Binding of methylene blue onto langmuir monolayers representing cell membranes may explain its efficiency as photosensitizer in photodynamic therapy

Langmuir

Volumn 31, Issue 14, 2015, Pages 4205-4212

  Schmidt, Thaís F ^a   Caseli, Luciano ^b   Oliveira, Osvaldo N ^c   Itri, Rosangela ^c  

^a UNIVERSIDADE FEDERAL DO ABC   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; AROMATIC COMPOUNDS; CELL MEMBRANES; CYTOLOGY; DYES; GAS GENERATORS; MAMMALS; MEMBRANES; MITOCHONDRIA; MONOLAYERS; PHOTOSENSITIZERS;

CELL MEMBRANE MODELS; INNER MITOCHONDRIAL MEMBRANES; LANGMUIR MONOLAYERS; MIXED LANGMUIR MONOLAYERS; POLARIZATION-MODULATED INFRARED REFLECTION-ABSORPTION SPECTROSCOPY; SINGLET OXYGEN GENERATION; SURFACE PRESSURE MEASUREMENTS; VIBRATIONAL MODES;

PHOTODYNAMIC THERAPY;

1,1',2,2'-TETRAOLEOYLCARDIOLIPIN; 1,2-OLEOYLPHOSPHATIDYLCHOLINE; CARDIOLIPIN; METHYLENE BLUE; PHOSPHATIDYLCHOLINE; PHOTOSENSITIZING AGENT;

CELL MEMBRANE; CHEMISTRY; METABOLISM; PHOTOCHEMOTHERAPY; STATIC ELECTRICITY;

CARDIOLIPINS; CELL MEMBRANE; METHYLENE BLUE; PHOSPHATIDYLCHOLINES; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; STATIC ELECTRICITY;

EID: 84927729658     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/acs.langmuir.5b00166     Document Type: Article

References (43)

