Perfluorooctyl bromide has limited membrane solubility and is located at the bilayer center. Locating small molecules in lipid bilayers through paramagnetic enhancements of NMR relaxation

Journal of Medicinal Chemistry

Volumn 45, Issue 25, 2002, Pages 5534-5542

  Ellena, Jeffrey F ^a   Obraztsov, Viktor V ^b   Cumbea, Valerie L ^a   Woods, Catherine M ^b   Cafiso, David S ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

^b Alliance Pharmaceutical Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 OLEOYL 1 PALMITOYLPHOSPHATIDYLCHOLINE; CHEMICAL COMPOUND; HEXANE; HYDROCARBON; OXYGEN; PERFLUOROOCTYL BROMIDE; PHOSPHORYLCHOLINE;

ARTICLE; BILAYER MEMBRANE; CHEMICAL PROCEDURES; CONCENTRATION (PARAMETERS); DEUTERON NUCLEAR MAGNETIC RESONANCE; ENVIRONMENT; LIPID BILAYER; MEMBRANE; MEMBRANE STRUCTURE; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; POLARIZATION; SOLUBILITY;

CELL MEMBRANE; FLUOROCARBONS; GADOLINIUM; LIPID BILAYERS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; OXYGEN; PHOSPHATIDYLCHOLINES; SOLUBILITY;

EID: 0037028021     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020278x     Document Type: Article

References (41)

