Making a match for valinomycin: Steroidal scaffolds in the design of electroneutral, electrogenic anion carriers

Accounts of Chemical Research

Volumn 46, Issue 12, 2013, Pages 2898-2909

  Valkenier, Hennie ^a   Davis, Anthony P ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; DRUG CARRIER; STEROID; VALINOMYCIN;

ARTICLE; BIOLOGICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; METABOLISM;

ANIONS; DRUG CARRIERS; DRUG DESIGN; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; STEROIDS; VALINOMYCIN;

EID: 84890620749     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar4000345     Document Type: Article

References (48)

1. Pressman, B. C. Biological applications of ionophores Annu. Rev. Biochem. 1976, 45, 501-530
2. Neupertlaves, K.; Dobler, M. Crystal-structure of a K+ complex of Valinomycin Helv. Chim. Acta 1975, 58, 432-442
3. Lauger, P. Carrier-mediated ion transport Science 1972, 178, 24-30
4. Lehn, J.-M. Supramolecular Chemistry-Scope and Perspectives Molecules, Supermolecules, and Molecular Devices Angew. Chem., Int. Ed. Engl. 1988, 27, 89-112
5. Ashcroft, F. M. Ion Channels and Disease; Academic Press: London, 2000.
6. Davis, A. P.; Sheppard, D. N.; Smith, B. D. Development of synthetic membrane transporters for anions Chem. Soc. Rev. 2007, 36, 348-357
7. 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)
8. Dietrich, B. Design of anion receptors: Applications Pure Appl. Chem. 1993, 65, 1457
9. Blanda, M. T.; Horner, J. H.; Newcomb, M. Macrocycles Containing Tin. Preparation of Macrobicyclic Lewis Acidic Hosts Containing Two Tin Atoms and 119Sn NMR Studies of their Chloride and Bromide Binding Properties in Solution J. Org. Chem. 1989, 54, 4626-4636
10. Yang, X.; Knobler, C. B.; Hawthorne, M. F. '[12]Mercuracarborand-4', the First Representative of a New Class of Rigid Macrocyclic Electrophiles: The Chloride Ion Complex of a Charge-Reversed Analogue of [12]Crown-4 Angew. Chem., Int. Ed. Engl. 1991, 30, 1507-1508
11. Worm, K.; Schmidtchen, F. P.; Schier, A.; Schafer, A.; Hesse, M. Macrotricyclic Borane-Amine Adducts: The First Uncharged Synthetic Host Compounds Without Lewis Acid Character, for anionic Guests Angew. Chem., Int. Ed. Engl. 1994, 33, 327-329 (Pubitemid 24986834)
12. Savage, P. B.; Holmgren, S. K.; Gellman, S. H. Anion and Ion Pair Complexation by a Macrocyclic Phosphine Oxide Disulfoxide J. Am. Chem. Soc. 1994, 116, 4069-4070 (Pubitemid 24980997)
13. Valiyaveettil, S.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. Synthesis and complexation studies of neutral anion receptors Angew. Chem., Int. Ed. Engl. 1993, 32, 900
14. Scheerder, J.; Fochi, M.; Engbersen, J.; Reinhoudt, D. N. Urea-derivatised p-tert-butylcalixarenes: Neutral ligands for selective anion complexation J. Org. Chem. 1994, 59, 7815
15. Davis, A. P.; Perry, J. J.; Williams, R. P. Anion recognition by tripodal receptors derived from cholic acid J. Am. Chem. Soc. 1997, 119, 1793-1794 (Pubitemid 27145529)
16. Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L. Thermodynamic And Kinetic Data For Macrocycle Interaction With Cations And Anions Chem. Rev. 1991, 91, 1721-2085
17. Davis, A. P. Cholaphanes et al.; Steroids as Structural Components in Molecular Engineering Chem. Soc. Rev. 1993, 22, 243-253
