Stereospecific Interaction of Bupivacaine Enantiomers with Lipid Membranes

Regional Anesthesia and Pain Medicine

Volumn 33, Issue 4, 2008, Pages 304-311

  Mizogami, Maki ^a   Tsuchiya, Hironori ^a   Ueno, Takahiro ^a   Kashimata, Masanori ^a   Takakura, Ko ^a  

^a ASAHI UNIVERSITY   (Japan)

Author keywords

Bupivacaine enantiomers; Lipid composition; Membrane disordering; Stereospecific membrane interaction

Indexed keywords

BUPIVACAINE; CHOLESTEROL; DIPALMITOYLPHOSPHATIDYLCHOLINE; PHOSPHOLIPID;

ARTICLE; ENANTIOMER; FLUORESCENCE POLARIZATION; HYDROPHOBICITY; LIPID COMPOSITION; LIPID MEMBRANE; NERVE CELL; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOSPECIFICITY; TURBIDITY;

ANESTHETICS, LOCAL; BUPIVACAINE; CELL MEMBRANE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROGEN BONDING; LIPID BILAYERS; LIPOSOMES; MEMBRANE LIPIDS; PHASE TRANSITION; STEREOISOMERISM;

EID: 48149099616     PISSN: 10987339     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.rapm.2007.05.011     Document Type: Article

References (30)

1. Nau C., and Strichartz G.R. Drug chirality in anesthesia. Anesthesiology 97 (2002) 497-502
2. Foster R.H., and Markham A. Levobupivacaine: a review of its pharmacology and use as a local anaesthetic. Drugs 59 (2000) 551-579
3. Lyons G., Columb M., Wilson R.C., and Johnson R.V. Epidural pain relief in labour: potencies of levobupivacaine and racemic bupivacaine. Br J Anaesth 81 (1998) 899-901
4. Dyhre H., Lang M., Wallin R., and Renck H. The duration of action of bupivacaine, levobupivacaine, ropivacaine and pethidine in peripheral nerve block in the rat. Acta Anaesthesiol Scand 41 (1997) 1346-1352
5. Lee-Son S., Wang G.K., Concus A., Crill E., and Strichartz G. Stereoselective inhibition of neuronal sodium channels by local anesthetics. Evidence for two sites of action?. Anesthesiology 77 (1992) 324-335
6. Vladimirov M., Nau C., Mok W.M., and Strichartz G. Potency of bupivacaine stereoisomers tested in vitro and in vivo: biochemical, electrophysiological, and neurobehavioral studies. Anesthesiology 93 (2000) 744-755
7. Heavner J.E. Cardiac toxicity of local anesthetics in the intact isolated heart model: a review. Reg Anesth Pain Med 27 (2002) 545-555
8. Valenzuela C., Snyders D.J., Bennett P.B., Tamargo J., and Hondeghem L.M. Stereoselective block of cardiac sodium channels by bupivacaine in guinea pig ventricular myocytes. Circulation 92 (1995) 3014-3024
9. Valenzuela C., Delpón E., Tamkun M.M., Tamargo J., and Snyders D.J. Stereoselective block of a human cardiac potassium channel (Kv1.5) by bupivacaine enantiomers. Biophys J 69 (1995) 418-427
10. Butterworth J.F., and Strichartz G.R. Molecular mechanisms of local anesthesia: a review. Anesthesiology 72 (1990) 711-734
11. Nau C., Vogel W., Hempelmann G., and Bräu M.E. Stereoselectivity of bupivacaine in local anesthetic-sensitive ion channels of peripheral nerve. Anesthesiology 91 (1999) 786-795
12. 2+ channels?. Anesth Analg 92 (2001) 496-501
13. Kopeikina L.T., Kamper E.F., Siafaka I., and Stavridis J. Modulation of synaptosomal plasma membrane-bound enzyme activity through the perturbation of plasma membrane lipid structure by bupivacaine. Anesth Analg 85 (1997) 1337-1343
14. Mizogami M., Tsuchiya H., and Harada J. Membrane effects of ropivacaine compared with those of bupivacaine and mepivacaine. Fundam Clin Pharmacol 16 (2002) 325-330
15. Goldstein D.B. The effects of drugs on membrane fluidity. Annu Rev Pharmacol Toxicol 24 (1984) 43-64
16. Alifimoff J.K., Bugge B., Forman S.A., and Miller K.W. Stereoselectivity of channel inhibition by secondary alkanol enantiomers at nicotinic acetylcholine receptors. Anesthesiology 79 (1993) 122-128
17. Tsuchiya H. Stereospecificity in membrane effects of catechins. Chem Biol Interact 134 (2001) 41-54
18. Korkmaz F., and Severcan F. Effect of progesterone on DPPC membrane: evidence for lateral phase separation and inverse action in lipid dynamics. Arch Biochem Biophys 440 (2005) 141-147
19. Tsuchiya H. Structure-specific membrane-fluidizing effect of propofol. Clin Exp Pharmacol Physiol 28 (2001) 292-299
20. Svennerholm L., Boström K., Fredman P., Jungbjer B., Månsson J.-E., and Rynmark B.-M. Membrane lipids of human peripheral nerve and spinal cord. Biochim Biophys Acta 1128 (1992) 1-7
21. 1H-NMR measurements. Biophys Chem 115 (2005) 11-18
22. Arnett E.M., Gold J.M., Harvey N., Johnson E.A., and Whitesell L.G. Stereoselective recognition in phospholipid monolayers. Adv Exp Med Biol 238 (1988) 21-36
23. Tsuchiya H., Mizogami M., and Takakura K. Reversed-phase liquid chromatographic retention and membrane activity relationships of local anesthetics. J Chromatogr A 1073 (2005) 303-308
24. Pesek J.J., Matyska M.T., Dawson G.B., Wilsdorf A., Marc P., and Padki M. Cholesterol bonded phase as a separation medium in liquid chromatography. Evaluation of properties and applications. J Chromatogr A 986 (2003) 253-262
25. Zhang J., Hadlock T., Gent A., and Strichartz G.R. Tetracaine-membrane interaction: effects of lipid composition and phase on drug partitioning, location, and ionization. Biophys J 92 (2007) 3988-4001
26. Lim Y., Ocampo C.E., and Sia A.T. A comparison of duration of analgesia of intrathecal 2.5 mg of bupivacaine, ropivacaine, and levobupivacaine in combined spinal epidural analgesia for patients in labor. Anesth Analg 98 (2004) 235-239
27. Burmester M.D., Schlüter K.-D., Daut J., and Hanley P.J. Enantioselective actions of bupivacaine and ropivacaine on coronary vascular resistance at cardiotoxic concentrations. Anesth Analg 100 (2005) 707-712
28. Brown R.E. Sphingolipid organization in biomembranes: what physical studies of model membranes reveal. J Cell Sci 111 (1998) 1-9
29. O'Connell K.M.S., Martens J.R., and Tamkun M.M. Localization of ion channels to lipid raft domains within the cardiovascular system. Trends Cardiovasc Med 14 (2004) 37-42
30. Gimpl G., Burger K., and Fahrenholz F. Cholesterol as modulator of receptor function. Biochemistry 36 (1997) 10959-10974