Weak intermolecular associations and anesthesia

Anesthesiology

Volumn 101, Issue 5, 2004, Pages 1225-1227

  Sandorfy, Camille ^a,b  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b NONE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANESTHETIC AGENT; CHLOROFORM; ENFLURANE; HALOCARBON; METHOXYFLURANE; NEUROTRANSMITTER RECEPTOR;

CHEMICAL BOND; DRUG POTENCY; DRUG STRUCTURE; GENERAL ANESTHESIA; HUMAN; HYDROGEN BOND; MOLECULAR INTERACTION; PRIORITY JOURNAL; QUANTUM CHEMISTRY; REVIEW; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS; VAN DER WAALS FORCE;

ANESTHESIA; ANESTHETICS; CHEMISTRY, PHYSICAL; HYDROGEN BONDING; PROTEIN BINDING;

EID: 7244247302     PISSN: 00033022     EISSN: None     Source Type: Journal    
DOI: 10.1097/00000542-200411000-00024     Document Type: Review

References (50)

1. Miller KW: The nature of the site of general anesthesia. Int Rev Neurobiol 1985; 27:1-61
2. Franks NP, Lieb WR: Molecular and cellular mechanisms of general anesthesia. Nature 1994; 367:607-14
3. Ueda I: Is there a receptor for volatile anesthetics? Prog Anest Mech (Japan) 1993; 1:1-20
4. Sandorfy C: Intermolecular interactions and anesthesia. ANESTHESIOLOGY 1978; 48:357-9
5. Urry DW, Sandorfy C: Chemical modulation of transmembrane proton structure and function. Drug and Anesthetic Effects on Membrane Structure and Function. Edited by Alois RC, Curtain CC, Gordon LM. New York, Wiley-Liss, 1991. pp 91-131
6. Lovinger DM: Alcohols and neurotransmitter gated ion-channels: Past, present and future. Naunyn-Schmiedebergs Arch Pharmacol 1997; 356:267-82
7. Pocock G, Richards CD: Excitatory and inhibitory synaptic mechanisms in anaesthesia. Br J Anaesth 1993; 71:134-47
8. Krasowski, MD, Harrison NL: General anesthetic actions on ligand-gated ion channels. Cell Mol Life Sci 1999; 55:1278-303
9. Belelli D, Pistis M, Peters JA, Lambert JJ: General anesthetic action at transmitter-gated inhibitory amino acid receptors. Trends Pharmacol Sci 1996; 20:496-502
10. Lis H, Sharon N: Lectins: Carbohydrate specific proteins that mediate cellular recognition. Chem Rev 1998; 98:637-74
11. Davis RH, Bagnall RD, Bell W, Jones WGM: The hydrogen bond proton donor properties of volatile halogenated hydrocarbons and ethers and their mode of action in anesthesia. Int J Quantum Chem, Quantum Biol Symp 1976; 3:171-85
12. Di Paolo T, Sandorfy C: Fluoro carbon anaesthetics break hydrogen bonds. Nature 1974; 252:471
13. Di Paolo T, Sandorfy C: Hydrogen bond breaking potency of fluorocarbon anesthetics. J Med Chem 1974; 17:809-14
14. Buchet R, Sandorfy C: The effect of anesthetics on hydrogen bonds: An infrared study at low anesthetic concentrations. Biophys Chem 1985; 22:249-54
15. Trudeau G, Cole KC, Massuda R, Sandorfy C: Anesthesia and hydrogen bonding: A semi-quantitative infrared study at room temperature. Can J Chem 1978; 56:1681-6
16. Trudeau G, Dumas JM, Dupuis P, Guerin M, Sandorfy C: Intermolecular interactions and anesthesia: Infrared spectroscopic studies. Top Curr Chem 1980; 93:91-125
17. Hobza P, Mulder F, Sandorfy C: Quantum chemical and statistical thermodynamic investigations of anesthetic activity. 1. The interaction between chloroform, fluoroform, cyclopropane and an O-H...O hydrogen bond. J Am Chem Soc 1981; 103:1360-6
18. Hobza P, Mulder F, Sandorfy C: Quantum chemical and statistical thermodynamic investigations of anesthetic activity. 2. The interaction between chloroform, fluoroform, cyclopropane and a N-H...O=C hydrogen bond. J Am Chem Soc 1982; 104:925-8
19. Brockerhoff H, Brockerhoff S, Box LL: Mechanism of anesthesia: The potency of four derivatives of octane corresponds to their hydrogen bonding capacity. Lipids 1986; 21:405-8
20. Abraham MH, Lieb WR, Franks NP: Role of hydrogen bonding in general anesthesia. J Pharma Sci 1991; 80:719-24
21. Jeffrey GA, Saenger W: Hydrogen Bonding in Biological Structures. Berlin: Springer-Verlag, 1991, p 19
22. Jones LH, Badger RM: The frequency of the third harmonic O-H band of methanol in various solvents, and the hydrogen bonding of methanol with aromatic hydrocarbons. J Am Chem Soc 1951; 73:3132-4
23. Josien ML, Sourisseau G: Contribution à l'étude des molécules aromatiques considérées comme accepteurs de proton. Hydrogen Bonding. Edited by Hadzi D. London, New York: Pergamon Press, 1959, pp 129-37
