Exposure of Chlorpromazine to 266 nm Laser Beam Generates New Species with Antibacterial Properties: Contributions to Development of a New Process for Drug Discovery

PLoS ONE

Volumn 8, Issue 2, 2013, Pages

  Pascu, Mihail Lucian ^a,e   Danko, Balazs ^b   Martins, Ana ^b   Jedlinszki, Nikoletta ^b   Alexandru, Tatiana ^a,e   Nastasa, Viorel ^a,e   Boni, Mihai ^a,e   Militaru, Andra ^a,e   Andrei, Ionut Relu ^a   Staicu, Angela ^a   Hunyadi, Attila ^b   Fanning, Seamus ^c   Amaral, Leonard ^d  

^a NATIONAL INSTITUTE FOR LASER   (Romania)

^b UNIVERSITY OF SZEGED   (Hungary)

^c UNIVERSITY COLLEGE DUBLIN   (Ireland)

^d INSTITUTO DE HIGIENE E MEDICINA TROPICAL   (Portugal)

^e UNIVERSITY OF BUCHAREST   (Romania)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORPROMAZINE; CHLORPROMAZINE SULFOXIDE; PROMAZINE;

ABSORPTION SPECTROSCOPY; ANTIBACTERIAL ACTIVITY; ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DIODE LASER; DRUG EXPOSURE; DRUG STRUCTURE; ENERGY YIELD; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LASER; NEW SPECIES; NONHUMAN; QUANTITATIVE ANALYSIS; SENSITIVITY ANALYSIS; SPECTROPHOTOMETRY; STAPHYLOCOCCUS AUREUS; TANDEM MASS SPECTROMETRY; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET RADIATION;

ANTI-BACTERIAL AGENTS; CHLORPROMAZINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; DOPAMINE ANTAGONISTS; DRUG DISCOVERY; LASERS; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCUS AUREUS; TANDEM MASS SPECTROMETRY;

EID: 84873529839     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0055767     Document Type: Article

References (60)

