Photodegradation of 2-chloro substituted phenothiazines in alcohols

Photochemistry and Photobiology

Volumn 85, Issue 1, 2009, Pages 160-170

  García, Carmelo ^a   Piñero, Luis ^a,b   Oyola, Rolando ^a   Arce, Rafael ^b  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^b UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CHLORINE DERIVATIVE; PHENOTHIAZINE; PHENOTHIAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; PHOTOLYSIS;

ALCOHOLS; CHLORINE COMPOUNDS; KINETICS; MOLECULAR STRUCTURE; PHENOTHIAZINES; PHOTOLYSIS;

EID: 58349090542     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2008.00412.x     Document Type: Article

References (45)

1. Kochevar, I. E. (1981) Phototoxicity mechanism: Chlorpromazine photosensitized damage to DNA and cell membranes. J. Invest. Dermatol. 76, 59 64.
2. Kochevar, I. E. (1987) Mechanisms of drug photosensitization. Photochem. Photobiol. 45, 891 895.
3. Kochevar, I. E. J. Hom (1983) Photoproducts of chlorpromazine that cause red blood cell lysis. Photochem. Photobiol. 37, 163 168.
4. Curry, S. H. (1970) Plasma protein binding of chlorpromazine. J. Pharm. Pharmacol. 22, 193 197.
5. Davis, A. K., S. Navaratnam G. O. Phillips (1976) Photochemistry of chlorpromazine (2-chloro-N-(3dimethylamino propyl) phenothiazine) in propan-2-ol solution. J. Chem. Soc. Perkin Trans. II 25, 25 29.
6. Grant, F. W. J. Green (1972) Phototoxicity and photonucleophilic aromatic substitution in chlorpromazine. Toxic. Appl. Pharmacol. 23, 71 74.
7. Epstein, S. (1968) Chlorpromazine photosensitivity, phototoxic and photoallergic reactions. Arch. Dermatol. 98, 354 363.
8. Kahn, G. B. P. Davis (1970) In vitro studies on longwave ultraviolet light dependent reactions of the skin photosensitizer chlorpromazine with nucleic acids. Purines and pyrimidines. J. Invest. Dermatol. 55, 47 53.
9. Ciulla, T. A., G. A. Epling I. E. Kochevar (1986) Photoaddition of chlorpromazine to guanosine-5'-monophosphate. Photochem. Photobiol. 43, 607 613.
10. Fujita, H., F. Yanagisawa, A. Endo K. Suzuki (1980) Photoreactivity of chlorpromazine with native DNA in an aqueous solution. J. Radiat. Res. 21, 279 287.
11. Fujita, H., A. Endo K. Suzuki (1981) Inactivation of bacteriophage lambda by near ultraviolet irradiation in the presence of chlorpromazine. Photochem. Photobiol. 33, 215 222.
12. Iwaoka, T. M. Kondo (1974) Mechanistic studies on the photooxidation of chlorpromazine in water and ethanol. Bull. Chem. Soc. Japan 47, 980 986.
13. Kochevar, I. E., F. Chung A. M. Jeffrey (1984) Photoaddition of chlorpromazine to DNA. Chem. Biol. Interact. 51, 273 284.
14. Ljunggren, B. H. Möller (1977) Phenothiazine phototoxicity: An experimental study on chlorpromazine and its metabolites. J. Invest. Dermatol. 68, 313 317.
15. Buettner, G. R., A. G. Motten, R. D. Hall C. F. Chignell (1986) Free radical production by chlorpromazine sulfoxide. An ESR spin trapping and flash photolysis study. Photochem. Photobiol. 44, 5 10.
16. Rosenthal, I., E. BenHur, A. Prager E. Riklis (1978) Photochemical reactions of chlorpromazine: Chemical and biochemical implications. Photochem. Photobiol. 28, 591 594.
17. Schoonderwoerd, S., G. Beijerbergen, V. Henegouwen J. Leijendijk (1988) Photobinding of chlorpromazine and its sulfoxide in vitro and in vivo. Photochem. Photobiol. 48, 621 626.
18. Kochevar, I. E., C. Garcia N. E. Geacintov (1998) Photoaddition to DNA by nonintercalated chlorpromazine molecules. Photochem. Photobiol. 68 (5 692 697.
19. García, C., G. A. Smith, M. Grant, I. E. Kochevar R. W. Redmond (1995) Mechanism and solvent dependence for the photoionization of promazine and chlorpromazine. J. Am. Chem. Soc. 117, 10871 10877.
20. García, C., R. Oyola, L. E. Piñero, R. Arce, J. Silva V. Sánchez (2005) Substitution and solvent effect on the photophysical properties of several series of 10-alkylated phenothiazine derivatives. J. Phys. Chem. A 109, 3360 3371.
21. Oyola, R. (2001) Design, construction and use of a nanosecond laser transient absorption spectrokinetic system for the study of the photochemical and photophysical properties of relevant biological molecules: dTpA, dApT and Tricyclic antidepressive drugs. Ph.D. thesis, University of Puerto Rico, Rio Piedras.
