Perturbing effects of carvedilol on a model membrane system: Role of lipophilicity and chemical structure

Biophysical Chemistry

Volumn 119, Issue 3, 2006, Pages 307-315

  Butler, Stephanie ^a   Wang, Rongwei ^a   Wunder, Stephanie L ^a   Cheng, Hung Yuan ^b,d   Randall, Cynthia S ^c  

^a Temple University   (United States)

^b GLAXOSMITHKLINE   (United States)

^c Sanofi Synthelabo   (United States)

^d Eksigent Technologies   (United States)

Author keywords

blocker; Antioxidant; Calorimetry; Carvedilol; Fluorescence; Liposome

Indexed keywords

ATENOLOL; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; CARBAZOLE DERIVATIVE; CARVEDILOL; LIPOSOME; PINDOLOL; PROPRANOLOL; TIMOLOL;

ANTIOXIDANT ACTIVITY; ARTICLE; ARTIFICIAL MEMBRANE; BILAYER MEMBRANE; CHEMICAL COMPOSITION; CONCENTRATION RESPONSE; DRUG BINDING; DRUG STRUCTURE; LIPOPHILICITY; PH; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TEMPERATURE SENSITIVITY;

ADRENERGIC BETA-ANTAGONISTS; CALORIMETRY, DIFFERENTIAL SCANNING; CARBAZOLES; CELL MEMBRANE; FLUORESCENT DYES; LIPID BILAYERS; LIPOSOMES; MEMBRANE FLUIDITY; MEMBRANE LIPIDS; MODELS, BIOLOGICAL; MODELS, MOLECULAR; PROPANOLAMINES; SPECTROMETRY, FLUORESCENCE;

EID: 32044435803     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2005.09.004     Document Type: Article

References (33)

