Anion transporters and biological systems

Accounts of Chemical Research

Volumn 46, Issue 12, 2013, Pages 2801-2813

  Gale, Philip A ^a   Pérez Tomás, Ricardo ^b   Quesada, Roberto ^c  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b UNIVERSITY OF BARCELONA   (Spain)

^c UNIVERSITY OF BURGOS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; ANTINEOPLASTIC AGENT; DRUG DERIVATIVE; ION CHANNEL; PRODIGININE; PRODIGIOSIN;

APOPTOSIS; ARTICLE; BIOLOGICAL MODEL; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECT; HUMAN; IC 50; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TRANSPORT AT THE CELLULAR LEVEL; TUMOR CELL LINE;

ANIONS; ANTINEOPLASTIC AGENTS; APOPTOSIS; BIOLOGICAL TRANSPORT; CELL LINE, TUMOR; CELL PROLIFERATION; HUMANS; INHIBITORY CONCENTRATION 50; ION CHANNELS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, BIOLOGICAL; PRODIGIOSIN;

EID: 84890785452     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar400019p     Document Type: Article

References (37)

1. Wenzel, M.; Hiscock, J. R.; Gale, P. A. Anion receptor chemistry: highlights from 2010 Chem. Soc. Rev. 2012, 41, 480-520
2. Davis, A. P.; Sheppard, D. N.; Smith, B. D. Development of synthetic membrane transporters for anions Chem. Soc. Rev. 2007, 36, 348-357
3. Davis, J. T.; Okunola, O.; Quesada, R. Recent advances in the transmembrane transport of anions Chem. Soc. Rev. 2010, 39, 3843-3862
4. Busschaert, N.; Gale, P. A. Small molecule lipid bilayer anion transporters for biological applications Angew. Chem., Int. Ed. 2013, 52, 1374-1382
5. Ashcroft, F. M. Ion Channels and Disease; Academic Press: San Diego, 2000.
6. -Symporters That Uncouple Proton Translocators J. Biol. Chem. 1998, 273, 21455-21462 (Pubitemid 28405312)
7. Davis, J. T.; Gale, P. A.; Okunola, O. A.; Prados, P.; Iglesias-Sanchez, J. C.; Torroba, T.; Quesada, R. Using smallmolecules to facilitate exchange of bicarbonate and chloride anions across liposomal membranes Nat. Chem. 2009, 1, 138-144
8. Matsuyama, S.; Llopis, J.; Deveraux, Q. L.; Tsien, R. Y.; Reed, J. C. Changes in intramitochondrial and cytosolic pH: early events that modulate caspase activation during apoptosis Nat. Cell Biol. 2000, 2, 318-325
9. Ohkuma, S.; Sato, T.; Okamoto, M.; Matsuya, H.; Arai, K.; Kataoka, T.; Nagai, K.; Wasserman, H. H. Prodigiosins uncouple lysosomal vacuolar-type ATPase through promotion of H+/Cl- symport Biochem. J. 1998, 334, 731-741 (Pubitemid 28457223)
10. 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 (Pubitemid 37010641)
11. Williamson, N. R.; Fineran, P. C.; Gristwood, T.; Chawrai, S. R.; Leeper, F. J.; Salmond, G. P. C. Anticancer and immunosuppressive properties of bacterial prodiginines Future Microbiol. 2007, 2, 605-618
12. Pérez-Tomás, R.; Viñas, M. New insights on the antitumoral properties of prodiginines Curr. Med. Chem. 2010, 17, 2222-2231
13. Sessler, J. L.; Eller, L. R.; Cho, W.-S.; Nicolaou, S.; Aguilar, A.; Lee, J. T.; Lynch, V. M.; Magda, D. J. Synthesis, Anion-Binding Properties, and In Vitro Anticancer Activity of Prodigiosin Analogues Angew. Chem., Int. Ed. 2005, 44, 5989-5992 (Pubitemid 41345917)
14. Davis, J. T. Anion Binding and Transport by Prodigiosin and Its Analogs Top. Heterocycl. Chem. 2010, 24, 145-176
15. Nguyen, M.; Marcellus, R. C.; Roulston, A.; Watson, M.; Serfass, L.; Madiraju, S. R. M.; Goulet, D.; Viallet, J.; Bélec, L.; Billot, X.; Acoca, S.; Purisima, E.; Wiegmans, A.; Cluse, L.; Johnstone, R. W.; Beauparlant, P.; Shore, G. C. Small molecule obatoclax (GX15-070) antagonizes MCL-1 and overcomes MCL-1-mediated resistance to apoptosis Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 19512-19517
16. Díaz De Greñu, B.; Iglesias-Hernández, P.; Espona, M.; Quiñonero, D.; Light, M. E.; Torroba, T.; Pérez-Tomás, R.; Quesada, R. Synthetic Prodiginine Obatoclax (GX15-070) and Related Analogues: Anion Binding, Transmembrane Transport, and Cytotoxicity Properties Chem.-Eur. J. 2011, 17, 14074-14083
