The fate of anticancer drug, ellipticine in DPPC and DMPC liposomes upon interaction with HSA: A photophysical approach

Journal of Photochemistry and Photobiology B: Biology

Volumn 130, Issue , 2014, Pages 122-131

  Thakur, Raina ^a   Das, Anupam ^a   Chakraborty, Anjan ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY INDORE   (India)

Author keywords

Binding; Ellipticine; HSA; Interaction; Liposomes; Penetration

Indexed keywords

DIMYRISTOYLPHOSPHATIDYLCHOLINE; DIPALMITOYLPHOSPHATIDYLCHOLINE; ELLIPTICINE; HUMAN SERUM ALBUMIN; LIPOSOME;

ARTICLE; BINDING AFFINITY; DIPOLE; DRUG BINDING; ENERGY TRANSFER; FLUORESCENCE SPECTROSCOPY; HIGH TEMPERATURE; HYDROPHOBICITY; LIPID BILAYER; PARTITION COEFFICIENT; PH; PHASE TRANSITION; PHOTOCHEMISTRY; PKA; PRIORITY JOURNAL; QUANTUM YIELD; STEADY STATE; TRANSITION TEMPERATURE;

BINDING; ELLIPTICINE; HSA; INTERACTION; LIPOSOMES; PENETRATION;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; ANTINEOPLASTIC AGENTS; DIMYRISTOYLPHOSPHATIDYLCHOLINE; ELLIPTICINES; HUMANS; LIPOSOMES; SERUM ALBUMIN; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 84890086168     PISSN: 10111344     EISSN: 18732682     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2013.10.016     Document Type: Article

References (56)

