Europium coordination complexes as potential anticancer drugs: Their partitioning and permeation into lipid bilayers as revealed by pyrene fluorescence quenching

Journal of Fluorescence

Volumn 23, Issue 1, 2013, Pages 193-202

  Trusova, Valeriya ^a   Yudintsev, Andrey ^a   Limanskaya, Ludmila ^a   Gorbenko, Galyna ^a   Deligeorgiev, Todor ^b  

^a V N KARAZIN KHARKIV NATIONAL UNIVERSITY   (Ukraine)

^b UNIVERSITY OF SOFIA   (Bulgaria)

Author keywords

Europium complexes; Lipid membranes; Liposomal formulations; Partitioning; Permeability

Indexed keywords

ANALYTICAL INSTRUMENT; ANIONIC LIPIDS; ANTI-TUMOR AGENTS; ANTICANCER DRUG; BILAYER COMPOSITIONS; CARDIOLIPINS; COMPLEX NATURE; COORDINATION COMPLEX; EUROPIUM COMPLEX; LIPID MEMBRANES; LIPID VESICLES; LIPOSOMAL FORMULATION; PARTITIONING; PERMEATION COEFFICIENTS; PHOSPHATIDYLCHOLINE; PYRENE FLUORESCENCE; ZWITTERIONIC LIPIDS;

DRUG PRODUCTS; EUROPIUM; FLUORESCENCE; LIPID BILAYERS; MECHANICAL PERMEABILITY; PHOSPHOLIPIDS; QUENCHING;

COORDINATION REACTIONS;

ANTINEOPLASTIC AGENT; EUROPIUM; ORGANOMETALLIC COMPOUND; PYRENE; PYRENE DERIVATIVE;

ANIMAL; ARTICLE; CELL MEMBRANE; CHEMICAL PHENOMENA; CHEMISTRY; LIPID BILAYER; PERMEABILITY; SPECTROFLUOROMETRY;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL MEMBRANE; EUROPIUM; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIPID BILAYERS; ORGANOMETALLIC COMPOUNDS; PERMEABILITY; PYRENES; SPECTROMETRY, FLUORESCENCE;

EID: 84873188615     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-012-1134-1     Document Type: Article

References (51)

