Photosensitizing properties of triplet β-lapachones in acetonitrile solution

Photochemistry and Photobiology

Volumn 85, Issue 1, 2009, Pages 153-159

  Netto Ferreira, José Carlos ^a,b   Lhiaubet Vallet, Virginie ^b   De Oliveira Bernardes, Bauer ^a   Ferreira, Aurelio Baird Buarque ^a   Miranda, Miguel Ángel ^b  

^a FEDERAL RURAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ACETONITRILE DERIVATIVE; BETA LAPACHONE; BETA-LAPACHONE; NAPHTHOQUINONE; PHOTOSENSITIZING AGENT; SINGLET OXYGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SOLUTION AND SOLUBILITY; SPECTROPHOTOMETRY;

ACETONITRILES; MOLECULAR STRUCTURE; NAPHTHOQUINONES; PHOTOSENSITIZING AGENTS; SINGLET OXYGEN; SOLUTIONS; SPECTROPHOTOMETRY;

EID: 58349095666     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2008.00410.x     Document Type: Article

References (58)

1. Docampo, R., F. S. Cruz, A. Boveris, R. P. Muniz D. M. Esquivel (1979) β-Lapachone enhancement of lipid peroxidation and superoxide anion and hydrogen peroxide formation by sarcoma 180 ascites tumor cells. Biochem. Pharmacol. 28, 723 728.
2. Schaffner-Sabba, K., K. H. Schmidt-Ruppin, W. Wehrli, A. R. Schuerch J. W. Wasley (1984) β-Lapachone: Synthesis of derivatives and activities in tumor models. J. Med. Chem. 27, 990 994.
3. Pink, J. J., S. M. Planchon, C. Tagliarino, M. E. Varnes, D. Siegel D. A. Boothman (2000) NAD(P)H:Quinone oxidoreductase activity is the principal determinant of β-lapachone cytotoxicity. J. Biol. Chem. 275, 5416 5424.
4. Planchon, S. M., S. Wuerzberger, B. Frydman, D. T. Witiak, P. Hutson, D. R. Church, G. Wilding D. A. Boothman (1995) β-Lapachone-mediated apoptosis in human promyelocytic leukemia (HL-60) and human prostate cancer cells: A p53-independent response. Cancer Res. 55, 3706 3711.
5. Planchon, S. M., J. J. Pink, C. Tagliarino, W. G. Bornmann, M. E. Varnes D. A. Boothman (2001) β-Lapachone-induced apoptosis in human prostate cancer cells: Involvement of NQO1/xip3. Exp. Cell Res. 267, 95 106.
6. Wuerzberger, S. M., J. J. Pink, S. M. Planchon, K. L. Byers, W. G. Bornmann D. A. Boothman (1998) Induction of apoptosis in MCF-7:WS8 breast cancer cells by β-lapachone. Cancer Res. 58, 1876 1885.
7. Pink, J. J., S. Wuerzberger-Davis, C. Tagliarino, S. Planchon, X. H. Yang, C. J. Froelich D. A. Boothman (2000) Activation of a cysteine protease in MCF-7 and T47D breast cancer cells during β-lapachone-mediated apoptosis. Exp. Cell Res. 255, 144 155.
8. Tagliarino, C., J. J. Pink, K. E. Reinicke, S. M. Simmers, S. M. Wuerzberger-Davis D. A. Boothman (2003) μ-Calpain activation in β-lapachone-mediated apoptosis. Cancer Biol. Ther. 2, 141 152.
9. Boothman, D. A. A. B. Pardee (1989) Inhibition of radiation induced neoplastic transformation by β-lapachone. Proc. Natl. Acad. Sci. U S A 86, 4963 4967.
10. Ross, D. D. Siegel (2004) NAD(P)H:quinone oxidoreductase 1 (NQO1, DT-diaphorase), functions and pharmacogenetics. Methods Enzymol. 382, 115 144.
11. Bentle, M. S., E. A. Bey, Y. Dong, K. E. Reinicke D. A. Boothman (2006) New tricks for old drugs: The anticarcinogenic potential of DNA repair inhibitors. J. Mol. Hist. 37, 203 218.
12. Netto-Ferreira, J. C., B. Bernardes, A. B. B. Ferreira M. A. Miranda (2008) Laser flash photolysis study of the triplet reactivity of β-lapachones. Photochem. Photobiol. Sci. 2008, 467 473.
13. Hubig, S. M., T. M. Bockman J. K. Kochi (1997) Identification of photoexcited singlet quinones and their ultrafast electron-transfer vs intersystem-crossing rates. J. Am. Chem. Soc. 119, 2926 2935.
14. Harada, Y., S. Watanabe, T. Suzuki T. Ichimura (2005) Photochemical reaction dynamics of 9,10-phenanthrenequinone and 1,2-naphthoquinone with hydrogen donors in solution. J. Photochem. Photobiol. A, Chem. 179, 161 167.
15. Pan, Y., Y. Fu, S. Liu, H. Yu, Y. Gao, Q. Guo S. Yu (2006) Studies on photoinduced H-atom and electron transfer reactions of o-naphthoquinones by laser flash photolysis. J. Phys. Chem. A. 110, 7316 7322.