1. D. Lichtenberg D.D. Lasic, Y. Barenholz, Liposomes as a Model for Solubilization and Reconstitution of Membranes 1995 CRC Press Boca Raton 199 218
2. A.D. Bangham, M.M. Standish, and J.C. Watkins Diffusion of univalent ions across the lamellae of swollen phospholipids J. Mol. Biol. 13 1965 238 252
3. S.K. Sahoo, and V. Labhasetwar Nanotech approaches to drug delivery and imaging Drug Discovery Today 8 2003 1112 1120 (Pubitemid 37547917)
4. T.M. Allen, and P.R. Cullis Drug delivery systems: entering the mainstream Science 303 2004 1818 1822 (Pubitemid 38374867)
5. R.D. Hofheinz, U. Grand-vogt, U. Beyer, and A. Hochhaus Liposomal encapsulated anti-cancer drugs Anticancer Drugs 16 2005 691 707 (Pubitemid 41104918)
6. P.M. Matos, T. Freitas, M.A.R.B. Castanho, and N.C. Santos The role of blood cell membrane lipids on the mode of action of HIV-1 fusion inhibitor sifuvirtide Biochem. Biophys. Res Commun. 403 2010 270 274
7. A. Chonn, S.C. Semple, and P.R. Cullis Association of blood proteins with large unilamellar liposomes in vivo. Relation to circulation lifetimes J. Biol. Chem. 267 1992 18759 18765
8. A.O. Pedersen, K.L. Mesenberg, and U. Kragh-Hansen Effects of ionic strength and pH on the binding of medium-chain fatty acids to human serum albumin Eur. J. Biochem. 233 1995 395 401
9. T. Peters Jr. All about Albumins: Biochemistry, Genetics, and Medical Applications 1996 Academic Press San Diego
10. D. Zhong, A. Douhal, and A.H. Zewail Femtosecond studies of protein-ligand hydrophobic binding and dynamics: Human serum albumin Proc. Natl. Acad. Sci. USA 97 2000 14056 14061 (Pubitemid 32016528)
11. S. Sugio, A. Kashima, S. Mochizuki, M. Noda, and K. Kobayashi Crystal structure of human serum albumin at 2.5 A resolution Protein Eng. 12 1999 439 446 (Pubitemid 29322441)
12. D.C. Carte, and J.X. Ho Structure of serum albumin Adv. Protein Chem. 45 1994 153 176
13. H.M. He, and D.C. Carter Atomic structure and chemistry of human serum albumin Nature 358 1992 209 215
14. T. Peters Serum albumin Adv. Protein Chem. 37 1985 161 245
15. S. Curry, P. Brick, and N.P. Frank Fatty acid binding to human serum albumin: new insights from crystallographic studies Biochim. Biophys. Acta 1441 1999 131 140 (Pubitemid 29537733)
16. I. Petitpas, T. Grune, A.A. Battacharya, and S. Curry Crystal structures of human serum albumin complexed with monounsaturated and polyunsaturated fatty acids J. Mol. Biol. 314 2001 955 960 (Pubitemid 34073060)
17. E.L. Gelamo, C.H.T.P. Silva, H. Imasato, and M. Tabak Interaction of bovine (BSA) and human (HSA) serum albumins with ionic surfactants: spectroscopy and modeling Biochim. Biophys. Acta 1594 2002 84 99 (Pubitemid 34131728)
18. V.T.G. Chuang, and M. Otagiri Flunitrazepam, a 7-nitro-1,4-benzodiazepine that is unable to bind to the indole-benzodiazepine site of human serum albumin Biochim. Biophys. Acta 1546 2001 337 345 (Pubitemid 32280829)
19. A.A. Bhattacharya, T. Grune, and S. Curry Crystallographic analysis reveals common modes of binding of medium and long-chain fatty acids to human serum albumin J. Mol. Biol. 303 2000 721 732
20. P. Toimila, G. Prieto, J. Mĩnones Jr, J.M. Trillo, and F. Sarmientoa Monolayer and brewster angle microscopy study of human serum albumin-dipalmitoyl phosphatidyl choline mixtures at the air-water interface Colloids Surf. B: Biointerfaces 92 2012 64 73
21. D. Hoekstra, and G. Scherphoft Effect of fetal calf serum and serum protein fractions on the uptake of liposomal phosphatidylcholine by rat hepatocytes in primary monolayer culture Biochim. Biophys. Acta 551 1979 109 121
22. J. Sabin, G. Prieto, J.M. Ruso, P.V. Messina, F.J. Salgado, M. Nogueira, M. Costas, and F.I. Sarmiento Interactions between DMPC liposomes and the serum blood proteins HSA and IgG J. Phys. Chem. B 113 2009 1655 1661
23. D. Charbonneau, M. Beauregard, and H.A. Tajmir-Riahi Structural analysis of human serum albumin complexes with cationic lipids J. Phys. Chem. B 113 2009 1777 1784
24. L.P. Tseng, H.J. Liang, T.W. Chung, Y.Y. Huang, and D.Z. Liu Liposomes incorporated with cholesterol for drug release triggered by magnetic field J. Med. Biol. Eng. 27 2007 29 34
25. M. Sikor, J. Sabin, A. Keyvanloo, M.F. Schneider, J.L. Thewalt, A.E. Bailey, and B.J. Frisken Interaction of a charged polymer with zwitterionic lipid vesicles Langmuir 26 2010 4095 4102
26. J. Hernandez, J. Estelrich, M.T. Montero, and O. Valls Interaction between human serum albumin and liposomes: a monolayer and liposome study Int. J. Pharm. 57 1989 211 215 (Pubitemid 20039365)
27. T.P.W. McMullen, and R.N. McElhaney Physical studies of cholesterol-phospholipid interactions Curr. Opin. Colloid Interface Sci. 1 1996 83 90
28. C. Rivalle, F. Wendling, P. Tambourin, J.M. Lhoste, E. Bisagni, and J.C. Chermann Structure-activity studies on the N-terminal region of growth hormone releasing factor J. Med. Chem. 28 1983 181 185
29. G.W. Gribble A. Brossi, The Alkaloid Chemistry and Pharmacology 1990 Academic Press San Diego, CA 239 328
