Characterization of the sources of protein-ligand affinity: 1-Sulfonato-8-(1 ′)anilinonaphthalene binding to intestinal fatty acid binding protein

Biophysical Journal

Volumn 70, Issue 1, 1996, Pages 69-83

  Kirk, William R ^a   Kurian, Elizabeth ^a   Prendergast, Franklyn G ^a,b  

^a MAYO CLINIC   (United States)

^b MAYO GRADUATE SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FATTY ACID; FATTY ACID BINDING PROTEIN;

ARTICLE; BINDING AFFINITY; BINDING SITE; CALORIMETRY; CRYSTAL STRUCTURE; ENTHALPY; ENTROPY; LIGAND BINDING; PROTEIN ANALYSIS; PROTEIN BINDING; SPECTROFLUOROMETRY; TEMPERATURE; X RAY CRYSTALLOGRAPHY;

ANILINO NAPHTHALENESULFONATES; ANIMALS; BINDING SITES; BIOPHYSICS; CARRIER PROTEINS; ELECTROCHEMISTRY; FATTY ACID-BINDING PROTEINS; FATTY ACIDS; FLUORESCENT DYES; HYDROGEN BONDING; LIGANDS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; MYELIN P2 PROTEIN; NEOPLASM PROTEINS; NERVE TISSUE PROTEINS; PROTEIN BINDING; RATS; RECOMBINANT PROTEINS; SPECTROMETRY, FLUORESCENCE; THERMODYNAMICS;

EID: 0030070010     PISSN: 00063495     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-3495(96)79592-9     Document Type: Article

References (58)

