Anion binding and transport by steroid-based receptors

Coordination Chemistry Reviews

Volumn 250, Issue 23-24, 2006, Pages 2939-2951

  Davis, Anthony P ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Anion recognition; Anion transport; Cholic acid; Hydrogen bonding; Steroids; Supramolecular chemistry

Indexed keywords

EID: 33750502923     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2006.05.008     Document Type: Review

References (71)

1. Virtanen E., and Kolehmainen E. Eur. J. Org. Chem. (2004) 3385
2. Zhu X.X., and Nichifor M. Acc. Chem. Res. 35 (2002) 539
3. Wallimann P., Marti T., Furer A., and Diederich F. Chem. Rev. 97 (1997) 1567
4. Li Y.X., and Dias J.R. Chem. Rev. 97 (1997) 283
5. Davis A.P., Bonar-Law R.P., and Sanders J.K.M. In: Murakami Y. (Ed). Comprehensive Supramolecular Chemistry, vol. 4, Supramolecular Reactivity and Transport: Bioorganic Systems (1996), Pergamon, Oxford 257
6. Davis A.P. Chem. Soc. Rev. 22 (1993) 243
7. Davis A.P., Perry J.J., and Wareham R.S. Tetrahedron Lett. 39 (1998) 4569
8. Davis A.P., Gilmer J.F., and Perry J.J. Angew. Chem. Int. Ed. Engl. 35 (1996) 1312
9. Davis A.P., and Lawless L.J. Chem. Commun. (1999) 9
10. Lawless L.J., Blackburn A.G., Ayling A.J., Pérez-Payán M.N., and Davis A.P. J. Chem. Soc., Perkin Trans. 1 (2001) 1329
11. Ayling A.J., Pérez-Payán M.N., and Davis A.P. J. Am. Chem. Soc. 123 (2001) 12716
12. Davis A.P., and Joos J.-B. Coord. Chem. Rev. 240 (2003) 143
13. 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., and Davis A.P. J. Am. Chem. Soc. 127 (2005) 10739
14. 2. For improved preparations of key intermediates see:
15. del Amo V., Siracusa L., Markidis T., Baragana B., Bhattarai K.M., Galobardes M., Naredo G., Pérez-Payán M.N., and Davis A.P. Org. Biomol. Chem. 2 (2004) 3320
16. del Amo V., Bhattarai K., Nissinen M., Rissanen K., Pérez-Payán M.N., and Davis A.P. Synlett (2005) 1319
17. Kyba E.P., Helgeson R.C., Madan K., Gokel G.W., Tarnowski T.L., Moore S.S., and Cram D.J. J. Am. Chem. Soc. 99 (1977) 2564
18. see also:
19. Ayling A.J., Broderick S., Clare J.P., Davis A.P., Pérez-Payán M.N., Lahtinen M., Nissinen M.J., and Rissanen K. Chem. Eur. J. 8 (2002) 2197
20. Abraham M.H., and Platts J.A. J. Org. Chem. 66 (2001) 3484
21. see also:
22. Hunter C.A. Angew. Chem. Int. Ed. 43 (2004) 5310
23. Dryfe R.A.W., Hill S.S., Davis A.P., Joos J.B., and Roberts E.P.L. Org. Biomol. Chem. 2 (2004) 2716
24. Fang L., Chan W.H., He Y.B., Kwong D.W.J., and Lee A.W.M. J. Org. Chem. 70 (2005) 7640
25. Liu S.Y., Fang L., He Y.B., Chan W.H., Yeung K.T., Cheng Y.K., and Yang R.H. Org. Lett. 7 (2005) 5825
26. Kim K.S., and Kim H.S. Bull. Korean Chem. Soc. 25 (2004) 1411
27. Shim J.H., Jeong I.S., Lee M.H., Hong H.P., On J.H., Kim K.S., Kim H.S., Kim B.H., Cha G.S., and Nam H. Talanta 63 (2004) 61
28. Kim K.S., and Kim H.S. Tetrahedron 61 (2005) 12366
29. K.M. Bhattarai, V. del Amo, G. Magro, A.L. Sisson, J.-B. Joos, J.P.H. Charmant, A. Kantacha, A.P. Davis, (2006) 2335.
30. Ghosh S., Choudhury A.R., Row T.N.G., and Maitra U. Org. Lett. 7 (2005) 1441
31. Meyerhoff M.E., Pretsch E., Welti D.H., and Simon W. Anal. Chem. 59 (1987) 144
32. Pyun N.J., Chu J.H., Jun Y.M., and Kim D.J. Bull. Korean Chem. Soc. 20 (1999) 112
