Glycol porphyrin derivatives as potent photodynamic inducers of apoptosis in tumor cells

Journal of Medicinal Chemistry

Volumn 51, Issue 19, 2008, Pages 5964-5973

  Králová, Jarmila ^a   Bříza, Tomáš ^b   Moserová, Irena ^a   Dolenský, Bohumil ^b   Vašek, Petr ^b   Poučková, Pavla ^c   Kejík, Zdeněk ^b   Kaplánek, Robert ^b   Martásek, Pavel ^c   Dvořák, Michal ^a   Král, Vladimír ^b,d  

^a INSTITUTE OF MOLECULAR GENETICS   (Czech Republic)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^c CHARLES UNIVERSITY   (Czech Republic)

^d Zentiva Prague   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

CASPASE; ETHYLENE GLYCOL; GLYCOL PORPHYRIN DERIVATIVE; HYDROXYGLYCOL PORPHYRIN; METHOXYGLYCOL PORPHYRIN; PHOTOSENSITIZING AGENT; PORPHYRIN DERIVATIVE; SIALIC ACID; TETRAPHENYLPORPHYRIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; APOPTOSIS; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; FLUORINATION; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PHOTODYNAMIC THERAPY; TUMOR CELL;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; FLOW CYTOMETRY; GLYCOLS; HUMANS; INJECTIONS, INTRAVENOUS; MICE; MICE, NUDE; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; NEOPLASMS, EXPERIMENTAL; PHOTOCHEMOTHERAPY; PORPHYRINS; STEREOISOMERISM; TIME FACTORS; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 53549097111     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8002119     Document Type: Article

References (49)