16. Barra, M., E. D. Harder J. P. Balfe (1999) Influence of solvent polarity on the photoreactivity of 2-4-ring aromatic ortho-quinones. J. Chem. Soc. Perkin Trans 2, 1439 1441.
17. Shimoishi, H., S. Tero-Kubota, K. Akiyama Y. Ikegami (1989) Influence of solvent polarity on the excited triplet states of non-phosphorescent 1,2-naphthoquinone and phosphorescent 9,10-phenanthrenequinone - Time resolved ESR and CIDEP studies. J. Phys. Chem. 93, 5410 5414.
18. Becker, R. S. L. V. Natarajan (1993) Comprehensive absorption, photophysical chemical, and theoretical study of 2-5-ring aromatic hydrocarbon diones. J. Phys. Chem. 97, 344 349.
19. Paternò, E. (1882) Ricerche sull'acido lapacico. Gazz. Chim. Ital. 12, 337 392.
20. Hooker, S. C. (1892) The constitution of lapachic acid (lapachol) and its derivatives. J. Chem. Soc. 61, 611 650.
21. 13C Nuclear magnetic resonance study of 1,2- and 1,4-naphthoquinones and their derivatives. J. Braz. Chem. Soc. 1, 55 57.
22. Hooker, S. C. (1936) Lomatiol. Part 11. Its occurrence, constitution, relation to and conversion into lapachol. Also a synthesis of lapachol. J. Am. Chem. Soc. 58, 1181 1190.
23. Pinto, A. V., M. C. F. R. Pinto C. G. T. Oliveira (1982) Synthesis of α-nor-lapachone and β-nor-lapachone in acid medium and reactions with N-bromosuccinimide. An. Acad. Brasil. Ciênc. 54, 107 114.
24. Fieser, L. F. (1948) Naphthoquinone antimalarials. 16. Water-soluble derivatives of alcoholic and unsaturated compounds. J. Amer. Chem. Soc. 70, 3232 3237.
25. Nonell, S., M. González F. R. Trull (1993) 1H-Phenalenone-1-one-2- sulfonic acid - an extremely efficient singlet molecular-oxygen sensitizer for aqueous media. Afinidad 50, 445 450.
26. 2). J. Phys. Chem. 92, 134 137.
27. Schuler, R. H., P. Neta, H. Zemel R. W. Fessenden (1976) Conversion of hydroxyphenyl to phenoxyl radicals - radiolytic study of reduction of bromophenols in aqueous solution. J. Am. Chem. Soc. 98, 3825 3831.
28. Stern, O. M. Volmer (1919) The fading time of fluorescence. Physik Z. 20, 183 188.
29. Pérez-Prieto, J., F. Boscá, R. E. Galian, A. Lahoz, L. R. Domingo M. A. Miranda (2003) Photoreaction between 2-benzoylthiophene and phenol or indole. J. Org. Chem. 68, 5104 5113.
30. Das, P. K., M. V. Encinas J. C. Scaiano (1981) Laser flash photolysis study of the reactions of carbonyl triplets with phenols and photochemistry of p-hydroxypropiophenone. J. Am. Chem. Soc. 103, 4154 4162.
31. Turro, N. J. R. Engel (1969) Quenching of biacetyl fluorescence and phosphorescence. J. Am. Chem. Soc. 91, 7113 7121.
32. Biczók, L., T. Bérces H. Linschitz (1997) Quenching processes in hydrogen-bonded pairs: Interactions of excited fluorenone with alcohols and phenols. J. Am. Chem. Soc. 119, 11071 11077.
33. Leigh, W. J., E. C. Lathioor M. J. St Pierre (1996) Photoinduced hydrogen abstraction from phenols by aromatic ketones. A new mechanism for hydrogen abstraction by carbonyl n,π* and π,π* triplets J. Am. Chem. Soc. 118, 12339 12348.
34. Miranda, M. A., A. Lahoz, F. Boscá, M. R. Metni, F. B. Abdelouahab J. Pérez-Prieto (2000) Regio- and stereo-selectivity in the intramolecular quenching of the excited benzoylthiophene chromophore by tryptophan. Chem. Commun. 22, 2257 2258.
35. Miranda, M. A., A. Lahoz, R. Matínez-Mañez, F. Boscá, J. V. Castell J. Pérez-Prieto (1999) Enantioselective discrimination in the intramolecular quenching of an excited aromatic ketone by a ground state phenol. J. Am. Chem. Soc. 121, 11569 11570.
36. de Lucas, N. C., R. J. Correa, A. C. C. Albuquerque, C. L. Firme, S. J. Garden, A. R. Bertoti J. C. Netto-Ferreira (2007) Laser flash photolysis of 1,2-diketopyracene and a theoretical study of the phenolic hydrogen abstraction by the triplet state of cyclic α-diketones. J. Phys. Chem. A 111, 1117 1122.
37. Lathioor, E. C. W. J. Leigh (2006) Bimolecular hydrogen abstraction from phenols by aromatic ketone triplets. Photochem. Photobiol. 82, 291 300.
38. Oliveira-Brett, A. M., M. O. F. Goulart F. C. Abreu (2002) Reduction of lapachones and their reaction with L-cysteine and mercaptoethanol on glassy carbon electrodes. Bioelectrochemistry 56, 53 55.
