Chelation-induced quenching of two-photon absorption of azacrown ether substituted distyryl benzene for metal ion sensing

Journal of Chemical Theory and Computation

Volumn 10, Issue 2, 2014, Pages 778-788

  Murugan, N Arul ^a   Zaleśny, Robert ^a,b   Kongsted, Jacob ^c   Ågren, Hans ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

^c UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84894167925     PISSN: 15499618     EISSN: 15499626     Source Type: Journal    
DOI: 10.1021/ct400924u     Document Type: Article

References (68)

1. Holm, R. H.; Kennepohl, P.; Solomon, E. I. Structural and Functional Aspects of Metal Sites in Biology Chem. Rev. 1996, 96, 2239-2314
2. Waldron, K. J.; Rutherford, J. C.; Ford, D.; Robinson, N. J. Metalloproteins and Metal Sensing Nature 1996, 460, 823-830
3. Andreini, C.; Bertini, I.; Cavallaro, G.; Holliday, G.; Thornton, J. Metal Ions in Biological Catalysis: from Enzyme Databases to General Principles J. Biol. Inorg. Chem. 2008, 13, 1205-1218
4. Casey, J. R.; Grinstein, S.; Orlowski, J. Sensors and Regulators of Intracellular pH Nat. Rev. Mol. Cell Biol. 2010, 11, 13518-13523
5. O'Halloran, T. V.; Culotta, V. C. Metallochaperones, an Intracellular Shuttle Service for Metal Ions J. Biol. Chem. 2000, 275, 25057-25060
6. Finney, L. A.; O'Halloran, T. V. Transition Metal Speciation in the Cell: Insights from the Chemistry of Metal Ion Receptors Science 2003, 300, 931-936
7. Barnham, K. J.; Bush, A. I. Metals in Alzheimer's and Parkinson's Diseases Curr. Opin. Chem. Biol. 2008, 12, 222-228
8. Robison, G.; Zakharova, T.; Fu, S.; Jiang, W.; Fulper, R.; Barrea, R.; Marcus, M. A.; Zheng, W.; Pushkar, Y. X-Ray Fluorescence Imaging: A New Tool for Studying Manganese Neurotoxicity PLoS One 2012, 7, e48899
9. Domaille, D. W.; Que, E. L.; Chang, C. J. Synthetic Fluorescent Sensors for Studying the Cell Biology of Metals Nat. Chem. Biol. 2008, 4, 168-175
10. Formica, M.; Fusi, V.; Giorgi, L.; Micheloni, M. New Fluorescent Chemosensors for Metal Ions in Solution Coord. Chem. Rev. 2012, 256, 170-192
11. Kim, H. M.; Cho, B. R. Two-Photon Fluorescent Probes for Metal Ions Chem.-Asian J. 2011, 6, 58-69
12. Ramirez, J.-Z.; Vargas, R.; Garza, J. The Role of Conformational Changes in the Signal Enhancement of a Selective Chemosensor of Pb2+ Phys. Chem. Chem. Phys. 2012, 14, 495-501
13. Zipfel, W. R.; Williams, R. M.; Webb, W. W. Nonlinear Magic: Multiphoton Microscopy in the Biosciences Nat. Biotechnol. 2003, 21, 1369-1377
14. Myung Kim, H.; Rae Cho, B. Two-Photon Materials with Large Two-Photon Cross Sections. Structure-Property Relationship Chem. Commun. 2009, 153-164
15. Dodani, S. C.; He, Q.; Chang, C. J. A Turn-On Fluorescent Sensor for Detecting Nickel in Living Cells J. Am. Chem. Soc. 2009, 131, 18020-18021
16. Zeng, L.; Miller, E. W.; Pralle, A.; Isacoff, E. Y.; Chang, C. J. A Selective Turn-On Fluorescent Sensor for Imaging Copper in Living Cells J. Am. Chem. Soc. 2006, 128, 10-11
17. Sumalekshmy, S.; Henary, M. M.; Siegel, N.; Lawson, P. V.; Wu; Schmidt, K.; Brédas, J.-L.; Perry, J. W.; Fahrni, C. J. Design of Emission Ratiometric Metal-Ion Sensors with Enhanced Two-Photon Cross Section and Brightness J. Am. Chem. Soc. 2007, 129, 11888-11889
18. Pond, S. J. K.; Tsutsumi, O.; Rumi, M.; Kwon, O.; Zojer, E.; Brédas, J.-L.; Marder, S. R.; Perry, J. W. Metal-Ion Sensing Fluorophores with Large Two-Photon Absorption Cross Sections: Aza-Crown Ether Substituted Donor-Acceptor-Donor Distyrylbenzenes J. Am. Chem. Soc. 2004, 126, 9291-9306
