α- and β-phosphorylated amines and pyrrolidines, a new class of low toxic highly sensitive 31P NMR pH indicators: Modeling of pK(}a and chemical shift values as a function of substituents

Journal of Biological Chemistry

Volumn 275, Issue 26, 2000, Pages 19505-19512

  Pietri, Sylvia ^a   Miollan, Malvina ^a   Martel, Sophie ^a   Le Moigne, François ^a   Blaive, Bruno ^a   Culcasi, Marcel ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; PHOSPHATE; PHOSPHONIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE;

ANIMAL TISSUE; ARTICLE; CELL PH; CHEMICAL BINDING; ISOLATED HEART; NONHUMAN; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; RAT; TEMPERATURE;

AMINES; ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; HEART; HYDROGEN-ION CONCENTRATION; INDICATORS AND REAGENTS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MODELS, STATISTICAL; MYOCARDIUM; PERFUSION; PHOSPHONIC ACIDS; PHOSPHORUS ISOTOPES; PHOSPHORYLATION; PROTEIN CONFORMATION; PROTEIN STRUCTURE, TERTIARY; PYRROLIDINES; RATS; RATS, WISTAR; REPRODUCIBILITY OF RESULTS; SENSITIVITY AND SPECIFICITY; SPIN LABELS; TEMPERATURE;

ANIMALIA;

EID: 0034733716     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M001784200     Document Type: Article

References (42)

