Biomimetic liposomes and planar supported bilayers for the assessment of glycodendrimeric porphyrins interaction with an immobilized lectin

Biochimica et Biophysica Acta - Biomembranes

Volumn 1808, Issue 3, 2011, Pages 656-666

  Makky, A ^a,b,d   Michel, J P ^a,b,d   Maillard, Ph ^a,b,c,d   Rosilio, V ^a,b,d  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

^c INSTITUT CURIE   (France)

^d CNRS GDR 3049 PHOTOMED   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CONCANAVALIN A; LECTIN; LIPOSOME; PORPHYRIN DERIVATIVE;

ADSORPTION; ARTICLE; BINDING AFFINITY; BINDING SITE; BIOMIMETICS; CELL MEMBRANE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; LIGHT SCATTERING; LIPID COMPOSITION; PARTICLE SIZE; PRIORITY JOURNAL; QUARTZ CRYSTAL MICROBALANCE; RETINA CELL; ZETA POTENTIAL;

BIOMIMETICS; CELL MEMBRANE; CONCANAVALIN A; HUMANS; LECTINS; LIPID BILAYERS; LIPOSOMES; MANNOSE; PORPHYRINS; QUARTZ CRYSTAL MICROBALANCE TECHNIQUES; RETINOBLASTOMA; TUMOR CELLS, CULTURED;

EID: 78650570160     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbamem.2010.11.028     Document Type: Article

References (74)