1. Chan, M. S.; Bolton, J. R. Structures, Reduction Potential and Absorption Maxima of Synthetic Dyes of Interest in Photochemical Solar Energy Storage Studies Sol. Energy 1980, 24, 561-574
2. Wainwright, M.; Crossley, K. B. Methylene Blue-A Therapeutic Dye for All Seasons? J. Chemother. 2002, 14, 431-443
3. Wright, R. O.; Lewander, W. J.; Woolf, A. D. Methemoglobinemia: Etiology, Pharmacology, and Clinical Management Ann. Emerg. Med. 1999, 34, 646-656
4. Orth, K.; Beck, G.; Genze, F.; Ruck, A. Methylene Blue Mediated Photodynamic Therapy in Experimental Colorectal Tumors in Mice J. Photochem. Photobiol., B 2000, 57, 186-190
5. Tardivo, J. P.; Del Giglio, A.; Paschoal, L. H.; Baptista, M. S. New Photodynamic Therapy Protocol to Treat Aids-Related Kaposi's Sarcoma Photomed. Laser Surg. 2006, 24, 528-531
6. Wagner, M.; Suarez, E. R.; Theodoro, T. R.; Machado, C. D. A. S.; Gama, M. F. M.; Tardivo, J. P.; Paschoal, F. M.; Pinhal, M. A. S. Methylene Blue Photodynamic Therapy in Malignant Melanoma Decreases Expression of Proliferating Cell Nuclear Antigen and Heparanases Clin. Exp. Dermatol. 2012, 37, 527-533
7. Wainwright, M.; Phoenix, D. A.; Gaskell, M.; Marshall, B. Photobactericidal Activity of Methylene Blue Derivatives Against Vancomycin-Resistant Enterococcus spp J. Antimicrob. Chemother. 1999, 44, 823-825
8. Tardivo, J. P.; Wainwright, M.; Baptista, M. S. Local Clinical Phototreatment of Herpes Infection in São Paulo Photodiag. Photodyn. Ther. 2012, 9, 118-121
9. Scwingel, A. R.; Barcessat, A. R. P.; Núñez, S. C.; Ribeiro, M. S. Antimicrobial Photodynamic Therapy in the Treatment of Oral Candidiasis in HIV-Infected Patients Photomed. Laser Surg. 2012, 30 (8) 429-432
10. Yolanda, G.; Carmen, A.; Carmen, A. M.; Elena, A.-C.; Blanca, F.; Revillo, M. J.; Hamblin, M. R.; Rezusta, A. Cutaneous Sporotrichosis Treated with Photodynamic Therapy: An In Vitro and In Vivo Study Photomed. Laser Surg. 2014, 32 (1) 54-57
11. Thorpe, W. P.; Toner, M.; Ezzell, R. M.; Tompkins, R. G.; Yarmush, M. L. Dynamics of Photoinduced Cell Plasma Membrane Injury Biophys. J. 1995, 68, 2198-2206
12. Itri, R.; Junqueira, H. C.; Mertins, O.; Baptista, M. S. Membrane Changes Under Oxidative Stress: the Impact of Oxidized Lipids Biophys. Rev. 2014, 6, 47-61
13. Caetano, W.; Haddad, P. S.; Itri, R.; Severino, D.; Vieira, V. C.; Baptista, M. S.; Schroder, A.; Marques, C. Photo-Induced Destruction of Giant Vesicles in Methylene Blue Solutions Langmuir 2007, 23, 1307-1314
14. Cwiklik, L.; Jungwirth, P. Massive Oxidation of Phospholipid Membranes Leads to Pore Creation and Bilayer Disintegration Chem. Phys. Lett. 2010, 48, 99-103
15. Mertins, O.; Bacellar, I. O. L.; Thalmann, F.; Marques, C. M.; Baptista, M.; Itri, R. Physical Damage on Giant Vesicles Membrane as a Result of Methylene Blue Photoirradiation Biophys. J. 2014, 106, 162-171
16. Wilkinson, F.; Helman, W. P.; Ross, A. B. Rate Constants for the Decay and Reactions of the Lowest Electronically Excited Singlet-State of Molecular-Oxygen in Solution-An Expanded and Revised Compilation J. Phys. Chem. Ref. Data 1995, 24, 663-1021
17. Gabrielli, D.; Belisle, E.; Baptista, M. S. Binding, Aggregation and Photochemical Properties of Methylene Blue in Mitochondrial Suspensions Photochem. Photobiol. 2004, 79, 227-232
18. Schlame, M.; Ren, M.; Xu, Y.; Greenberg, M. L.; Haller, Y. Molecular Symmetry in Mitochondrial Cardiolipins Chem. Phys. Lipids 2005, 138, 38-49
19. Schlame, M. Cardiolipin Synthesis for the Assembly of Bacterial and Mitochondrial Membranes J. Lipid Res. 2008, 49, 1607-1620
20. Epand, R. F.; Pollard, J. E.; Wright, J. O.; Savage, P. B.; Epand, R. M. Depolarization, Bacterial Membrane Composition, and the Antimicrobial Action of Ceragenins Antimicrob. Agents Chemother. 2010, 54, 3708-3713
21. Brockman, H. Lipid Monolayers: Why Use Half a Membrane to Characterize Protein-Membrane Interactions? Curr. Opin. Struct. Biol. 1999, 9, 438-444
22. Buffeteau, T.; Desbat, B.; Turlet, J. M. Polarization Modulation FT-IR Spectroscopy of Surfaces and Ultra-Thin Films: Experimental Procedure and Quantitative Analysis Appl. Spectrosc. 1991, 45, 380-389
23. Mendelshon, R.; Mao, G.; Flach, C. R. Infrared Reflection-Absorption Spectroscopy: Principles and Applications to Lipid-Protein Interaction in Langmuir Films Biochim. Biophys. Acta 2010, 1798, 788-800
