Photochemistry of pheomelanin building blocks and model chromophores: Excited-state intra- and intermolecular proton transfer

Journal of Physical Chemistry Letters

Volumn 5, Issue 12, 2014, Pages 2094-2100

  El Nahhas, Amal ^a   Pascher, Torbjörn ^a   Leone, Loredana ^b   Panzella, Lucia ^b   Napolitano, Alessandra ^b   Sundström, Villy ^a  

^a LUND UNIVERSITY   (Sweden)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

6 (2 amino 2 carboxyethyl) 4 hydroxy 1,3 benzothiazole (BT); 6 (2 amino 2 carboxyethyl) 4 hydroxy 1,3 benzothiazole 2 carboxylic acid (BTCA); excited state proton transfer; pheomelanin; time resolved fluorescence

Indexed keywords

CHEMICAL REACTIONS; CHROMOPHORES; FLUORESCENCE SPECTROSCOPY; PROTON TRANSFER;

6-(2-AMINO-2-CARBOXYETHYL)-4-HYDROXY-1,3-BENZOTHIAZOLE (BT); 6-(2-AMINO-2-CARBOXYETHYL)-4-HYDROXY-1,3-BENZOTHIAZOLE-2-CARBOXYLIC ACID (BTCA); EXCITED-STATE PROTON TRANSFER; PHEOMELANIN; TIME-RESOLVED FLUORESCENCE;

EXCITED STATES;

EID: 84903144136     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz500720g     Document Type: Article

References (27)