1. D.E. Dolmans, D. Fukumura, and R.K. Jain Photodynamic therapy for cancer Nat. Rev. Cancer 3 2003 380 387 (Pubitemid 37328858)
2. H. Stephan, R. Boeloeni, A. Eggert, N. Bornfeld, and A. Schueler Photodynamic therapy in retinoblastoma: effects of verteporfin on retinoblastoma cell lines Invest. Ophthalmol. Vis. Sci. 49 2008 3158 3163
3. M. Lupu, C.D. Thomas, Ph. Maillard, B. Loock, B. Chauvin, I. Aerts, A. Croisy, E. Belloir, A. Volk, and J. Mispelter Na-23 MRI longitudinal follow-up of PDT in a xenograft model of human retinoblastoma Photodiag. Photodyn. Ther. 6 2009 214 220
4. P. Maillard, M. Lupu, C.D. Thomas, and J. Mispelter Vers un nouveau traitement du rétinoblastome? Ann. Pharm. Fr. 68 2010 195 202
5. I. Aerts, P. Leuraud, J. Blais, A.-L. Pouliquen, Ph. Maillard, C. Houdayer, J. Couturier, X. (in press). Sastre-Garau, F. Doz, M.-F. Poupon, In vivo efficacy of photodynamic therapy in three new xenograft models of human retinoblastoma., Photodiag. Photodyn. Ther. 7 (2010) 275-283.
6. R. van Hillegersberg, W.J. Kort, and J.H. Wilson Current status of photodynamic therapy in oncology Drugs 48 1994 510 527
7. T.J. Dougherty, C.J. Gomer, B.W. Henderson, G. Jori, D. Kessel, M. Korbelik, J. Moan, and Q. Peng Photodynamic therapy J. Natl Cancer Inst. 90 1998 889 905 (Pubitemid 28304157)
8. R. Bonnett Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy Chem. Soc. Rev. 24 1995 19 33
9. R.F. Pasternack, P.R. Huber, P. Boyd, G. Engasser, L. Francesconi, E. Gibbs, P. Fasella, G. Cerio Venturo, and L.D. Hinds Aggregation of meso-substituted water-soluble porphyrins JACS 94 1972 4511 4517
10. G. Csík, E. Balog, I. Voszka, F. Tölgyesi, D. Oulmi, P. Maillard, and M. Momenteau Glycosylated derivatives of tetraphenyl porphyrin: photophysical characterization, self-aggregation and membrane binding J. Photochem. Photobiol. B Biol. 44 1998 216 224 (Pubitemid 28466439)
11. D. Oulmi, P. Maillard, C. Vever-Bizet, M. Momenteau, and D. Brault Glycosylated porphyrins: characterization of association in aqueous solutions by absorption and fluorescence spectroscopies and determination of singlet oxygen yield in organic media Photochem. Photobiol. 67 1998 511 518 (Pubitemid 128472273)
12. M. Momenteau, P. Maillard, M.A. De Belinay, D. Carrez, and A. Croisy Tetrapyrrolic glycosylated macrocycles for an application in PDT J. Biomed. Opt. 4 1999 298 318
13. I. Laville, T. Figueiredo, B. Loock, S. Pigaglio, Ph. Maillard, D.S. Grierson, D. Carrez, A. Croisy, and J. Blais Synthesis, cellular internalization and photodynamic activity of glucoconjugated derivatives of tri and tetra(meta-hydroxyphenyl)chlorins Bioorg. Med. Chem. 11 2003 1643 1652 (Pubitemid 36349145)
14. I. Laville, S. Pigaglio, J.C. Blais, B. Loock, Ph. Maillard, D.S. Grierson, and J. Blais A study of the stability of tri(glucosyloxyphenyl) chlorin, a sensitizer for photodynamic therapy, in human colon tumoural cells: a liquid chromatography and MALDI-TOF mass spectrometry analysis Bioorg. Med. Chem. 12 2004 3673 3682 (Pubitemid 38746870)
15. I. Laville, S. Pigaglio, J.C. Blais, F. Doz, B. Loock, Ph. Maillard, D.S. Grierson, and J. Blais Photodynamic efficiency of diethylene glycol-linked glycoconjugated porphyrins in human retinoblastoma cells J. Med. Chem. 49 2006 2558 2567
16. P. Maillard, B. Loock, D.S. Grierson, I. Laville, J. Blais, F. Doz, L. Desjardins, D. Carrez, J.L. Guerquin-Kern, and A. Croisy In vitro phototoxicity of glycoconjugated porphyrins and chlorins in colorectal adenocarcinoma (HT29) and retinoblastoma (Y79) cell lines Photodiag. Photodyn. Ther. 4 2007 261 268 (Pubitemid 350161878)
17. X. Chen, and C.M. Drain Photodynamic therapy using carbohydrate conjugated porphyrins Drug Des. Rev. Online 1 2004 215 234