19. Olsen, J. M.; Aidas, K.; Kongsted, J. Excited States in Solution through Polarizable Embedding J. Chem. Theory Comput. 2010, 6, 3721-3734
20. Olsen, J. M. H.; Kongsted, J. Molecular Properties through Polarizable Embedding Adv. Quantum Chem. 2011, 61, 107-143
21. Barone, V.; Baiardi, A.; Biczysko, M.; Bloino, J.; Cappelli, C.; Lipparini, F. Implementation and Validation of a Multi-Purpose Virtual Spectrometer for Large Systems in Complex Environments Phys. Chem. Chem. Phys. 2012, 14, 12404-12422
22. Biczysko, M.; Bloino, J.; Brancato, G.; Cacelli, I.; Cappelli, C.; Ferretti, A.; Lami, A.; Monti, S.; Pedone, A.; Prampolini, G.; Puzzarini, C.; Santoro, F.; Trani, F.; Villani, G. Integrated Computational Approaches for Spectroscopic Studies of Molecular Systems in the Gas Phase and in Solution: Pyrimidine As a Test Case Theor. Chem. Acc. 2012, 131, 1201
23. Warshel, A.; Levitt, M. Theoretical Studies of Enzymic Reactions: Dielectric, Electrostatic and Steric Stabilization of the Carbonium Ion in the Reaction of Lysozyme J. Mol. Biol. 1976, 103, 227-249
24. Field, M. J.; Bash, P. A.; Karplus, M. A Combined Quantum Mechanical and Molecular Mechanical Potential for Molecular Dynamics Simulations J. Comput. Chem. 1990, 11, 700-733
25. Tomasi, J.; Mennucci, B.; Cammi, R. Quantum Mechanical Continuum Solvation Models Chem. Rev. 2005, 105, 2999-3094
26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Parandekar, P. V.; Mayhall, N. J.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fo, D. J. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
27. DALTON, a molecular electronic structure program, ReleaseDalton 2011. See http://daltonprogram.org/ (accessed May 20, 2013).
28. Breneman, C.; Wiberg, K. Determining Atom-Centered Monopoles from Molecular Electrostatic Potentials. The Need for High Sampling Density in Formamide Conformational Analysis J. Comput. Chem. 1990, 11, 361-373
29. Wang, J.; Wolf, R.; Caldwell, J.; Kollman, P.; Case, D. Development and Testing of a General AMBER force field J. Comput. Chem. 2004, 34, 1157-1174
30. Case, D. A.; Darden, T. A.; Cheatham, T. E.; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Crowley, M.; Walker, R. C.; Zhang, W.; Merz, K. M.; Wang, B.; Hayik, S.; Roitberg, A.; Seabra, G.; Kolossvai, I.; Wong, K. F.; Paesani, F.; Vanicek, J.; Wu, X.; Brozell, S. R.; Steibrecher, T.; Gohlke, H.; Yang, L.; Tan, C.; Mongan, J.; Hornak, V.; Cui, G.; Mathews, D. H.; Seetin, M. G.; Sagui, C.; Babin, V.; Kollman, P. A. Amber 11; University of California: San Francisco, CA, 2010.
31. Nielsen, C. B.; Christiansen, O.; Mikkelsen, K. V.; Kongsted, J. Density Functional Self-Consistent Quantum Mechanics/Molecular Mechanics Theory for Linear and Nonlinear Molecular Properties: Applications to Solvated Water and Formaldehyde J. Chem. Phys. 2007, 126, 154112
32. Hutter, J.; Parrinello, M.; Marx, D.; Focher, P.; Tuckerman, M.; Andreoni, W.; Curioni, A.; Fois, E.; Röthlisberger, U.; Giannozzi, P.; Deutsch, T.; Alavi, A.; Sebastiani, D.; Laio, A.; VandeVondele, J.; Seitsonen, A.; Billeter, S. Computer code CPMD, version 3.11; Copyright IBM Corp. and MPI-FKF Stuttgart, 1990-2002.
33. van Gunsteren, W. F.; Billeter, S. R.; Eising, A. A.; Hünenberger, P. H.; Krüger, P.; Mark, A. E.; Scott, W. R. P.; Tironi, I. Biomolecular Simulation: The GROMOS96 Manual and User Guide; Vdf Hochschulverlag AG an der ETH Zürich: Zürich, 1996.
