Nanomolar protein sensing with embedded receptor molecules

Journal of the American Chemical Society

Volumn 127, Issue 3, 2005, Pages 904-915

  Zadmard, Reza ^a   Schrader, Thomas ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; CHEMICAL SENSORS; CONCENTRATION (PROCESS); HYDROGEN BONDS; INTERFACES (MATERIALS); LIPIDS; MONOLAYERS; PATTERN RECOGNITION; STEARIC ACID;

AIR-WATER INTERFACE; AMPHIPHILIC RECEPTOR MOLECULES; CHARGED FUNCTIONAL GROUPS; NANOMOLAR PROTEIN SENSING;

PROTEINS;

AMPHOPHILE; CALIXARENE; FUNCTIONAL GROUP; LIPID; PEPTIDE DERIVATIVE; RECEPTOR; STEARIC ACID;

AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); HYDROGEN BOND; MODEL; MOLECULAR RECOGNITION; PROTEIN ANALYSIS; PROTEIN BINDING;

AMINO ACIDS; BENZYL COMPOUNDS; BIOSENSING TECHNIQUES; CALIXARENES; MODELS, MOLECULAR; PHENOLS; PHOSPHONIC ACIDS; PROTEIN BINDING; PROTEINS; QUATERNARY AMMONIUM COMPOUNDS; STEARIC ACIDS; SUBSTRATE SPECIFICITY;

EID: 12444283730     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045785d     Document Type: Article

References (76)

