Study of the photochemical and phototoxic properties of lonidamine [1-(2,4-dichlorobenzyl)-1H-indazol-3-carboxylic acid]

Journal of Photochemistry and Photobiology B: Biology

Volumn 41, Issue 1-2, 1997, Pages 11-21

  Chekulayev, Vladimir ^a   Shevchuk, Igor ^a   Chekulayeva, Lyudmila ^a   Kahru, Anne ^b  

^a TALLINN UNIVERSITY OF TECHNOLOGY   (Estonia)

^b NATIONAL INSTITUTE OF CHEMICAL PHYSICS AND BIOPHYSICS   (Estonia)

Author keywords

Lonidamine; Phototoxicity; Tumour cells; Ultraviolet radiation

Indexed keywords

ANTINEOPLASTIC AGENT; ANTISPERMATOGENIC AGENT; LIPID; LONIDAMINE; OXIDOREDUCTASE; OXYGEN; PHOTOSENSITIZING AGENT;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CELL MEMBRANE; CELL MEMBRANE PERMEABILITY; CONTROLLED STUDY; EHRLICH ASCITES TUMOR; ENZYME INHIBITION; FEMALE; LIPID OXIDATION; MITOCHONDRION; MOUSE; NONHUMAN; OXYGEN CONSUMPTION; PHOTOCHEMISTRY; PHOTOOXIDATION; PHOTOPHOBIA; PHOTOSENSITIVITY DISORDER; PHOTOTOXICITY; PRIORITY JOURNAL; ULTRAVIOLET RADIATION;

ANIMALS; FEMALE; INDAZOLES; MICE; MOLECULAR STRUCTURE; NADP; RADIATION-SENSITIZING AGENTS; TRYPTOPHAN; TUMOR CELLS, CULTURED; ULTRAVIOLET RAYS;

EID: 0031435531     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1011-1344(97)00062-6     Document Type: Article

References (48)