1. Long, D. M.; Long, D. C.; Mattrey, R. F.; Long R. A.; Burgan, A. R.; Herrick, W. C.; Shellhamer, D. F. An overview of perfluorooctylbromide - Application as a synthetic oxygen carrier and imaging agent for x-ray, ultrasound, and nuclear magnetic resonance. Biomater., Artif. Cells, Artif. Organs 1988, 16, 411-420.
2. Nesti, F. D.; Fuhrman, B. P.; Steinhorn, D. M.; Papo, M. C.; Hernan, L. J.; Duffy, L. C.; Fisher, J. E.; Leach, C. L.; Paczan, P. R.; Burak, B. A. Perfluorocarbon-associated gas exchange in gastric aspiration. Crit. Care Med. 1994, 22, 1445-1452.
3. Tutuncu, A. S.; Faithfull, N. S.; Lachmann, B. Comparison of ventilatory support with intratracheal perfluorocarbon administration and conventional mechanical ventilation in animals with acute respiratory failure. Am. Rev. Respir. Dis. 1993, 148, 785-792.
4. Riess, J. Fluorochemical emulsions. In Fluorine Chemistry at the Millenium; Banks, R. E., Ed.; Elsevier: Amsterdam, 2000; pp 385-430.
5. Obraztsov, V. V.; Grishanova, A. Y.; Shekhtman, D. G.; Sklifas, A. N.; Makarov, K. N. Interaction of perfluorooctylbromide with liver microsomal monooxygenase. Biokhimiya 1993, 58, 879-883.
6. Wolfson, M. R.; Greenspan, J. S.; Shaffer, T. H. Liquid assisted ventilation: An alternative respiratory modality. Pediatr. Pulmonol. 1998, 16, 42-63.
7. Keipert, P. E. Perfluorochemical emulsions: Future alternatives to transfusion. In Blood Substitutes: Principles, Methods, Products and Clinical Trials; Chang, T. M. S., Ed.; Karger Landes Systems: Basel, Switzerland, 1998; pp 127-156.
8. Spahn, D. R.; van Brempt, R.; Theilmeier, G.; Reibold, J.-P.; Welte, M.; Heinzerling, H.; Birck, K. M.; Keipert, P. E.; Messmer, K. Perflubron emulsion delays blood transfusions in orthopedic surgery. Anesthesiology 1999, 91, 1195-1208.
9. Hirschl, R. B.; Tooley, R.; Parent, A. C.; Johnson, K.; Bartlett, R. H. Improvement of gas exchange, pulmonary function, and lung injury with partial liquid ventilation. Chest 1995, 108, 500-508.
10. Leach, C. L.; Greenspan, J. S.; Rubenstein, S. D.; Shaffer, T. H.; Wolfson, M. R.; Jackson, J. C.; Delamos, R.; Furman, B. P. Partial liquid ventilation with perflubron in premature infants with severe respiratory distress syndrome. N. Engl. J. Med. 1996, 335, 761-767.
11. Colton, D.; Hirschl, R.; Johnson, K.; Till, G.; Bartlett, R. Neutrophil infiltration is reduced during partial perfluorocarbon liquid ventilation in the setting of lung injury. Surg. Forum 1994, 1055, 668-670.
12. Croce, M. A.; Fabian, T. C.; Patton, J. H., Jr.; Melton, S. M.; Moore, M.; Trenthem, L. L. Partial liquid ventilation decreases the inflammatory response in the alveolar environment of trauma patients. J. Trauma 1998, 45, 273-280.
13. Steinhorn, D. M.; Papo, M. C.; Rotta, A. T.; Aljada, A.; Fuhrman, B. P.; Dandona, P. Liquid ventilation attenuates pulmonary oxidative damage. J. Crit. Care 1999, 14, 20-28.
14. Smith, D.; Sun, X.; Neslund, G.; Flaim, S. F. Effects of perflubron (liquivent) on human leukocyte activation in vitro. Am. J. Respir. Crit. Care Med. 1997, 155, A752.
15. Thomassen, M. J.; Buhrow, L. T.; Wiedemann, H. P. Perflubron decreases cytokine production by human alveolar macrophages. Crit. Care Med. 1997, 25, 2045-2047.
16. Woods, C. M.; Neslund, G.; Kornbrust, E. S.; Flaim, S. F. Perflubron attenuates neutrophil adhesion to activated endothelial cells in vitro. Am. J. Physiol.: Lung Cell. Mol. Physiol. 2000, 278, L1008-L1017.
17. Obraztsov, V. V.; Neslund, G. G.; Kornbrust, E. S.; Flaim, S. F.; Woods, C. M. In vitro cellular effects of perfluorochemicals correlate with their lipid solubility. Am. J. Physiol.: Lung Cell. Mol. Physiol. 2000, 278, 1018-1024.
18. Koblin, D. D.; Chortkoff, B.; Laster, M. J.; Eger, E. I.; Halsey, M. J.; Ionescu, P. Polyhalogenated and perfluoroinated compounds that disobey the meyer-overton hypothesis. Anesth. Analg. 1994, 79, 1043-1048.
19. North, C.; Cafiso, D. Contrasting membrane localization and behavior of halogenated cyclobutanes that follow or violate the meyer-overton hypothesis of general anesthetic potency. Biophys. J. 1997, 72, 1754-1761.
20. 19F NMR study. Biophys. J. 1997, 72, 1676-1682.
21. 19F NMR probes of oxygen tension and temperature. J. Magn. Reson. 1995, B106, 131-141.
22. Bergelson, L. D. Paramagnetic hydrophilic probes in NMR investigations of membrane systems. In Methods in Membrane Biology; Korn, E. D., Ed.; Plenum Press: New York, 1978; Vol. 9, pp 275-335.
23. Subczynski, W. K.; Hyde, J. S.; Kusumi, A. Oxygen permeability of phosphatidylcholine-cholesterol membranes. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 4474-4478.
24. Marsh, D. Polarity and permation profiles in lipid membranes. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 7777-7782.
25. 2H NMR as a method to study structure, dynamics, and interactions. Acc. Chem. Res. 1987, 20, 221-228.
26. Bloom, M.; Evans, E.; Mouritsen, O. G. Physical properties of the fluid lipid-bilayer component of cell membranes: A perspective. Q. Rev. Biophys. 1991, 24, 293-397.
27. Macdonald, P. M. Deuterium NMR and the topography of surface electrostatic charge. Acc. Chem. Res. 1997, 30, 196-203.
28. Huster, D.; Arnold, K.; Gawrisch, K. Investigation of lipid organization in biological membranes by two-dimensional nuclear overhauser enhancement spectroscopy. J. Phys. Chem. B. 1999, 103, 243-251.
29. Huster, D.; Gawrisch, K. NOESY NMR crosspeaks between lipid headgroups and hydrocarbon chains: Spin diffusion or molecular disorder? J. Am. Chem. Soc. 1999, 121, 1992-1993.
30. Hubbell, W. L.; Cafiso, D. S.; Altenbach, C. Identifying conformational changes with site-directed spin labeling. Nat. Struct. Biol. 2000, 7, 735-739.
31. 19F NMR. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 9967-9971.
32. 19F NMR study. Biophys. J. 2001, 80, 1406-1416.
33. White, S. H.; Wimley, W. C. Hydrophobic interactions of peptides with membrane interfaces. Biochim. Biophys. Acta 1998, 1376, 339-352.
34. Kaiser, R. D.; London, E. Location of diphenylhexatriene (dph) and its derivatives within membranes: Comparison of different fluorescence quenching analyses of membrane depth. Biochemistry 1998, 37, 8180-8190.
35. 19F NMR spectroscopy. J. Am. Chem. Soc. 2002, 124, 1778-1781.
36. Cui, S. T.; Siepmann, H. D.; Cochran, H. D.; Cummings, P. T. Intermolecular potentials and vapor-liquid phase equilibria of perfluorinated alkanes. Fluid Phase Equilib. 1998, 146, 51-61.
37. Freeman, R.; Hill, H. D. W.; Kaptein, R. An Adaptive scheme for measuring NMR spin-lattice relaxation times. J. Magn. Reson. 1972, 7, 82-98.
38. 2H NMR. Biochim. Biophys. Acta 1983, 737, 117-171.
39. Rance, M.; Byrd, R. A. Obtaining high fidelity spin-1/2 powder spectra in anisotropic media: Phase-cycled hahn echo spectroscopy. J. Magn. Reson. 1983, 52, 221-240.
40. Solomon, I. Relaxation processes in a system of two spins. Phys. Rev. 1955, 99, 559-565.
41. 1 processes. J. Chem. Phys. 1978, 68, 4034-4037.