1. Stites, W. E. Chem. Rev. 1997, 97, 1233-1250.
2. (a) Bloomer, A. C.; Champness, J. N.; Bricogne, G.; Staden, R.; Klug, A. Nature 1978, 276, 362-368.
3. (b) Namba, K.; Stubbs, G. Science 1986, 231, 1401-1406.
4. Baldwin, J. Trends Biochem. Sci. 1980, 5, 224-228.
5. (b) Perutz, M. F.; Fermi, G.; Luisi, B.; Shaanan, B.; Liddington, R. C. Acc. Chem. Res. 1987, 20, 309-321.
6. (a) Wakil, S. J.; Stoops, J. K.; Joshi, V. C. Annu. Rev. Biochem. 1983, 52, 537-579.
7. (b) Wakil, S. J. Biochemistry 1989, 28, 4523-4530.
8. (a) Walker, J. E. Les Prix Nobel; The Nobel Foundation: Stockholm, Sweden, 1997; pp 208-234.
9. (b) Walker, J. E. Angew. Chem., Int. Ed. 1998, 37, 2308-2319.
10. (c) Stock, D.; Leslie, A. G. W.; Walker, J. E. Science 1999, 286, 1700-1705.
11. (a) Cushman, M.; Kanamathareddy, S.; De Clerq, E.; Schols, D.; Goldman M. E.; Bowen, J. A. J. Med. Chem. 1991, 34, 337-342.
12. (b) Regan, J. McGarry, D.; Bruno, J.; Green, D.; Newman, J.; Hsu, C. Y.; Kline, J. Barton, J.; Travis, J.; Choi, Y. M.: Volz, F.; Pauls, H.; Harrison, R. Zilberstein, A.; Ben-Sasson, S. A.; Chang, M. J. Med. Chem. 1997, 40, 3408-3422.
13. For a comprehensive review about the stabilization of α-helices and β-sheets, see: Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169-2187.
14. (a) Peczuh, M. W.; Hamilton, A. D.; Sanchez-Quesada, J.; Mendoza, J. D.; Haack, T.; Giralt, E. J. Am. Chem. Soc. 1997, 119, 9327-9328.
15. (b) Tabet, M.; Labroo, V.; Sheppard, P.; Sasaki, T. J. Am. Chem. Soc. 1993, 115, 3866-3868.
16. (a) Hamuro, Y.; Calama, M. C.; Park, H. S.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 2680-2683.
17. (b) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8-13.
18. (c) Lin, Q.; Park, H. S.; Hamuro, Y.; Lee, C. S.; Hamilton, A. D. Biopolymers 1998, 47, 285-297.
19. For an overview and first examples, see: Ariga, K.; Kunitake, T. Acc. Chem. Res. 1998, 31, 371-378.
20. (a) Cha, X.; Ariga, K.; Onda, M.; Kunitake, T. J. Am. Chem. Soc. 1995, 117, 11833.
21. (b) Ariga, K.; Kamino, A.; Cha, X.; Kunitake, T. Langmuir 1999, 15, 3875-3885.
22. Kimzuka, N.: Baba, A.; Kunitake, T. J. Am. Chem. Soc. 2001, 123, 1764-1765.
23. Sakai, N.; Matile, S. J. Am. Chem. Soc. 2003, 125, 14348-14356.
24. Lee, M.; An, W. G.; Kim, J.-H.; Choi, H.-J.; Kim, S.-H.; Han, M.-H.; Koh, K. Mater. Sci. Eng., C 2004, 24, 123-126.
25. Zamah, A. M.; Delahunty, M.; Luttrell, L. M.; Louis, M.; Lefkowitz, R. J. J. Biol. Chem. 2002, 277, 31249-31256.
26. Schmitt, L.; Bohanon, T. M.; Denzinger, S.; Ringsdorf, H.; Tampé, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 317-320.
27. For embedded isolated artificial receptors in lipid layers, see: (a) Kolusheva, S.; Shahal, T.: Jelinek, R. J. Am. Chem. Soc. 2000, 122, 776-780.
28. (b) Sasaki, D. Y.; Waggoner, T. A.; Last, J. A.; Alam, T. M. Langmuir 2002, 18, 3714.
29. (c) Lahiri, J.; Fate, G. D.; Ungashe, S. B.; Groves, J. T. J. Am. Chem. Soc. 1996, 118, 2347.
30. For a self-assembled receptor at the air-water interface, see: Higuchi, M.; Koga, T.; Taguchi, K.; Kinoshita, T. Langmuir 2002, 18, 813-818.
31. Zadmard, R.; Schrader, T.; Grawe, T.; Kraft, A. Org. Lett. 2002, 4, 1687-1690.
32. The solution studies offer the advantage of a precise determination of association constants, stoichiometries, and complex geometries. This characterization becomes much more difficult in a lipid monolayer.
33. (a) Sansone, F.; Barboso, F.; Casnati, A.; Saciotto, D.; Ungaro, R. Tetrahedron Lett. 1999, 40, 4741-4744.
34. (b) Da Silva, E.; Coleman, A. W. Tetrahedron 2003, 59, 7357-7364.
35. (a) Gansey, M. H. B. G.; de Haan, A. S.; Bos, E. S.; Verboom, W.; Reinhoudt, D. N. Bioconjugate Chem. 1999, 10, 613-623.
36. (b) Da Silva, E.; Shahgaldian, P.; Coleman, A. W. Int. J. Pharm. 2004, 273, 57-62.
37. (a) Schneider, H. J.; Kramer, R.: Simova, S.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6442.
38. (b) Wilcox. C. S. In Frontiers in Supramoleculur Chemistry; Schneider. H. J., Ed.: Verlag Chemie: Weinheim. Germany. 1991; p 123.
39. MacroModel 7.0; Schrödinger Inc. Force-field: Amber*, water, 3000 Steps.
40. a value places it above all other bisphosphonates described earlier as arginine receptors.
41. (a) Selkti, N. M.; Coleman, A. W.; Nicolis, I.; Douteau-Guével, N.; Villain, F.; Tomas, A.; De Rango, C. Chem. Commun. 2000, 161.
42. (b) Douteau-Guével, N.; Perret, F.; Coleman, A. W.; Morel, J.-P.; Morel-Desrosiers, N. J. Chem. Soc., Perkin Trans. 2 2002, 524-532.