1. Ehrlich P (1959-60) Papers reprinted in The Collected Papers of Paul Ehrlich (Editors F. Himmelweit, M. Marquardt and H. H. Dale), vol III. London: Pergamon. 1913 Chemo-therapy 3: 505-518.
2. Amaral L, Viveiros M, Molnar J, Kristiansen JE, (2011) Effective Therapy with the Neuroleptic Thioridazine as an Adjunct to Second Line of Defence Drugs, and the Potential that Thioridazine Offers for New Patents that Cover a Variety of "New Uses". Recent Patents Anti-Infective Drug Discovery 6: 284-287.
3. Kyle DE, Milhous WK, Rossan RN, (1993) Reversal of Plasmodium falciparum resistance to chloroquine in Panamanian Aotus monkeys. Am J Trop Med Hyg 48: 126-133.
4. Kristiansen JE, Amaral L, (1997) The potential management of resistant infections with non-antibiotics. J Antimicrob Chemother 40: 319-327.
5. Amaral L, Kristiansen JE, Abebe LS, Millett W, (1996) Inhibition of the respiration of multi-drug resistant clinical isolates of Mycobacterium tuberculosis by thioridazine: potential use for initial therapy of freshly diagnosed tuberculosis. J Antimicrob Chemother 38: 1049-1053.
6. Amaral L, Martins A, Molnar J, Kristiansen JE, Martins M, et al. (2010) Phenothiazines, bacterial efflux pumps and targeting the macrophage for enhanced killing of intracellular XDRTB. In Vivo 24: 409-424.
7. Amaral L, Martins M, Viveiros M, Molnar J, Kristiansen JE, (2008) Promising therapy of XDR-TB/MDR-TB with thioridazine an inhibitor of bacterial efflux pumps. Curr Drug Targets 9: 816-819.
8. Martins M, Viveiros M, Kristiansen JE, Molnar J, Amaral L, (2007) The curative activity of thioridazine on mice infected with Mycobacterium tuberculosis. In Vivo 21: 771-775.
9. Amaral L, Viveiros M, Kristiansen JE, (2006) "Non-Antibiotics": alternative therapy for the management of MDRTB and MRSA in economically disadvantaged countries. Curr Drug Targets 7: 887-891.
10. Viveiros M, Martins M, Couto I, Kristiansen JE, Molnar J, et al. (2005) The in vitro activity of phenothiazines against Mycobacterium avium: potential of thioridazine for therapy of the co-infected AIDS patient. In Vivo 19: 733-736.
11. Ordway D, Viveiros M, Leandro C, Bettencourt R, Almeida J, et al. (2003) Clinical concentrations of thioridazine kill intracellular multidrug-resistant Mycobacterium tuberculosis. Antimicrob Agents Chemother 47: 917-922.
12. Amaral L, Viveiros M, Kristiansen JE, (2001) Phenothiazines: potential alternatives for the management of antibiotic resistant infections of tuberculosis and malaria in developing countries. Trop Med Int Health 6: 1016-1022.
13. Amaral L, Kristiansen JE, Viveiros M, Atouguia J, (2001) Activity of phenothiazines against antibiotic-resistant Mycobacterium tuberculosis: a review supporting further studies that may elucidate the potential use of thioridazine as anti-tuberculosis therapy. J Antimicrob Chemother 47: 505-511.
14. Amaral L, Kristiansen JE, (2000) Phenothiazines: an alternative to conventional therapy for the initial management of suspected multidrug resistant tuberculosis. A call for studies. Int J Antimicrob Agents 14: 173-176.
15. Minder R, Schnetzer F, Bickel MH, (1971) Hepatic and extrahepatic metabolism of the psychotropic drugs, chlorpromazine, imipramine, and imipramine-N-oxide. Archives of Pharmacol 268: 334-347.
16. Nałe{ogonek}cz-Jawecki G, Wójcik T, Sawicki J, (2008) Evaluation of in vitro biotransformation of propranolol with HPLC, MS/MS, and two bioassays. Environmental Toxicology 23 (1): 52-58 DOI: 10.1002/tox.20310.
17. Arce R, Garcia C, Oyola R, Piñero L, Nieves I, et al. (2003) Photophysical and photochemical properties of amitriptyline and notriptyline hydrochloride: a 266 nm nanosecond laser flash and theoretical study. J Photochem Photobiol A: Chem 154: 245-257.
18. García C, Oyola R, Piñero LE, Cruz N, Alejando F, et al. (2002) Photophysical, electrochemical and theoretical study of protriptyline in several solvents. J Phys Chem B 106: 9794-9801.
