Membrane-active calixarenes: toward 'gating' transmembrane anion transport

Tetrahedron

Volumn 63, Issue 44, 2007, Pages 10743-10750

  Okunola, Oluyomi A ^a   Seganish, Jennifer L ^a   Salimian, Kevan J ^a   Zavalij, Peter Y ^a   Davis, Jeffery T ^a  

^a Bldg 142   (United States)

Author keywords

Anion transport; Calix 4 arene; Transmembrane

Indexed keywords

CALIXARENE; CHLORIDE ION; ESTER; LIPOSOME; PHENOL;

ANION TRANSPORT; ARTICLE; CHLORIDE TRANSPORT; ISOMER; MEMBRANE TRANSPORT; PH; PHOSPHOLIPID MEMBRANE; PRIORITY JOURNAL; SYNTHESIS;

EID: 34548702892     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.06.124     Document Type: Article

References (63)

1. Seganish J.L., Santacroce P.V., Salimian K.J., Fettinger J.C., Zavalij P., and Davis J.T. Angew. Chem., Int. Ed. 45 (2006) 3334-3338
2. MacKinnon R. Angew. Chem., Int. Ed. 43 (2004) 4265-4277
3. Dutzler R., Campbell E.B., Cadene M., Chait B.T., and MacKinnon R. Nature 415 (2003) 287-294
4. Sheppard D.N., Rich D.P., Ostedgaard L.S., Gregory R.J., Smith A.E., and Welsh M.J. Nature 362 (1993) 160-164
5. For a recent review on synthetic pores and channels, see:. Sisson A.L., Shah M.R., Bhosale S., and Matile S. Chem. Soc. Rev. 35 (2006) 1269-1286
6. Davis A.P., Sheppard D.N., and Smith B.D. Chem. Soc. Rev. 36 (2007) 348-357
7. Broughman J.R., Shank L.P., Takeguchi W., Schultz B.D., Iwamoto T., Mitchell K.E., and Tomich J.M. Biochemistry 41 (2002) 7350-7358
8. Schlesinger P.H., Ferdani R., Liu J., Pajewska J., Pajewki R., Saito M., Shabany H., and Gokel G.W. J. Am. Chem. Soc. 124 (2002) 1848-1849
9. You L., Ferdani R., Pajewski R., and Gokel G.W. Chem. Commun. (2006) 603-605
10. Sadownik A., Deng G., Janout V., and Regen S.L. J. Am. Chem. Soc. 117 (1995) 6138-6139
11. Otto S., Osifchin M., and Regen S.L. J. Am. Chem. Soc. 121 (1999) 7276-7277
12. Jiang C., Lee E.R., Lane M.B., Xiao Y.-F., Harris D.J., and Cheng S.H. Am. J. Physiol. 281 (2001) L1164-L1172
13. Koulov A.V., Lambert T.N., Shukla R., Jain M., Bood J.M., Smith B.D., Li H.Y., Sheppard D.N., Joos J.-B., Clare J.P., and Davis A.P. Angew. Chem., Int. Ed. 42 (2003) 4931-4933
14. Clare J.P., Ayling A.J., Joos J.-B., Sisson A.L., Magro G., Perez-Payan M.N., Lambert T.N., Shukla R., Smith B.D., and Davis A.P. J. Am. Chem. Soc. 127 (2005) 10739-10746
15. Madhavan N., Robert E.C., and Gin M.S. Angew. Chem., Int. Ed. 44 (2005) 7584-7587
16. Furstner A. Angew. Chem., Int. Ed. 42 (2003) 3582-3603
17. Gale P.A., Light M.E., McNally B., Navakhum K., Sliwinski K.I., and Smith B.D. Chem. Commun. (2005) 3773-3775
18. Sessler J.L., Eller L.R., Cho W.-S., Nicolaou S., Aguilar A., Lee J.T., Lynch V.M., and Magda D.J. Angew. Chem., Int. Ed. 45 (2005) 5989-5992
19. Seganish J.L., and Davis J.T. Chem. Commun. (2005) 5781-5783
20. Sáez Díaz R.I., Regourd J., Santacroce P.V., Davis J.T., Jakeman D.L., and Thompson A. Chem. Commun. (2007) 10.1039/b701919j
21. Santacroce P.V., Davis J.T., Light M.E., Gale P.A., Iglesia-Sanchez J.C., Prados P., and Quesada R. J. Am. Chem. Soc. 129 (2007) 1886-1887
22. Li X., Shen B., Yao X.-Q., and Yang D. J. Am. Chem. Soc. (2007) 10.1021/ja071961h
23. Sidorov V., Kotch F.W., Abdrakhmanova G., Mizani R., Fettinger J.C., and Davis J.T. J. Am. Chem. Soc. 124 (2002) 2267-2278
24. Sidorov V., Kotch F.W., Lam Y., Kuebler J.L., and Davis J.T. J. Am. Chem. Soc. 125 (2003) 2840-2841
25. Seganish J.L., Fettinger J.C., and Davis J.T. Supramolecular Chem. 18 (2006) 257-264
26. Iqbal K.S.J., and Cragg P.J. J. Chem. Soc. Dalton Trans. (2007) 26-32
27. Tanaka Y., Kobuke Y., and Sokabe M. Angew. Chem., Int. Ed. 34 (1995) 693-694
28. Yoshino N., Satake A., and Kobuke Y. Angew. Chem., Int. Ed. 40 (2001) 457-459
29. Chen W.H., Nishikawa M., Tan S.D., Yamamura M., Satake A., and Kobuke Y. Chem. Commun. (2004) 872-873
30. de Mendoza J., Cuevas F., Prados P., Meadows E.S., and Gokel G.W. Angew. Chem., Int. Ed. 37 (1998) 1534-1537
31. Paquet V., Zumbuehl A., and Carreira E.M. Bioconjugate Chem. 17 (2006) 1460-1463
