Ecotoxicology of narcosis: Stereoselectivity and potential target sites

Chemosphere

Volumn 72, Issue 9, 2008, Pages 1256-1259

  Sandermann, Heinrich ^a,b  

^a ecotoxfreiburg   (Germany)

^b INSTITUTE OF EPIDEMIOLOGY   (Germany)

Author keywords

Etomidate; GABAA channel; Lipid protein interface; Propofol; Stereoselectivity; Tadpole narcosis

Indexed keywords

LIPIDS;

ECO-TOXICOLOGY; TARGET SITES;

STEREOSELECTIVITY;

ETOMIDATE; OCTANOL;

ANESTHETIC; ECOTOXICOLOGY; EXPERIMENTAL STUDY; FROG; JUVENILE; SLEEP;

ANESTHESIA; ANIMAL EXPERIMENT; ARTICLE; CALIBRATION; ECOTOXICOLOGY; ENANTIOMER; LIPOPHILICITY; NONHUMAN; PROTEIN LIPID INTERACTION; RECEPTOR BINDING; STEREOCHEMISTRY; TADPOLE;

ANESTHETICS, INTRAVENOUS; ANIMALS; CHEMISTRY, PHYSICAL; ENVIRONMENTAL POLLUTANTS; LARVA; PROPOFOL; RANA TEMPORARIA; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; STUPOR; XENOPUS LAEVIS;

EID: 46149083203     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2008.05.002     Document Type: Article

References (39)