24. Vargaftik, N. B.; Volkov, B. N.; Voljak, L. D. International Tables of the Surface Pressure of Water J. Phys. Chem. Ref. Data 1983, 12, 817-820
25. Liljeblad, J. F. D.; Bulone, V.; Tyrode, E.; Rutland, M. W.; Magnus Johnson, C. Phospholipid Monolayers Probed by Vibrational Sum Frequency Spectroscopy: Instability of Unsaturated Phospholipids Biophys. J. 2010, 98, L50-L52
26. Yamins, H. G.; Zisman, W. A. A New Method of Studying the Electrical Properties of Monomolecular Films on Liquids J. Chem. Phys. 1933, 1, 656-661
27. Dicko, A.; Bourque, H.; Pézolet, M. Study by Infrared Spectroscopy of the Conformation of Dipalmitoylphosphatidylglyrecol Monolayers at the Air-Water Interface and Transferred on Solid Substrates Chem. Phys. Lipids 1998, 96, 125-139
28. Blaudez, D.; Turlet, J. M.; Dufourcq, J.; Bard, D.; Buffeteau, T.; Desbat, B. Investigations at the Air/Water Interface Using Polarization Modulation IR Spectroscopy J. Chem. Soc., Faraday Trans. 1996, 92, 525-530
29. Urakawa, A.; Bürgi, T.; Baiker, A. Modulation Excitation PM-IRRAS: A New Possibility for Simultaneous Monitoring of Surface and Gas Species and Surface Properties Chimia 2006, 60, 231-233
30. Vié, V.; Legardinier, S.; Chieze, L.; Le Bihan, O.; Oin, Y.; Sarkis, J.; Hubert, J. F.; Renault, A.; Desbat, B.; Le Rumeur, E. Specific Anchoring Modes of Two Distinct Dystrophin Rod Sub-Domains Interacting in Phospholipid Langmuir Films Studied by Atomic Force Microscopy and PM-IRRAS Biochim. Biophys. Acta, Biomembr. 2010, 1798, 1503-1511
31. Aguayo, D.; González-Nilo, F. D.; Chipot, C. Insight into the Properties of Cardiolipin Bilayers from Molecular Dynamics Simulations, Using a Hybrid All-Atom/United Atom Force Field J. Chem. Theory Comput. 2012, 8, 1765-1773
32. Niño, M. R. R.; Caro, A. L.; Patino, J. M. R. Structural, Topographical, and Rheological Characteristics of β-Casein-Dioleoyl Phosphatidylcholine (DOPC) Mixed Monolayers Colloids Surf., B 2009, 69, 15-25
33. Broniatowski, M.; Flasiński, M.; Zieba, K.; Mis̈kowiec, P. Langmuir Monolayer Studies of the Interaction of Monoamphiphilic Pentacyclic Triterpenes With Anionic Mitochondrial and Bacterial Membrane Phospholipids - Searching for the Most Active Terpene Biochim. Biophys. Acta 2014, 1838, 2460-2472
34. Gaines, Jr., G. L. Insoluble Monolayers at Liquid-Gas Interfaces; Wiley: New York, 1966.
35. Domènech, O.; Torrent-Burgués, J.; Merino, S.; Sanz, F.; Montero, M. T.; Hernández-Borrel, J. Surface Thermodynamics Study of Monolayers Formed with Heteroacid Phospholipids of Biological Interest Colloids Surf., B 2005, 41, 233-238
36. Nichols-Smith, S.; Teh, S. Y.; Kuhl, T. L. Thermodynamic and Mechanical Properties of Model Mitochondrial Membranes Biochim. Biophys. Acta 2004, 1663, 82-88
37. Aoki, P. H. B.; Volpati, D.; Caetano, W.; Constantino, C. J. L. Study of the Interaction Between Cardiolipin Bilayers and Methylene Blue in Polymer-Based Layer-by-Layer and Langmuir Films Applied as Membrane Mimetic Systems Vib. Spectrosc. 2010, 54, 93-102
38. Zawisza, I.; Lachenwitzer, A.; Zamlynny, V.; Horswell, S. L.; Goddard, J. D.; Lipkowski, J. Electrochemical and Photon Polarization Modulation Infrared Reflection Absorption Spectroscopy Study of the Electric Field Driven Transformations of a Phospholipid Bilayer Supported at a Gold Electrode Surface Biophys. J. 2003, 85, 4055-4075
39. Hasegawa, T.; Konk, V.; Leblanc, R. M. In Vibrational Spectroscopy of Biological and Polymeric Materials; Gregoriou, V. G.; Braiman, M. S., Eds.; CRC Taylor & Francis Group: Boca Raton, FL, 2006; Chapter 3.
40. Yu, Z.; Chuang, S. S. C. Probing Methylene Blue Photocatalytic Degradation by Adsorbed Ethanol with In Situ IR J. Phys. Chem. C 2007, 111, 13813-1382
41. Vácha, R.; Jurkiewicz, P.; Petrov, M.; Berkowitz, M. L.; Bockmann, R. A.; Barucha-Kraszewska, J.; Hof, M.; Jungwirth, P. Mechanism of Interaction of Monovalent Ions with Phosphatidylcholine Lipid Membranes J. Phys. Chem. B 2010, 114, 9504-9509
42. Christoforou, M.; Leontidis, E.; Brezesinski, G. Effects of Sodium Salts of Lyotropic Anions on Low-Temperature, Ordered Lipid Monolayers J. Phys. Chem. B 2012, 116, 14602-14612
43. Barbosa, L. R. S.; Caetano, W.; Itri, R.; Homem-de-Mello, P.; Santiago, P. S.; Tabak, M. Interaction of Phenothiazine Compounds with Zwitterionic Lysophosphatidylcholine Micelles: Small Angle X-Ray Scattering, Electronic Absorption Spectroscopy, and Theoretical Calculations J. Phys. Chem. B 2006, 110, 13086-13093