18. J. Cavaleiro, J. Tomé, and M. Faustino Synthesis of glycoporphyrins E. El Ashry, Heterocycles from carbohydrate precursors vol. 7 2007 Springer Berlin/Heidelberg 179 248
19. X. Zheng, and R.K. Pandey Porphyrin-carbohydrate conjugates: impact of carbohydrate moieties in photodynamic therapy (PDT) Anti Canc. Agents Med. Chem. 8 2008 241 268 (Pubitemid 351761431)
20. M. Monsigny, A.C. Roche, and P. Midoux Endogenous lectins and drug targeting Ann. NY Acad. Sci. 551 1988 399 413 discussion 413-394
21. R. Lotan, and A. Raz Lectins in cancer cells Ann. NY Acad. Sci. 551 1988 385 398 (Pubitemid 19172156)
22. S. Ballut, A. Makky, B. Loock, J.P. Michel, Ph. Maillard, and V. Rosilio New strategy for targeting of photosensitizers. Synthesis of glycodendrimeric phenylporphyrins, incorporation into a liposome membrane and interaction with a specific lectin Chem. Commun. 2009 224 226
23. S. Griegel, M.F. Rajewsky, T. Ciesiolka, and H.J. Gabius Endogenous sugar receptor (lectin) profiles of human retinoblastoma and retinoblast cell lines analyzed by cytological markers, affinity chromatography and neoglycoprotein-targeted photolysis Anticancer Res. 9 1989 723 730 (Pubitemid 19194307)
24. S. Ballut, B. Loock, Ph. Maillard, New strategy for the targeting of photosensitizers. Synthesis, characterisation and photobiological property of porphyrins bearing glycodendrimeric moieties, J. Org. Chem. accepted.
25. J. Spikes, and G. Jori Photodynamic therapy of tumours and other diseases using porphyrins Laser Med. Sci. 2 1987 3 15 (Pubitemid 18075805)
26. M.C. Desroches, A. Kasselouri, M. Meyniel, P. Fontaine, M. Goldmann, P. Prognon, Ph. Maillard, and V. Rosilio Incorporation of glycoconjugated porphyrin derivatives into phospholipid monolayers: a screening method for the evaluation of their Interaction with a cell membrane Langmuir 20 2004 11698 11705 (Pubitemid 40049644)
27. A.A. Hidalgo, M. Tabak, and O.N. Oliveira Jr. The interaction of meso-tetraphenylporphyrin with phospholipid monolayers Chem. Phys. Lipids 134 2005 97 108 (Pubitemid 40387389)
28. F. Ricchelli, and G. Jori Distribution of porphyrins in the various compartments of unilamellar liposomes of dipalmitoyl-phosphatidylcholine as probed by fluorescence spectroscopy Photochem. Photobiol. 44 1986 151 157
29. M. Hoebeke The importance of liposomes as models and tools in the understanding of photosensitization mechanisms J. Photochem. Photobiol. B. Biol. 28 1995 189 196
30. F. Ricchelli Photophysical properties of porphyrins in biological membranes J. Photochem. Photobiol. B Biol. 29 1995 109 118
31. F. Ricchelli, S. Gobbo, G. Moreno, C. Salet, L. Brancaleon, and A. Mazzini Photophysical properties of porphyrin planar aggregates in liposomes Eur. J. Biochem. 253 1998 760 765 (Pubitemid 28223545)
32. D. Brault Physical chemistry of porphyrins and their interactions with membranes: the importance of pH J. Photochem. Photobiol. B Biol. 6 1990 79 86
33. K. Kuzelova, and D. Brault Interactions of dicarboxylic porphyrins with unilamellar lipidic vesicles: drastic effects of pH and cholesterol on kinetics Biochemistry 34 1995 11245 11255
34. N. Maman, and D. Brault Kinetics of the interactions of a dicarboxylic porphyrin with unilamellar lipidic vesicles: interplay between bilayer thickness and pH in rate control Biochim. Biophys. Acta Biomembr. 1414 1998 31 42 (Pubitemid 28511037)
35. B. Ehrenberg, and E. Gross The effect of liposomes membrane composition on the binding of the photosensitizers HPD and PHOTOFRIN II Photochem. Photobiol. 48 1988 461 466
36. E. Gross, and B. Ehrenberg The partition and distribution of porphyrins in liposomal membranes. A spectroscopic study Biochim. Biophys. Acta Biomembr. 983 1989 118 122 (Pubitemid 19180035)
37. A. Lavi, H. Weitman, R.T. Holmes, K.M. Smith, and B. Ehrenberg The depth of porphyrin in a membrane and the membrane's physical properties affect the photosensitizing efficiency Biophys. J. 82 2002 2101 2110 (Pubitemid 34280823)