24. Levitt M, Perutz MF: Aromatic rings act as hydrogen bond acceptors. J Mol Biol 1988; 201:751-4
25. Steiner T, Koellner G: Hydrogen bonds with π-acceptors in proteins: frequencies and role in stabilizing local 3D structures. J Mol Biol 2001; 305:535-57
26. Perutz MF: The role of aromatic rings as hydrogen-bond acceptors in molecular recognition. Phil Trans Roy Soc Ser A 1993; 345:105-12
27. Desiraju GR, Steiner T: The Weak Hydrogen Bond. Oxford University Press, 1989
28. Singh J, Thornton JM: An automated method for the analysis of the preferred packing arrangements between protein groups. J Mol Biol 1990; 211:595-615
29. Mitchell JBO, Nandi CL, McDonald LK, Thornton JM, Price SL: Amino/ aromatic interactions in proteins: is the evidence stacked against hydrogen bonding? J Mol Biol 1994; 239:315-31
30. Gursky O, Fontano E, Bhyravbhatla B, Caspar DLD: Stereospecific dihaloalkane binding of a pH-sensitive cavity in cubic insulin crystals. Proc Natl Acad Sci U S A 1994; 91:12388-92
31. Burley SK, Petsko GA: Amino-aromatic interactions in proteins. FEBS Lett 1986; 203:139-43
32. Burley SK, Petsko GA: Aromatic-aromatic interaction: a mechanism of protein structure stabilization. Science 1985; 229:23-28
33. Berger I, Egli M: The role of backbone oxygen atoms in the organization of nucleic acid tertiary structure: Zippers, networks, champs and C-H...O hydrogen bonds. Chem Eur J 1997; 3:1400-4
34. Atwood JL, Hamada F, Robinson KD, Orr GW, Vincent RL: X-ray diffraction evidence for aromatic π hydrogen bonding to water. Nature 1991; 349:683-4
35. Kiessling LL, Young T, Mortell KH: Multivalency in protein-carbohydrate recognition, Glycoscience-Chemistry and Chemical Biology. Berlin: Springer-Verlag, 2001, pp 1818-61
36. Weis WI, Drickamer K: Structural basis of lectin-carbohydrate recognition. Annu Rev Biochem 1996; 65:441-73
37. Sandorfy C: Towards a comprehensive theory of general anesthesia. In Molecular and Basic Mechanism of Anesthesia. Edited by Urban BW, Barann M. Lengerich, Pabst Science Publishers, 2002, pp 66-73
38. Eckenhoff RG: Amino acid resolution of halothane binding sites in serum albumin. J Biol Chem 1996; 271:15521-6
39. Eckenhoff RG, Johansson JS: Interactions between inhaled anesthetics and proteins. Pharmacol Rev 1997; 49:343-67
40. Johansson JS, Scharf D, Davies LA, Reddy KS, Eckenhoff RG: A designed four-α-helix bundle that binds the volatile general anesthetic halothane with high affinity. Biophys J 78:982-93
41. Manderson, CA, Johannson JS: Role of aromatic side chains in the binding of volatile general anesthetics to a four-α-helix bundle. Biochemistry 2002; 41:4080-7
42. Johansson JS, Eckenhoff RG: Minimum structural requirements for an inhalational anesthetic binding site on a protein site. Biochim Biophys Acta 1996; 1290:63-8
43. Johansson JS, Scharf D: Towards an understanding of how general anesthetics alter central nervous system protein function. Reg Anesth Pain Med 2001; 26:267-7
44. Johansson JS, Gibney BR, Rabanal F, Reddy KF, Dutton PL: A designed cavity in the hydrophobic core of a four α-helix bundle improves volatile anesthetic affinity. Biochimistry 1998; 37:1421-9
45. Yoshida T, Okabayashi H, Takahashi A, Ueda I: A proton nuclear magnetic study on the release of bound water by inhalation anesthetics in water-in-oil emulsion. Biochim Biophys Acta 1984; 772:102-7
46. Trudell JR, Bertaccini E: Molecular modeling of specific and non-specific anaesthetic interactions. Br J Anaesth 2002; 89:32-40
47. Jones OT, McNamee M: Annular and nonannular binding sites for cholesterol associated with the nicotinic acetylcholine receptor. Biochemistry 1988; 27:2364-74
48. Corbin J, Wang HH, Blanton MP: Identifying the cholesterol binding domain in the nicotinic acetylcholine receptor with [1251]azido-cholesterol. Biochim Biophys Acta 1998; 1414:65-74
49. Rankin SE, Addona GH, Kloczewiak, MA, Bugge B, Miller KW: The cholesterol dependence of activation and fast desensitization of the nicotinic acid receptor. Biophys J 1997; 73:2446-55
50. Mercier P, Sandorfy C, Vocelle D: Perturbation of the hydrogen-bond equilibrium between cholesterol and esters or amides by chlorofluorocarbons. J Phys Chem 1983; 87:3670-4