Type 1 phototherapeutic agents. 2. Cancer cell viability and ESR studies of tricyclic diarylamines

ACS Medicinal Chemistry Letters

Volumn 3, Issue 4, 2012, Pages 284-288

  Rajagopalan, Raghavan ^a   Lin, Tien Sung ^b   Karwa, Amolkumar S ^a   Poreddy, Amruta R ^a   Asmelash, Bethel ^a   Dorshow, Richard B ^a  

^a MEDTRONIC INC   (United States)

^b WASHINGTON UNIVERSITY   (United States)

Author keywords

Diarylamines; ESR; photosensitizers; radicals; ROS; type 1; type 2

Indexed keywords

9 PHENYLACRIDAN; ACRIDAN; AMINE; ANTINEOPLASTIC AGENT; PHOTOSENSITIZING AGENT; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CELL VIABILITY; DRUG EFFICACY; DRUG POTENCY; ELECTRON SPIN RESONANCE; IC 50; LIGHT EXPOSURE; PHOTOTOXICITY; PRIORITY JOURNAL; ULTRAVIOLET A RADIATION; ULTRAVIOLET B RADIATION;

EID: 84859772673     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200266v     Document Type: Article

References (30)

1. Nyst, H. J.; Tan, B. I.; Stewart, F. A.; Balm, A. J. M. Is Photodynamic Therapy a Good Alternative to Surgery and Radiotherapy in the Treatment of Head and Neck Cancer? Photodiagn. Photodyn Ther. 2009, 6, 3-11
2. Tierney, E.; Baker, A.; Ahdout, J.; Hanke, C. W.; Moy, R. L.; Kouba, D. J. Photodynamic Therapy for the Treatment of Neoplasia, Inflammatory Disorders, and Photoaging Dermatol. Surg. 2009, 35, 725-746
3. Moore, A. C. E.; Ortel, B.; Hasan, T. Mechanisms of Photodynamic Therapy. In Photodynamic Therapy; Patrice, T., Ed.; RSC: Cambridge, 2003; pp 19-57.
4. O'Connor, A. E.; Gallagher, W. M.; Byrne, A. T. Porphyrin and Non-porphyrin Photosensitizes in Oncology: Preclinical and Clinical Advances in Photodynamic Therapy Photochem. Photobiol. 2009, 85, 1053-1074
5. Rahmanto, A. S.; Morgan, P. E.; Hawkins, C. L.; Davies, M. J. Cellular Effects of Photogenerated Oxidants and Long-Lived, Reactive, Hydroperoxide Photoproducts Free Radical Biol. Med. 2010, 49, 1505-1515
6. Huang, A. A Review of progress in Clinical Photodynamic Therapy Technol. Cancer Res. Treat. 2005, 4, 283-293
7. Karwa, A.; Poreddy, A. R.; Asmelash, B.; Lin, T.-S.; Dorshow, R. B.; Rajagopalan, R. Type 1 Phototherapeutic Agents, Part I. Preparation and Cancer Cell Viability Studies of Novel Photolabile Sufenamides ACS Med. Chem. Lett. 2011, 2, 828-833
8. Wardman, P.; Dennis, M. F.; Everett, S. A.; Patel, K. B.; Stratford, M. R. L.; Tracy, M. Radicals from One-electron Reduction of Nitro Compounds, Aromatic N-Oxides, and Quinones: The Kinetic Basis for Hypoxia-Selective, Bioreductive Drugs. In Free Radicals and Oxidative Stress: Environment, Drugs, and Food Additives; Rice-Evans, C.; Halliwell, B.; Gunt, G. G., Eds.; Portland Press: London, 1995; pp- 171-194.
9. Hahn, S. M.; Wilson, L.; Krishna, C. M.; Leibman, J.; DeGraff, W.; Gamson, J.; Samuni, A.; Venzon, D.; Mitchell, J. B. Identification of Nitroxide Radioprotectors Radiat. Res. 1992, 132, 87-93
10. Lin, T.-S.; Retsky, J. ESR Studies of Photochemical Reactions of Diphenylamines, Phenothiazines and Phenoxazines J. Phys. Chem. B 1986, 90, 2687-2689
