Structural and photophysical properties of peptide micro/nanotubes functionalized with hypericin

Journal of Physical Chemistry B

Volumn 117, Issue 9, 2013, Pages 2605-2614

  Souza, Márcia I ^a   Jaques, Ygor M ^a   De Andrade, Gislaine P ^a   Ribeiro, Anderson O ^a   Da Silva, Emerson R ^a   Fileti, Eudes E ^b   Ávilla, Érick De Souza ^c   Pinheiro, Maurício V B ^c   Krambrock, Klaus ^c   Alves, Wendel A ^a  

^a UNIVERSIDADE FEDERAL DO ABC   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

^c FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

MAGNETIC RESONANCE; MOLECULAR DYNAMICS; NUCLEAR PHYSICS; PARAMAGNETISM; PEPTIDES; PHOTODYNAMIC THERAPY; PHOTOSENSITIZERS;

CHARACTERISTIC FLUORESCENCE; MOLECULAR DYNAMICS SIMULATIONS; PHOTODYNAMIC THERAPY (PDT); PHOTOPHYSICAL BEHAVIOR; PHOTOPHYSICAL PROPERTIES; REACTIVE OXYGEN SPECIES; SPATIAL ORGANIZATION; SUPRAMOLECULAR STRUCTURE;

FLUOROPHORES;

EID: 84875045748     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp3113655     Document Type: Article

References (45)