38. A.J. Fliesler, and R.E. Anderson Chemistry and metabolism of lipids in the vertebrate retina Prog. Lipid Res. 22 1983 79 131
39. D. Huster, K. Arnold, and K. Gawrisch Influence of docosahexaenoic acid and cholesterol on lateral lipid organization in phospholipid mixtures Biochemistry 37 1998 17299 17308 (Pubitemid 29013788)
40. D. Huster, K. Arnold, and K. Gawrisch Strength of Ca2+ binding to retinal lipid membranes: consequences for lipid organization Biophys. J. 78 2000 3011 3018 (Pubitemid 30396931)
41. M.A. Yorek, P.H. Figard, T.L. Kaduce, and A.A. Spector A comparison of lipid metabolism in two human retinoblastoma cell lines Invest. Ophthalmol. Vis. Sci. 26 1985 1148 1154 (Pubitemid 15003358)
42. A. Makky, J.P. Michel, S. Ballut, A. Kasselouri, Ph. Maillard, and V. Rosilio Effect of cholesterol and sugar on the penetration of glycodendrimeric phenylporphyrins into biomimetic models of retinoblastoma cells membranes Langmuir 26 2010 11145 11156
43. A. Makky, J.P. Michel, A. Kasselouri, E. Briand, Ph. Maillard, and V. Rosilio Evaluation of the specific interactions between glycodendrimeric porphyrins, free or incorporated into liposomes, and concanavaline A by fluorescence spectroscopy, surface pressure, and QCM-D measurements Langmuir 26 2010 12761 12768
44. S. Mordon, J.M. Devoisselle, and S. Soulié Fluorescence spectroscopy of pH in vivo using a dual-emission fluorophore (C-SNAFL-1) J. Photochem. Photobiol. B Biol. 28 1995 19 23
45. 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 IN226-IN227
46. V. Faivre, V. Rosilio, P. Boullanger, L. Martins Almeida, and A. Baszkin Fucosyled neoglycolipids: synthesis and interaction with a phospholipid Chem. Phys. Lipids 109 2001 91 101 (Pubitemid 32121745)
47. V. Faivre, M.L. Costa, P. Boullanger, A. Baszkin, and V. Rosilio Specific interaction of lectins with liposomes and monolayers bearing neoglycolipids Chem. Phys. Lipids 125 2003 147 159 (Pubitemid 37130153)
48. J.N. Sanders, S.A. Chenoweth, and F.P. Schwarz Effect of metal ion substitutions in concanavalin A on the binding of carbohydrates and on thermal stability J. Inorg. Biochem. 70 1998 71 82 (Pubitemid 28340606)
49. Y. Nakano, M. Mori, S. Nishinohara, Y. Takita, S. Naito, H. Kato, M. Taneichi, K. Komuro, and T. Uchida Surface-linked liposomal antigen induces IgE-selective unresponsiveness regardless of the lipid components of liposomes Bioconj. Chem. 12 2001 391 395 (Pubitemid 32464185)
50. G. Liu, and Y. Lin Nanomaterial labels in electrochemical immunosensors and immunoassays Talanta 74 2007 308 317 (Pubitemid 350192537)
51. H. Chen, V. Torchilin, and R. Langer Lectin-bearing polymerized liposomes as potential oral vaccine carriers Pharm. Res. 13 1996 1378 1383 (Pubitemid 26344985)
52. J.W. Becker, G.N. Reeke Jr., J.L. Wang, B.A. Cunningham, and G.M. Edelman The covalent and three-dimensional structure of concanavalin A. III. Structure of the monomer and its interactions with metals and saccharides J. Biol. Chem. 250 1975 1513 1524
53. H.M.L.R. Santos, F.B. de Queiroz, R.M.S. Maior, S.C. do Nascimento, and N.S.S. Magalhães Cytotoxicity of doxorubicin-loaded Con A-liposomes Drug Dev. Res. 67 2006 430 437
54. A.A. Bogdanov jr, A.L. Klibanov, and V.P. Torchilin Protein immobilization on the surface of liposomes via carbodiimide activation in the presence of N-hydroxysulfosuccinimide. New strategy for the targeting of photosensitizers. Synthesis, characterisation and photobiological property of porphyrins bearing glycodendrimeric moieties. FEBS Lett. 231 1988 381 384
55. Z.V. Leonenko, A. Carnini, and D.T. Cramb Supported planar bilayer formation by vesicle fusion: the interaction of phospholipid vesicles with surfaces and the effect of gramicidin on bilayer properties using atomic force microscopy Biochim. Biophys. Acta Biomembr. 1509 2000 131 147