34. Laio, A.; VandeVondele, J.; Rothlisberger, U. A Hamiltonian Electrostatic Coupling Scheme for Hybrid Car-Parrinello Molecular Dynamics Simulations J. Chem. Phys. 2006, 116, 6941
35. Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior Phys. Rev. A 1988, 38, 3098-3100
36. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density Phys. Rev. B 1988, 37, 785-789
37. Yanai, T.; Tew, D. P.; Handy, N. C. A New Hybrid Exchange-Correlation Functional Using the Coulomb-Attenuating Method (CAM-B3LYP) Chem. Phys. Lett. 2004, 393, 51-57
38. Peach, M. J. G.; Helgaker, T.; Sagek, P.; Keal, T. W.; Lutnæs, O. B.; Tozer, D. J.; Handy, N. C. Assessment of a Coulomb-Attenuated Exchange-Correlation Energy Functional Phys. Chem. Chem. Phys. 2006, 8, 558-562
39. Reichardt, C. Solvatochromic Dyes as Solvent Polarity Indicators Chem. Rev. 1994, 94, 2319-2358
40. Wielgus, M.; Zaleśny, R.; Arul Murugan, N.; Kongsted, J.; Ågren, H.; Samoc, M.; Bartkowiak, W. Two-Photon Solvatochromism II: Experimental and Theoretical Study of Solvent Effects on the Two-Photon Absorption Spectrum of Reichardt's Dye Chem. Phys. Chem. 2013, 14, 3731-3739
41. Olesiak-Banska, J.; Matczyszyn, K.; Zaleśny, R.; Arul Murugan, N.; Kongsted, J.; Ågren, H.; Bartkowiak, W.; Samoc, M. Revealing Spectral Features in Two-Photon Absorption Spectrum of Hoechst 33342: A Combined Experimental and Quantum-Chemical Study J. Phys. Chem. B 2013, 117, 12013-12019
42. Schafer, A.; Huber, C.; Ahlrichs, R. Fully Optimized Contracted Gaussian Basis Sets of Triple Zeta Valence Quality for Atoms Li to Kr J. Chem. Phys. 1994, 100, 5829-5835
43. Murugan, N. A.; Olsen, J. M. H.; Kongsted, J.; Rinkevicius, Z.; Aidas, K.; Ågren, H. Amyloid Fibril-Induced Structural and Spectral Modifications in the Thioflavin-T Optical Probe J. Phys. Chem. Lett. 2013, 4, 70-77
44. Murugan, N. A.; Kongsted, J.; Rinkevicius, Z.; Ågren, H. Color Modeling of Protein Optical Probes Phys. Chem. Chem. Phys. 2012, 14, 1107-1112
45. Murugan, N. A.; Kongsted, J.; Rinkevicius, Z.; Aidas, K.; Mikkelsen, K. V.; Ågren, H. Hybrid Density Functional Theory/Molecular Mechanics Calculations of Two-Photon Absorption of Dimethylamino Nitro Stilbene in Solution Phys. Chem. Chem. Phys. 2011, 13, 12506-12516
46. Murugan, N. A.; Kongsted, J.; Ågren, H. pH Induced Modulation of One and Two-Photon Absorption Properties in a Naphthalene Based Molecular Probe J. Chem. Theory Comput. 2013, 9, 36603669
47. Gagliardi, L.; Lindh, R.; Karlström, G. Local Properties of Quantum Chemical Systems: The LoProp Approach J. Chem. Phys. 2004, 121, 4494-4500
48. Aquilante, F.; De Vico, L.; Ferré, N.; Ghigo, G.; Malmqvist, P.-A.; Neogrády, P.; Pedersen, T. B.; Pitoňák, M.; Reiher, M.; Roos, B. O.; Serrano-Andrés, L.; Urban, M.; Veryazov, V.; Lindh, R. MOLCAS 7: The Next Generation J. Comput. Chem. 2010, 31, 224-247
49. Bourhill, G.; Bredas, J.-L.; Cheng, L.-T.; Marder, S. R.; Meyers, F.; Perry, J. W.; Tiemann, B. G. Experimental Demonstration of the Dependence of the First Hyperpolarizability of Donor-Acceptor-Substituted Polyenes on the Ground-State Polarization and Bond Length Alternation J. Am. Chem. Soc. 1994, 116, 2619-2620
50. Meyers, F.; Marder, S. R.; Pierce, B. M.; Bredas, J. L. Electric Field Modulated Nonlinear Optical Properties of Donor-Acceptor Polyenes: Sum-Over-States Investigation of the Relationship between Molecular Polarizabilities (.alpha.,.beta., and.gamma.) and Bond Length Alternation J. Am. Chem. Soc. 1994, 116, 10703-10714