1. J. Cheng, K. Kamiya, and I. Kodama Carvedilol: molecular and cellular basis for its multifaceted therapeutic potential Cardiovasc. Drug Rev. 19 2001 152 171
2. E.R. Schwarz, P.H. Kersting, T. Reffelmann, D.A. Meven, R. Al-Dashti, E.C. Skobel, B. Klosterhalfen, and P. Hanrath Cardioprotection by carvedilol: antiapoptosis effect is independent of beta-adrenoceptor blockage in the rat heart J. Cardiovasc. Pharmacol. Ther. 8 2003 207 215
3. L. Herbette, A.M. Katz, and J.M. Sturtevant Comparisons of the interaction of propranolol and timolol with model and biological membranes Mol. Pharmacol. 24 1983 259 269
4. G. Albertini, C. Donati, R.S. Phadke, M.G. Ponzi Bossi, and F. Rustichelli Thermodynamic and structural effects of propranolol on DPPC liposomes Chem. Phys. Lipids 55 1990 331 337
5. A. Colotto, P. Mariani, M.G. Ponzi Bossi, F. Rustichelli, G. Albertini, and L.Q. Amaral Lipid-drug interaction: a structural analysis of pindolol effects on model membranes Biochim. Biophys. Acta 1107 1991 165 174
6. S.L. Krill, K.Y. Lau, W.Z. Plachy, and S.J. Rehfeld Penetration of dimyristoylcholine monolayers and bilayers by model β-blocker agents of varying lipophilicity J. Pharm. Sci. 87 1998 751 756
7. H.-Y. Cheng, C.S. Randall, W.W. Holl, P.P. Constantinides, T.-L. Yue, and G.Z. Feuerstein Carvedilol-liposome interactions: evidence for strong association with the hydrophobic region of the bilayers Biochim. Biophys. Acta 1284 1996 20 28
8. P.G. Lysko, K.A. Lysko, C.L. Webb, G. Feuerstein, P.E. Mason, M.F. Walter, and R.P. Mason Neuroprotective activities of carvedilol and a hydroxylated derivative Biochem. Pharmacol. 56 1998 1645 1656
9. G.V. Betageri, S.A. Jenkins, and D.L. Parsons Liposome Drug Delivery Systems 1993 Technomic Publishing Lancaster, PA
10. T. Heimburg A model for the lipid pretransition: coupling of ripple formation with the chain-melting transition Biophys. J. 78 2000 1154 1165
11. G. Caron, G. Steyaert, A. Pagliara, F. Reymond, P. Crivori, P. Gaillard, P.-A. Carrupt, A. Avdeef, J. Comer, K.J. Box, H.H. Girault, and B. Testa Structure-lipophilicity relationships of neutral and protonated beta-blockers: Part 1 Helv. Chim. Acta 82 1999 1211 1222
12. M.R. Tota, and C.D. Strader Characterization of the binding domain of the β-adrenergic receptor with the fluorescent antagonist carazolol J. Biol. Chem. 265 1990 16891 16897
13. M.K. Jain, and M.N. Wu Effects of small molecules on the dipalmitoyl lecithin liposomal bilayer: III. Phase transitions in lipid bilayers J. Membr. Biol. 34 1977 157 201
14. S. Girke, K. Mohr, and S. Schrape Comparison between the activities of cationic amphiphilic drugs to affect phospholipid membranes and to depress cardiac function Biochem. Pharmacol. 38 1989 2487 2496
15. S.-J. Bae, S. Kitamura, L.G. Herbette, and J.M. Sturtevant The effects of calcium channel blockers on the thermotropic behavior of dimyristoyl phosphatidylcholine Chem. Phys. Lipids 51 1989 1 7
16. S.D. Kramer, A. Braun, C. Jakits-Deiser, and H. Wunderli-Allenspach Towards the predictability of drug-lipid membrane interactions: the pH-dependent affinity of propranolol to phosphatidylinositol containing liposomes Pharm. Res. 15 1998 739 744
17. R. Hanpft, and K. Mohr Influence of cationic amphiphilic drugs on the phase transition temperature of phospholipids with different polar head groups Biochim. Biophys. Acta 814 1985 156 162
18. M.S. Webb, J.J. Wheeler, M.B. Bally, and L.D. Mayer The cationic lipid stearylamine reduces the permeability of the cationic drugs verapamil and prochloroperazine to lipid bilayers-implications for drug delivery Biochim. Biophys. Acta 1238 1995 147 155
19. R. Mannhold The impact of lipophilicity in drug research: a case report on β-blockers Mini-Rev. Med. Chem. 5 2005 187 205
20. B. Kursch, H. Lullmann, and K. Mohr Influence of various cationic amphiphilic drugs on the phase transition temperature of phosphatidylcholine liposomes Biochem. Pharmacol. 32 1983 2589 2594
21. E.A. Haigh, K.R. Thulborn, L.W. Nichol, and W.H. Sawyer Uptake of n-(9-anthroyloxy) fatty acid fluorescent probes into lipid bilayers Aust. J. Biol. Sci. 31 1978 447 457
22. A. Coutinho, J. Costa, J.L. Fabria, M.N. Berberan-Santos, and M.J.E. Prieto Dibucaine interaction with phospholipid vesicles Eur. J. Biochem. 189 1990 387 393
23. J.S. Hinzmann, R.L. McKenna, T.S. Pierson, F. Han, F.J. Kezdy, and D.E. Epps Interactions of antioxidants with depth-dependent fluorescence quenchers and energy transfer probes in lipid bilayers Chem. Phys. Lipids 62 1992 123 138
24. K.K. Jensen, B. Albinsson, M. Van der Auweraer, E. Vuorimaa, and H. Lemmetyinen Interlayer energy transfer between carbazole and two 9-anthroyloxy derivatives in Langmuir-Blodgett films J. Phys. Chem. 103 1999 8514 8523
25. A. Hjalmarson Cardioprotection with beta-adrenoceptor blockers. Does lipophilicity matter? Basic Res. Cardiol. 95 Suppl. 1 2000 41 45
26. Z.Y. Yuan, K. Shioji, Y. Kihara, H. Takenaka, Y. Onozawa, and C. Kishimoto Cardioprotective effects of carvedilol on acute autoimmune myocarditis: anti-inflammatory effects associated with antioxidant property Am. J. Physiol, Heart Circ. Physiol. 286 2004 H83 H90
27. K. Yasunari, K. Maeda, M. Nakamura, T. Watanabe, J. Yoshikawa, and A. Asada Effects of carvedilol on oxidative stress in polymorphonuclear and mononuclear cells in patients with essential hypertension Am. J. Med. 116 2004 460 465
28. I.T. Mak, and W.B. Weglicki Potent antioxidant properties of 4-hydroxyl-propranolol J. Pharmacol. Exp. Ther. 308 2004 85 90
29. L. Rossig, J. Haendeler, Z. Mallat, B. Hugel, J.-M. Freyssinet, A. Tedgui, S. Dimmeler, and A.M. Zeiher Congestive heart failure induces endothelial cell apoptosis: protective role of carvedilol J. Am. Coll. Cardiol. 36 2000 2081 2089
30. S. Stolc Indole derivatives as neuroprotectants Life Sci. 65 1999 1943 1950
31. E. Migliavacca, J. Ancerewicz, P.-A. Carrupt, and B. Testa Theoretical parameters to characterize antioxidants: Part 2. The cases of melatonin and carvedilol Helv. Chim. Acta 81 1998 1337 1348
32. A.P. Rolo, P.J. Oliveira, A.J. Moreno, and C.M. Palmeira Chenodeoxylate induction of mitochondrial permeability transition pore is associated with increased membrane fluidity and cytochrome c release: protective role of carvedilol Mitochondrion 2 2003 305 311
33. Y. Suzuki, M. Tanaka, M. Sohmiya, T. Yoshida, and K. Okamoto Antioxidant properties of carvedilol: Inhibition of lipid peroxidation, protein oxidation, and superoxide generation Neurol. Res. 25 2003 749 753