1. Bünzli JG, Piguet C (2005) Taking advantage of luminescent lanthanide ions. Chem Soc Rev 34:1048-1077
2. Vogler A, Kunkely H (2006) Excited state properties of lanthanide complexes: beyond ff states. Inorg Chim Acta 359:4130-4138
3. Maas H, Currao A, Calzaferri G (2002) Encapsulated lanthanides as luminescent materials. Angew Chem Int Ed 41:2495-2497
4. 3+ using a fluorescent siderophore: an assay displacement approach. Sensors 10:1326-1337
5. Yuan J, Wang G (2005) Lanthanide complex-based fluorescence label for time-resolved fluorescence bioassay. J Fluoresc 15:559-568
6. Bakker BH, Goes M, Hoebe N, van Ramesdonk HJ, Verhoeven JW, Werts MHV, Hofstraat JW (2000) Luminescent materials and devices: lanthanide azatriphenylene complexes and electroluminescent charge transfer systems. Coord Chem Rev 208:3-16
7. Dean Sherry A (1989) Lanthanide chelates as magnetic resonance imaging contrast agents. J Less Common Met 149:133-141
8. Thompson K, Orvig C (2006) Lanthanide compounds for therapeutic and diagnostic applications. Chem Soc Rev 35:499-499
9. Kostova I (2005) Lanthanides as anticancer drugs. Curr Med Chem Anticancer Agents 5:591-602
10. Evans CH (1983) Interesting and useful biochemical properties of lanthanides. Trends Biochem Sci 8:445-449
11. Momekov G, Deligeorgiev T, Vasilev A, Peneva K, Konstantinov S, Karaivanova M (2006) Evaluation of the cytotoxic and pro-apoptotic activities of Eu(III) complexes with appended DNA intercalators in a panel of human malignant cell lines. Med Chem 2:439-445
12. Chonn A, Cullis P (1995) Recent advances in liposomal drug-delivery systems. Curr Opin Biotechnol 6:698-708
13. Maurer N, Fenske D, Cullis P (2001) Developments in liposomal drug delivery systems. Expert Opin Biol Ther 1:1-25
14. Mickova A, Buzgo M, Benada O, Rampichova M, Fisar Z, Filova E, Tesarova M, Lukas D, Amler E (2012) Core/shell nanofibers with embedded liposomes as a drug delivery system. Biomacromolecules 13:952-962
15. Ladokhin AS, Selsted ME, White SH (1997) Bilayer interactions of indolicidin, a small antimicrobial peptide rich in tryptophan, proline, and basic amino acids. Biophys J 72:794-805
16. Word RC, Smejtek P (2005) Partitioning of tetrachlorophenol into lipid bilayers and sarcoplasmic reticulum: effect of length of acyl chains, carbonyl group of lipids and biomembrane structure. J Membrane Biol 203:127-142
17. Santos NC, Prieto M, Castanho M (2003) Quantifying molecular partition into model systems of biomembranes: an emphasis on optical spectroscopic methods. Biochim Biophys Acta 1612:123-135
18. Wang J, Gambhir A, Hangyas-Mihalyne G, Murray D, Golebiewska U, McLaughlin S (2002) Lateral sequestration of phosphatidylinositol 4,5-bisphosphate by the basic effector domain of myristoylated alanine-rich C kinase substrate is due to nonspecific electrostatic interactions. J Biol Chem 277:34401-34412
19. Lakowicz JR (2006) Principles of fuorescence spectroscopy. Plenum Press, New York
20. Lakowicz JR, Hogen D, Omann G (1977) Diffusion and partitioning of a pesticide, lindane, into phosphatidylcholine bilayers: a new fluorescence quenching method to study chlorinated hydrocarbo membrane interactions. Biochim Biophys Acta 471:401-411
21. Mui B, Chow L, Hope MJ (2003) Extrusion technique to generate liposomes of defined size. Meth Enzymol 367:3-14
22. Bartlett G (1959) Phosphorus assay in column chromatography. J Biol Chem 234:466-468
23. Mathai J, Tristam-Nagle S, Nagle J, Zeidel M (2008) Structural determinants of water permeability through the lipid membrane. J Gen Physiol 131:69-76
24. Dobretsov GE (1989) Fluorescent probes for the cell, membrane and lipoprotein studies. Nauka, Moscow
25. Inada T, Funasaka Y, Kikuchi K, Takahashi Y, Ikeda H (2006) Electron-transfer fluorescence quenching of aromatic hydrocarbons by europium and ytterbium ions in acetonotrile. J Phys Chem A 110:2595-2600
26. Nakamura T, Kira A, Imamura M (1982) Enhancement of the intersystem crossing of pyrene by metal ions in sodium dodecyl sulfate micelle solutions. J Phys Chem 86:3359-3363
27. + exciplex formation in aqueous and ethanolic solutions. J Photochem Photobiol A 167:141-148