11. Gilbert, B. C.; Chiu, M. F.; Hanson, P. Electron Spin Resonance of Some Heterocyclic Radicals Containing Elements of Group VI J. Chem. Soc. [Sect. B]: Phys. Org. 1970, 9, 1700-1708
12. Rahn, R.; Schroeder, J.; Troe, J.; Grellman, K. H. Intensity-Dependent Ultraviolet Laser Flash Excitation of Diphenylamine in Methanol: A Two-Photon Ionization Mechansim Involving the Triplet State J. Phys. Chem. 1989, 93, 7841-7856
13. Martin, M.; Breheret, E.; Tfibel, F.; Lacourbas, B. Two-Photon Stepwise Dissociation of Carbazole in Solution J. Phys. Chem. 1980, 84, 70-72
14. Shukla, D.; Rege, de F.; Wan, P.; Johnston, L. J. Laser Flash Photolysis and Product Studies of the Photoionization of N-Methylacridan in aqueous solution J. Phys. Chem. 1991, 95, 10240-10246
15. Wang, Z.; McGimpsey, W. G. One- and Two-Laser Photochemistry of Iminodibenzyl J. Phys. Chem. 1993, 97, 9668-9672
16. Brede, O.; Maroz, A.; Hermann, R.; Naumov, S. Ionization of Cyclic Aromatic Amines by Free Electron Transfer: Products Are Governed by Molecule Flexibility J. Phys. Chem. 2005, 109, 8081-8087-9672
17. Viola, G.; Miolo, G.; Vedaldi, D.; Dall'Acqua, F. In Vitro Studies of the Phototoxic Potential of the Antidepressant Drug Amitriptyline and Imipramine Farmaco 2000, 55, 211-218 (Pubitemid 30488844)
18. Dutta, B.; Kar, G. K.; Ray, J. K. Direct Regioselective Phenylation of Acridine Derivatives with Phenyllithium Tetrahedron Lett. 2003, 44, 8641-8643 (Pubitemid 37324768)
19. Charbit, J. J.; Galy, A. M.; Galy, J. P.; Barbe, J. Preparation of Some New N-Substituted 9,10-Dihydroacridine Derivatives J. Chem. Eng. Data 1989, 34, 136-137
20. Allinger, N. L.; Youngdale, G. A. Aromatic and Pseudoaromatic Non-benzenoid Systems. III. The Synthesis of some Ten p-Electron Systems J. Am. Chem. Soc. 1962, 84, 1020-1026
21. Breslow, R.; Rajagopalan, R.; Schwarz, J. Selective Functionalization of Doubly Coordinated Flexible Chains J. Am. Chem. Soc. 1981, 103, 2905-2907
22. Hopff, H.; Gutenberg, H. 2-Vinylthianthrene and Its Polymerization Products Makromol. Chem. 1963, 60, 129-138
23. Janzen, E. G. Radical Addition Reactions of 5,5-Dimethyl-l-pyrroline-l- oxide. ESR Spin Trapping with a Cyclic Nitrone J. Magn. Reson. 1973, 9, 510-512
24. Migita, C. T.; Migita, K. Spin Trapping of the Nitrogen Radicals Chem. Lett. 2003, 32, 466-467
25. Xu, H. J.; Lin, S. Q.; Shen, S. Y.; Chen, D. W.; Xu, G. Z. Radical Mechanism in the Photoinduced Oxygen Transfer from Acridine N-Oxide to Cyclohexene J. Photochem. Photobiol., A: Chem. 1989, 48, 53-59
26. Cann, M. C. Formation of Acridine from the reaction of Dibenz[b,f]azepine with Silver(I): Formation of an Aromatic Nitrenium Ion? J. Org. Chem. 1988, 53, 1112-1113
27. Bausch, M. J.; Gostowski, R. Homolytic and Heterolytic Bond Strengths J. Org. Chem. 1991, 56, 6260-6262
28. Eyer, P. The Red Cell as a Sensitive Target for Activated Toxic Arylamines Arch. Toxicol., Suppl. 1983, 6, 3-12 (Pubitemid 13026863)
29. Harada, A. Cytotoxicity of Aniline Derivatives Igakkai Zasshi 1990, 99, 233-247
30. Pinto-Basto, D.; Silva, J. P.; Queiroz, M. J.; Moreno, A. J.; Coutinho, O. P. Antioxidant Activity of Synthetic Diarylamiines: A Mitochondrial and Cellular Approach Mitochondrion 2009, 9, 17-26