Carbazole-based bis-ureas and thioureas as electroneutral anion transporters

References

• Davis JT, Gale PA, Quesada R. Advances in anion transport and supramolecular medicinal chemistry. Chem. Soc. Rev. 2020;49:6056–6086.
   Web of Science ®Google Scholar
• Li H, Valkenier H, Judd LW, et al. Efficient, non-toxic anion transport by synthetic carriers in cells and epithelia. Nat. Chem. 2016;8:24–32.
   PubMed Web of Science ®Google Scholar
• Li H, Valkenier H, Thorne AG, et al. Anion carriers as potential treatments for cystic fibrosis: transport in cystic fibrosis cells, and additivity to channel-targeting drugs. Chem. Sci. 2019;10:9663–9672.
   PubMed Web of Science ®Google Scholar
• Jowett LA, Howe EN, Soto-Cerrato V, et al. Indole-based perenosins as highly potent HCl transporters and potential anti-cancer agents. Sci. Rep. 2017;7:9397.
   PubMed Web of Science ®Google Scholar
• Park S-H, Park S-H, Howe EN, et al. Determinants of ion-transporter cancer cell death. Chem.2019;5:2079–2098.
   PubMed Web of Science ®Google Scholar
• Tapia L, Pérez Y, Bolte M, et al. pH-dependent chloride transport by pseudopeptidic cages for the selective killing of cancer cells in acidic microenvironments. Angew. Chem. Int. Ed. 2019;58:12465–12468.
   Google Scholar
• Zhang S, Wang Y, Xie W, et al. Squaramide-based synthetic chloride transporters activate TFEB but block autophagic flux. Cell Death Dis. 2019;10:242.
   PubMed Web of Science ®Google Scholar
• Brotherhood PR, Davis AP. Steroid-based anion receptors and transporters. Chem. Soc. Rev. 2010;39:3633–3647.
   PubMed Web of Science ®Google Scholar
• Brooks SJ, Gale PA, Light ME. ortho-Phenylenediamine bis-urea–carboxylate: a new reliable supramolecular synthon. CrystEngComm. 2005;7:586–591.
   Web of Science ®Google Scholar
• Karagiannidis LE, Haynes CJ, Holder KJ, et al. Highly effective yet simple transmembrane anion transporters based upon ortho-phenylenediamine bis-ureas. Chem. Commun. 2014;50:12050–12053.
   PubMed Web of Science ®Google Scholar
• Moore SJ, Haynes CJ, González J, et al. Chloride, carboxylate and carbonate transport by ortho-phenylenediamine-based bisureas. Chem. Sci. 2013;4:103–117.
   Web of Science ®Google Scholar
• Dias CM, Valkenier H, Davis AP. Anthracene bisureas as powerful and accessible anion carriers. Chem. Eur. J. 2018;24:6262–6268.
   PubMed Web of Science ®Google Scholar
• Hussain S, Brotherhood PR, Judd LW, et al. Diaxial diureido decalins as compact, efficient, and tunable anion transporters. J. Am. Chem. Soc. 2011;2011:1614–1617.
   Google Scholar
• McNally BA, Koulov AV, Lambert TN, et al. Structure–activity relationships in cholapod anion carriers: enhanced transmembrane chloride transport through substituent tuning. Chem. Eur. J. 2008;14:9599–9606.
   PubMed Web of Science ®Google Scholar
• Gale PA. Synthetic indole, carbazole, biindole and indolocarbazole-based receptors: applications in anion complexation and sensing. Chem Commun. 2008;38:4525–4540.
   PubMed Web of Science ®Google Scholar
• Bąk KM, Chabuda K, Montes H, et al. 1,8-Diamidocarbazoles: an easily tuneable family of fluorescent anion sensors and transporters. Org. Biomol. Chem. 2018;16:5188–5196.
   PubMed Web of Science ®Google Scholar
• Pomorski R, García-Valverde M, Quesada R, et al. Transmembrane anion transport promoted by thioamides. RSC Adv. 2021;11:12249–12253.
   Web of Science ®Google Scholar
• Martin K, Nõges J, Haav K, et al. Exploring selectivity of 22 acyclic urea‐, carbazole‐ and indolocarbazole‐based receptors towards 11 monocarboxylates. Eur. J. Org. Chem. 2017;2017:5231–5237.
   Web of Science ®Google Scholar
• Chmielewski MJ. A short, multigram synthesis of 1,8-diaminocarbazole. Synthesis. 2010;2010:3067–3069.
   Web of Science ®Google Scholar
• Pujol E, Blanco-Cabra N, Julián E, et al. Pentafluorosulfanyl-containing triclocarban analogs with potent antimicrobial activity. Molecules. 2018;23:2853.
   Web of Science ®Google Scholar
• Available from: http://app.supramolecular.org/bindfit/ (February 2021)
   Google Scholar
• Thordarson P. Determining association constants from titration experiments in supramolecular chemistry. Chem. Soc. Rev. 2011;40:1305–1323.
   PubMed Web of Science ®Google Scholar
• Jowett LA, Gale PA. Supramolecular methods: the chloride/nitrate transmembrane exchange assay. Supramol. Chem. 2019;31:297–312.
   Web of Science ®Google Scholar
• Boiocchi M, Del Boca L, Esteban‐Gómez D, et al. Anion‐induced urea deprotonation. Chem. Eur. J. 2005;11:3097–3104.
   PubMed Web of Science ®Google Scholar
• Wu X, Small JR, Cataldo A, et al. Voltage‐switchable HCl transport enabled by lipid headgroup–transporter interactions. Angew Chem. Int. Ed. 2019;58:15142–15147.
   Google Scholar
• Herschede SR, Gneid H, Dent T, et al. Bactericidal urea crown ethers target phosphatidylethanolamine membrane lipids. Org. Biomol. Chem. 2021;19:3838–3843.
   PubMed Web of Science ®Google Scholar
• Kamp F, Hamilton JA. pH gradients across phospholipid membranes caused by fast flip-flop of un-ionized fatty acids. Proc. Nat. Acad. Sci. USA. 1992;89:11367–11370.
   PubMed Web of Science ®Google Scholar
• Jowett LA, Howe ENW, Wu X, et al. New insights into the anion transport selectivity and mechanism of tren‐based tris‐(thio) ureas. Chem. Eur. J. 2018;24:10475–10487.
   PubMed Web of Science ®Google Scholar
• Wu X, Gale PA. Measuring anion transport selectivity: a cautionary tale. Chem. Commun. 2021;57:3979–3982.
   PubMed Web of Science ®Google Scholar
• Wu X, Wang P, Turner P, et al. Tetraurea macrocycles: aggregation-driven binding of chloride in aqueous solutions. Chem. 2019;5:1210–1222.
   Web of Science ®Google Scholar