56. E. Kalb, J. Engel, and L.K. Tamm Binding of proteins to specific target sites in membranes measured by total internal reflection fluorescence microscopy Biochemistry 29 1990 1607 1613 (Pubitemid 20063395)
57. M. Grandbois, H. Clausen-Schaumann, and H. Gaub Atomic force microscope imaging of phospholipid bilayer degradation by phospholipase A2 Biophys. J. 74 1998 2398 2404 (Pubitemid 28225236)
58. M. Ross, C. Steinem, H.J. Galla, and A. Janshoff Visualization of chemical and physical properties of calcium-induced domains in DPPC/DPPS Langmuir-Blodgett layers Langmuir 17 2001 2437 2445 (Pubitemid 35330120)
59. C.A. Keller, and B. Kasemo Surface specific kinetics of lipid vesicle adsorption measured with a quartz crystal microbalance Biophys. J. 75 1998 1397 1402 (Pubitemid 28397608)
60. C. Steinem, A. Janshoff, W.P. Ulrich, M. Sieber, and H.J. Galla Impedance analysis of supported lipid bilayer membranes: a scrutiny of different preparation techniques Biochim. Biophys. Acta Biomembr. 1279 1996 169 180 (Pubitemid 26080847)
61. E. Reimhult, F. Höök, and B. Kasemo Intact vesicle adsorption and supported biomembrane formation from vesicles in solution: influence of surface chemistry, vesicle size, temperature, and osmotic pressure Langmuir 19 2002 1681 1691
62. 2: dependence on vesicle size J. Chem. Phys. 117 2002 7401 7405
63. 3 single crystals Langmuir 16 2000 10301 10308 (Pubitemid 32086284)
64. R. Richter, A. Mukhopadhyay, and A. Brisson Pathways of lipid vesicle deposition on solid surfaces: a combined QCM-D and AFM study Biophys. J. 85 2003 3035 3047 (Pubitemid 37345791)
65. B. Seantier, C. Breffa, O. Felix, and G. Decher Dissipation-enhanced quartz crystal microbalance studies on the experimental parameters controlling the formation of supported lipid bilayers J. Phys. Chem. B 109 2005 21755 21765 (Pubitemid 41784806)
66. R.P. Richter, R. Bérat, and Alain R. Brisson Formation of solid-supported lipid bilayers: an integrated view Langmuir 22 2006 3497 3505 (Pubitemid 43672517)
67. 2 Langmuir 22 2006 3313 3319
68. A.R. Patel, and C.W. Frank Quantitative analysis of tethered vesicle assemblies by quartz crystal microbalance with dissipation monitoring: binding dynamics and bound water content Langmuir 22 2006 7587 7599 (Pubitemid 44373430)
69. H. Brochu, and P. Vermette Liposome layers characterized by quartz crystal microbalance measurements and multirelease delivery Langmuir 23 2007 7679 7686 (Pubitemid 47116433)
70. F. Hook, B. Kasemo, T. Nylander, C. Fant, K. Sott, and H. Elwing Variations in coupled water, viscoelastic properties, and film thickness of a Mefp-1 protein film during adsorption and cross-linking: a quartz crystal microbalance with dissipation monitoring, ellipsometry, and surface plasmon resonance study Anal. Chem. 73 2001 5796 5804 (Pubitemid 34042194)
71. A.K. Dutta, A. Nayak, and G. Belfort Viscoelastic properties of adsorbed and cross-linked polypeptide and protein layers at a solid-liquid interface J. Colloid Interface Sci. 324 2008 55 60
72. J.J. Ramsden Biomimetic protein immobilization using lipid bilayers Biosens. Bioelectron. 13 1998 593 598 (Pubitemid 28500050)
73. P. Calvez, S. Bussieres, E. Demers, and C. Salesse Parameters modulating the maximum insertion pressure of proteins and peptides in lipid monolayers Biochimie 91 2009 718 733
74. H. Ibrahim, A. Kasselouri, C. You, Ph. Maillard, V. Rosilio, R. Pansu, and P. Prognon Glycoconjugated porphyrins usable in photodynamic therapy: self-aggregation, association with albumin, and localisation in DMPC liposomes as a simplified cell membrane model J. Photochem. Photobiol. Chem. 2010 10.1016/j.jphotochem.2010.09.008