including a rare perfectly paired three-way junction (3WJ). This complex secondary structure serves as a primitive but highly effective strategy for thermal control of gene expression. Here, we report the first small molecule modulators of the E. coli σ32 mRNA temperature sensor.

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Section: Figurementioning

confidence: 99%

Modulation of the E. coli rpoH Temperature Sensor with Triptycene‐Based Small Molecules

2016

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“…the ruthenium trisdiimine complex NQ418 (439); two new triptycene derivatives XX-67 (543) and XX-32 (544), whose synthesis will be described elsewhere (A. Granzhan et al), structurally close to the compounds previously studied by D. Chenoweth and coworkers; 25,26 and a newly reported organometallic cage Rec-(AN)-DONQ (562). 34 Classical DNA intercalators are also identified, notably two porphyrins, TMPyP4 (545) 35 and TEGPy (546), 36 and two cationic pyrene derivatives, AZ03 (414) and AZ04 (415), 37 owing to their innate ability to interact with negatively charged nucleic acids.…”

Section: Selection Of Chemical Libraries For Twj-screen Evaluationsmentioning

confidence: 91%

Identification of Three-Way DNA Junction Ligands through Screening of Chemical Libraries and Validation by Complementary in Vitro Assays

et al. 2019

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The human genome is replete with repetitive DNA sequences that can fold into thermodynamically stable secondary structures such as hairpins and quadruplexes. Cellular enzymes exist to cope with these structures whose stable accumulation would result in DNA damage through interference with DNA transactions such as transcription and replication. Therefore, chemical stabilization of secondary DNA structures offers an attractive way to foster DNA transaction-associated damages to trigger cell death in proliferating cancer cells. While much emphasis has been recently given to DNA quadruplexes, we focused here on three-way DNA junctions (TWJ) and report on a strategy to identify TWJ-targeting agents through a combination of in vitro techniques (TWJ-Screen, PAGE, FRET-melting, ESI-MS, dialysis equilibrium and SRB assays). We designed a complete workflow and screened 1200 compounds to identify promising TWJ-ligands selected on stringent criteria in terms of TWJ folding ability, affinity and selectivity.

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Section: Figurementioning

confidence: 99%

Modulation of the E. coli rpoH Temperature Sensor with Triptycene‐Based Small Molecules

2016

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Regulation of the heat shock response (HSR) is essential in all living systems. In E. coli, the HSR is regulated by an alternative s factor, s 32 , which is encoded by the rpoH gene. The mRNA of rpoH adopts a complex secondary structure that is critical for the proper translation of the s 32 protein. At low temperatures, the rpoH gene transcript forms a highly structured mRNA containing several three-way junctions, including a rare perfectly paired three-way junction (3WJ). This complex secondary structure serves as a primitive but highly effective strategy for the thermal control of gene expression. In this work, the first small-molecule modulators of the E. coli s 32 mRNA temperature sensor are reported.

show abstract

Recognition of Nucleic Acid Junctions Using Triptycene‐Based Molecules

Cited by 48 publications

References 92 publications

Modulation of the E. coli rpoH Temperature Sensor with Triptycene‐Based Small Molecules

Modulation of the E. coli rpoH Temperature Sensor with Triptycene‐Based Small Molecules

Identification of Three-Way DNA Junction Ligands through Screening of Chemical Libraries and Validation by Complementary in Vitro Assays

Modulation of the E. coli rpoH Temperature Sensor with Triptycene‐Based Small Molecules

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