Crystallographic observation of 'induced fit' in a cryptophane host-guest model system

Nature Communications

Volumn 1, Issue 9, 2010, Pages

  Taratula, Olena ^a   Hill, P Aru ^a   Khan, Najat S ^a   Carroll, Patrick J ^a   Dmochowski, Ivan J ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CHLOROFORM; CRYPTOPHANE A; METHANOL; UNCLASSIFIED DRUG; WATER; XENON;

ARTICLE; CONFORMATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; MOLECULE; NONHUMAN; X RAY CRYSTALLOGRAPHY;

EID: 79251576449     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms1151     Document Type: Article

References (46)

1. Koshland, D. E. Application of a theory of enzyme specificity to protein synthesis. Proc. Natl Acad. Sci. USA 44, 98-104 (1958).
2. Deutman, A. B. C. et al. Squaring cooperative binding circles. Proc. Natl Acad. Sci. USA 106, 10471-10476 (2009).
3. Pluth, M. D., Fiedler, D., Mugridge, J. S., Bergman, R. G. & Raymond, K. N. Encapsulation and characterization of proton-bound amine homodimers in a water-soluble, self-assembled supramolecular host. Proc. Natl Acad. Sci. USA 106, 10438-10443 (2009).
4. Feringa, B. L. From molecules to molecular systems. Chimia 63, 254-256 (2009).
5. Kim, B. S. et al. Water soluble cucurbit[6]uril derivative as a potential Xe carrier for Xe-129 NMR-based biosensors. Chem. Commun. 2756-2758 (2008).
6. Brotin, T. & Dutasta, J. P. Cryptophanes and their complexes-present and future. Chem. Rev. 109, 88-130 (2009).
7. Garel, L., Dutasta, J. P. & Collet, A. Complexation of methane and chlorofluorocarbons by cryptophane-A in organic solution. Angew. Chem. Int. Ed. 32, 1169-1171 (1993).
8. Mecozzi, S. & Rebek, J. The 55% solution: a formula for molecular recognition in the liquid state. Chem. Eur. J. 4, 1016-1022 (1998).
9. Bartik, K., Luhmer, M., Dutasta, J. P., Collet, A. & Reisse, J. Xe-129 and H-1 NMR study of the reversible trapping of xenon by cryptophane-A in organic solution. J. Am. Chem. Soc. 120, 784-791 (1998).
10. Cavagnat, D. et al. Raman microspectrometry as a new approach to the investigation of molecular recognition in solids: chloroform-cryptophane complexes. J. Phys. Chem. B 108, 5572-5581 (2004).
11. 3 complex, a stable van der Waals molecule. Angew. Chem. Int. Ed. Engl. 28, 1246-1248 (1989).
12. 2 cavitate. J. Chem. Soc., Chem. Commun. 361-363 (1985).
13. 2 cavitate. J. Chem. Soc., Chem. Commun. 339-341 (1986).
14. *xenon. J. Chem. Soc., Chem. Commun. 119, 939-940 (1997).
15. Enright, G. D., Udachin, K. A., Moudrakovski, I. L. & Ripmeester, J. A. Thermally programmable gas storage and release in single crystals of an organic van der Waals host. J. Am. Chem. Soc. 125, 9896-9897 (2003).
16. Miyahara, Y., Abe, K. & Inazu, T. 'Molecular' molecular sieves: lid-free decamethylcucurbit[5]uril absorbs and desorbs gases selectively. Angew. Chem. Int. Ed. 41, 3020-3023 (2002).
17. Schiltz, M., Fourme, R. & Prange, T. Use of noble gases xenon and krypton as heavy atoms in protein structure determination. Methods Enzymol. 374, 83-119 (2003).
18. 129Xe-cryptophane biosensor complexed with human carbonic anhydrase II. J. Am. Chem. Soc. 130, 6942-6943 (2008).
19. Berthault, P., Huber, G. & Desvaux, H. Biosensing using laser-polarized xenon NMR/MRI. Progr. Nucl. Magn. Reson. Spectrosc. 55, 35-60 (2009).
20. Taratula, O. & Dmochowski, I. J. Functionalized Xe-129 contrast agents for magnetic resonance imaging. Curr. Opin. Chem. Biol. 14, 97-104 (2010).
21. Meldrum, T. et al. A xenon-based molecular sensor assembled on an MS2 viral capsid scaffold. J. Am. Chem. Soc. 132, 5936-5937 (2010).