33. Pyun H.J., Chu J.H., Yoon W., Jun Y.M., and Kim D.J. Bull. Korean Chem. Soc. 20 (1999) 179
34. Lee H.J., Yoon I.J., Yoo C.L., Pyun H.J., Cha G.S., and Nam H. Anal. Chem. 72 (2000) 4694
35. Choi Y.S., Lvova L., Shin J.H., Oh S.H., Lee C.S., Kim B.H., Cha G.S., and Nam H. Anal. Chem. 74 (2002) 2435
36. Song F.Y., Ha J.H., Park B., Kwak T.H., Kim I.T., Nam H., and Cha G.S. Talanta 57 (2002) 263
37. Sisson A.L., Clare J.P., Taylor L.H., Charmant J.P.H., and Davis A.P. Chem. Commun. (2003) 2246
38. Hofmeister F. Arch. Exp. Path. Pharmakol. 24 (1888) 247
39. Cacace M.G., Landau E.M., and Ramsden J.J. Quart. Rev. Biophys. 30 (1997) 241
40. Sisson A.L., Clare J.P., and Davis A.P. Chem. Commun. (2005) 5263
41. Savage P.B. Eur. J. Org. Chem. (2002) 759
42. Ding B.W., Yin N., Liu Y., Cardenas-Garcia J., Evanson R., Cirsak T., Fan M.J., Turin G., and Savage P.B. J. Am. Chem. Soc. 126 (2004) 13642
43. Willemen H.M., de Smet L., Koudijs A., Stuart M.C.A., Heikamp-de Jong I., Marcelis A.T.M., and Sudholter E.J.R. Angew. Chem. Int. Ed. 41 (2002) 4275
44. Kolehmainen E., Koivukorpi J., Sievanen E., and Král V. Supramol. Chem. 17 (2005) 437
45. Baragaña B., Blackburn A.G., Breccia P., Davis A.P., de Mendoza J., Padron-Carrillo J.M., Prados P., Riedner J., and de Vries J.G. Chem. Eur. J. 8 (2002) 2931
46. Siracusa L., Hurley F.M., Dresen S., Lawless L.J., Pérez-Payán M.N., and Davis A.P. Org. Lett. 4 (2002) 4639
47. Hayes J.M., Stein M., and Weiser J. J. Phys. Chem. A 108 (2004) 3572
48. Leading Refs.:
49. Iuliano A., and Ruffini A. Tetrahedron Asymm. 16 (2005) 3820
50. Vaton-Chanvrier L., Oulyadi H., Combret Y., Coquerel G., and Combret J.C. Chirality 13 (2001) 668
51. Takeuchi T., Chu J., and Miwa T. Chromatographia 47 (1998) 183
52. Prodigiosins:
53. Fürstner A. Angew. Chem. Int. Ed. 42 (2003) 3582
54. Pamamycins:
55. Jeong E.J., Kang E.J., Sung L.T., Hong S.K., and Lee E. J. Am. Chem. Soc. 124 (2002) 14655
56. See for example:
57. Boon J.M., and Smith B.D. Curr. Opin. Chem. Biol. 6 (2002) 749
58. Sessler J.L., Camiolo S., and Gale P.A. Coord. Chem. Rev. 240 (2003) 17
59. Broughman J.R., Shank L.P., Takeguchi W., Schultz B.D., Iwamoto T., Mitchell K.E., and Tomich J.M. Biochemistry 41 (2002) 7350
60. 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., and Davis A.P. Angew. Chem. Int. Ed. 42 (2003) 4931
61. Sisson A.L., del Amo Sanchez V., Magro G., Griffin A.M.E., Shah S., Charmant J.P.H., and Davis A.P. Angew. Chem. Int. Ed. 44 (2005) 6878
62. McNally B.A., Koulov A.V., Smith B.D., Joos J.B., and Davis A.P. Chem. Commun. (2005) 1087
63. Boon J.M., and Smith B.D. J. Am. Chem. Soc. 121 (1999) 11924
64. Lambert T.N., Boon J.M., Smith B.D., Pérez-Payán M.N., and Davis A.P. J. Am. Chem. Soc. 124 (2002) 5276
65. Merritt M., Lanier M., Deng G., and Regen S.L. J. Am. Chem. Soc. 120 (1998) 8494
66. Sakai N., and Matile S. Tetrahedron Lett. 38 (1997) 2613
67. Janout V., Jing B.W., Staina I.V., and Regen S.L. J. Am. Chem. Soc. 125 (2003) 4436
68. Leading Refs.:
69. Janout V., Jing B.W., and Regen S.L. J. Am. Chem. Soc. 127 (2005) 15862
70. Boon J.M., Lambert T.N., Sisson A.L., Davis A.P., and Smith B.D. J. Am. Chem. Soc. 125 (2003) 8195
71. DiVittorio K.M., Lambert T.N., and Smith B.D. Bioorg. Med. Chem. 13 (2005) 4485