22. Felmeister, A. C. A. Discher (1964) Photodegradation of chlorpromazine hydrochloride. J. Pharm. Sci. 53, 756 762.
23. Bunce, N. J., Y. Kumar L. Ravanal (1979) Phototoxicity of chlorpromazine. J. Med. Chem. 22, 202 204.
24. Moore, D. S. Tamat (1980) Photosensitization by drugs: Photolysis of some chlorine-containing drugs. J. Pharm. Pharmacol. 32, 172 177.
25. Kricka, L. J. A. Ledwith (1972) Reactions of condensed N-heteroaromatic molecules. Part I. Alkylation by thallium(I)ethoxide. J. Chem. Soc. Perkin Trans. 1, 2292 2293.
26. Wang, Z. W. G. McGimpsey (1993) One and two laser photochemistry of iminodibenzyl. J. Phys. Chem. 97, 9668 9672.
27. Kuhn, H. J., S. E. Braslavsky R. Schmidt (1989) Chemical actinometry. Pure Appl. Chem. 61 (2 187 210.
28. García, C., R. Oyola, L. E. Piñero, N. Cruz, F. Alejando, R. Arce I. Nieves (2002) Photophysical, electrochemical and theoretical study of protriptyline in several solvents. J. Phys. Chem. B 106, 9794 9801.
29. Benson, S. W. (1976) Thermochemical Kinetics: Methods for the Estimation of Thermochemical Data and Rate Parameter. John Wiley & Sons, New York.
30. McMillen, D. F. D. M. Golden (1982) Hydrocarbon bond dissociation energies. Annu. Rev. Phys. Chem. 33, 493 532.
31. (NISTWebBook) (2005) NIST Standard Reference Database Number 69. http://webbook.nist.gov/chemistry. Accessed June 2008.
32. Wedenejew, V. W., L. W. Gurwitsch, W. H. Kondratjew, W. A. Medwedew E. L. Frankenwitsch (1971) Energien chemischer bindungen, Ionisationspotentiale und Elektronenaffinitae VEB Deutcher Verlag Fuer Grundstoffindustrie. Leipzig, Germany.
33. Mäuser, H. (1974) Formale Kinetic: Experimentelle Methoden der Physik und der Chemie. Bertelsmann Universitätsverlag 1, 297 363.
34. Daniil, D., G. Gauglitz H. Meier (1977) Kinetic investigation of the photolysis of 2-oxo-2,5-dihydro-1,3,4-oxadiazoles. Photochem. Photobiol. 26, 225 229.
35. Mäuser, H. G. Gauglitz (1998) Photokinetics: Theoretical fundamentals and applications. In Comprehensive Chemical Kinetics, Vol. 36 (Edited by R. G. Compton G. Hancock pp. 342 369. Elsevier Science Publishers, New York.
36. Aaron, J., M. Maafi, C. Kersebet, C. Párkányi, A. M. Shafik N. Motohashi (1996) A solvatochromic study of new benzo [a] phenothiazines for the determination of dipole moments and specific solute solvent interactions in the first excited singlet state. J. Photochem. Photobiol. A, Chem. 101, 127 136.
37. Casarotto, M. G. D. J. Craick (2001) Ring flexibility within tricyclic antidepressant drugs. J. Pharm. Pharmac. Sci. 90, 713 721.
38. 13C NMR studies of the solution molecular dynamics of Tricyclic antidepressants. Magn. Reson. Chem. 28, 533 540.
39. Elisei, F., L. Latterini, G. G. Aloisi, U. Mazzucato, G. Viola, G. Miolo, D. Vedaldi F. Dall'Acqua (2002) Excited state properties and in vitro phototoxicity studies of three phenothiazine derivatives. Photochem. Photobiol. 75 (1 11 21.
40. Turro, N J, I. V. Khudyakov H. v. Willigen (1995) Photoionization of phenothiazine: EPR detection of reactions of the polarized solvated electron. J. Am. Chem. Soc. 117 (49 12273 12280.
41. Barra, M., G. S. Calabrese, M. T. Allen, R. W. Redmond, R. Sinta, A. A. Lamola, R. D. Small J. Scaiano (1991) Photophysical and photochemical studies of phenothiazine and some derivatives: Explanatory studies of novel photosensitizers for photoresist technology. Chem. Mater. 3, 610 616.
42. Toth, M. (1980) Triplet-triplet absorption of cyclohexadiene-1,3 and ergosterol-Sensitized total ground state depletion of dienes by triplet energy transfer from the ruby laser excited 2fluorenylphenylketone. Chem. Phys. Lett. 46, 437 443.
43. Wright, J. S., E. R. Johnson G. A. DiLabio (2001) Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants. J. Am. Chem. Soc. 123, 1173 1183.
44. Piñero, L. E. (2006) Synthesis, characterization, photophysics, and photochemistry of 2chlorinated phenothiazine derivatives in several solvents. Master thesis, University of Puerto Rico, Rio Piedras, Puerto Rico.
45. Chignell, C. F. (1972) Application of physicochemical and analytic techniques to the study of drug interactions with biological systems. CRC Crit. Rev. Toxicol. 413 465.