22. Chambers, J. M. et al. Cryptophane xenon-129 nuclear magnetic resonance biosensors targeting human carbonic anhydrase. J. Am. Chem. Soc. 131, 563-569 (2009).
23. Seward, G. K., Wei, Q. & Dmochowski, I. J. Peptide-mediated cellular uptake of cryptophane. Bioconjug. Chem. 19, 2129-2135 (2008).
24. Hill, P. A., Wei, Q., Troxler, T. & Dmochowski, I. J. Substituent effects on xenon binding affinity and solution behavior of water-soluble cryptophanes. J. Am. Chem. Soc. 131, 3069-3077 (2009).
25. Bouchet, A., Brotin, T., Cavagnat, D. & Buffeteau, T. Induced chiroptical changes of a water-soluble cryptophane by encapsulation of guest molecules and counterion effects. Chem. Eur. J. 16, 4507-4518 (2010).
26. Brotin, T., Cavagnat, D. & Buffeteau, T. Conformational changes in cryptophane having C-1-symmetry studied by vibrational circular dichroism. J. Phys. Chem. A 112, 8464-8470 (2008).
27. Murakami, Y., Kikuchi, J., Hisaeda, Y. & Hayashida, O. Artificial enzymes. Chem. Rev. 96, 721-758 (1996).
28. Rekharsky, M. V. & Inoue, Y. Complexation thermodynamics of cyclodextrins. Chem. Rev. 98, 1875-1917 (1998).
29. Fan, Z. et al. Encapsulation of quinine by beta-cyclodextrin: excellent model for mimicking enzyme-substrate interactions. J. Org. Chem. 71, 1244-1246 (2006).
30. Bondi, A. Van der Waals volumes + radii. J. Phys. Chem. 68, 441-451 (1964).
31. Kirchhoff, P. D. et al. Structural fluctuations of a cryptophane host: a molecular dynamics simulation. J. Am. Chem. Soc. 118, 3237-3246 (1996).
32. Huber, G. et al. Water soluble cryptophanes showing unprecedented affinity for xenon: candidates as NMR-based biosensors. J. Am. Chem. Soc. 128, 6239-6246 (2006).
33. Mough, S. T., Goeltz, J. C. & Holman, K. T. Isolation and structure of an 'imploded' cryptophane. Angew. Chem. Int. Ed. 43, 5631-5635 (2004).
34. Collet, A. Cyclotriveratrylenes and cryptophanes. Tetrahedron 43, 5725-5759 (1987).
35. Brotin, T. & Dutasta, J. P. Xe@cryptophane complexes with C-2 symmetry: synthesis and investigations by Xe-129 NMR of the consequences of the size of the host cavity for xenon encapsulation. Eur. J. Org. Chem. 973-984 (2003).
36. Fogarty, H. A. et al. A cryptophane core optimized for xenon encapsulation. J. Am. Chem. Soc. 129, 10332-10333 (2007).
37. Guex, N. & Peitsch, M. C. SWISS-MODEL and the Swiss PdbViewer: an environment for comparative protein modeling. Electrophoresis 18, 2714-2723 (1997).
38. Duchamp, D. J. CrystMol, Version 2.1. (DandA Consulting LLC, 2004).
39. Huber, J. G. et al. NMR study of optically active monosubstituted cryptophanes and their interaction with xenon. J. Phys. Chem. A 108, 9608-9615 (2004).
40. Luhmer, M. et al. Study of xenon binding in cryptophane-A using laser-induced NMR polarization enhancement. J. Am. Chem. Soc. 121, 3502-3512 (1999).
41. 2@bis-cryptophane complex. New J. Chem. 28, 502-512 (2004).
42. Desvaux, H., Huber, J. G., Brotin, T., Dutasta, J. P. & Berthault, P. Magnetization transfer from laser-polarized xenon to protons with spin-diffusion quenching. ChemPhysChem 4, 384-387 (2003).
43. Brotin, T., Cavagnat, D., Dutasta, J. P. & Buffeteau, T. Vibrational circular dichroism study of optically pure cryptophane-A. J. Am. Chem. Soc. 128, 5533-5540 (2006).
44. Hill, P. A. Synthesis of functionalized cryptophane-A derivatives and assessment of their xenon-binding properties for the construction of hyperpolarized xenon-129 biosensors. University of Pennsylvania, Philadelphia, PA (2008).
45. Hill, P. A., Wei, Q., Eckenhoff, R. G. & Dmochowski, I. J. Thermodynamics of xenon binding to cryptophane in water and human plasma. J. Am. Chem. Soc. 129, 9262-9263 (2007).
46. Sheldrick, G. M. SHELXL-97. Acta. Cryst. A64, 112-122 (2008).