17. Carté, B.; Faulkner, D. J. Defensive Metabolites from Three Nembrothid Nudibranchs J. Org. Chem. 1983, 48, 2314-2318
18. Davis, R. A.; Carroll, A. R.; Quinn, R. J. The Synthesis of a Combinatorial Library Using a Tambjamine Natural Product Template Aust. J. Chem. 2001, 54, 355-359 (Pubitemid 33694052)
19. Cavalcanti, B. C.; Junior, H. V. N.; Seleghim, M. H. R.; Berlinck, R. G. S.; Cunha, G. M. A.; Moraes, M. O.; Pessoa, C. Chem.-Biol. Interact. 2008, 174, 155-162
20. Kojiri, K.; Nakajima, S.; Suzuki, H.; Okura, A.; Suda, H. New Antitumor Substance, BE-18591, Produced by a Streptomycete J. Antibiot. 1993, 46, 1799-1803
21. Iglesias-Hernández, P.; Moreno, D.; Araujo Javier, A.; Torroba, T.; Pérez-Tomás, R.; Quesada, R. Tambjamine alkaloids and related synthetic analogs: efficient transmembrane anion transporters Chem. Commun. 2012, 48, 1556-1558
22. McNally, B. A.; Koulov, A. V.; Lambert, T. N.; Smith, B. D.; Joos, J. B.; Sisson, A. L.; Clare, J. P.; Sgarlata, V.; Judd, L. W.; Magro, G.; Davis, A. P. Structure-Activity Relationships in Cholapod Anion Carriers: Enhanced Transmembrane Chloride Transport through Substituent Tuning Chem.-Eur. J. 2008, 14, 9599-9606
23. Saggiomo, V.; Otto, S.; Marques, I.; Félix, V.; Torroba, T.; Quesada, R. The Role of Lipophilicity in Transmembrane Anion Transport Chem. Commun. 2012, 48, 5274-5276
24. Haynes, C. J. E.; Moore, S. J.; Hiscock, J. R.; Marques, I.; Costa, P. J.; Félix, V.; Gale, P. A. Tunable transmembrane chloride transport by bis-indolylureas Chem. Sci. 2012, 3, 1436-1444
25. VCCLAB, Virtual Computational Chemistry Laboratory, http://www.vcclab. org, 2005.
26. Gale, P. A. From anion receptors to transporters Acc. Chem. Res. 2011, 44, 216-226
27. Busschaert, N.; Gale, P. A.; Haynes, C. J. E.; Light, M. E.; Moore, S. J.; Tong, C. C.; Davis, J. T.; Harrell, W. A., Jr. Tripodal transmembrane transporters for bicarbonate Chem. Commun. 2010, 46, 6252-6254
28. Custelcean, R.; Bock, A.; Moyer, B. A. Selectivity Principles in Anion Separation by Crystallization of Hydrogen-Bonding Capsules J. Am. Chem. Soc. 2010, 132, 7177-7185
29. 2 as carbonate in a capsule of a neutral receptor and its release under mild conditions Chem. Commun. 2010, 46, 1082-1084 and references cited therein
30. Wu, B.; Liang, J.; Yang, J.; Jia, C.; Yang, X.-J.; Zhang, H.; Tang, N.; Janiak, C. Sulfate ion encapsulation in caged supramolecular structures assembled by second-sphere coordination Chem. Commun. 2008, 1762-1764 (Pubitemid 351479189)
31. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Fluorine in medicinal chemistry Chem. Soc. Rev. 2008, 37, 320-330
32. Smart, B. E. Fluorine substituent effects (on bioactivity) J. Fluorine Chem. 2001, 109, 3-11 (Pubitemid 33618184)
33. Busschaert, N.; Wenzel, M.; Light, M. E.; Iglesias-Hernández, P.; Pérez-Tomás, R.; Gale, P. A. Structure-activity relationships in tripodal anion transporters: the effect of fluorination J. Am. Chem. Soc. 2011, 133, 14136-14148
34. Kerns, E. H.; Di, L. Drug-like properties: concepts, structure design and methods from ADME to toxicity optimization; Academic Press: Burlington, MA, 2008.
35. Andrews, N. J.; Haynes, C. J. E.; Light, M. E.; Moore, S. J.; Tong, C. C.; Davis, A. P.; Harrell, W. A.; Gale, P. A. Structurally simple lipid bilayer transport agents for chloride and bicarbonate Chem. Sci. 2011, 2, 256-260
36. Moore, S. J.; Wenzel, M.; Light, M. E.; Morley, R.; Bradberry, S. J.; Gómez-Iglesias, P.; Soto-Cerrato, V.; Pérez-Tomás, R.; Gale, P. A. Towards "drug-like" indole-based transmembrane anion transporters Chem. Sci. 2012, 3, 2501-2508
37. Moore, S. J.; Haynes, C. J. E.; González, J.; Sutton, J. L.; Brooks, S. J.; Light, M. E.; Herniman, J.; Langley, G. J.; Soto-Cerrato, V.; Pérez-Tomás, R.; Marques, I.; Costa, P. J.; Félix, V.; Gale, P. A. Chloride, carboxylate and carbonate transport by ortho -phenylene diamine-based bis-ureas Chem. Sci. 2013, 4, 103-117