1. Si, W.; Hu, X.-B.; Liu, X.-H.; Fan, R.; Chen, Z.; Weng, L.; Hou, J.-L. Self-Assembly and Proton Conductance of Organic Nanotubes from Pillar[5]arenes Tetrahedron Lett. 2011, 52, 2484-2487
2. Toksöz, S.; Guler, M. O. Self-Assembled Peptidic Nanostructures Nano Today 2009, 4, 458-469
3. Demirel, G.; Buyukserin, F. Surface-Induced Self-Assembly of Dipeptides onto Nanotextured Surfaces Langmuir 2011, 27, 12533-12538
4. Reches, M.; Gazit, E. Casting Metal Nanowires Within Discrete Self-Assembled Peptide Nanotubes Science 2003, 300, 625-627 (Pubitemid 36520583)
5. Tamamis, P.; Adler-Abramovich, L.; Reches, M.; Marshall, K.; Sikorski, P.; Serpell, L.; Gazit, E.; Archontis, G. Self-Assembly of Phenylalanine Oligopeptides: Insights from Experiments and Simulations Biophys. J. 2009, 96, 5020-5029
6. Yemini, M.; Reches, M.; Rishpon, J.; Gazit, E. Novel Electrochemical Biosensing Platform Using Self-Assembled Peptide Nanotubes Nano Lett. 2004, 5, 183-186
7. Yan, X.; Su, Y.; Li, J.; Früh, J.; Möhwald, H. Uniaxially Oriented Peptide Crystals for Active Optical Waveguiding Angew. Chem., Int. Ed. 2011, 50, 11186-11191
8. Yan, X.; Zhu, P.; Fei, J.; Li, J. Self-Assembly of Peptide-Inorganic Hybrid Spheres for Adaptive Encapsulation of Guests Adv. Mater. 2010, 22, 1283-1287
9. Yan, X.; Cui, Y.; Qi, W.; Su, Y.; Yang, Y.; He, Q.; Li, J. Self-Assembly of Peptide-Based Colloids Containing Lipophilic Nanocrystals Small 2008, 4, 1687-1693
10. Yan, X.; Zhu, P.; Li, J. Self-Assembly and Application of Diphenylalanine-Based Nanostructures Chem. Soc. Rev. 2010, 39, 1877-1890
11. de la Rica, R.; Matsui, H. Applications of Peptide and Protein-Based Materials in Bionanotechnology Chem. Soc. Rev. 2010, 39, 3499-3509
12. Matos, I. O.; Alves, W. A. Electrochemical Determination of Dopamine Based on Self-Assembled Peptide Nanostructure ACS Appl. Mater. Interfaces 2011, 3, 4437-4443
13. de la Rica, R.; Mendoza, E.; Matsui, H. Bioinspired Target-Specific Crystallization on Peptide Nanotubes for Ultrasensitive Pb Ion Detection Small 2010, 6, 1753-1756
14. Ryu, J.; Park, C. B. Synthesis of Diphenylalanine/Polyaniline Core/Shell Conducting Nanowires by Peptide Self-Assembly Angew. Chem., Int. Ed. 2009, 48, 4820-4823
15. Kim, J. H.; Lim, S. Y.; Nam, D. H.; Ryu, J.; Ku, S. H.; Park, C. B. Self-Assembled, Photoluminescent Peptide Hydrogel as a Versatile Platform for Enzyme-Based Optical Biosensors Biosens. Bioelectron. 2011, 26, 1860-1865
16. Cipriano, T.; Takahashi, P.; de Lima, D.; Oliveira, V.; Souza, J.; Martinho, H.; Alves, W. A. Spatial Organization of Peptide Nanotubes for Electrochemical Devices J. Mater. Sci. 2010, 45, 5101-5108
17. Martins, T. D.; Souza, M. I.; Cunha, B. B.; Takahashi, P. M.; Ferreira, F. F.; Souza, J. A.; Fileti, E. E.; Alves, W. A. Influence of pH and Pyrenyl on the Structural and Morphological Control of Peptide Nanotubes J. Phys. Chem. C 2011, 115, 7906-7913
18. Karioti, A.; Bilia, A. R. Hypericins as Potential Leads for New Therapeutics Int. J. Mol. Sci. 2010, 11, 562-594
19. Gbur, P.; Dedic, R.; Chorvat, D., Jr.; Miskovsky, P.; Hala, J.; Jancura, D. Time-Resolved Luminescence and Singlet Oxygen Formation After Illumination of the Hypericin-Low-Density Lipoprotein Complex Photochem. Photobiol. 2009, 85, 816-823
20. Sánchez-Cortés, S.; Miskovsky, P.; Jancura, D.; Bertoluzza, A. Specific Interactions of Antiretroviraly Active Drug Hypericin with DNA as Studied by Surface-Enhanced Resonance Raman Spectroscopy J. Phys. Chem. 1996, 100, 1938-1944 (Pubitemid 126790018)
21. Guedes, R. C.; Eriksson, L. A. Theoretical Study of Hypericin J. Photochem. Photobiol., A 2005, 172, 293-299 (Pubitemid 40652178)
22. Arabei, S. M.; Galaup, J. P.; Jardon, P. Analysis of the Site Selected Fluorescence and the Phosphorescence Spectrum of Hypericin in Ethanol Chem. Phys. Lett. 1997, 270, 31-36 (Pubitemid 127169304)
23. Weiner, L.; Mazur, Y. EPR Studies of Hypericin. Photogeneration of Free Radicals and Superoxide J. Chem. Soc., Perkin Trans. 1992, 2, 1439-1442