1. A. Floridi, M.G. Paggi, M.L. Marcante, B, Silvestrini, A. Caputo, C. De Martino, Lonidamine, a selective inhibitor of aerobic glycolysis of murine tumor cells, JNCI, 66 (1981) 497-499.
2. A. Floridi, A.L. Lehninger, Action of the antitumor and antispermatogenic agent lonidamine on electron transport in Ehrlich ascites tumor mitochondria, Arch. Biochem. Biophys., 226 (1983) 73-83.
3. A. Floridi, M.G. Paggi, S. D' Atri, C. De Martino, L. Marcante, B. Silvestrini, A. Caputo, Effect of lonidamine on the energy metabolism of Ehrlich ascites tumor cells, Cancer Res., 41 (1981) 4661-4666.
4. A. Floridi, A. Alexandre, M.G. Paggi, L. Pellegrini, M.L. Marcante, B. Silvestrini, A. Caputo, A.L. Lehninger, Mechanisms of rnitochondrial swelling induced by lonidamine, in T. Galeotti, A. Cittadini, G. Neri, S. Papa and L.A. Smets (eds.), Cell Membranes and Cancer, Elsevier Science, Amsterdam, 1985, pp. 217-221.
5. W. Malorni, G. Arancia, C. De Martino, A. Nista, L. Accinni, R. Masella, A. Cantafora, On the mechanism of action of lonidamine. A study on human erythrocyte membrane, Exp. Mol. Pathol., 49 (1988) 361-372.
6. W.K. Evans, F.A. Shepherd, B. Mullis, Phase II evaluation of Lonidamine in patients with advanced malignancy, Oncology, 41 (Suppl. 1) (1984) 69-77.
7. G. Robustelli della Cuna, P. Pedrazzoli, Toxicity and clinical tolerance of lonidamine, Seminars in Oncology, 18 (No. 2 Suppl. 4) (1991) 18-22.
8. W.E. Bloch, B.L. Lokeshwar, S.M. Ferrell, N.L. Block, Enhancement of hyperthermic toxicity by lonidamine in the Dunning R3327G rat prostatic adenocarcinoma, Prostate, 24 (1994) 131-138.
9. L. Magno, F. Terraneo, F. Bertoni, M. Tordiglione, D. Bardelli, M.T. Rosignoli, G.B. Ciottoli, Double-blind randomized study of lonidamine and radiotherapy in head and neck cancer, Int. J. Radiation Oncology, Biology, Physics, 29 (1994) 45-55.
10. I. Shevchuk, V. Chekulayev, J. Moan, K. Berg, Effects of the inhibitors of energy metabolism, lonidamine and levamisole, on 5-aminolevulinic acid induced photochemotherapy, Int. J. Cancer, 67 (1996) 791-799.
11. G. Buccheri, D. Ferrigno, A. Rosso, A phase II study of methotrexate, doxorubicin, cyclophosphamide, and lomustine chemotherapy and lonidamine in advanced non-small cell lung cancer, Cancer, 72 (1993) 1564-1572.
12. R. Forster, A. Campana, E. D'Onofrio, L. Henderson, P. Mosesso, P. Scorza Barcellona, Lonidamine: a non-mutagenic antitumor agent, Carcinogenesis, 11 (1990) 1509-1515.
13. C.W. Young, V.E. Currie, J.H. Kim, M.A. O'Hehir, F.M. Farag, J.E. Kinahan, Phase 1 and clinical pharmacologic evaluation of lonidamine in patients with advanced cancer, Oncology, 41 ((Suppl. 1)) (1984) 60-65.
14. T. Battelli, P. Manocchi, L. Giustini, R. Mattioli, A. Ginnetti, M. De Gregorio, C. De Martino, B. Silvestrini, A long-term clinical experience with lonidamine, Oncology, 41 ((Suppl. 1)) (1984) 39-47.
15. R.M. Tyrrell, Induction of pyrimidine dimers in bacterial DNA by 365 nm radiation, Photochem. Photobiol., 17 (1973) 69-73.
16. R.M. Tyrrell, R.D. Ley, R.B. Webb, Induction of single strand breaks (alkali-labile bonds) in bacterial and phage DNA by near-UV (365 nm) radiation, Photochem. Photobiol., 20 (1974) 395-399.
17. A. Han, M.J. Peak, J.G. Peak, Induction of DNA-protein cross-linking in Chinese hamster cells by monochromatic 365 nm and 405 nm light, Photochem. Photobiol., 39 (1984) 343-348.
18. R.B. Webb, M.S. Brown, Action spectra for oxygen-dependent and independent inactivation of Escherichia coli WP 2s from 254 to 460 nm, Photochem. Photobiol., 29 (1979) 407-409.
19. H.J. Danpure, R.M. Tyrrell, Oxygen-dependence of near UV (365 nm) lethality and the interaction of near UV and X-Rays in two mammalian cell lines, Photochem. Photobiol., 23 (1976) 171-177.
20. M. Keyse, S.H. Moss, D.J.G. Davies, Action spectra for inactivation of normal and xeroderma pigmentosum human skin fibroblasts by ultraviolet radiations, Photochem. Photobiol., 37 (1983) 307-312.
21. R.M. Tyrrell, M. Pidoux, Singlet oxygen involvement in the inactivation of cultured human fibroblasts by UVA (334 nm, 365 nm) and near-visible (405 nm) radiations, Photochem. Photobiol., 49 (1989) 407-412.
22. A.V. Putvinsky, Ya. A. Potapenko, E.O. Puchkov, D.I. Roshchupkin, Yu. A. Vladimirov, Study of the effect of ultra-violet light on biomembranes VI. Increase in the ion permeability of mitochondrial and artificial lipid membranes, Studia biophysica, 64 (1977) 17-32.
23. D.I. Roshchupkin, A.I. Marzoev, E.O. Puchkov, Yu.A. Vladimirov, L.V. Khripach, Study of the effect of ultra-violet light on biomembranes V. Photolysis of lipids and sulfur-containing groups and its role in the inactivation of respiration of isolated mitochondria, Studia Biophysica, 48 (1975) 67-75.