32. Wright A.J., Matthews S.E., Fischer W.B., and Beer P.D. Chem.-Eur. J. 7 (2001) 3474-3481
33. Jin T. J. Chem. Soc., Perkin Trans. 2 (2002) 151-154
34. Maulucci N., De Riccardis F., Botta C.B., Casapullo A., Cressina E., Fregonese M., Tecilla P., and Izzo I. Chem. Commun. (2005) 1354-1356
35. For recent reviews on calixarenes as anion receptors, see:
36. Lhotak P. Top. Curr. Chem. 255 (2005) 65-95
37. Matthews S.E., and Beer P.D. Supramolecular Chem. 17 (2005) 411-435
38. Sidorov V., Kotch F.W., El-Kouedi M., and Davis J.T. Chem. Commun. (2000) 2369-2370
39. Kotch F.W., Sidorov V., Lam Y.F., Kayser K.J., Li H., Kaucher M.S., and Davis J.T. J. Am. Chem. Soc. 125 (2003) 15140-15150
40. Neutral amides are ligands for coordinating anions:
41. Beer P.D., and Gale P.A. Angew. Chem., Int. Ed. 40 (2001) 487-516
42. Kang S.O., Begum R.A., and Bowman-James K. Angew. Chem., Int. Ed. 45 (2001) 7882-7894
43. For some references on stimuli-responsive transporters, see:
44. Fyles T.M., Loock D., and Zhou X. J. Am. Chem. Soc. 120 (1998) 2997-3003
45. Goto C., Yamamura M., Satake A., and Kobuke Y. J. Am. Chem. Soc. 123 (2001) 12152-12159
46. Gorteau V., Perret F., Bollot G., Mareda J., Lazar A.N., Coleman A.W., Tran D.-H., Sakai N., and Matile S. J. Am. Chem. Soc. 126 (2004) 13592-13593
47. Chen W.H., and Regen S.L. J. Am. Chem. Soc. 127 (2005) 6538-6539
48. Dutzler R., Campbell E.B., and MacKinnon R. Science 300 (2003) 108-112
49. Chang S.K., Kwon S.K., and Cho I. Chem. Lett. (1987) 947-948
50. Nomura E., Takagaki M., Nakaoka C., Uchida M., and Tanaguchi H. J. Org. Chem. 64 (1999) 3151-3156
51. Arnaud-Neu F., Collins E.M., Deasy M., Ferguson G., Harris S.J., Kaitner B., Lough A.J., McKervey A., Marques E., Ruhl B.L., Schwing-Weill M.J., and Seward E.M. J. Am. Chem. Soc. 111 (1989) 8681-8691
52. Gutsche C.D., and Lin L.-G. Tetrahedron 42 (1986) 1633-1640
53. Percec V., Bera T.K., De B.B., Sanai Y., Smith J., Holerca M.N., Barboiu B., Grubbs R.B., and Fréchet J.M.J. J. Org. Chem. 66 (2001) 2104-2117
54. Iwamoto K., Araki K., and Shinkai S. J. Org. Chem. 56 (1991) 4955-4962
55. Ungaro R. In: Mandolini L., and Ungaro R. (Eds). Calixarenes in Action (2000), Imperial College, London, UK 5-10 and references therein
56. The NMR data for TAC-OH 3 closely matches that of a related triamido phenolic cone calixarene previously reported by Vicens and colleagues:. Abidi R., Oueslati I., Amri H., Thuery P., Nierlich M., Asfari Z., and Vicens J. Tetrahedron Lett. (2001) 1685-1689
57. -1. Data were collected on a Bruker SMART 1000 CCD diffractometer at 233(2) K. The structure refined to convergence [Δ/σ≤0.001] with R(F)=5.81%, wR(F2)=11.14%, GOF=1.017 for all 4378 unique reflections. Crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication # CCDC-649435. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK. E-mail: deposit@ccdc.cam.ac.uk.
58. -1. Data were collected on a Bruker SMART 1000 CCD diffractometer at 240(2) K. The structure refined to convergence [Δ/σ≤0.001] with R(F)=5.53%, wR(F2)=12.91%, GOF=0.814 for all 5489 unique reflections. Crystallographic data for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication # CCDC-649436. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK. E-mail: deposit@ccdc.cam.ac.uk.
59. The crystal structures of cone-H 2a and TAC-OEster 4 are similar to a structure previously reported for a tetra-substituted secondary ethyl-amide with t-Bu groups on its upper rim:. Arnaud-Neu F., Barboso S., Fanni S., Schwing-Weill M.-J., McKee V., and McKervey M.A. Ind. Eng. Chem. Res. 39 (2000) 3489-3492
60. The NMR association constant for TAC-OH 3 was determined, assuming a 1:1 binding stoichiometry, using the program 'Associate 1.6' from the F. N. Diederich group at ETH.
61. Biwersi J., Tulk B., and Verkman A.S. Anal. Biochem. 219 (1994) 139-143
62. McNally B.A., Koulov A.V., Smith B.D., Joos J.-B., and Davis A.P. Chem. Commun. (2005) 1087-1088
63. Araki K., Iwamoto K., Shinkai S., and Matsuda T. Bull. Chem. Soc. Jpn. 63 (1990) 3480-3485