18. Davis, A. P.; Perry, J. J.; Wareham, R. S. Anion recognition by alkyl cholates: Neutral anionophores closely related to a natural product Tetrahedron Lett. 1998, 39, 4569-4572 (Pubitemid 28255285)
19. Davis, A. P.; Gilmer, J. F.; Perry, J. J. A steroid-based cryptand for halide anions Angew. Chem., Int. Ed. Engl. 1996, 35, 1312-1315
20. Davis, A. P.; Dresen, S.; Lawless, L. J. Mitsunobu reactions with methanesulfonic acid; The replacement of equatorial hydroxyl groups by azide with net retention of configuration Tetrahedron Lett. 1997, 38, 4305-4308 (Pubitemid 27244031)
21. Broderick, S.; Davis, A. P.; Williams, R. P. The ″Triamino- analogue″ of Methyl Cholate; A Facial Amphiphile and Scaffold with Potential for Combinatorial and Molecular Recognition Chemistry Tetrahedron Lett. 1998, 39, 6083-6086 (Pubitemid 28358024)
22. Davis, A. P.; Pérez-Payán, M. N. The ″triamino- analogue″ of methyl cholate; A practical, large- scale synthesis Synlett 1999, 991-993
23. del Amo, V.; Siracusa, L.; Markidis, T.; Baragana, B.; Bhattarai, K. M.; Galobardes, M.; Naredo, G.; Pérez-Payán, M. N.; Davis, A. P. Differentially-protected steroidal triamines; scaffolds with potential for medicinal, supramolecular, and combinatorial chemistry Org. Biomol. Chem. 2004, 2, 3320-3328
24. Davis, A. P.; Perry, J. J.; Williams, R. P. Anion recognition by tripodal receptors derived from cholic acid J. Am. Chem. Soc. 1997, 119, 1793-1794 (Pubitemid 27145529)
25. Kyba, E. P.; Helgeson, R. C.; Madan, K.; Gokel, G. W.; Tarnowski, T. L.; Moore, S. S.; Cram, D. J. Host-Guest Complexation. 1. Concept and Illustration J. Am. Chem. Soc. 1977, 99, 2564-2571
26. Ayling, A. J.; Broderick, S.; Clare, J. P.; Davis, A. P.; Pérez-Payán, M. N.; Lahtinen, M.; Nissinen, M. J.; Rissanen, K. An extraction-based assay for neutral anionophores: The measurement of high binding constants to steroidal receptors in a nonpolar solvent Chem.-Eur. J. 2002, 8, 2197-2203 (Pubitemid 34534444)
27. Clare, J. P.; Ayling, A. J.; Joos, J. B.; Sisson, A. L.; Magro, G.; Pérez-Payán, M. N.; Lambert, T. N.; Shukla, R.; Smith, B. D.; Davis, A. P. Substrate discrimination by cholapod anion receptors: Geometric effects and the ″affinity-selectivity principle″ J. Am. Chem. Soc. 2005, 127, 10739-10746 (Pubitemid 41061448)
28. Romeo, R.; Arena, G.; Scolaro, L. M.; Plutino, M. R. Ion-pair mechanism in square planar substitution. Reactivity of cationic platinum(II) complexes with negatively charged nucleophiles in solvents of high, medium and low polarity Inorg. Chim. Acta 1995, 240, 81-92
29. Ayling, A. J.; Pérez-Payán, M. N.; Davis, A. P. New "cholapod" anionophores; high-affinity halide receptors derived from cholic acid J. Am. Chem. Soc. 2001, 123, 12716-12717 (Pubitemid 33140412)
30. Dryfe, R. A. W.; Hill, S. S.; Davis, A. P.; Joos, J. B.; Roberts, E. P. L. Electrochemical quantification of high-affinity halide binding by a steroid-based receptor Org. Biomol. Chem. 2004, 2, 2716-2718
31. Mascal, M. A statistical analysis of halide center dot center dot center dot H-A (A = OR, NR2, N+R3) hydrogen bonding interactions in the solid state J. Chem. Soc., Perkin Trans. 2 1997, 1999-2001 (Pubitemid 127443421)
32. Bhattarai, K. M.; del Amo, V.; Magro, G.; Sisson, A. L.; Joos, J. B.; Charmant, J. P. H.; Kantacha, A.; Davis, A. P. The "triamino-analogue" of methyl allocholate; a rigid, functionalised scaffold for supramolecular chemistry Chem. Commun. 2006, 2335-2337 (Pubitemid 43846369)