51. De Mitri, N.; Monti, S.; Prampolini, G.; Barone, V. Absorption and Emission Spectra of a Flexible Dye in Solution: A Computational Time-Dependent Approach J. Chem. Theory Comput. 2013, 9, 4507-4516
52. Jacquemin, D.; Planchat, A.; Adamo, C.; Mennucci, B. TD-DFT Assessment of Functionals for Optical 00 Transitions in Solvated Dyes J. Chem. Theory Comput. 2012, 8, 2359-2372
53. Adamo, C.; Jacquemin, D. The Calculations of Excited-State Properties with Time-Dependent Density Functional Theory Chem. Soc. Rev. 2013, 42, 845-856
54. Olsen, J. M.; Aidas, K.; Mikkelsen, K. V.; Kongsted, J. Solvatochromic Shifts in Uracil: A Combined MD-QM/MM Study J. Chem. Theory Comput. 2010, 6, 249-256
55. Kongsted, J.; Osted, A.; Mikkelsen, K. V.; Åstrand, P.-O.; Christiansen, O. Solvent Effects on the n→π* Electronic Transition in Formaldehyde: A Combined Coupled Cluster/Molecular Dynamics Study J. Chem. Phys. 2004, 121, 8435
56. Murugan, N. A.; Rinkevicius, Z.; Ågren, H. Modeling Solvatochromism of Nile Red in Water Int. J. Quantum Chem. 2011, 111, 1521-1530
57. Albota, M. Design of Organic Molecules with Large Two-Photon Absorption Cross Sections Science 1998, 281, 1653-1656
58. Poulsen, T. D.; Frederiksen, P. K.; Jorgensen, M.; Mikkelsen, K. V.; Ogilby, P. R. Two-Photon Singlet Oxygen Sensitizers: Quantifying, Modeling, and Optimizing the Two-Photon Absorption Cross Section J. Phys. Chem. A 2001, 105, 11488-11495
59. Nayyar, I. H.; Masunov, A. E.; Tretiak, S. Comparison of TD-DFT Methods for the Calculation of Two-Photon Absorption Spectra of Oligophenylvinylenes J. Phys. Chem. C 2013, 117, 18170-18189
60. Day, P. N.; Nguyen, K. A.; Pachter, R. TDDFT Study of One- and Two-Photon Absorption Properties: π Donor-p-Acceptor Chromophores J. Phys. Chem. B 2005, 109, 1803-1814
61. Day, P. N.; Nguyen, K. A.; Pachter, R. Calculation of Two-Photon Absorption Spectra of Donor - Acceptor Compounds in Solution Using Quadratic Response Time-Dependent Density Functional Theory J. Chem. Phys. 2006, 125, 094103
62. Silva, D. L.; Murugan, N. A.; Kongsted, J.; Rinkevicius, Z.; Canuto, S.; Ågren, H. The Role of Molecular Conformation and Polarizable Embedding for One- and Two-Photon Absorption of Disperse Orange 3 in Solution J. Phys. Chem. B 2012, 116, 8169-8181
63. Kamada, K.; Iwase, Y.; Sakai, K.; Kondo, K.; Ohta, K. Cationic Two-Photon Absorption Chromophores with Double- and Triple-Bond Cores in Symmetric/Asymmetric Arrangements J. Phys. Chem. C 2009, 113, 11469-11474
64. Ohta, K.; Yamada, S.; Kamada, K.; Slepkov, A. D.; Hegmann, F. A.; Tykwinski, R. R.; Shirtcliff, L. D.; Haley, M. M.; Saek, P.; Gelmukhanov, F.; Ågren, H. Two-Photon Absorption Properties of Two-Dimensional-Conjugated Chromophores: Combined Experimental and Theoretical Study J. Phys. Chem. A 2011, 115, 105-117
65. Macoas, E.; Marcelo, G.; Pinto, S.; Caneque, T.; Cuadro, A. M.; Vaquero, J. J.; Martinho, J. M. G. A V-shaped cationic dye for nonlinear optical bioimaging Chem. Commun. 2011, 47, 7374-7376
66. Wilson, J. N.; Bunz, U. H. F. Switching of Intramolecular Charge Transfer in Cruciforms: Metal Ion Sensing J. Am. Chem. Soc. 2005, 127, 4124-4125
67. Cronstrand, P.; Luo, Y.; Ågren, H. Effects of Dipole Alignment and Channel Interference on Two-Photon Absorption Cross Sections of Two-Dimensional Charge-Transfer Systems J. Chem. Phys. 2002, 117, 11102
68. Alam, M. M.; Chattopadhyaya, M.; Chakrabarti, S. Enhancement of Twist Angle Dependent Two-Photon Activity through the Proper Alignment of Ground to Excited State and Excited State Dipole Moment Vectors J. Phys. Chem. A 2012, 116, 8067-8073