19. García C, Oyola R, Piñero LE, Hernández D, Arce R, (2008) Photophysics and photochemistry of imipramine, desimipramine and clomipramine in several solvents: a fluorescence, 266 nm laser flash and theoretical study. J Phys Chem A 112: 168-178.
20. Kochevar IE, (1980) Posible mechanisms of toxicity due to photochemical products of protriptyline. Toxic. Appl Pharmacol 54: 258-264.
21. Piñero LE, García C, Lhiaubet-Vallet V, Oyola R, Miranda MA, (2009) Photophysics and phototchemistry of Z-Chlorprothixene in acetonitrile. Photochem Photobiol 85: 895-900.
22. García C, Oyola R, Piñero LE, Arce R, Silva J, et al. (2005) Substitution and solvent effect on the photophysical properties of several series of 10-alkylatedphenothiazine derivatives. J Phys Chem A 109: 3360-3371.
23. García C, Piñero L, Oyola R, Arce R, (2009) Photodegradation of 2-chloro substituted phenothiazines in alcohols. Photochem Photobiol 85: 160-170.
24. McIntosh M, Leona N, Katneni K, Morizzi J, Schackleford D, et al. (2010) Impact of chlorpromazine self-association on its apparent binding constant with cyclodextrins: effect of SBE7-b-CD on the disposition of chlorpromazine in the rat. J Pharm Sc 99: 2999-3008.
25. Kochevar IE, Lamola AA, (1979) Chlorpromazine and protriptyline phototoxicity: photosensitized oxygen independent red cell hemolysis. Photochem Photobiol 29: 791-795.
26. Kochevar IE, Chung F, Jeffrey AM, (1984) Photoaddition of chlorpromazine to DNA. Chem Biol Interactions 51: 273-284.
27. Kochevar IE, Garcia C, Geacintov NE, (1998) Photoaddition to DNA by nonintercalated chlorpromazine molecules. Photochem Photobiol 68(5): 692-697.
28. Ciamician G, Silber P, (1908) Chemische Lichtwirkungen. Chemische Berichte 41 (2) (): 1928 DOI:10.1002/cber.19080410272.
29. Nałecz-Jawecki G, Hajnas A, Sawicki J, (2008) Photodegradation and phototoxicity of thioridazine and chlorpromazine evaluated with chemical analysis and aquatic organisms. Ecotoxicology 17 (1) (): 13-20 PMID 17929167.
30. Drucker AM, Rosen CF, (2011) Drug-induced photosensitivity: culprit drugs, management and prevention. Drug Saf 34: 821-837.
31. Chignell CF, Motten AG, Buettner GR, (1985) Photoinduced free radicals from chlorpromazine and related phenothiazines: relationship to phenothiazine-induced photosensitization. Environ Health Perspect 64: 103-110.
32. Buettner GR, Hall RD, Chignell CF, Motten AG, (1989) The stepwise biphotonic photoionization of chlorpromazine as seen by laser flash photolysis. Photochem Photobiol 49: 249-256.
33. Navartnam S, Parsons BJ, Phillips GO, Davies AK, (1978) Laser flash photolysis study of the photoionisation of chlorpromazine and promazine in solution. J Chem Soc, Faraday Trans 1 74: 1811-1819 DOI: 10.1039/F19787401811.
34. Kochevar I E, Hom J, (1983) Photoproducts of chlorpromazine that cause red blood cell lisis. Photochem Photobiol 37: 163-168.
35. García C, Smith G A, Grant M, Kochevar IE, Redmond RW, (1995) Mechanism and solvent dependence for the photoionization of promazine and chlorpromazine. J Am Chem Soc 117: 10871-10877.
36. Caber-Ud-Din M, Al-Ahmadi D A, Naqvi AZ, Akram M, (2009) Micellar properties of phenothiazine drug in presence of additives. Colloid Journal 71: 498-502 DOI:10.1134/S1061933X09040115.
37. Pascu ML, Nastasa V, Smarandache A, Militaru A, Martins A, et al. (2011) Direct modification of bioactive phenothiazines by exposure to laser radiation. Recent Patents on Anti-Infective Drug Discovery 6 (2) (): 147-157.
38. Binford JS, Palm WH, (1994) Absorption of surfactants by membranes: Erythrocytes versus synthetic vesicles. Biophysical Journal 66: 2024-2028.
39. Odian G (2004) Principles of polymerization. Fourth Edition, Wiley -Interscience, Hoboken, New Jersey page 352.
40. McIntosh MP, Leong N, Katneni K, Morizzi J, Shackleford DM, et al. (2010) Impact of chlorpromazine self-association on its apparent binding constants with cyclodextrins: effect of SBE7-b-CD on the disposition of chlorpromazine in the rat. J Pharm Sci 99: 2999-3008 DOI 10.1002/jps.22064.