1. Napolitano, A.; Panzella, L.; Leone, L.; d'Ischia, M. Red Hair Benzothiazines and Benzothiazoles: Mutation-Inspired Chemistry in the Quest for Functionality Acc. Chem. Res. 2013, 46, 519-528
2. Rouzaud, F.; Kadekaro, A. L.; Abdel-Malek, Z. A.; Hearing, V. J. MC1R and the Response of Melanocytes to Ultraviolet Radiation Mutat. Res. 2005, 571, 133-152
3. Chedekel, M. R.; Smith, S. K.; Post, P. W.; Pokora, A.; Vessel, D. L. Photodestruction of Pheomelanin: Role of Oxygen Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 5395-5399
4. Panzella, L.; Szewczyk, G.; d'Ischia, M.; Napolitano, A.; Sarna, T. Zinc-Induced Structural Effects Enhance Oxygen Consumption and Superoxide Generation in Synthetic Pheomelanins on UVA/Visible Light Irradiation Photochem. Photobiol. 2010, 86, 757-764
5. Takeuchi, S.; Zhang, W.; Wakamatsu, K.; Ito, S.; Hearing, V. J.; Kraemer, K. H.; Brash, D. E. Melanin Acts as a Potent UVB Photosensitizer to Cause an Atypical Mode of Cell Death in Murine Skin Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 15076-15081
6. Wenczl, E.; Van der Schans, G. P.; Roza, L.; Kolb, R. M.; Timmerman, A. J.; Smit, N. P.; Pavel, S.; Schothorst, A. A. (Pheo)melanin Photosensitizes UVA-Induced DNA Damage in Cultured Human Melanocytes J. Invest. Dermatol. 1998, 111, 678-682
7. Napolitano, A.; Memoli, S.; Crescenzi, O.; Prota, G. Oxidative Polymerization of the Pheomelanin Precursor 5-Hydroxy-1,4-benzothiazinylalanine: a New Hint to the Pigment Structure J. Org. Chem. 1996, 61, 598-604
8. Greco, G.; Panzella, L.; Verotta, L.; d'Ischia, M.; Napolitano, A. Uncovering the Structure of Human Red Hair Pheomelanin: Benzothiazolylthiazinodihydroisoquinolines as Key Building Blocks J. Nat. Prod 2011, 74, 675-682
9. Wakamatsu, K.; Nakanishi, Y.; Miyazaki, N.; Kolbe, L.; Ito, S. UVA-induced Oxidative Degradation of Melanins: Fission of Indole Moiety in Eumelanin and Conversion to Benzothiazole Moiety in Pheomelanin Pigm. Cell Melanoma Res. 2012, 25, 434-445
10. Greco, G.; Wakamatsu, K.; Panzella, L.; Ito, S.; Napolitano, A.; d'Ischia, M. Isomeric Cysteinyldopas Provide a (Photo)degradable Bulk Component and a Robust Structural Element in Red Human Hair Pheomelanin Pigm. Cell Melanoma Res. 2009, 22, 319-327
11. Becker, R. S.; Lenoble, C.; Zein, A. A Comprehensive Investigation of the Photophysics and Photochemistry of Salicylideneaniline and Derivatives of Phenylbenzothiazole Including Solvent Effects J. Phys. Chem. 1987, 91, 3509-3511
12. Potter, C. A. S.; Brown, R. G.; Vollmer, F.; Rettig, W. Role of Twisted Intramolecular Charge-Transfer States in the Decay of 2-(2′-Hydroxyphenyl) benzothiazole following Excited-State Intramolecular Proton Transfer J. Chem. Soc., Faraday Trans. 1994, 90, 59-67
13. Luber, S.; Adamczyk, K.; Nibbering, E. T. J.; Batista, V. S. Photoinduced Proton Coupled Electron Transfer in 2-(2′-Hydroxyphenyl)-Benzothiazole J. Phys. Chem. A 2013, 117, 5269-5279
14. Douhal, A.; Sanza, M.; Tormo, L.; Organero, J. A. Femtochemistry of Inter- and Intramolecular Hydrogen Bonds ChemPhysChem 2005, 6, 419-423
15. Greco, G.; Panzella, L.; Napolitano, A.; d'Ischia, M. Biologically Inspired One-pot Access Routes to 4-Hydroxybenzothiazole Amino Acids, Red Hair-Specific Markers of UV Susceptibility and Skin Cancer Risk Tetrahedron Lett. 2009, 50, 3095-3097
16. Catallo, W. J.; Junk, T. Transformation of Benzothiazole in Estauarine Sediments J. Environ. Qual. 2005, 34, 1746-1754
17. Todesco, P. E.; Vivarelli, P. Research on Benzothiazoles. VI. Acidity of Benzothiazole-2-carboxylic acid Gazz. Chim. Ital. 1964, 94, 372-381
18. Berg, J. M.; Tymoczko, J. L.; Stryer, L. Biochemistry; W. H. Freeman and Company: New York, 2002.
19. Feng, P. K.; Fernando, Q. Stabilities of Divalent Metal Complexes of 4-Hydroxybenzothiazole J. Org. Chem. 1960, 82, 2115-2118
20. Potter, C. A. S.; Brown, R. G. Excited-State Intramolecular Proton Transfer in Polar Solutions of 2-(2′-Hydroxyphenyl)benzothiazole Chem. Phys. Lett. 1988, 153, 7-12
21. Gauden, M.; Pezzella, A.; Panzella, L.; Neves-Petersen, M.; Skovsen, E.; Petersen, S. B.; Mullen, K. M.; Napolitano, A.; d'Ischia, M.; Sundström, V. Role of Solvent, pH, and Molecular Size in Excited-State Deactivation of Key Eumelanin Building Blocks: Implications for Melanin Pigment Photostability J. Am. Chem. Soc. 2008, 130, 17038-17043
22. Gauden, M.; Pezzella, A.; Panzella, L.; Napolitano, A.; d'Ischia, M.; Sundström, V. Ultrafast Excited State Dynamics of 5,6-Dhydroxyindole, a Key Eumelanin Building Block: Nonradiative Decay Mechanism J. Phys. Chem. B 2009, 113, 12575-12580
23. Huijser, A.; Pezzella, A.; Hannestad, J. K.; Panzella, L.; Napolitano, A.; d'Ischia, M.; Sundström, V. UV-Dissipation Mechanisms in the Eumelanin Building Block DHICA ChemPhysChem 2010, 11, 2424-2431
24. Corani, A.; Huijser, A.; Iadonisi, A.; Pezzella, A.; Sundström, V.; d'Ischia, M. Bottom- Up Approach to Eumelanin Photoprotection: Emission Dynamics in Parallel Sets of Water-Soluble 5,6-Dihydroxyindole-Based Model Systems J. Phys. Chem. B 2012, 116, 13151-13158
25. Corani, A.; Pezzella, A.; Pascher, T.; Gustavsson, T.; Markovitsi, D.; Huijser, A.; d'Ischia, M.; Sundström, V. Excited-State Proton-Transfer Processes of DHICA Resolved: From Sub-Picoseconds to Nanoseconds J. Phys. Chem. Lett. 2013, 4, 1383-1388
26. Leupold, D.; Scholz, M.; Stankovic, G.; Reda, J.; Buder, S.; Eichhorn, R.; Wessler, G.; Stucker, M.; Hoffmann, K.; Bauer, J. The Stepwise Two-Photon Excited Melanin Fluorescence Is a Unique Diagnostic Tool for the Detection of Malignant Transformation in Melanocytes Pigm. Cell Melanoma Res. 2011, 24, 438-445
27. Nighswander-Rempel, S. P. Quantitative Fluorescence Spectra and Quantum Yield Map of Synthetic Pheomelanin Biopolymers 2006, 82, 631-637