1. Aktories K., Förstermann M., Hofmann J., and Starke K. Allgemeine und spezielle Pharmakologie und Toxikologie (2005), Urban & Fischer, München, Germany pp. 278-279
2. Altschuh J., Walcher S., and Sandermann H. The lipid/protein interface as xenobiotic target site. Kinetic analysis of tadpole narcosis. FEBS J. 272 (2005) 2399-2406
3. A receptor. Mol. Pharmacol. 65 (2004) 68-76
4. Belelli D., Lambert J.J., Peters J.A., Wafford K., and Whiting P.J. The interaction of the general anesthetic etomidate with the γ-aminobutyric acid type A receptor is influenced by a single amino acid. Proc. Natl. Acad. Sci. USA 94 (1997) 11031-11036
5. Bosnan R., Gong D., Cotton J., Yost C.S., Eger II E.I., and Sonner J.M. Chirality in anesthesia II: stereoselective modulation of ion channel function by secondary alcohol enantiomers. Anesth. Analg. 103 (2006) 86-91
6. Bright D.P., Adham S.D., Lemaire L.C.J.M., Benavides R., Gruss M., Taylor G.W., Smith E.H., and Franks N.P. Identification of anesthetic binding sites on human serum albumin using a novel etomidate photolabel. J. Biol. Chem. 282 (2007) 12038-12047
7. Campagna J.A., Miller K.W., and Forman S.A. Mechanisms of action of inhaled anesthetics. New Engl. J. Med. 348 (2003) 2110-2124
8. Eger II E.I., Koblin D.D., Laster M.J., Schurig V., Juza M., Ionescu P., and Gong D. Minimum alveolar anesthetic concentration values for the enantiomers of isoflurane differ minimally. Anesth. Analg. 85 (1997) 188-192
9. Escher B.I., and Hermens J.L.M. Modes of action in ecotoxicology: their role in body burdens, species sensitivity, QSARs, and mixture effects. Environ. Sci. Technol. 36 (2002) 4201-4217
10. Franks N.P. Molecular targets underlying general anesthesia. Br. J. Pharmacol. 147 (2006) S72-S81
11. Franks N.P., and Lieb W.R. Do general anesthetics act by competitive binding to specific receptors?. Nature 310 (1984) 599-601
12. Franks N.P., and Lieb W.R. Stereospecific effects of inhalational general anesthetic optical isomers on nerve ion channels. Science 254 (1991) 427-430
13. Franks N.P., and Lieb W.R. Molecular and cellular mechanisms of general anesthesia. Nature 367 (1994) 607-614
14. Harrison N.L. Optical isomers open a new window on anesthetic mechanism. Anesthesiology 88 (1998) 566-567
15. Hemmings H.C., Akabas M.H., Goldstein P.A., Trudell J.R., Orser B.A., and Harrison N.L. Emerging molecular mechanisms of general anesthetic action. Trends Pharmacol. Sci. 26 (2005) 503-510
16. Husain S.S., Forman S.A., Kloczewiak M.A., Addona G.H., Olsen R.W., Pratt M.B., Cohen J.B., and Miller K.W. Synthesis and properties of 3-(2-hydroxyethyl)-3-n-pentyldiazirine, a photoactivable general anesthetic. J. Med. Chem. 42 (1999) 3300-3307
17. Husain S.S., Ziebell M.R., Ruesch D., Hong F., Arevalo E., Kosterlitz J.A., Olsen R.W., Forman S.A., Cohen J.B., and Miller K.W. 2-(3-Methyl-3H-diaziren-3-yl)-ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate: a derivative of the stereoselective general anesthetic etomidate for photolabelling ligand-gated ion channels. J. Med. Chem. 46 (2003) 1257-1265
18. Husain S.S., Nirthanan S., Ruesch D., Solt K., Cheng Q., Li G.-D., Arevalo E., Olsen R.W., Raines D.E., Forman S.A., Cohen J.B., and Miller K.W. Synthesis of trifluoromethylaryl diazirine and benzophenone derivatives of etomidate that are potent general anesthetics and effective photolabels for probing sites on ligand-gated ion channels. J. Med. Chem. 49 (2006) 4818-4825
19. Kelz M.B., Sun Y., Chen J., Meng Q.C., Moore J.T., Veasey S.C., Dixon S., Thornton M., Funato H., and Yanagisawa M. An essential role for orexins in emergence from general anesthesia. Proc. Natl. Acad. Sci. USA 105 (2008) 1309-1314
20. A receptor but not with lipid solubility. J. Pharmacol. Exp. Ther. 297 (2001) 338-351
21. A receptor anesthetic binding site at subunit interfaces by photolabelling with an etomidate analog. J. Neurosci. 26 (2006) 11599-11605
22. A and glycine receptors. Nature 389 (1997) 385-389
23. Miller K.W. The nature of the site of general anesthesia. Int. Rev. Neurobiol. 27 (1985) 1-61
24. Mohr J.T., Gribble G.W., Lin S.S., Eckenhoff R.G., and Cantor R.S. Anesthetic potency of two novel synthetic polyhydric alkanols longer than the n-alkanol cutoff: evidence for a bilayer-mediated mechanism of anesthesia. J. Med. Chem. 48 (2005) 4172-4176
25. Öberg T. A QSAR for baseline toxicity: validation, domain of application, and prediction. Chem. Res. Toxicol. 17 (2004) 1630-1637
26. Overton C.E. In: Lipnick R.L. (Ed). Studies of Narcosis (1991), Chapman and Hall, London
27. 2 subunit M4 segment is a determinant of γ-aminobutyric acid type A receptor sensitivity to propofol. Anesthesiology 107 (2007) 412-418
28. Roberts M.T., Phelan R., Erlichman B.S., Pillai R.N., Ma L., Lopreato G.F., and Mihic S.J. Occupancy of a single anesthetic binding pocket is sufficient to enhance glycine receptor function. J. Biol. Chem. 281 (2006) 3305-3311
29. Sandermann H., Duncan T.M., McIntyre J.O., and Fleischer S. Cooperative regulation of membrane enzymes by lipids. In: Watts A. (Ed). Protein-Lipid Interactions (1993), Elsevier, Amsterdam 67-85
30. Seeman P. The membrane actions of anesthetics and tranquilizers. Pharmacol. Rev. 24 (1972) 583-655
31. Solt K., and Forman S.A. Correlating the clinical actions and molecular mechanisms of general anesthetics. Curr. Opin. Anesthesiol. 20 (2007) 300-306
32. Tang P., and Xu Y. Large-scale molecular dynamics simulations of general anesthetic effects on the ion channel in the fully hydrated membrane: The implication of molecular mechanisms of general anesthesia. Proc. Natl. Acad. Sci. USA 99 (2002) 16035-16040
33. Tomlin S.L., Jenkins A., Lieb W.R., and Franks N.P. Stereoselective effects of etomidate optical isomers on gamma-aminobutyric acid type A receptors and animals. Anesthesiology 88 (1998) 708-717
34. Tonner P.H., Poppers D.M., and Miller K.W. The general anesthetic potency of propofol and its dependence on hydrostatic pressure. Anesthesiology 77 (1992) 926-931
35. Tonner P.H., Scholz J., Lamberz L., Schlamp N., and Schulte Esch N. Inhibition of nitric oxide synthase decreases anesthetic requirements of intravenous anesthetics in Xenopus laevis. Anesthesiology 87 (1997) 1479-1485
36. Van Wezel A.P., and Opperhuizen A. Narcosis due to environmental pollutants in aquatic organisms: residue-based toxicity, mechanisms and membrane burdens. Crit. Rev. Toxicol. 25 (1995) 255-279
37. Vemparala S., Saiz L., Eckenhoff R.G., and Klein M.L. Partitioning of anesthetics into a lipid bilayer and their interaction with membrane-bound peptide bundles. Biophys. J. 91 (2006) 2815-2825
38. Wang X., Dong Y., Wang L., and Han S. Acute toxicity of substituted phenols to Rana japonica tadpoles and mechanism-based quantitative structure-activity relationship (QSAR) study. Chemosphere 44 (2001) 447-455
39. Yamakura T., Bertaccini E., Trudell J.R., and Harris R.A. Anesthetics and ion channels: molecular models and sites of action. Annu. Rev. Pharmacol. Toxicol. 41 (2001) 23-51