41. Schreier S, Malheiros SVP, de Paula E, (2000) Surface active drugs: self-association and interaction with membranes and surfactants. Physicochemical and biological aspects. Biochimica et Biophysica Acta 1508: 210-234.
42. Beijersbergen Van Henegouwen GMJ (1997) Medicinal Photochemistry: Phototoxic and Photothrrapeutic Aspects and Drugs. In Advances in Drug Research,. vol.29, page 119, Testa B, Meyer UA (Eds), Academic Press, San Diego, Ca (USA).
43. Clinical and Laboratory Standards Institute (2007) Performance Standards for Antimicrobial Susceptibility Testing. 17th Informational Supplement. Document M100-s17. Wayne, AO: CLSI.
44. Koenig JL (1999) Spectroscopy of Polymers, 2nd ed.;.Elsevier Science: New York.
45. Würthner F, Kaiser TE, Saha-Möller CR, (2011) J-Aggregates: From Serendipitous Discovery to Supramolecular Engineering of Functional Dye Materials. Angewandte Chemie International Edition 50: 3376-3410 DOI: 10.1002/anie.201002307.
46. Ray RS, Agrawal N, Sharma A, Hans RK, (2008) Use of L-929 cell line for phototoxicity assessment. Toxicol In Vitro 22: 1775-1781.
47. Davies AK, Navaratnam S, Phillips GO, (1976) Photochemistry of chlorpromazine [2-chloro-N-(3-dimethylaminopropyl) phenothiazinel in propan-2-ol solution. J Chem Soc Perkin II: 25-29.
48. Huang CL, (1962) Isolation and characterization of chlorpromazine derivatives produced by UV irradiation. Psychopharmacol Serv Cent Bull 2: 54-55.
49. Felmeister A, Discher CA, (1964) Photodegradation of chlorpromazine hydrochloride. J Pharm Sci 53: 756-762.
50. Grant FW, Greene J, (1972) Phototoxicity and photonucleophilic aromatic substitution in chlorpromazine. Toxicol Appl Pharmacol 23: 71-74.
51. Motten AG, Buettner GR, Chignell CF, (1983) Spectroscopic studies of cutaneous photosensitizing agents, VIII. A spin trapping study of light induced free radicals from chlorpromazine and promazine. Photochem Photobiol 42: 9-16.
52. Buettner GR, Motten AG, Hall RD, Chignell CF, (1986) Free radical production by chlorpromazine sulfoxide, an ESR spin-traping and flash photolysis study. Photochem Potobiol 4 (1) (): 5-10 DOI(2008): 10.1111/j.1751-1097.1986.tb03556.x.
53. Prema K, Gopinathan KP, (1974) Involvement of the superoxide anion in sulphoxidation. Biochem J 137: 119-121.
54. Martins M, Bleiss W, Marko A, Ordway D, Viveiros M, et al. (2004) Clinical concentrations of thioridazine enhance the killing of intracellular methicillin-resistant Staphylococcus aureus: an in vivo, ex vivo and electron microscopy study. In Vivo 18: 787-794.
55. Sala C, Haouz A, Saul FA, Miras I, Rosenkrands I, et al. (2009) Genome-wide regulon and crystal structure of BlaI (Rv1846c) from Mycobacterium tuberculosis. Mol Microbiol 71: 1102-1116.
56. Arakaki AK, Tian W, Skolnick J, (2006) High precision multi-genome scale reannotation of enzyme function by EFICAz. BMC Genomics 7: 315.
57. Itou H, Okada U, Suzuki H, Yao M, Wachi M, et al. (2005) The CGL2612 protein from Corynebacterium glutamicum is a drug resistance-related transcriptional repressor: structural and functional analysis of a newly identified transcription factor from genomic DNA analysis. J Biol Chem 280 (46) (): 38711-9.
58. Peschel A, Jack RW, Otto M, Collins LV, Staubitz P, et al. (2001) Staphylococcus aureus resistance to human defensins and evasion of neutrophil killing via the novel virulence factor MprF is based on modification of membrane lipids with l-lysine. J Exp Med 193: 1067-1076.
59. Spengler G, Molnar J, Viveiros M, Amaral L, (2011) Thioridazine induces apoptosis of multidrug-resistant mouse lymphoma cells transfected with the human ABCB1 and inhibits the expression of P-Glycoprotein. Anticancer Res 31: 4201-4205.
60. Yde CW, Clausen MP, Bennetzen MV, Lykkesfeldt AE, Mouritsen OG, et al. (2009) The antipsychotic drug chlorpromazine enhances the cytotoxic effect of tamoxifen in tamoxifen-sensitive and tamoxifen-resistant human breast cancer cells. Anticancer Drugs 20: 723-735.