43. (a) Schrader, T. Chem.-Eur. J. 1997, 3, 1537.
44. (b) Rensing, S.; Springer. A.; Grawe, T.; Schrader, T. J. Org. Chem. 2001, 66, 5814-5821.
45. (c) Rensing, S.; Schrader, T. Org. Lett. 2002, 4, 2161-2164.
46. For related work, see: Schrader, T. Chem.-Eur. J. 1997, 3, 1537.
47. Sakurai, M.; Tamagawa, H.; Inoue, Y.; Ariga, K.; Kunitake, T. J. Phys. Chem. B 1997, 101, 4810-4817.
48. Quite recently, calixarene 1,3-bisphosphonates with alternating hydrophilic and Hydrophobie groups have been prepared and integrated into monolayers entirely consisting of two-dimensional condensed-phase domains: Vollhardt, D.; Gloede, J.; Weidemann, G.; Rudert, R. Langmuir 2003, 19, 4228-4234.
49. Honig, D.; Möbius, D. J. Phys. Chem. 1991, 95, 4590.
50. Liu, F.; Lu, G.-Y.; He, W.-J.: Liu, M-H.; Zhu, L.-G.; Wu, H.-M. New J. Chem. 2002, 26, 601-606.
51. Ulman, A. An Introduction to Uhrathin Organic Films from Langmuir-Blodgett to Self-assembly; Academic Press: New York, 1991.
52. -8 M equimolar aqueous solution of the histone protein with the calixarene host, we obtained a clean ESI-MS spectrum. It featured prominent molecular ion peaks for the 1:1, 1:2, and 1:3 complex, with the highest intensity residing in the 1:2 peaks.
53. In high excess, NaCl and HEPES themselves interact with the receptor molecule and are less pronounced with the stearic acid monolayer; however, the large additional increase with NaCl, due to the specific calixarene protein interaction, remains constant throughout the entire concentration range: (a) Shahgaldian, P.; Coleman, A. W. Langmuir 2001, 17, 6851-6854.
54. (b) Houel, E.; Lazar, A.; Da Silva, E.; Coleman, A. W.; Solovyov, A.; Cherenok, S.; Kalchenko, V. I. Langmuir 2002, 18, 1374-1379.
55. (c) Da Silva, E.; Nouar, F.; Coleman, A. W.; Rather, B.; Zaworotko, M. J. J. Inclusion Phenom. Macrocycl. Chem. 2003, 46, 161-166.
56. (a) Carter, D. C.; He, X. M.; Munson, S. H.; Twigg, P. D.; Gernert, K. M.; Broom, M. B.; Miller, T. Y. Science 1989, 244, 1195-1198.
57. (b) Carter, D. C.; Ho, J. X. Adv. Protein Chem. 1994, 45, 153-203.
58. Dps is DNA protecting protein of starving bacteria.
59. 2 (ferritin is composed of 24 identical subunits, each of which has a comparable size to the other monomeric basic proteins).
60. -8 M. This is clearly related to what BSA does in nature: it binds to fatty acids which have been released to the blood stream and leads to a 1000-fold increase in their solubility. Apart from BSA, thrombin, and to a small extent ferritine, the dodecamer and chymotrypsin also interact with the stearic acid monolayer.
61. 2 observed area increase ∼3%.
62. Diaminocalix[4]arenes were recently shown to interact with nucleotides at the air-water interface: Liu, F.; Lu, G.-Y.; He, W.-J.; Liu, M. H.; Zhu, L.-G. Thin Solid Films 2002, 414, 72-77.
63. Potentiometric titrations were carried out in water/DMSO (benzylammonium) or 2:1 water/methanol (anilinium) solvent mixtures at 25 °C and an ionic strength of 0.1 M (KCl). For details of the analytical procedure, see: Kraft, A. J. Chem. Educ. 2003, 80, 554-559 and references therein.
64. This corresponds well with ESl-MS measurements carried out by Coleman et al. on the related complex between BSA and tetrasulfonatocalixarenes: Memmi, L.; Lazar, A.: Brioude, A.; Ball, V.; Coleman, A. W. Chem. Commun. 2001, 2474-2475.
65. Kodadek, T. Chem. Biol. 2001, 8, 105-115.
66. Zhu, H.; Snyder, M. Curr. Opin. Chem. Biol. 2001, 5, 40-45.
67. Boder, E. T.; Midelfort, K. S.; Wittrup, K. D. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 10701-10705.
68. de Wildt, R. M. T.; Mundy, C. R.; Gorick, B. D.; Tomlinson, I. M. Nat. Biotechnol. 2000, 18, 989-994.
69. Hesselberth, J.; Robertson, M. P.; Jhaveri, S.; Ellington, A. D. Rev. Mol. Biotechnol 2000, 74, 15-25.
70. (a) Connolly, M. L. Science 1983, 221, 709.
71. (b) Connolly, M. L. J. Appl. Crystallogr. 1983, 16, 548.
72. (a) Wei, Y.; McLendon, G. L.; Hamilton, A. D.; Case, M. A.; Purring, C. B.; Lin, Q.; Park, H. S.; Lee, C.-S.; Yu, T. Chem. Commun. 2001, 1580-1581.
73. (b) Park, H. S.; Lin, Q.; Hamilton, A. D. J. Am. Chem. Soc. 1999, 121, 8-13.
74. Pechkova, E.; Nicolini, C. J. Cell. Biochem. 2002, 85, 243-251.
75. For FMN recognition by a mixed monolayer, see: Ariga, K.; Kamino, A.; Koyano, H.; Kunitake, T. J. Mater. Chem. 1997, 7, 1155.
76. Kim, Y.-C.; Jacobson, K. J. Med. Chem. 2000, 43, 746-755.