Bupivacaine, but not lidocaine, disrupts cardiolipin-containing small biomimetic unilamellar liposomes

Chemico-Biological Interactions

Volumn 169, Issue 3, 2007, Pages 154-159

  Önyüksel, Hayat ^a   Sethi, Varun ^a   Weinberg, Guy L ^a,b   Dudeja, Pradeep K ^a,b   Rubinstein, Israel ^a,b  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b JESSE BROWN VA MEDICAL CENTER   (United States)

Author keywords

Bupivacaine; Carboxyfluorescein; Cholesterol; Lidocaine; Membrane; Mitochondria; Permeability; Phosphatidylcholine; Phospholipids

Indexed keywords

BUPIVACAINE; CARBOXYFLUORESCEIN; CARDIOLIPIN; CHOLESTEROL; LIDOCAINE; LIPOSOME; PHOSPHATIDYLCHOLINE;

ARTICLE; CONTROLLED STUDY; DISPERSION; DRUG EFFECT; DRUG MECHANISM; DRUG PROTEIN BINDING; FLUORESCENCE; HEART MUSCLE CELL; MEMBRANE PERMEABILITY; MICELLE; NONHUMAN; PHOSPHOLIPID BILAYER;

BIOMIMETIC MATERIALS; BUPIVACAINE; CARDIOLIPINS; LIDOCAINE; UNILAMELLAR LIPOSOMES;

EID: 34548306674     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2007.06.002     Document Type: Article

References (29)

1. Groban L.D.S., Zvara D.A., and Oaks T. Thoracic epidural analgesia: its role in postthoracotomy atrial arrhythmias. J. Cardiothorac. Vasc. Anesth. 14 (2000) 662-665
2. Weinberg G.L. Current concepts in resuscitation of patients with local anesthetic cardiac toxicity. Reg. Anesth. Pain Med. 27 (2002) 568-575
3. Butterworth J., and Groban L. Central nervous system and cardiac effects from long-acting amide local anesthetic toxicity in the intact animal model. Reg. Anesth. Pain Med. 28 (2003) 167-169
4. Heavner J.E. Cardiac toxicity of local anesthetics in the intact isolated heart model: a review. Reg. Anesth. Pain Med. 28 (2003) 3-11
5. Grouselle M., Tueux O., Dabadie P., Georgescaud D., and Mazat J.P. Effect of local anaesthetics on mitochondrial membrane potential in living cells. Biochem. J. 271 (1990) 269-272
6. Irwin W., Fontaine E., Agnolucci L., Penzo D., Betto R., Bortolotto S., Reggiani C., Salviati G., and Bernard P. Bupivacaine myotoxicity is mediated by mitochondria. J. Biol. Chem. 277 (2002) 12221-12227
7. Sztark F., Malgat M., Dabadie P., and Mazat J.P. Comparison of the effects of bupivacaine and ropivacaine on heart cell mitochondrial bioenergetics. Anesthesiology 88 (1998) 1340-1349
8. Weinberg G.L., Palmer J.W., VadeBoncouer T.R., Zuechner M.B., Edelman G., and Hoppel C.L. Bupivacaine inhibits acylcarnitine exchange in cardiac mitochondria. Anesthesiology 92 (2000) 523-528
9. Chazotte B., and Vanderkooi G. Multiple sites of inhibition of mitochondrial electron transport by local anesthetics. Biochim. Biophys. Acta 636 (1981) 153-161
10. Hoch F.L. Cardiolipins and biomembrane function. Biochim. Biophys. Acta 1113 (1992) 71-133
11. Hatch G.M. Cardiolipin: biosynthesis, remodeling and trafficking in the heart and mammalian cells. Int. J. Mol. Med. 1 (1998) 33-41
12. Noel H. An essential requirement of cardiolipin for mitochondrial carnitine acylcarnitine translocase activity. Lipid requirement of carnitine acylcarnitine translocase. Eur. J. Biochem. 155 (1986) 99-102
13. Xia W.J., and Önyüksel H. Mechanistic studies on surfactant-induced membrane permeability enhancement. Pharm. Res. 17 (2000) 612-618
14. Stewart J.C. Colorimetric determination of phospholipids with ammonium ferrothiocyanate. Anal. Biochem. 104 (1980) 10-14
15. New R.R.C. Liposomes: A Practical Approach (1990), New York: IRL Press; Oxford University Press, Oxford; New York p. xvi, 301
16. Ohki S. Adsorption of local anesthetics on phospholipid membranes. Biochim. Biophys. Acta 777 (1984) 56-66
17. Seelig A., Allegrini P.R., and Seelig J. Partitioning of local anesthetics into membranes: surface charge effects monitored by the phospholipid head-group. Biochim. Biophys. Acta 939 (1988) 267-276
18. Dullenkopf A., Ekatodramis G., Nagy L., and Borgeat A. Local anesthetics. Differences and similarities in the "-cains". Anesthesiology 99 (2003) 436-442
19. Grouls R.J., Ackerman E.W., Korsten H.H., Hellebrekers L.J., and Breimer D.D. Partition coefficients (n-octanol/water) of N-butyl-p-aminobenzoate and other local anesthetics measured by reversed-phase high-performance liquid chromatography. J. Chromatogr. B: Biomed. Sci. Appl. 694 (1997) 421-425
20. Pardo L., Blanck T.J., and Recio-Pinto E. The neuronal membrane permeability was markedly increased by bupivacaine and mildly affected by lidocaine and ropivacaine. Eur. J. Pharmacol. 455 (2002) 81-90
21. Shimooka T., Seto S., and Terada H. Increase in water permeability of negatively charged liposomal membrane by local anesthetics. Chem. Pharm. Bull. (Tokyo) 40 (1992) 1880-1882
22. a values of clinically used drugs. Anesth. Analg. 71 (1990) 158-170
23. Frezzatti Jr. W.A., Toselli W.R., and Schreier S. Spin label study of local anesthetic-lipid membrane interactions. Phase separation of the uncharged form and bilayer micellization by the charged form of tetracaine. Biochim. Biophys. Acta 860 (1986) 531-538
24. Shibata A., Ikawa K., and Terada H. Site of action of the local anesthetic tetracaine in a phosphatidylcholine bilayer with incorporated cardiolipin. Biophys. J. 69 (1995) 470-477
25. Shimooka T., Shibata A., and Terada H. The local anesthetic tetracaine destabilizes membrane structure by interaction with polar headgroups of phospholipids. Biochim. Biophys. Acta 1104 (1992) 261-268
26. Goormaghtigh E., Huart P., Praet M., Brasseur R., and Ruysschaert J.M. Structure of the adriamycin-cardiolipin complex. Role in mitochondrial toxicity. Biophys. Chem. 35 (1990) 247-257
27. Marcillat O., Zhang Y., and Davies K.J. Oxidative and non-oxidative mechanisms in the inactivation of cardiac mitochondrial electron transport chain components by doxorubicin. Biochem. J. 259 (1989) 181-189
28. Fernandez M.S. Formation of micelles and membrane action of the local anesthetic tetracaine hydrochloride. Biochim. Biophys. Acta 597 (1980) 83-91
29. Ueda I., Chiou J.S., Krishna P.R., and Kamaya H. Local anesthetics destabilize lipid membranes by breaking hydration shell: infrared and calorimetry studies. Biochim. Biophys. Acta 1190 (1994) 421-429