33. Lambert, T. N.; Boon, J. M.; Smith, B. D.; Perez-Payan, M. N.; Davis, A. P. Facilitated phospholipid flip-flop using synthetic steroid- derived translocases J. Am. Chem. Soc. 2002, 124, 5276-5277 (Pubitemid 34506918)
34. Boon, J. M.; Lambert, T. N.; Sisson, A. L.; Davis, A. P.; Smith, B. D. Facilitated phosphatidylserine (PS) flip-flop and thrombin activation using a synthetic PS scramblase J. Am. Chem. Soc. 2003, 125, 8195-8201 (Pubitemid 36828582)
35. Merritt, M.; Lanier, M.; Deng, G.; Regen, S. L. Sterol-polyamine conjugates as synthetic ionophores J. Am. Chem. Soc. 1998, 120, 8494-8501 (Pubitemid 28420473)
36. Sakai, N.; Matile, S. Transmembrane ion transport mediated by amphiphilic polyamine dendrimers Tetrahedron Lett. 1997, 38, 2613-2616 (Pubitemid 27154347)
37. Schlesinger, P. H.; Ferdani, R.; Liu, J.; Pajewska, J.; Pajewski, R.; Saito, M.; Shabany, H.; Gokel, G. W. SCMTR: A chloride-selective, membrane-anchored peptide channel that exhibits voltage gating J. Am. Chem. Soc. 2002, 124, 1848-1849 (Pubitemid 34215290)
38. Sidorov, V.; Kotch, F. W.; Abdrakhmanova, G.; Mizani, R.; Fettinger, J. C.; Davis, J. T. Ion channel formation from a calix 4 arene amide that binds HCl J. Am. Chem. Soc. 2002, 124, 2267-2278 (Pubitemid 34267113)
39. Sisson, A. L.; Clare, J. P.; Taylor, L. H.; Charmant, J. P. H.; Davis, A. P. Perturbing the Hofmeister series: a steroid-based anion receptor with preorganised quaternary ammonium and H-bond donor groups Chem. Commun. 2003, 2246-2247 (Pubitemid 37076136)
40. Koulov, A. V.; Lambert, T. N.; Shukla, R.; Jain, M.; Boon, J. M.; Smith, B. D.; Li, H. Y.; Sheppard, D. N.; Joos, J. B.; Clare, J. P.; Davis, A. P. Chloride transport across vesicle and cell membranes by steroid-based receptors Angew. Chem., Int. Ed. 2003, 42, 4931-4933 (Pubitemid 37345394)
41. 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
42. McNally, B. A.; Koulov, A. V.; Smith, B. D.; Joos, J. B.; Davis, A. P. A fluorescent assay for chloride transport; identification of a synthetic anionophore with improved activity Chem. Commun. 2005, 1087-1089 (Pubitemid 40363481)
43. Judd, L. W.; Davis, A. P. From cholapod to cholaphane transmembrane anion carriers: accelerated transport through binding site enclosure Chem. Commun. 2010, 46, 2227-2229
44. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 1997, 23, 3-25 (Pubitemid 27046991)
45. Jones, J. B.; Dodds, D. R. Enzymes in Organic-Synthesis 0.37. Preparation and Characterization of Potential Decalindione Substrates of Horse Liver Alcohol-Dehydrogenase Can. J. Chem. 1987, 65, 2397-2404
46. Hussain, S.; Brotherhood, P. R.; Judd, L. W.; Davis, A. P. Diaxial Diureido Decalins as Compact, Efficient, and Tunable Anion Transporters J. Am. Chem. Soc. 2011, 133, 1614-1617
47. Andrews, N. J.; Haynes, C. J. E.; Light, M. E.; Moore, S. J.; Tong, C. C.; Davis, J. T.; Harrell, W. A.; Gale, P. A. Structurally simple lipid bilayer transport agents for chloride and bicarbonate Chem. Sci. 2011, 2, 256-260
48. Busschaert, N.; Kirby, I. L.; Young, S.; Coles, S. J.; Horton, P. N.; Light, M. E.; Gale, P. A. Squaramides as Potent Transmembrane Anion Transporters Angew. Chem., Int. Ed. 2012, 51, 4426-4430