30. C.L. Arteaga, D.L. Kisner, A. Goodman, and D.D. Von Hoff Elliptinium, a DNA intercalating agent with broad antitumor activity in a human tumor cloning system Eur J. Cancer Clin. Oncol. 23 1987 1621 1626 (Pubitemid 18044639)
31. S.Y. Fung, J. Duhamel, and P. Chen Solvent effect on the photophysical properties of the anticancer agent ellipticine J. Phys. Chem. A 110 2006 11446 11454 (Pubitemid 44626474)
32. Z. Miskolczy, L. Biczok, and I. Jablonkai Effect of hydroxylic compounds on the photophysical properties of ellipticine and its 6-methyl derivative: The origin of dual fluorescence Chem. Phys. Lett. 427 2006 76
33. S. Banerjee, A. Pabbathi, M. Chandra Sekhar, and A. Samanta Dual fluorescence of ellipticine: excited state proton transfer from solvent versus solvent mediated intramolecular proton transfer J. Phys. Chem. A 115 2011 9217 9225
34. S.J.F. Ammon, W.P. Marcia, N. Osheroff, and R.B. Thompson Topoisomerase II binds to ellipticine in the absence or presence of DNA J. Biol. Chem. 270 1995 14998 15004
35. S. Cros, R. Sorbara, C. Moisand, N.D. Xuong, P. Lecointe, and C. Paoletti Toxicological and pharmacological studies on 9-hydroxy-ellipticine in mice Toxicol. Appl. Pharmacol. 33 1975 484 497
36. El.H. Chahine, J.P. Bertiguy, and M.A. Schwaller Kinetics and thermodynamics of the formation of inclusion complexes between cyclodextrins and DNA-intercalating agents. Inclusion of ellipticine in y-cyclodextrin J. Chem. Soc. Perkin Trans. II 1989 629 633
37. S.Y. Fung, H. Yang, P.T. Bhola, P. Sadatmousavi, E. Muzar, M. Liu, and P. Chen Self-assembling peptide as a potential carrier for hydrophobic anticancer drug ellipticine: complexation, release and in vitro delivery Adv. Funct. Mater. 19 2009 74 83
38. X. Xu, and E. London The effect of sterol structure on membrane lipid domains reveals how cholesterol can induce lipid domain formation Biochemistry 39 2000 843 849 (Pubitemid 30075310)
39. E.M. Mashak, C. Paoletti, and J.F. Tocanne Interactions between ellipticine and some derivatives and phospholipids in model membranes FEBS Lett. 107 1980 155 159
40. R. Thakur, A. Das, and A. Chakraboty Photophysical and photodynamical study of ellipticine: an anticancer drug molecule in bile salt modulated in vitro created liposome Phys. Chem. Chem. Phys. 14 2012 15369 15378
41. M. Mohapatra, and A.K. Mishra Photophysical behavior of fisetin in dimyristoylphosphatidylcholine liposome membrane J. Phys. Chem. B 115 2011 9962 9970
42. R. Thakur, A. Mallick, and A. Chakraborty Photophysical and photodynamical study of fluoroquinolone drug molecule in bile salt aggregates Photochem. Photobiol. 88 2012 1248 1255
43. F. Terce, J.F. Tocanne, and G. Laneelle Localization of ellipticine derivatives interacting with membranes Eur. J. Biochem. 133 1983 349 354
44. R. Thakur, A. Das, and A. Chakraborty Fate of anticancer drug ellipticine in reverse micelles in aqueous and methanolic environment: a photophysical approach Chem. Phys. Lett. 563 2013 37 42
45. H.A. Benesi, and J.H. Hildebrand A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons J. Am. Chem. Soc. 71 1949 2703 2707
46. E. Daniel, and G. Weber Cooperative effects in binding by bovine Serum albumin. I. The binding of 1-Anilino-8-naphthalenesulfonate. fluorimetric titrations Biochemistry 5 1966 1893 1900
47. D.C. Turner, and L. Brand Quantitative estimation of protein binding site polarity. Fluorescence of N-arylaminonaphthalenesulfonates Biochemistry 7 1968 3381 3390
48. L.A. Bagatolli, S.C. Kivatinitz, F. Anguilar, M.A. Soto, S. Patricio, and G.D. Fidelio Two distinguishable fluorescent modes of 1-anilino-8- naphthalenesulfonate bound to human albumin J. Fluoresc. 6 1996 33 40 (Pubitemid 126713208)
49. I. Petitpas, A.A. Bhattacharya, S. Twine, M. East, and S. Curry Crystal structure analysis of warfarin binding to human serum albumin: anatomy of drug site I J. Biol. Chem. 276 2001 22804 22809
50. U. Kragh-Hansen, V.T.G. Chuang, and M. Otagiri Practical aspects of the ligand-binding and enzymatic properties of human serum albumin Biol. Pharm. Bull. 25 2002 695 704 (Pubitemid 40036701)
51. B.A.C. Horta, A.H. Vries, and P.H. Hunenberger Simulating the transition between gel and liquid-crystal phases of lipid bi-layers: dependence of the transition temperature on the hydration level J. Chem. Theory Comput. 6 2010 2488 2500
52. N.C. Santos, M. Prieto, and M.A.R.B. Catanho Interaction of the major epitope region of HIV protein gp41 with membrane model systems. A fluorescence spectroscopy study Biochemistry 37 1998 8674 8682 (Pubitemid 28299605)
53. M.N. Dimitrova, H. Matsumura, V. Neitchev, and K. Furusawa Temperature dependence of protein-induced flocculation of phosphatidylcholine liposomes Langmuir 14 1998 5438 5445 (Pubitemid 128590373)
54. M.N. Dimitrova, H. Matsumura, and V. Neitchev Kinetics of protein-induced flocculation of phosphatidylcholine liposomes Langmuir 13 1997 6516 6523 (Pubitemid 127592069)
55. A.A. Spector Fatty acid binding to plasma albumin J. Lipid Res. 16 1975 165 179
56. R. Galantai, and I. Bárdos-Nagy The interaction of human serum albumin and model membranes Int. J. Pharm. 195 2000 207 218 (Pubitemid 30089505)