Sensitivity of opioid receptor binding to N-substituted maleimides and methanethiosulfonate derivatives

Neurochemical Research

Volumn 21, Issue 11, 1996, Pages 1295-1299

  Shahrestanifar, M S ^a   Howells, R D ^a  

^a RUTGERS NEW JERSEY MEDICAL SCHOOL   (United States)

Author keywords

maleimides; methane thiosulfonate; Opioid receptors

Indexed keywords

(2 AMINOETHYL)METHANETHIOSULFONATE; BREMAZOCINE; DELTA OPIATE RECEPTOR; MALEIMIDE DERIVATIVE; MU OPIATE RECEPTOR; OPIATE RECEPTOR; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; EMBRYO; HUMAN; HUMAN CELL; PRIORITY JOURNAL; RECEPTOR BINDING; SITE DIRECTED MUTAGENESIS;

EID: 0029908852     PISSN: 03643190     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02532370     Document Type: Article

References (26)

1. Strader, C. D., Fong, T. M., Graziano, M. P., and Tola, M. R. 1995. The family of G-protein-coupled receptors. FASEB J. 9: 745-754.
2. Schwartz, T. W., Gether, U., Schambye, H. T., and Hjorth, S. A. 1995. Molecular mechanism of action of non-peptide ligands for peptide receptors. Curr. Pharmaceut. Design 1:325-342.
3. Knapp, R. J., Malatynska, E., Collins, N., Fang, L., Wang, J. Y., Hruby, V. J., Roeske, W. R., and Yamamura, H. I. 1995. Molecular biology and pharmacology of cloned opioid receptors. FASEB J. 9:516-525.
4. Reisine, T. 1995. Opiate receptors. Neuropharmacology 34:463-472.
5. Simon, E. J., Miller, J. M., and Edelman, I. 1973. Stereospecific binding of the potent narcotic analgesic 3H-etorphine to rat brain homogenate. Proc. Natl. Acad. Sci. USA 70:1947-1949.
6. Pasternak, G. W., Wilson, H. A., and Snyder, S. H. 1975. Differential effects of protein-modifying reagents on receptor binding of opiate agonists and antagonists. MoI. Pharmacol. 11:340-351.
7. Simon, E. J., and Groth, J. 1975. Kinetics of opiate receptor inactivation by sulfhydryl reagents: evidence for conformational change in presence of sodium ions. Proc. Natl. Acad. Sci. USA 72:2404-2407.
8. Mulliken-Kilpatrick, D., Larsen, N. E., and Blume, A. J. 1983. Protection of opiate receptors in NG108-15 cells against modification by N-ethylmaleimide. J. Neurosci. 3:145-152.
9. Childers, S. R. 1984. Interaction of opiate receptor binding sites and guanine nucleotide regulatory sites: selective protection from N-ethylmaleimide. J. Pharmacol. Exp. Ther. 230:684-691.
10. Shahrestanifar, M., and Howells, R. D. 1994. Sensitivity of μ and δ opioid receptor binding to N-ethylmaleimide. Reg. Peptides 54: 269-270.
11. Shahrestanifar, M., Wang, W. W., and Howells, R. D. 1996. Studies on inhibition of μ and δ opioid receptor binding by dithiothreitol and N-ethylmaleimide: His223 is critical for μ opioid receptor binding and inactivation by N-ethylmaleimide. J. Biol. Chem. 271:5505-5512.
12. Howells, R. D., Gioannini, T., Hiller, J. M., and Simon, E. J. 1982. Solubilization and characterization of active opiate binding sites from mammalian brain. J. Pharmacol. Exp. Ther. 222:629-634.
13. Bradford, M. M. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:248-254.
14. Heitz, J. R., Anderson, C. D., and Anderson, B. M. 1968. Inactivation of yeast alcohol dehydrogenase by N-alkylmaleimides. Arch. Biochem. Biophys. 127:627-636.
15. Offri, D., and Simon, E. J. 1992. Sulfhydryl groups on opioid receptors revisted. Evidence for two sulfhydryl groups at or near the active site of the mu opioid receptor. Receptor 2:109-119.
16. Fonda, M. L., and Anderson, B. M. 1969. D-Amino acid oxidase IV. Inactivation by maleimides. J. Biol. Chem. 244:666-674.
17. Anderson, B. M., Vercellotti, S. V., and Fischer, T. L. 1974. Maleimide inactivation of lactate dehydrogenase isozymes. Biochim. Biophys. Acta 350:135-140.
18. Anderson, B. M., and Vasini, E. C. 1970. Nonpolar effects in reactions of the sulfhydryl group of papain. Biochemistry 9:3348-3352.
19. Pongsawasdi, P., and Anderson, B. M. 1984. Inactivation of rat ovarian 20a-hydro.\ysteroid dehydrogenase by N-alkylmaleimides. Arch. Biochem. Biophys. 233:481-488.
20. Dubler, R. E., and Anderson, B. M. 1981. Simultaneous inactivation of the catalytic activities of yeast glutathione reductase by N-alkylmaleimides. Biochim. Biophys. Acta 659:70-85.
21. Beier, K. H., Anderson, C. D., and Anderson, B. M. 1989. Non-polar interactions in the modification of an essential sulfhydryl of sorbitol dehydrogenase by N-alkylmaleimides. Biochim. Biophys. Acta 997:236-241.
22. Anderson, B. M., and Dubler, R. E. 1980. Inactivation of chicken liver D-3-phosphoglycerate dehydrogenase by N-alkylmaleimides. Arch. Biochem. Biophys. 200:583-589.
23. Noble, C. Jr., and Anderson, B. M. 1977. Interactions of inhibitors at the coenzyme binding site of 6-phosphogluconate dehydrogenase. Arch. Biochem. Biophys. 178:26-33.
24. Kieffer, B. L., Befort, K., Gaveriaux-Ruff, C., and Hirth, C. 1992. The δ-opioid receptor: isolation of a cDNA by expression cloning and pharmacological characterization. Proc. Natl. Acad. Sci. USA 89:12048-12052.
25. Javitch, J. A., Fu, D., Chen, J., and Karlin, A. 1995. Mapping the binding-site crevice of the dopamine D2 receptor by the substituted-cysteine accessibility method. Neuron 14:825-831.
26. Javitch, J. A., Fu, D., and Chen, J. 1995. Residues in the fifth membrane-spanning segment of the dopamine D2 receptor exposed in the binding-site crevice. Biochemistry 34:16433-16439.