28. Dederen J, Auweraer M, Schryver F (1981) Fluorescence quecnhing of solubilized pyrene and pyrene derivatives by metal ions in SDS micelles. J Phys Chem 85:1198-1202
29. Lemmetyinen H, Yliperttula M, Mikkola J, Kinnunen P (1989) Quenching of fluorescence of pyrene-substituted lecithin by tetracyanoquinodimethane in liposomes. Biophys J 55:885-895
30. de Paula E, Schreier S (1995) Use of a novel method for determination of partition coefficients to compare the effect of local anesthetics on membrane structure. Biochim Biophys Acta 1240:25-33
31. Zhang J, Hadlock T, Gent A, Strichartz G (2007) Tetracaine-membrane interactions: effects of lipid composition and phase on drug partitioning, location, and ionization. Biophys J 92:3988-4001
32. De Castro B, Gameiro P, Lima J, Matos C, Reis S (2001) Location and partition coefficients of anti-inflammatory drugs in EPC liposomes. A fluorescence quenching study using n-(9-anthroyloxy)-stearic probes. Colloids Surf A 190:205-212
33. Takegami S, Kitamura K, Kitade T, Takashima M, Ito M, Nakagawa E, Sone M, Sumitani R, Yasuda Y (2005) Effects of phosphatidylserine and phosphatidylethanolamine content on partitioning of triflupromazine and chlorpromazine between phosphatidylcholine-aminophospholipid bilayer vesicles and water studied by second-derivative spectrophotometry. Chem Pharm Bull 53:147-150
34. Avdeef A (2003) Absorption and drug development. Wiley, New Jersey
35. Sandhya KV, Devi G, Mathew S (2008) Liposomal formulations of serratiopeptidase: in vitro studies using PAMPA and Caco-2 models. Mol Pharm 5:92-97
36. Pasenkiewicz-Gierula M, Rog T, Kitamura K, Kusumi A (2000) Cholesterol effects on the phosphatidylcholine bilayer polar region: a molecular simulation study. Biophys J 78:1376-1389
37. Kinnunen PKJ, Koiv A, Lehtonen JYA, Mustonen P (1994) Lipid dynamics and peripheral interactions of proteins with membrane surfaces. Chem Phys Lett 73:181-207
38. Marrink SJ, Sok RM, Berendsen HJC (1996) Free volume properties of a simulated lipid membrane. J Chem Phys 104:9090-9099
39. Merkle H, Subczynski WK, Kusumi A (1987) Dynamic fluorescence quenching studies on lipid mobilities in phosphotidylcholine-cholesterol membranes. Biochim Biophys Acta 897:238-348
40. Bittman R, Blau L (1972) The phospholipid-cholesterol interaction. Kinetics of water permeability in liposomes. Biochemistry 11:4831-4839
41. Bach D, Miller IR (1998) Hydration of phospholipid bilayers in the presence and absence of cholesterol. Biochim Biophys Acta 1368:216-224
42. Rog T, Pasenkiewicz-Gierula M (2001) Cholesterol effects on the phosphatidylcholine bilayer nonpolar region: a molecular simulation study. Biophys J 81:2190-2202
43. Demel RA, de Kruijff B (1976) The function of sterols in membranes. Biochim Biophys Acta 457:109-132
44. van Balen G, Martinet C, Caron G, Bouchard G, Reist M, Carrupt PA, Fruttero R, Gasco A, Testa B (2004) Liposome/water lipophilicity: methods, information content, and pharmaceutical applications. Med Res Rev 3:299-324
45. Giaginis C, Tsantili-Kakoulidou A (2008) Alternative measure of lipophilicity: from octanol-water partitioning to IAM retention. J Pharm Sci 97:2984-3004
46. Tetko IV, Gasteiger J, Todeschini R, Mauri A, Livingstone D, Ertl P, Palyulin VA, Radchenko EV, Zefirov NS, Makarenko AS, Tanchuk VY, Prokopenko VV (2005) Virtual computational chemistry laboratory - design and description. J Comput Aid Mol Des 19:453-463
47. Tetko IV (2005) Computing chemistry on the web DOI:10.1016/S1359-6446(05) 03584-1. Drug Discov Today 10:1497-1500
48. Camenisch G, Folkers G, van de Waterbeemd H (1998) Shapes of membrane permeability-lipophilicity curves: extention of theoretical models with an aqueous pore pathway. Eur J Pharm Sci 6:325-329
49. Camenisch G, Folkers G, van de Waterbeemd H (1996) Review of theoretical passive drug absorption models: historical background, recent developments and limitations. Pharm Acta Helv 71:309-327
50. Ioffe VM, Gorbenko GP (2005) Lysozyme effect on structural state of model membranes as revealed by pyrene excimerization studies. Biophys Chem 114:199-204
51. Shibata A, Ikawa K, Shimooka T, Terada H (1994) Significant stabilization of the phosphatidylcholine bilayer structure by incorporation of small amounts of cardiolipin. Biochim Biophys Acta 1192:71-78