24. Sgarbossa, A.; Lenci, F. Spectroscopic Study of Visible-Light Effects on Hypericin-Lens Proteins Systems Photochem. Photobiol. 2001, 74, 196-200
25. Hamblin, M. R.; Hasan, T. Photodynamic Therapy: A New Antimicrobial Approach to Infectious Disease? Photochem. Photobiol. Sci. 2004, 3, 436-450 (Pubitemid 38855151)
26. Asilian, A.; Davami, M. Comparison Between the Efficacy of Photodynamic Therapy and Topical Paromomycin in the Treatment of Old World Cutaneous Leishmaniasis: A Placebo-Controlled, Randomized Clinical Trial Clin. Exp. Dermatol. 2006, 31, 634-637 (Pubitemid 44086787)
27. Enk, C. D.; Fritsch, C.; Jonas, F.; Nasereddin, A.; Ingber, A.; Jaffe, C. L.; Ruzicka, T. Treatment of Cutaneous Leishmaniasis with Photodynamic Therapy Arch. Dermatol. 2003, 139, 432-434 (Pubitemid 36427606)
28. Gardlo, K.; Horska, Z.; Enk, C. D.; Rauch, L.; Megahed, M.; Ruzicka, T.; Fritsch, C. Treatment of Cutaneous Leishmaniasis by Photodynamic Therapy J. Am. Acad. Dermatol. 2003, 48, 893-896 (Pubitemid 36706223)
29. Gardlo, K.; Hanneken, S.; Ruzicka, T.; Neumann, N. J. Photodynamic Therapy of Cutaneous Leishmaniasis. A Promising New Therapeutic Modality Hautarzt 2004, 55, 381-383 (Pubitemid 38661284)
30. Bramanti, E.; Lenci, F.; Sgarbossa, A. Effects of Hypericin on the Structure and Aggregation Properties of β -Amyloid Peptides Eur. Biophys. J. 2010, 39, 1493-1501
31. Falk, H.; Meyer, J.; Oberreiter, M. A Convenient Semisynthetic Route to Hypericin Monatsh. Chem. 1993, 124, 339-341
32. Huygens, A.; Kamuhabwa, A. R.; de Witte, P. A. Stability of Different Formulations and Ion Pairs of Hypericin Eur. J. Pharm. Biopharm. 2005, 59, 461-468 (Pubitemid 40342520)
33. Wilcox, C. S. Effects of Tempol and Redox-Cycling Nitroxides in Models of Oxidative Stress Pharmacol. Ther. 2010, 126, 119-145
34. Görbitz, C. H. Nanotube Formation by Hydrophobic Dipeptides Chem.-Eur. J. 2001, 7, 5153-5159 (Pubitemid 34555642)
35. Görbitz, C. H. The Structure of Nanotubes Formed by Diphenylalanine, the Core Recognition Motif of Alzheimer's β -Amyloid Polypeptide Chem. Commun. 2006, 2332-2334 (Pubitemid 43846368)
36. Hess, B.; Kutzner, C.; van der Spoel, D.; Lindahl, E. GROMACS 4: Algorithms for Highly Efficient, Load-Balanced, and Scalable Molecular Simulation J. Chem. Theory Comput. 2008, 4, 435-447
37. MacKerell, A. D.; Bashford, D.; Bellott, M.; Dunbrack, R. L.; Evanseck, J. D.; Field, M. J.; Fischer, S.; Gao, J.; Guo, H.; Ha, S. All-Atom Empirical Potential for Molecular Modeling and Dynamics Studies of Proteins J. Phys. Chem. B 1998, 102, 3586-3616 (Pubitemid 128576688)
38. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. Comparison of Simple Potential Functions for Simulating Liquid Water J. Chem. Phys. 1983, 79, 926-935
39. Sgarbossa, A.; Buselli, D.; Lenci, F. In Vitro Perturbation of Aggregation Processes in β -Amyloid Peptides: A Spectroscopic Study FEBS Lett. 2008, 582, 3288-3292
40. Larson, A. C.; Von Dreele, R. B. General Structure Analysis System (GSAS) (Report LAUR 86-748); Los Alamos National Laboratory: Los Alamos, NM, 2001.
41. Toby, B. H.; EXPGUI, A. Graphical User Interface for GSAS J. Appl. Crystallogr. 2001, 34, 210-213
42. Spiller, W.; Kliesch, H.; Wohrle, D.; Hackbarth, S.; Roder, B.; Schnurpfeil, G. Singlet Oxygen Quantum Yields of Different Photosensitizers in Polar Solvents and Micellar Solutions J. Porphyrins Phthalocyanines 1998, 2, 145-158 (Pubitemid 128543116)
43. Engelmann, F. M.; Mayer, I.; Araki, K.; Toma, H. E.; Baptista, M. S.; Maeda, H.; Osuka, A.; Furuta, H. Photochemistry of Doubly N -Confused Porphyrin Bonded to Non-Conventional High Oxidation State Ag(III) and Cu(III) Ions J. Photochem. Photobiol., A 2004, 163, 403-411
44. Redmond, R. W.; Land, E. J.; Truscott, T. G. Aggregation Effects on the Photophysical Properties of Porphyrins in Relation to Mechanisms Involved in Photodynamic Therapy Adv. Exp. Med. Biol. 1985, 193, 293-302
45. Falk, H.; Meyer, J. On the Homo- and Heteroassociation of Hypericin Monatsh. Chem. 1994, 125, 753-762