39. Neder, K., L. J. Marton, L. F. Liu B. Frydman (1998) Reaction of β-lapachone and related naphthoquinones with 2-mercaptoethanol: A biomimetic model of topoisomerase II poisoning by quinones, Cell. Mol. Biol. 44, 465 474.
40. Steenken, S. S. V. Jovanovic (1997) How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution. J. Am. Chem. Soc. 119, 617 618.
41. Misiaszeck, R., C. Crean, N. E. Geacintov V. Shafirovich (2005) Combination of nitrogen dioxide radicals with 8-oxo-7,8-dihydroguanine and guanine radicals in DNA: Oxidation and nitration end-products. J. Am. Chem. Soc. 127, 2191 2200.
42. Ci, X. H., R. S. Silva, D. E. Nicodem D. G. Whitten (1989) Electron and hydrogen-atom transfer mechanisms for the photo-reduction of ortho-quinones - Visible light induced photoreactions of β-lapachone with amines, alcohols, and amino-alcohols. J. Am. Chem. Soc. 111, 1337 1343.
43. Goulart, M. O. F., C. L. Zani, J. Tonholo, L. R. Freitas, F. C. de Abreu, A. B. Oliveira, D. S. Raslan, S. Starling E. Chiari (1997) Trypanocidal activity and redox potential of heterocyclic and 2-hydroxy-naphthoquinones Bioorg. Med. Chem. Lett. 7, 2043 2048.
44. Lhiaubet-Vallet, V., N. Belmadoui, M. J. Climent M. A. Miranda (2007) The long-lived triplet excited state of an elongated ketoprofen derivative and its interactions with amino acids and nucleosides. J. Phys. Chem. B 111, 8277 8282.
45. Rehm, D. A. Weller (1970) Kinetics of fluorescence quenching by electron and H-atom transfer. Isr. J. Chem. 8, 259 271.
46. Encinas, S., N. Belmadoui, M. J. Climent, S. Gil M. A. Miranda (2004) Photosensitization of thymine nucleobase by benzophenone derivatives as models for photoinduced DNA damage: Paternò-Büchi vs energy and electron transfer processes. Chem. Res. Toxicol. 17, 857 862.
47. Belmadoui, N., S. Encinas, M. J. Climent, S. Gil M. A. Miranda (2006) Intramolecular interactions in the triplet excited states of benzophenone-thymine dyads. Chem. Eur. J. 12, 553 561.
48. Joseph, A., G. Prakash D. E. Falvey (2000) Model studies of the (6-4) photoproduct photolyase enzyme: Laser flash photolysis experiments confirm radical ion intermediates in the sensitized repair of thymine oxetane adducts. J. Am. Chem. Soc. 122, 11219 11225.
49. Nakatani, K., T. Yoshida I. Saito (2002) Photochemistry of benzophenone immobilized in a major groove of DNA: Formation of thermally reversible interstrand cross-link. J. Am. Chem. Soc. 124, 2118 2119.
50. Lhiaubet-Vallet, V., S. Encinas M. A. Miranda (2005) Excited state enantiodifferentiating interactions between a chiral benzophenone derivative and nucleosides. J. Am. Chem. Soc. 127, 12774 12775.
51. Burrows, C. J. J. G. Muller (1998) Oxidative nucleobase modifications leading to strand scission. Chem. Rev. 98, 1109 1151.
52. Wilkinson, F., W. P. Helman A. B. Ross (1995) Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution - An expanded and revised compilation. J. Phys. Chem. Ref. Data 24, 663 1021.
53. Darmanyan, A. P. C. S. Foote (1993) Solvent effects on singlet oxygen yield from nπ* and ππ* triplet carbonyl compounds. J. Phys. Chem. 97, 5032 5035.
54. Redmond, R. W. S. E. Braslavsky (1988) Time-resolved thermal lensing and phosphorescence studies on photosensitized singlet molecular oxygen formation - Influence of the electronic configuration of the sensitizer on sensitization efficiency. Chem. Phys. Lett. 148, 523 529.
55. g) sensitization. J. Photochem. Photobiol. A, Chem. 79, 11 17.
56. Oliveros, E., P. Suardi-Murasecco, T. Aminian-Saghafi, A. M. Braun H.-J. Hansen (1991) 1H-Phenalen-1-one - Photophysical properties and singlet oxygen production. Helv. Chim. Acta 74, 79 90.
57. Nau, W. M. J. C. Scaiano (1996) Oxygen quenching of excited aliphatic ketones and diketones. J. Phys. Chem. 100, 11360 11367.
58. Hora Machado, A. E., J. A. Miranda, A. M. F. Oliveira-Campos, D. Severino D. E. Nicodem (2001) Photophysical properties of two new psoralen analogs. J. Photochem. Photobiol. A, Chem. 146, 75 81.