Octaoctyl-substituted lutetium bisphthalocyanine for NADH biosensing

Journal of Physical Chemistry B

Volumn 117, Issue 48, 2013, Pages 15033-15040

  Pal, C ^a   Sharma, A K ^b   Cammidge, A N ^c   Cook, M J ^c   Ray, A K ^a  

^a BRUNEL UNIVERSITY   (United Kingdom)

^b USAF   (United States)

^c UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BISPHTHALOCYANINE; CYCLIC VOLTAMMETRIC; DIHYDRONICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCTION PROCESS; UV VISIBLE ABSORPTION SPECTRUM; UV-VIS ABSORPTIONS; UV-VIS SPECTROSCOPIC MEASUREMENT; VIBRATIONAL MODES;

NITROGEN COMPOUNDS;

LUTETIUM;

BIOMIMETIC MATERIAL; COORDINATION COMPOUND; INDOLE DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMICAL ANALYSIS; GENETIC PROCEDURES; OXIDATION REDUCTION REACTION; RAMAN SPECTROMETRY;

BIOMIMETIC MATERIALS; BIOSENSING TECHNIQUES; COORDINATION COMPLEXES; ELECTROCHEMICAL TECHNIQUES; INDOLES; MOLECULAR STRUCTURE; NAD; OXIDATION-REDUCTION; SPECTRUM ANALYSIS, RAMAN;

EID: 84890082823     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp4078568     Document Type: Article

References (43)