1. Giovannetti, A.; Pierdominici, M.; Di Iorio, A.; Cianci, R.; Murdaca, G.; Puppo, F.; Pandolfi, F.; Paganelli, R. Apoptosis in the homeostasis of the immune system and in human immune mediated diseases. Curr. Pharm. Des. 2008, 14, 253-268.
2. Van Cruchten, S.; Van Den Broeck, W. Morphological and biochemical aspects of apoptosis, oncosis and necrosis. Anat., Histol., Embryol. 2002, 31, 214-223.
3. Kroemer, G.; Galluzzi, L.; Brenner, C. Mitochondrial membrane permeabilization in cell death. Physiol. Rev. 2007, 87, 99-163.
4. Kaufmann, S. H.; Gores, G. J. Apoptosis in cancer: cause and cure. BioEssays 2000, 22, 1007-17.
5. Alkhalaf, M.; El-Mowafy, A.; Renno, W.; Rachid, O.; Ali, A.; Al-Attyiah, R. Resveratrol-induced apoptosis in human breast cancer cells is mediated primarily through the caspase-3-dependent pathway. Arch. Med. Res. 2008, 39, 162-168.
6. Balakin, K. V.; Ivanenkov, Y. A.; Kiselyov, A. S.; Tkachenko, S. E. Histone deacetylase inhibitors in cancer therapy: latest developments, trends and medicinal chemistry perspective. Anti-Cancer Agents Med. Chem. 2007, 7, 576-592.
7. Danson, S.; Dean, E.; Dive, C.; Ranson, M. IAPs as a target for anticancer therapy. Curr. Cancer Drug Targets 2007, 7, 785-794.
8. Díaz-Gavilán, M.; Gómez-Vidal, J. A.; Rodríguez-Serrano, F.; Marchal, J. A.; Caba, O.; Aránega, A.; Gallo, M. A.; Espinosa, A.; Campos, J. M. Anticancer activity of (1,2,3,5-tetrahydro-4,1-benzoxazepine-3-yl)-pyrimidines and -purines against the MCF-7 cell line: preliminary cDNA microarray studies. Bioorg. Med. Chem. Lett. 2008, 18, 1457-1460.
9. Dong, L. F.; Swettenham, E.; Eliasson, J.; Wang, X. F.; Gold, M.; Medunic, Y.; Stantic, M.; Low, P.; Prochazka, L.; Witting, P. K.; Turanek, J.; Akporiaye, E. T.; Ralph, S. J.; Neuzil, J. Vitamin E analogues inhibit angiogenesis by selective induction of apoptosis in proliferating endothelial cells: the role of oxidative stress. Cancer Res. 2007, 67, 11906-11913.
10. Fulda, S. Inhibitor of apoptosis proteins as targets for anticancer therapy. Expert Rev. Anticancer Ther. 2007, 7, 1255-1264.
11. Heikaus, S.; Matuszek, K. S.; Suschek, C. V.; Ramp, U.; Reinecke, P.; Grinstein, E.; Haremza, J.; Gabbert, H. E.; Mahotka, C. Paclitaxel (Taxol)-induced apoptosis in human epithelioid sarcoma cell lines is enhanced by upregulation of CD95 ligand (FasL/Apo-1L). J. Cancer Res. Clin. Oncol. 2007, 134, 689-695.
12. Kawanishi, S.; Hiraku, Y. Amplification of anticancer drug-induced DNA damage and apoptosis by DNA-binding compounds. Curr. Med. Chem.: Anti-Cancer Agents 2004, 4, 415-419.
13. Kumar, A.; D'Souza, S. S.; Gaonkar, S. L.; Rai, K. M.; Salimath, B. P. Growth inhibition and induction of apoptosis in MCF-7 breast cancer cells by a new series of substituted-1,3,4-oxadiazole derivativesInvest. New Drugs, published online Jan 29 2008, http://dx.doi.org/10.1007/s10637-008-9116-5.
14. Mosley, C. A.; Liotta, D. C.; Snyder, J. P. Highly active anticancer curcumin analogues. Adv. Exp. Med. Biol. 2007, 595, 77-103.
15. Russo, A.; Fratto, M. E.; Bazan, V.; Schiro, V.; Agnese, V.; Cicero, G.; Vincenzi, B.; Tonini, G.; Santini, D. Targeting apoptosis in solid tumors: the role of bortezomib from preclinical to clinical evidence. Expert Opin. Ther. Targets 2007, 11, 1571-1586.
16. Thongphasuk, P.; Stremmel, W.; Chamulitrat, W. Potent direct or TNF-α-promoted anticancer effects of 2,3-dehydrosilybin: comparison study with silybin. Chemotherapy 2008, 54, 23-30.
17. Allison, R. R.; Bagnato, V. S.; Cuenca, R.; Downie, G. H.; Sibata, C. H. The future of photodynamic therapy in oncology. Future Oncol. 2006, 2, 53-71.
18. Castano, A. P.; Mroz, P.; Hamblin, M. R. Photodynamic therapy and anti-tumour immunity. Nat. Rev. Cancer 2006, 6, 535-545.
19. Wilson, B. C.; Patterson, M. S. The physics of photodynamic therapy. Phys. Med. Biol. 1986, 31, 327-360.
20. Henderson, B. W.; Dougherty, T. J. How does photodynamic therapy work? Photochem. Photobiol. 1992, 55, 145-157.
21. Niedre, M.; Patterson, M. S.; Wilson, B. C. Direct near-infrared luminescence detection of singlet oxygen generated by photodynamic therapy in cells in vitro and tissues in vivo. Photochem. Photobiol. 2002, 75, 382-391.
22. Oleinick, N. L.; Evans, H. H. The photobiology of photodynamic therapy: cellular targets and mechanisms. Radiat. Res. 1998, 150, S146-S156.
23. Almeida, R. D.; Manadas, B. J.; Carvalho, A. P.; Duarte, C. B. Intracellular signaling mechanisms in photodynamic therapy. Biochim. Biophys. Acta 2004, 1704, 59-86.
24. Oleinick, N. L.; Morris, R. L.; Belichenko, I. The role of apoptosis in response to photodynamic therapy: what, where, why, and how. Photochem. Photobiol. Sci. 2002, 1, 1-21.
25. Lavie, G.; Kaplinsky, C.; Toren, A.; Aizman, I.; Meruelo, D.; Mazur, Y.; Mandel, M. A photodynamic pathway to apoptosis and necrosis induced by dimethyl tetrahydroxyhelianthrone and hypericin in leukaemic cells: possible relevance to photodynamic therapy. Br. J. Cancer 1999, 79, 423-432.
26. Kessel, D.; Luo, Y.; Deng, Y.; Chang, C. K. The role of subcellular localization in initiation of apoptosis by photodynamic therapy. Photochem. Photobiol. 1997, 65, 422-426.
