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Research Article

Roseophilin-inspired derivatives as transmembrane anion carriers

ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon
Pages 550-558 | Received 26 May 2022, Accepted 29 Jun 2022, Published online: 18 Jul 2022

References

  • Davis JT, Gale PA, Quesada R. Advances in anion transport and supramolecular medicinal chemistry. Chem Soc Rev. 2020;49:6056–6086.
  • Wu X, Gilchrist AM, Gale PA. Prospects and challenges in anion recognition and transport. Chem. 2020;6:1296–1309.
  • Busschaert N, Caltagirone C, Van Rossom W, et al. Applications of supramolecular anion recognition. Chem Rev. 2015;115:8038–8155.
  • Bickerton LE, Johnson TG, Kerckhoffs A, et al. Supramolecular chemistry in lipid bilayer membranes. Chem Sci. 2021;12:11252–11274.
  • Spooner MJ, Li H, Marques I, et al. Fluorinated synthetic anion carriers: experimental and computational insights into transmembrane chloride transport. Chem Sci. 2019;10(7):1976–1985.
  • Picci G, Marchesan S, Caltagirone C. Ion channels and transporters as therapeutic agents: from biomolecules to supramolecular medicinal chemistry. Biomedicines. 2022;10(4):885–908.
  • Roy A, Talukdar P. Recent advances in bioactive artificial ionophores. Chem Bio Chem. 2021;22:2925–2940.
  • Akhtar N, Biswas O, Manna D. Biological applications of synthetic anion transporters. Chem Commun. 2020;56:14137–14153.
  • Akhtar N, Pradhan N, Saha A, et al. Tuning the solubility of ionophores: glutathione-mediated transport of chloride ions across hydrophobic membranes. Chem Commun. 2019;55:8482–8485.
  • Ko SK, Kim SK, Share A, et al. Synthetic ion transporters can induce apoptosis by facilitating chloride anion transport into cells. Nat Chem. 2014;6(10):885–892.
  • Rodilla L, Korrodi-Gregório AM, Hernando E, et al. Synthetic tambjamine analogues induce mitochondrial swelling and lysosomal dysfunction leading to autophagy blockade and necrotic cell death in lung cancer. Biochem Pharmacol. 2017;126:23–33.
  • Park S-H, Park S-H, Howe ENW, et al. Determinants of Ion-transporter cancer cell death. Chem. 2019;5:2079–2098.
  • Carreira-Barral I, Rumbo C, Mielczarek M, et al. Small molecule anion transporters display in vitro antimicrobial activity against clinically relevant bacterial strains. Chem Commun. 2019;55:10080–10083.
  • Cossu C, Fiore M, Baroni D, et al. Anion-transport mechanism of a triazole-bearing derivative of prodigiosine: a candidate for cystic fibrosis therapy. Front Pharmacol. 2018;9:852–865.
  • 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(42):9663–9672.
  • Gianotti A, Capurro V, Delpiano L, et al. Small molecule anion carriers correct abnormal airway surface liquid properties in cystic fibrosis airway Epithelia. Int J Mol Sci. 2020;21:1488–1502.
  • Fürstner A. Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years. Angew Chem Int Ed. 2003;42:3582–3603.
  • Pinkerton DM, Banwell MG, Willis AC. Total syntheses of tambjamines C, E, F, G, H, I and J, BE-18591, and a related alkaloid from the marine bacterium pseudoalteromonas tunicate. Org Lett. 2007;9:5127–5130.
  • Sakai-Kawada FE, Ip CG, Hagiwara KA, et al. Biosynthesis and bioactivity of prodiginine analogs in marine bacteria, pseudoalteromonas: a mini review. Front Microbiol. 2019;10:1715–1723.
  • Hayakawa Y, Kawakami K, Seto H, et al. Structure of a new antibiotic, roseophilin. Tetrahedron Lett. 1992;33:2701–2704.
  • Zhang X, Zhang C, Wang X, et al. Mild Friedel–crafts reactions enable a robust synthesis of roseophilin. Org Lett. 2019;21:3357–3360.
  • Fürstner A, Weintritt H. Total synthesis of roseophilin. J Am Chem Soc. 1998;120:2817–2825.
  • Fürstner A, Grabowski EJ. Studies on DNA cleavage by cytotoxic pyrrole alkaloids reveal the distinctly different behavior of roseophilin and prodigiosin derivatives. ChemBioChem. 2001;2:706–709.
  • Haynes SW, Sydor PK, and Stanley AE, et al. Role and substrate specificity of the Streptomyces coelicolor RedH enzyme in undecylprodiginine biosynthesis Chem Commun . 2008 ; 1865–1867. DOI: 10.1039/B801677A.
  • Daïri K, Yao Y, Faley M, et al. A scalable process for the synthesis of the bcl inhibitor obatoclax. Org Process Res Dev. 2007;11:1051–1054.
  • Aldrich LN, Dawson ES, Lindsley CW. Evaluation of the biosynthetic proposal for the synthesis of marineosins A and B. Org Lett. 2010;12:1048–1051.
  • Jowett LA, Gale PA. Supramolecular methods: the chloride/nitrate transmembrane exchange assay. Supramol Chem. 2019;31(5):297–312.
  • García-Valverde M, Alfonso I, Quiñonero D, et al. Conformational analysis of a model synthetic prodiginine. J Org Chem. 2012;77:6538–6544.
  • Jeffrey GA. An introduction to hydrogen bonding. Oxford, UK: Oxford University Press; 1997.
  • Steiner T. The hydrogen bond in the solid state. Angew Chem Int Ed. 2002;41:48–76.
  • Carreira-Barral I, Mielczarek M, Alonso-Carrillo D, et al. Click-tambjamines as efficient and tunable bioactive anion transporters. Chem Commun. 2020;56:3218–3221.
  • de Greñu B D, Iglesias Hernández P, Espona M, et al. Synthetic prodiginine obatoclax (GX15-070) and related analogues: anion binding, transmembrane transport, and cytotoxicity properties. Chem Eur J. 2011;17:14074–14083.
  • Knight NJ, Hernando E, Haynes CJE, et al. QSAR analysis of substituent effects on tambjamine anion transporters. Chem Sci. 2016;7:1600–1608.

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