24. A. Floridi, A. Delpino, A. Nista, R. Feriozzi, M.L. Marcante, B. Silvestrini, A. Caputo, Effect of lonidamine on protein synthesis in neoplastic cells, Exp. Mol. Pathol., 42 (1985) 293-305.
25. C. De Martino, T. Battelli, M.G. Paggi, A. Nista, M.L. Marcante, S. D'Atri, W. Malorni, M. Gallo, A. Floridi, Effects of lonidamine on murine and human tumor cells in vitro: a morphological and biochemical study, Oncology, 41 (1984) 15-29.
26. A. Floridi, S. D'Atri, M.G. Paggi, M.L. Marcante, C. De Martino, B. Silvestrini, A. Caputo, A.L. Lehninger, Binding of lonidamine to Ehrlich ascites tumor and liver mitochondria, in Membranes in Tumor Growth, T. Galeotti et al. (eds.), Elsevier Science, Amsterdam, 1982, pp. 559-565.
27. J.K. Wilson, J.M. Sargent, A.W. Elgie, J.G. Hill, C.G. Taylor, A feasibility study of the MTT assay for chemosensitivity testing in ovarian malignancy, Br. J. Cancer, 62 (1990) 189-194.
28. A. Kahru, M. Liiders, K. Vanatalu, R. Vilu, Adenylate energy charge during batch culture of Thermoactinomyces vulgaris, Arch. Microbiol., 133 (1982) 142-144.
29. 6 trimethyl ester. The effect of L-buthionine-[S,R]-sulfoximine on the photosensitized damage of tumor cells, Proc. Estonian Acad. Sci. Chem., 41 (1992) 52-61.
30. P. Walrant, R. Santus, N-formyl-kynurenine, a tryptophan photo-oxidation product, as a photodynamic sensitizer, Photochem. Photobiol., 19 (1974) 411-417.
31. M. Rougee, R.V. Bensasson, E.J. Land, R. Pariente, Deactivation of singlet molecular oxygen by thiols and related compounds, possible protectors against skin photosencitivity, Photochem. Photobiol., 47 (1988) 485-489.
32. V. Chekulayev, I. Shevchuk, L. Chekulayeva, A. Kahru, Personal communication, 1996.
33. 2+ in toxic cell killing, TiPS, 10 (1989) 281-285.
34. 2+ and cell killing in hepatoma 1c1c7 cells exposed to chemical anoxia, FASEB J., 3 (1989) 59-64.
35. W. Kuhne, M. Besselmann, T. Noll, A. Muhs, H. Watanabe, H.M. Piper, Desintegration of cytoskeletal structure of actin filaments in energy-depleted endothelial cells, Am. J. Physiol., 264 (1993) 1599-1608.
36. R.M. Tyrrell, M. Pidoux, Correlation between endogenous glutathione content and sensitivity of cultured human skin cells to radiation at defined wavelengths in the solar ultraviolet range, Photochem. Photobiol., 47 (1988) 405-412.
37. D.I. Roshchupkin, A.B. Pelenitsyn, A.Y. Potapenko, V.V. Talitsky, Y.A. Vladimirov, Study of the effects of oxygen on the UV-induced haemolysis and lipid peroxidation in rat erythrocytes and liposomes, Photochem. Photobiol., 21 (1975) 63-69.
38. C. Vever-Bizet, M. Dellinger, D. Brault, M. Rougee, R.V. Bensasson, Singlet molecular oxygen quenching by saturated and unsaturated fatty-acids and by cholesterol, Photochem. Photobiol., 50 (1989) 321-325.
39. T.M.A.R. Dubbelman, A.F.P.M. De Goeij, J. Van Steveninck, Photodynamic effects of protoporphyrin on human erythrocytes. Nature of the cross-linking of membrane proteins, Biochim. Biophys. Acta, 511 (1978) 141-151.
40. G. Bellomo, F. Mirabelli, A. Salis, M. Vairetti, P. Richelmi, G. Finardi, H. Thor, S. Orrenius, Oxidative stress-induced plasma membrane blebbing and cytoskeletal alterations in normal and cancer cells, Membrane in cancer cells, Ann. N.Y. Acad. Sci., 551 (1988) 128-130.
41. R.V. Bensasson, E.J. Land and T.G. Truscott (eds.), Excited states and free radicals in biology and medicine, Oxford University Press, Oxford, 1993.
42. E. Kohen, R. Santus and J.G Hirscberg (eds.), Photobiology, Academic Press, San Diego, 1995.
43. S. Takagi, N. Mizuno, K. Adachi, T. Wakabayashi, Effects of dimethylchlortetracycline phototoxicity on the structure and functions of rat liver mitochondria, Photochem. Photobiol., 51 (1990) 175-183.
44. C.R. Shea, D. Whitaker, G.F. Murphy, T. Hasan, Ultrastructure and dynamics of selective mitochondrial injury in carcinoma cells after doxycycline photosensitization in vitro, Am. J. Pathol., 133 (1988) 381-388.
45. H. Schmidt, W. Siems, M. Müller, R. Dumdey, M. Jakstadt, S.M. Rapoport, Balancing of mitochondrial and glycolytic ATP production and of the ATP-consuming processes of Ehrlich mouse ascites tumour cells in a high phosphate medium, Biochemistry Int., 19 (1989) 985-992.
46. 2+-ATPase in R3230AC mammary adenocarcinomas, Cancer Res., 48 (1988) 3360-3366.
47. J. Moan, K. Berg, Photochemotherapy of cancer: experimental research, Photochem. Photobiol., 55 (1992) 931-948.
48. 2+ by lonidamine, Biochem. Pharmacol., 46 (1993) 330-332.