1. Banaszak, L., N. Winter, Z. Xu, D. Bernlohr, S. Cowan, and T Jones. 1994. Lipid-binding proteins: a family of fatty acid, and retinoid binding proteins. Adv. Prot. Chem. 45:89-151.
2. Ben-Naim, A. 1983. Hydrophobic Interactions. Plenum Press, New York.
3. Bockris, J., and A. Reddy. 1977. Modern Electrochemistry. Plenum Press, New York.
4. Brand, L., and B. Witholt. 1967. Fluorescence measurements. Methods Enzymol. 11:776-856.
5. Brandts, J. 1993. ITC Data Analysis in Origin, Appendix. Microcal Systems, Northampton, MA.
6. Cantor, C., and P. Schimmel. 1980. Biophysical Chemistry, Part II. W H. Freeman, New York.
7. Chevernak, M., and E. Toone. 1994. A direct measurement of the contribution of solvent reorganization to the enthalpy of ligand binding. J. Am. Chem. Soc. 116:10533-10539.
8. Connelly, P., R. Aldape, F. Bruzzese, S. Chamber, M. Fitzgibbon, M. Fleming, S. Itoh, D. Livingston, M. Navia, J. Thomson, and K. Wilson. 1994. Enthalpy of hydrogen bond formation in a protein-ligand binding reaction. Proc. Natl. Acad. Sci. USA. 91:1964-1968.
9. Cornish-Bowden, A. 1995. Analysis of Enzyme Kinetic Data. Oxford University Press, Oxford.
10. Demas, J., and G. Crosby. 1971. The measurement of photoluminescence quantum yields: a review. J. Phys. Chem. 75:991-1024.
11. Dill, K. 1990. The meaning of hydrophobicity Science. 250:297.
12. Dodiuk, H., H. Kanety, and E. Kosower. 1979. The apomyoglobin-arylaminonaphthalene-sulfonate system, insight into fluorescent probe responses by substituent modulation. J. Phys. Chem. 83:515-521.
13. Douglas, A. 1966. Anomalously long radiative lifetimes of molecular excited states. J. Chem. Phys. 45:1007-1015.
14. Ernst, J., R. Clubb, H.-X. Zhou, A. Gronenborn, and G. Clore. 1995. Demonstration of positionally disordered water within a protein hydrophobic cavity. Science. 267:1813-1817.
15. Finney, J. 1979. The organization of water in protein crystals. In Water: A Comprehensive Treatise, Vol. 6. F. Franks, editor. Plenum Press, New York. 47-122.
16. Fœrster, T., and K. Rokos. 1967. A deuterium isotope solvent effect on fluorescence. Chem. Phys. Lett. 1:279-280.
17. Franks, F. 1975. The hydrophobic effect. In Water: A Comprehensive Treatise, Vol. 4. F Franks, editor. Plenum Press, New York. 1-115.
18. Friedman, H., and C. Krishnan. 1973. Thermodynamics of ionic hydration In Water: A Comprehensive Treatise, Vol. 3. F. Franks, editor. Plenum Press. New York. 1-118.
19. Goldberg, M., G. Semisotnov, B. Friguet, K Kuwajima, O. Ptitsyn, and S Sugai. 1990. An early immunoreactive folding intermediate of the tryptophan synthase β2 subunit is a "molten globule" FEBS Lett. 263:51-56.
20. Guilbault, G. 1973. Practical Fluorescence: Theory, Methods and Techniques. Marcel Dekker, New York.
21. Hertz, H. 1977. Velocity correlations in aqueous electrolyte solutions from diffusion, conductance and transference data. Part 1. Theory. Ber. Bunsenges. Physik. Chemie. 81:656-674.
22. Jakoby V. M., K. Miller, J Toner, A. Bauman, L. Cheng, E. Li, and D Cistola 1993. Ligand-binding electrostatic interactions govern the specificity of retinol- and fatty acid-binding proteins. Biochemistry. 32. 872-878.
23. Jencks, W. 1975 Binding energy, specificity, and enzymic catalysis. Adv Enzymol. Relat. Areas Mol. Biol. 43:219-410
24. Johnson, J., M. El-Bayoumi, L. Weber, and A. Tulinsky. 1979. Interaction of α-chymotrypsin with the fluorescent probe 1-anilinonaphthalene-8-sulfonate in solution. Biochemistry. 18:1292-1295.
25. Kirk, W., E. Kurian, and F. Prendergast. 1995. Thermodynamics of (1, 8) ANS binding to intestinal fatty acid binding protein (IFABP) Biophys J. 68:A196.
26. Kirk, W., W. Wessels, and F. Prendergast. 1993. Lanthanide-dependent perturbations of luminescence in indolylethylenediaminetetraacetic acid-lanthanide chelate. J. Phys. Chem. 97:10326-10340.
27. Kirkwood, J. 1934. Theory of solutions of molecules containing widely separated charges with special application to zwitterions. J. Chem. Phys. 3:351-360.
28. Klotz, I 1982. Number of receptor sites from scatchard graphs: facts and fantasies. Science. 217:1247-1250.
29. LaLonde, J., M. Levenson, J. Roe, D. Bernlohr, and L. Banaszak. 1994. Adipocyte lipid binding protein complexed with fatty acid. J. Biol. Chem. 269:25339-25347.
30. Levitt, M., and B. Park. 1993. Water: now you see it, now you don't. Structure. 1:223-226.