1. Weiss, R.; Fischer, J. In The porphyrin handbook; Kadish, K. M., Smith, K. M.; Guilard, R., Eds.; Academic Press: San Diego, CA, 2003; Vol. 16 pp 171-246.
2. Valli, L. Phthalocyanine-based Langmuir-Blodgett films as chemical sensors Adv. Colloid Interface Sci. 2005, 116, 13-44
3. Martin, M. G.; Rodriguez-Mendez, M. L.; de Saja, J. A. Films of Lutetium Bisphthalocyanine Nanowires as Electrochemical Sensors Langmuir 2010, 26, 19217-19224
4. Apetrei, C.; Alessio, P.; Constantino, C. J. L.; de Saja, J. A.; Rodriguez-Mendez, M. L.; Pavinatto, F. J.; Fernandes, E. G. R.; Zucolotto, V.; Oliveira, O. N. Biomimetic biosensor based on lipidic layers containing tyrosinase and lutetium bisphthalocyanine for the detection of antioxidants Biosens. Bioelectron. 2011, 26, 2513-2519
5. Durmus, M.; Yesilot, S.; Cosut, B.; Gurek, A. G.; Kilic, A.; Ahsen, V. Comparison of Photophysicochemical Properties of Hexaphenoxycyclotriphosphazenyl-Substituted Metal-free, Mono- And Bis-Lutetium Phthalocyanines Synth. Met. 2010, 160, 436-444
6. Rodriguez-Mendez, M. L.; Gay, M.; de Saja, J. A. New Insights into Sensors Based on Radical Bisphthalocyanines J. Porphyrins Phthalocyanines 2009, 13, 1159-1167
7. Bariain, C.; Matias, I. R.; Fernandez-Valdivielso, C.; Arregui, F. J.; Rodriguez-Mendez, M. L.; de Saja, J. A. Optical Fiber Sensor Based on Lutetium Bisphthalocyanine for the Detection of Gases using Standard Telecommunication Wavelengths Sens. Actuators, B 2003, 93, 153-158
8. Fernandes, E. G. R.; Brazaca, L. C.; Rodriguez-Mendez, M. L.; de Saja, J. A; Zucolotto, V. Immobilization of Lutetium Bisphthalocyanine in Nanostructured Biomimetic Sensors using the LbL Technique for Phenol Detection Biosens. Bioelectron. 2011, 26, 4715-4719
9. Pavinatto, F. J.; Fernandes, E. G. R.; Alessio, P.; Constantino, C. J. L.; de Saja, J. A.; Zucolotto, V.; Apetrei, C.; Oliveira, O. N., Jr.; Rodriguez-Mendez, M. L. Optimized Architecture for Tyrosinase-Containing Langmuir-Blodgett Films to Detect Pyrogallol J. Mater. Chem. 2011, 21, 4995-5003
10. Mayevsky, A.; Barbiro-Michaely, E. Shedding light on mitochondrial function by real time monitoring of NADH fluorescence: II: human studies J. Clin. Monitor. Comp. 2013, 27, 125-145
11. Mayevsky, A.; Barbiro-Michaely, E. Shedding Light on Mitochondrial Function by Real Time Monitoring of NADH Fluorescence: I. Basic Methodology and Animal Studies J. Clin. Monitor. Comp. 2013, 27, 1-34
12. Ghosh, D.; LeVault, K. R.; Barnett, A. J.; Brewer, G. J. A Reversible Early Oxidized Redox State That Precedes Macromolecular ROS Damage in Aging Nontransgenic and 3xTg-AD Mouse Neurons J. Neurosci. 2012, 32, 5821-5832
13. Nadlinger, K.; Westerthaler, W.; Storga-Tomic, D.; Birkmayer, J. G. D. Extracellular metabolisation of NADH by blood cells correlates with intracellular ATP levels Biochim. Biophys. Acta, Gen. Subj. 2002, 1573, 177-182
14. Yin, C.; Zhou, F. Y.; Wang, Y. R.; Luo, W. H.; Luo, Q. M.; Li, P. C. Simultaneous detection of hemodynamics, mitochondrial metabolism and light scattering changes during cortical spreading depression in rats based on multi-spectral optical imaging Neuroimage 2013, 76, 70-80
15. Birkmayer, G. D.; Kay, G. G.; Vürre, E. Stabilized NADH (ENADA) improves jet lag-induced cognitive performance deficit Wien. Med. Wochenschr. 2002, 152, 450-454
16. Kuila, T.; Bose, S.; Khanra, P.; Mishra, A. K.; Kim, N. H. Recent advances in graphene-based biosensors Biosens. Bioelectron. 2011, 26, 4637-4648
17. Shao, Y.; Wang, J.; Wu, H.; Liu, J.; Aksay, I. A.; Lin, Y. H. Graphene Based Electrochemical Sensors and Biosensors: A Review Electroanalysis 2010, 22, 1027-1036
18. Radoi, A.; Compagnone, D. Recent advances in NADH electrochemical sensing design Bioelectrochemistry 2009, 76, 126-134
19. Basova, T.; Gurek, A. G.; Ahsen, V.; Ray, A. K. Electrochromic lutetium phthalocyanine films for in situ detection of NADH Opt. Mater. 2013, 35, 634-637
20. Basova, T.; Jushina, I.; Guerek, A. G.; Ahsen, V.; Ray, A. K. Use of the electrochromic behaviour of lanthanide phthalocyanine films for nicotinamide adenine dinucleotide detection J. R. Soc. Interface 2008, 5, 801-806
21. Pal, C.; Cammidge, A. N.; Cook, M. J.; Sosa-Sanchez, J. L.; Sharma, A. K.; Ray, A. K. In situ chemichromic studies of interactions between a lutetium bis-octaalkyl-substituted phthalocyanine and selected biological cofactors J. R. Soc. Interface 2012, 9, 183-189
22. Chaure, N. B.; Sosa-Sanchez, J. L.; Cammidge, A. N.; Cook, M. J.; Ray, A. K. Solution processable lutetium phthalocyanine organic field-effect transistors Org. Electron. 2010, 11, 434-438
23. Wang, H. L.; Kobayashi, N.; Jiang, J. Z. New Sandwich-Type Phthalocyaninato-Metal Quintuple-Decker Complexes Chem.-Eur. J. 2012, 18 (4) 1047-1049
