Furazan bis-ureas: a heterocyclic scaffold for anion binding and transport

William G. Ryder; Emilie G. Wu; Lijun Chen; Mohamed Fares; Daniel A. McNaughton; Karen Tran; Chengzhong Yu; Philip A. Gale

doi:10.1039/d3qo01956j

Furazan bis-ureas: a heterocyclic scaffold for anion binding and transport

William G. Ryder
, Emilie G. Wu
, Lijun Chen
, Mohamed Fares
, Daniel A. McNaughton
, Karen Tran
, Chengzhong Yu
, Philip A. Gale^*

^*Corresponding author for this work

University of Sydney
University of Technology Sydney
University of Queensland

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

The incorporation of hydrogen bonding motifs surrounding a central cyclic scaffold has proven to be an effective method in the design of synthetic anion transpoters. Herein, we report a novel and synthetically accessible architecture centred around an oxadiazole ring. The series was found to effectively mediate the perturbation of liposomal pH gradients at micromolar concentrations via a H⁺/Cl⁻ transport mechanism and a wide range of cytotoxicities were exhibited against cancerous and normal cell lines.

Original language	English
Pages (from-to)	1290-1298
Number of pages	9
Journal	Organic Chemistry Frontiers
Volume	11
Issue number	5
DOIs	https://doi.org/10.1039/d3qo01956j
State	Published - 2 Jan 2024
Externally published	Yes

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SDG 3 Good Health and Well-being

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10.1039/d3qo01956j

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title = "Furazan bis-ureas: a heterocyclic scaffold for anion binding and transport",

abstract = "The incorporation of hydrogen bonding motifs surrounding a central cyclic scaffold has proven to be an effective method in the design of synthetic anion transpoters. Herein, we report a novel and synthetically accessible architecture centred around an oxadiazole ring. The series was found to effectively mediate the perturbation of liposomal pH gradients at micromolar concentrations via a H+/Cl− transport mechanism and a wide range of cytotoxicities were exhibited against cancerous and normal cell lines.",

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doi = "10.1039/d3qo01956j",

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T2 - a heterocyclic scaffold for anion binding and transport

AU - Ryder, William G.

AU - Wu, Emilie G.

AU - Chen, Lijun

AU - Fares, Mohamed

AU - McNaughton, Daniel A.

AU - Tran, Karen

AU - Yu, Chengzhong

AU - Gale, Philip A.

PY - 2024/1/2

Y1 - 2024/1/2

N2 - The incorporation of hydrogen bonding motifs surrounding a central cyclic scaffold has proven to be an effective method in the design of synthetic anion transpoters. Herein, we report a novel and synthetically accessible architecture centred around an oxadiazole ring. The series was found to effectively mediate the perturbation of liposomal pH gradients at micromolar concentrations via a H+/Cl− transport mechanism and a wide range of cytotoxicities were exhibited against cancerous and normal cell lines.

AB - The incorporation of hydrogen bonding motifs surrounding a central cyclic scaffold has proven to be an effective method in the design of synthetic anion transpoters. Herein, we report a novel and synthetically accessible architecture centred around an oxadiazole ring. The series was found to effectively mediate the perturbation of liposomal pH gradients at micromolar concentrations via a H+/Cl− transport mechanism and a wide range of cytotoxicities were exhibited against cancerous and normal cell lines.

UR - https://www.scopus.com/pages/publications/85181478466

U2 - 10.1039/d3qo01956j

DO - 10.1039/d3qo01956j

M3 - 文章

AN - SCOPUS:85181478466

SN - 2052-4110

VL - 11

SP - 1290

EP - 1298

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 5

ER -

Furazan bis-ureas: a heterocyclic scaffold for anion binding and transport

Abstract

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