1. Moon, R. B., and Richards, J. H. (1973) J. Biol. Chem. 248, 7276-7278
2. Gillies, R. J., Alger, J. R., den Hollander, J. A., and Shulman, R. G. (1982) in Intracellular pH: Its Measurement, Regulation, and Utilization in Cellular Functions (Nuccitelli, E., and Deamer, D. W., eds) pp. 79-104, Alan R. Liss, New York
3. Schlisefeld, L. H., Burt, C. T., and Labotka, R. J. (1982) Biochemistry 21, 317-320
4. Robitaille, P. M. L., Robitaille, P. A., Brown, G. G., Jr., and Brown, G. G. (1991) J. Magn. Reson. 92, 73-84
5. Labotka, R. J., and Kleps, R. A. (1983) Biochemistry 22, 6089-6095
6. DeFronzo, M., and Gillies, R. J. (1987) J. Biol. Chem. 262, 11032-11037
7. Brénot, F., Aubry, L., Martin, J. B., Satre, M., and Klein, G. (1992) Biochimie (Paris) 74, 883-895
8. Satre, M., Martin, J. B., and Klein, G. (1989) Biochimie [Paris] 71, 941-948
9. Stewart, I. M., Chapman, B. E., Kirk, K., Kuchel, P. W., Lovric, V. A., and Raftos, J. E. (1986) Biochim. Biophys. Acta 885, 23-33
10. Gillies, R. J., Liu, Z., and Bhujwalla, Z. (1994) Am. J. Physiol. 267, C195-C203
11. Szwergold, B. S., Brown, T. R., and Freed, J. J. (1989) J. Cell. Physiol. 138, 227-235
12. Thoma, W. J., Steiert, J. G., Crawford, R. L., and Ugurbil, K. (1986) Biochem. Biophys. Res. Commun. 138, 1106-1109
13. Fisher, M. J., and Dillon, P. F. (1987) Circ. Res. 60, 472-477
14. Clarke, K., Stewart, L. C., Neubauer, S., Balschi, J. A., Smith, T. W., Ingwall, J. S., Nédelec, J. S., Humphrey, S. M., Kléber, A. G., and Springer, C. S. (1993) NMR Biomed. 6, 278-286
15. Clarke, K., Anderson, R. E., Nédélec, J. F., Foster, D. O., and Ally, A. (1994) Magn. Res. Med. 32, 181-188
16. Bruynseels, K., Gillis, N., Van Hecke, P., and Vanstapel, F. (1997) NMR Biomed. 10, 263-270
17. Fréjaville, C., Karoui, H., Tuccio, B., Le Moigne, F., Culcasi, M., Pietri, S., Lauricella, R., and Tordo, P. (1995) J. Med. Chem. 38, 258-265
18. Barbati, S., Clément, J. L., Olive, G., Roubaud, V., Tuccio, B., and Tordo, P. (1997) NATO ASI Ser. Ser. A Life Sci. 27, 39-47
19. Karoui, H., Nsanzumuhire, C., Le Moigne, F., and Tordo, P. (1999) J. Org. Chem. 64, 1471-1477
20. Pietri, S., Miollan, M., Le Moigne, F., and Culcasi, M. (March 18, 1998) French Patent CNRS 98,03317
21. Afarinkia, K., Rees, C. W., and Cadogan, J. I. G. (1990) Tetrahedron 46, 7175-7196
22. Medved, T. Y., and Kabachnik, M. I. (1954) Izv. Akad. Nauk. SSSR Otd. Khim. Nauk. 255-261; Engl. Transl. (1954) Bull. Acad. Sci. USSR Div. Chem. Sci. 314-320
23. Medved, T. Y., and Kabachnik, M. I. (1954) Izv. Akad. Nauk. SSSR Otd. Khim. Nauk. 255-261; Engl. Transl. (1954) Bull. Acad. Sci. USSR Div. Chem. Sci. 314-320
24. Medved, T. Y., and Kabachnik, M. I. (1954) Izv. Akad. Nauk. SSSR Otd. Khim. Nauk. 255-261; Engl. Transl. (1954) Bull. Acad. Sci. USSR Div. Chem. Sci. 314-320
25. Fields, E. K. (1952) J. Am. Chem. Soc. 74, 1528-1531
26. Dawson, N. D., and Burger, A. (1952) J. Am. Chem. Soc. 74, 5312-5314
27. Abdel-Magid, A. F., Maryanoff, C. A., and Carson, K. G. (1990) Tetrahedron Lett. 31, 5595-5598
28. Grimaldi, S. (1997) Ph. D. Thesis, Université d'Aix-Marseille III, France
29. Gordon, A. J., and Ford, R. A. (1972) The Chemist's Companion: A Handbook of Practical Data, Techniques, and References, pp. 55-81, Wiley-Inter-science, New York
30. Sosnovsky, G., and Bell, P. (1998) Life Sci. 62, 639-648
31. Grabenstetter, R. J., Quimby, O. T., and Flautt, T. J. (1967) J. Phys. Chem. 71, 4194-4202
32. Deutsch, C. J., and Taylor, J. S. (1987) Ann. N. Y. Acad. Sci. 508, 33-47
33. Deutsch, C. J., and Taylor, J. S. (1989) Biophys. J. 55, 799-804
34. Szwergold, B. S. (1992) Annu. Rev. Physiol. 54, 775-798
35. Anderson, R. G. W., and Orci, L. (1988) J. Cell Biol. 106, 539-543
36. Wadsworth, S. J., and van Rossum, G. D. V. (1994) J. Membr. Biol. 142, 21-34
37. Gorenstein, D. G. (1984) in Phosphorus-31 NMR: Principles and Applications (Gorenstein, D. G., ed) pp. 7-36, Academic Press, Orlando, FL
38. Ohia, K. (1992) Bull. Chem. Soc. Jpn 65, 2543-2545
39. Maurelli, E., Culcasi, M., Delmas-Beauvieux, M. C., Miollan, M., Gallis, J. L., Tron, T., and Pietri, S. (1999) Free Radic. Biol. & Med. 27, 34-41
40. Seo, Y., Murakami, M., Watari, H., Imai, Y., Yoshizaki, K., Nishikawa, H., and Morimoto, T. (1983) J. Biochem. 94, 729-734
41. Roberts, J. K. M., Wade-Jardetsky, N., and Jardetzky, O. (1981) Biochemistry 20, 5389-5394
42. U.S. Department of Health and Human Services (1985) NIH publication 85-23