24. Sergeyev, S.; Pouzet, E.; Debever, O.; Levin, J.; Gierschner, J.; Cornil, J.; Aspe, R. G.; Geerts, Y. H. Liquid crystalline octaalkoxycarbonyl phthalocyanines: design, synthesis, electronic structure, self-aggregation and mesomorphism J. Mater. Chem. 2007, 17 (18) 1777-1784
25. Swarts, J. C.; Langner, E. H. G.; Krokeide-Hove, N.; Cook, M. J. Synthesis and electrochemical characterisation of some long chain 1,4,8,11,15,18,22,25-octa-alkylated metal-free and zinc phthalocyanines possessing discotic liquid crystalline properties J. Mater. Chem. 2001, 11 (2) 434-443
26. Kadish, K. M.; Nakanishi, T.; Gurek, A.; Ahsen, V.; Yilmaz, I. Electrochemistry of a double-decker lutetium(III) phthalocyanine in aqueous media. The first evidence for five reductions J. Phys. Chem. B 2001, 105 (40) 9817-9821
27. Neudeck, A.; Marken, F.; Compton, R. G. Complex electron transfer kinetic data from convolution analysis of cyclic voltammograms. Theory and application to diamond electrodes Electroanalysis 1999, 11, 1149-1154
28. Zhu, P. H.; Lu, F. L.; Pan, N.; Arnold, D. P.; Zhang, S. Y.; Jiang, J. Z. Comparative electrochemical study of unsubstituted and substituted bis(phthalocyaninato) rare earth(III) complexes Eur. J. Inorg. Chem. 2004, 3, 510-517
29. Quentel, F. l.; Elleouet, C.; Mirceski, V.; Hernandez, V. A.; L'Her, M.; Lovric, M.; Komorsky-Lovric, S.; Scholz, F. J. Studying ion transfers across a room temperature ionic liquid vertical bar aqueous electrolyte interface driven by redox reactions of lutetium bis(tetra-tert-butylphthalocyaninato) Electroanal. Chem. 2007, 611, 192-200
30. Martin, M. G.; de Saja, J. A.; Munoz, R.; Rodriguez-Mendez, M. L. Multisensor system based on bisphthalocyanine nanowires for the detection of antioxidants Electrochim. Acta 2012, 68, 88-94
31. Nakanishi, T.; Yilmaz, I.; Nakashima, N.; Kadish, K. M. Thermodynamic Study of Ion-Pairing Effects Between Reduced Double-Decker Lutetium(III) Phthalocyanines and A Cationic Matrix J. Phys. Chem. B 2003, 107, 12789-12796
32. Li, X. F.; Zhang, S. X.; Sun, C. Q. Fabrication of a covalently attached multilayer film electrode containing cobalt phthalocyanine and its electrocatalytic oxidation of hydrazine J. Electroanal. Chem. 2003, 553, 139-145
33. Orti, E.; Bredas, J. L.; Clarisse, C. Electronic-Structure of Phthalocyanines-Theoretical Investigation of the Optical-Properties of Phthalocyanine Monomers, Dimers, and Crystals J. Chem. Phys. 1990, 92, 1228-1235
34. Rousseau, R.; Aroca, R.; Rodriguez-Mendez, M. L. Extended Huckel Molecular-Orbital Model for Lanthanide Bisphthalocyanine Complexes J. Mol. Struct. 1995, 356, 49-62
35. Bao, M.; Wang, R. M.; Rintoul, L.; Liu, Q. Y.; Arnold, D. P.; Ma, C. Q.; Jiang, J. Z. Vibrational Spectroscopy of Phthalocyanine and Naphthalocyanine in Sandwich-Type (Na)Phthalocyaninato and Porphyrinato Rare Earth Complexes-Part 12-Part 13. The Raman Characteristics of Phthalocyanine in Unsubstituted and Peripherally Octa(Octyloxy) -Substituted Homoleptic Bis(Phthalocyaninato) Rare Earth Complexes Polyhedron 2006, 25, 1195-1203
36. Vivas, M. G.; Fernandes, E. G. R.; Rodriguez-Mendez, M. L.; Mendonca, C. R. Study of Singlet Excited State Absorption Spectrum of Lutetium Bisphthalocyanine using the Femtosecond Z-Scan Technique Chem. Phys. Lett. 2012, 531, 173-176
37. Takamatsu, S.; Ishikawa, N. A Theoretical Study of a Drastic Structural Change of Bis(Phthalocyaninato)Lanthanide by Ligand Oxidation: Towards Control of Ligand Field Strength and Magnetism of Single-Lanthanide-Ionic Single Molecule Magnet Polyhedron 2007, 26, 1859-1862
38. 2(Oac)(2) Chem. Phys. 2007, 340, 283-292
39. Deore, B. A.; Freund, M. S. Reactivity of poly(anilineboronic acid) with NAD(+) and NADH Chem. Mater. 2005, 17, 2918-2923
40. Bao, M.; Wang, R. M.; Rintoul, L.; Arnold, D. P.; Jiang, J. Z. Vibrational spectroscopy of phthalocyanine and naphthalocyanine in sandwich-type (na)phthalocyaninato and porphyrinato rare earth complexes-Part 14. The infrared and Raman characteristics of phthalocyanine in "pinwheel- like" homoleptic bis[1,8,15,22-tetrakis(3-pentyloxy)phthalocyaninato] rare earth(III) double-decker complexes Vib. Spectrosc. 2006, 40, 47-54
41. Tran-Thi, T. H.; Mattioli, T. A.; Chabach, D.; de Cian, A.; Weiss, R. Hole Localization or Delocalization-An Optical, Raman, and Redox Study of Lanthanide Porphyrin-Phthalocyanine Sandwich-Type Heterocomplexes J. Phys. Chem. 1994, 98, 8279-8288
42. Jiang, J. Z.; Bao, M.; Rintoul, L.; Arnold, D. P. Vibrational spectroscopy of phthalocyanine and naphthalocyanine in sandwich-type (na)phthalocyaninato and porphyrinato rare earth complexes Coord. Chem. Rev. 2006, 250, 424-448
43. Jiang, J. Z.; Rintoul, L.; Arnold, D. P. Raman spectroscopic characteristics of phthalocyanine and naphthalocyanine in sandwich-type (na)phthalocyaninato and porphyrinato rare earth complexes Polyhedron 2000, 19, 1381-1394