27. Král, V.; Králová, J.; Kaplánek, R.; Bříza, T.; Martásek, P. Quo vadis porphyrin chemistry? Physiol. Res. 2006, 55 (Suppl. 2), S3-S26.
28. Banfi, S.; Caruso, E.; Caprioli, S.; Mazzagatti, L.; Canti, G.; Ravizza, R.; Gariboldi, M.; Monti, E. Photodynamic effects of porphyrin and chlorin photosensitizers in human colon adenocarcinoma cells. Bioorg. Med. Chem. 2004, 12, 4853-4860.
29. Samaroo, D.; Vinodu, M.; Chen, X.; Drain, C. M. meso-Tetra(pentafluorophenyl)porphyrin as an efficient platform for combinatorial synthesis and the selection of new photodynamic therapeutics using a cancer cell line. J. Comb. Chem. 2007, 9, 998-1011.
30. Synytsya, A.; Král, V.; Volka, K.; Sessler, J. L. In vitro interaction of macrocyclic photosensitizers with intact mitochondria: a spectroscopic study. Biochim. Biophys. Acta 2003, 1620, 85-96.
31. Král, V.; Rusin, O.; Charvatova, J.; Anzenbacher, P.; Fogl, J. Porphyrin phosphonates: novel anionic receptors for saccharide recognition. Tetrahedron Lett. 2000, 41, 10147-10151.
32. Králová, J.; Synytsya, A.; Poučková, P.; Koc, M.; Dvořák, M.; Král, V. Novel porphyrin conjugates with a potent photodynamic antitumor effect: differential efficacy of mono- and bis-beta-cyclodextrin derivatives in vitro and in vivo. Photochem. Photobiol. 2006, 82, 432-438.
33. Rusin, O.; Hub, M.; Král, V. Novel water-soluble porphyrin-based receptors for saccharide recognition. Mater. Sci. Eng., C 2001, 18, 135-140.
34. Sibrian-Vazquez, M.; Jensen, T. J.; Vicente, M. G. Synthesis and cellular studies of PEG-functionalized meso-tetraphenylporphyrins. J. Photochem. Photobiol., B 2007, 86, 9-21.
35. Crupi, V.; Giordano, R.; Majolino, D.; Migliardo, P.; Venuti, V.; Micali, N.; Villari, V.; Mineo, P.; Vitalini, D.; Scamporrino, E. Spectroscopic evidence of aggregation processes in porphyrin-based star-polymers in agueous solutions. Mol. Phys. 2003, 101, 1517-1526.
36. Swamy, N.; Purohit, A.; Fernandez-Gacio, A.; Jones, G. B.; Ray, R. Nuclear estrogen receptor targeted photodynamic therapy: selective uptake and killing of MCF-7 breast cancer cells by a C17α-alkynylestradiol-porphyrin conjugate. J. Cell. Biochem. 2006, 99, 966-977.
37. Tkadlecova, M.; Foltynova, J.; Valik, M.; Král, V. Spectroscopic binding studies of novel fluorescent distamycin derivatives. Tetrahedron Lett. 2008, 49, 323-326.
38. Kobayashi, N.; Nakai, K. Application of magnetic circular dichroism spectroscopy to porphyrins and phthalocyanines. Chem. Commun. 2007, 40, 4077-4092.
39. Surewicz, W. K. Electron spin resonance study on the mechanism of polyethylene glycol-membrane interaction. FEBS Lett. 1983, 151, 228-232.
40. Kirk, K. L. Fluorine in medicinal chemistry: recent therapeutic applications of fluorinated small molecules. J. Fluorine Chem. 2006, 127, 1013-1029.
41. Weitman, H.; Schatz, S.; Gottlieb, H. E.; Kobayashi, N.; Ehrenberg, B. Spectroscopic probing of the acid-base properties and photosensitization of a fluorinated phthalocyanine in organic solutions and liposomes. Photochem. Photobiol. 2001, 73, 473-481.
42. Biffinger, J. C.; Kim, H. W.; DiMagno, S. G. The polar hydrophobicity of fluorinated compounds. ChemBioChem 2004, 5, 622-627.
43. Kim, D.; Wang, L.; Beconi, M.; Eiermann, G. J.; Fisher, M. H.; He, H.; Hickey, G. J.; Kowalchick, J. E.; Leiting, B.; Lyons, K.; Marsilio, F.; McCann, M. E.; Patel, R. A.; Petrov, A.; Scapin, G.; Patel, S. B.; Roy, R. S.; Wu, J. K.; Wyvratt, M. J.; Zhang, B. B.; Zhu, L.; Thornberry, N. A.; Weber, A. E. (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4, 3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine: a potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. J. Med. Chem. 2005, 48, 141-151.
44. Králová, J.; Dvořák, M.; Koc, M.; Král, V. p38 MAPK plays an essential role in apoptosis induced by photoactivation of a novel ethylene glycol porphyrin derivative. Oncogene 2008, 27, 3010-3020.
45. Hirohara, S.; Obata, M.; Ogata, S.; Ohtsuki, C.; Higashida, S.; Ogura, S.; Okura, I.; Takenaka, M.; Ono, H.; Sugai, Y.; Mikata, Y.; Tanihara, M.; Yano, S. Cellular uptake and photocytotoxicity of glycoconjugated chlorins in HeLa cells. J. Photochem. Photobiol., B 2005, 78, 7-15.
46. Banfi, S.; Caruso, E.; Buccafurni, L.; Murano, R.; Monti, E.; Gariboldi, M.; Papa, E.; Gramatica, P. Comparison between 5,10,15,20-tetraaryl-and 5,15-diarylporphyrins as photosensitizers: synthesis, photodynamic activity, and quantitative structure-activity relationship modeling. J. Med. Chem. 2006, 49, 3293-3304.
47. Fabris, C.; Valduga, G.; Miotto, G.; Borsetto, L.; Jori, G.; Garbisa, S.; Reddi, E. Photosensitization with zinc (II) phthalocyanine as a switch in the decision between apoptosis and necrosis. Cancer Res. 2001, 61, 7495-7500.
48. Dougherty, T. J.; Gomer, C. J.; Henderson, B. W.; Jori, G.; Kessel, D.; Korbelik, M.; Moan, J.; Peng, Q. Photodynamic therapy. J. Natl. Cancer Inst. 1998, 90, 889-905.
49. Králová, J.; Dvořák, M.; Král, V. Novel cationic transport agents for oligonucleotide delivery into primary leukemic cells. J. Med. Chem. 2003, 46, 2049-2056.