31. Marcus, R. A. 1965. On the theory of electron transfer reactions. VI. Unified treatment for homogeneous and electrode reactions. J. Chem. Phys. 43:679-701.
32. Nemethy, G., and H. Scheraga. 1962. The structure of water and hydrophobic bonding in proteins. III. The thermodynamic properties of hydrophobic bonds in proteins. J. Phys. Chem. 66:1773-1789.
33. Oakenfull, D., and D. Fenwick. 1975. Hydrophobic interaction in deuterium Oxide. Aust. J. Chem. 28:715-720.
34. O'Connor, D., and W. Ware. 1976. Exciplex photophysics. III. Kinetics of fluorescence quenching of α-cyanonaphthalene by dimethylcyclopenten-1,2 in hexane. J. Am. Chem. Soc. 98:4706-4709.
35. Okubo, T., and N. Ise. 1969. The solubilities of naphthalene and biphenyl in aqueous polymer solutions. J. Phys. Chem. 73:1488-1494.
36. Oyashiki, T., and T. Sekine 1979. Fluorometric studies on conformational changes in tropomyosin associated with depolymerization. J Biochem. 85:575-580.
37. Parker, C., and C. Osterland. 1970. Hydrophobic binding sites on immunoglobulins. Biochemistry. 9:1074-1082.
38. Pratt, L., and D. Chandler. 1977. Theory of the hydrophobic effect. J. Chem. Phys. 67:3683-3703.
39. Pratt, L., and D. Chandler. 1980. Effect of solute-solvent attractive forces on hydrophobic correlations. J. Chem. Phys. 73:3434-3441.
40. Privalov, P., and S. Gill. 1988. Stability of protein structure and hydrophobic interaction. Adv. Protein Chem. 39:191-234.
41. Rahman, A., and F. Stillinger. 1971. Molecular dynamics study of liquid water. J. Chem. Phys. 55:3336-3348.
42. Richieri, G., R. Ogata, and A. Kleinfeld 1992. A fluorescently labeled intestinal fatty acid binding protein. Interactions with fatty acids and its use in monitoring free fatty acids. J Biol. Chem. 267:23495-23501.
43. Robinson, G., R. Robbins, G. Fleming, J. Morris, A. Knight, and B. Morrison. 1978. Picosecond studies of the fluorescent probe molecule 8-anilino-1-naphthalenesulfonic acid J. Am. Chem. Soc. 100: 7145-7150.
44. Sacchettini, J., L. Banaszak, and J. Gordon. 1990. Expression of rat intestinal fatty acid binding protein in E. coli and its subsequent structural analysis: a model system for studying the molecular details of fatty acid-protein interaction. J. Mol. Cell. Biochem. 98:81-93.
45. Sacchettini, J. C., J. I. Gordon, and L. J. Banaszak. 1989. Crystal structure of rat intestinal fatty-acid-binding protein. Refinement and analysis of the Escherichia coli-derived protein with bound palmitate. J. Mol. Biol. 208:327-339.
46. Sambrook, J., E. Fritsch, and T. Maniatis. 1989. Molecular Cloning: A Laboratory Manual, 2nd Ed., Vol 3. Cold Spring Harbor Laboratory, Plainview, NY.
47. Scapin, G., J. Gordon, and J. Sacchettini. 1992. Refinement of the structure of recombinant rat intestinal fatty acid binding protein at 1.2 Å resolution. J. Biol. Chem. 267:4253-4269.
48. Sirangelo, I., E. Bismuto, and G. Irace. 1994. Solvent and thermal denaturation of the acidic compact state of apomyoglobin. FEBS Lett. 338: 11-15.
49. Slavik, J. 1982. Anilinonaphthalene sulfonate as a probe of membrane composition and function. Biochim. Biophys. Acta. 694:1-25.
50. Strickler, S., and R. Berg. 1962. Relationship between absorption intensity and fluorescence lifetime of molecules. J. Chem. Phys. 37:814-822.
51. Stryer, L. 1965. The interaction of a naphthalene dye with apomyoglobin and apohemoglobin. A fluorescent probe of nonpolar binding sites. J. Mol. Biol. 13:482-495.
52. Tanford, C. 1973. The Hydrophobic Effect. Wiley, New York.
53. Warshel, A. 1987. What about protein polarity? Nature. 330:15-16.
54. Weber, G. 1952. Polarization of the fluorescence of macromolecules. 2. Fluorescent conjugates of ovalbumin and bovine serum albumin. Biochem. J. 51:155-167.
55. Weber, G., and D. Laurence. 1954. Fluorescent indicators of adsorption in aqueous solution and on the solid phase. Biochem. J. 56:xxxi
56. Weber, L., A. Tulinsky, J. Johnson, and M. El-Bayoumi. 1979. Expression of functionality of α-chymotrypsin. The structure of a fluorescent probe-α-chymotrypsin complex and the nature of its pH dependence. Biochemistry. 18:1297-1303.
57. Xu, Z., M. Buelt, L. Banaszak, and D. Bemlohr. 1991. Expression, purification, and crystallization of the adipocyte lipid binding protein. J. Biol. Chem. 266 14367-14370.
58. Yang, M., S. Ghosh, and D. Millar. 1994. Direct measurement of thermodynamic and kinetic parameters of DNA triple helix formation by fluorescence spectroscopy. Biochemistry. 33:15329-15337.