Low concentrations of a non-hydrolysable tetra-S-glycosylated porphyrin and low light induces apoptosis in human breast cancer cells via stress of the endoplasmic reticulum

Photochemical and Photobiological Sciences

Volumn 7, Issue 11, 2008, Pages 1415-1421

  Thompson, Sebastian ^a   Chen, Xin ^a   Hui, Li ^a   Toschi, Alfredo ^a   Foster, David A ^a   Drain, Charles Michael ^a,b  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b ROCKEFELLER UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALCIUM; CASPASE 3; CYTOCHROME C; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; PORPHYRIN;

APOPTOSIS; ARTICLE; BREAST CANCER; CANCER CELL; CELL DEATH; CHROMATIN CONDENSATION; CONFOCAL MICROSCOPY; CONTROLLED STUDY; CYTOSOL; ENDOPLASMIC RETICULUM; ENDOPLASMIC RETICULUM STRESS; HUMAN; HUMAN CELL; LIGHT; MITOCHONDRION; PHOTODYNAMIC THERAPY; PRIORITY JOURNAL;

TETRA;

EID: 55149110320     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b806536e     Document Type: Article

References (42)

1. G. Kroemer B. Dallaporta M. Resche-Rigon The mitochondrial death/life regulator in apoptosis and necrosis Annu. Rev. Physiol. 1998 60 619 642
2. A. Lawen Apoptosis-an introduction BioEssays 2003 25 888 896
3. E. D. Sternberg C. Bruckner D. Dolphin Porphyrin-based photosensitizers for use in photodynamic therapy Tetrahedron 1998 54 4151 4202
4. J. Osterloh M. G. H. Vicente Mechanisms of porphyrinoid localization in tumors J. Porphyrins Phthalocyanines 2002 6 305 324
5. R. Bonnett Photosensitizers of the porphyrin the phthalocyanine series for photodynamic therapy Chem. Soc. Rev. 1995 24 19 32
6. N. L. Oleinick R. L. Morris I. Belichenko The role of apoptosis in response to photodynamic therapy: what, where, why, and how Photochem. Photobiol. Sci. 2002 1 1 21
7. D. Kessel Y. Luo Photodynamic therapy: A mitochondrial inducer of apoptosis Cell Death Differentiation 1999 6 28 35
8. X. Chen L. Hui D. A. Foster C. M. Drain Efficient synthesis and photodynamic activity of porphyrin-saccharide conjugates: targeting and incapacitating cancer cells Biochemistry 2004 43 10918 10929
9. M. E. Varnes S.-M. Chiu L.-Y. Xue N. L. Oleinick Photodynamic therapy-induced apoptosis in lymphoma cells: Translocation of cytochrome c causes inhibition of respiration as well as caspase activation Biochem. Biophys. Res. Commun. 1999 255 673 679
10. D. J. Granville D. W. C. Hunt Porphyrin-mediated photosensitization - Taking the apoptosis fast lane Curr. Opin. Drug Discovery Develop. 2000 3 232 243
11. I. Yslas M. G. Alvarez C. Marty G. Mori E. N. Durantini V. Rivarola Expression of Fas antigen and apoptosis caused by 5,10,15,20-tetra(4- methoxyphenyl)porphyrin (TMP) on carcinoma cells: implication for photodynamic therapy Toxicology 2000 149 69 74
12. D. Kessel Y. Luo Intracellular sites of photodamage as a factor in apoptotic cell death J. Porphyrins Phthalocyanines 2001 5 181 184
13. T. J. McGarrity L. P. Peiffer D. J. Granville C. M. Carthy J. G. Levy M. Khandelwal D. W. C. Hunt Apoptosis associated with esophageal adenocarcinoma: influence of photodynamic therapy Cancer Lett. 2001 163 33 41
14. D. Nowis M. Makowski T. Stoklosa M. Legat T. Issat J. Golab Direct tumor damage mechanisms of photodynamic therapy Acta Biochim. Polonica 2005 52 339 352
15. C. N. Lunardi A. C. Tedesco Synergic photosensitizers: A new trend in photodynamic therapy Curr. Org. Chem. 2005 9 813 821
16. K. Plaetzer T. Kiesslich C. B. Oberdanner B. Krammer Apoptosis following photodynamic tumor therapy: Induction, mechanisms and detection Curr. Pharm. Design 2005 11 1151 1165
17. R. D. Almeida B. J. Manadas A. P. Carvalho C. B. Duarte Intracellular signaling mechanisms in photodynamic therapy Biochim. Biophys. Acta - Rev. Cancer 2004 1704 59 86
18. T.-I. Peng C.-J. Chang M.-J. Guo Y.-H. Wang J.-S. Yu H.-Y. Wu M.-J. Jou Mitochondria-targeted photosensitizer enhances the photodynamic effect-induced mitochondrial dysfunction and apoptosis Ann. N. Y. Acad. Sci. 2005 1042 419 428
19. E. Buytaert M. Dewaele P. Agostinis Molecular effectors of multiple cell death pathways initiated by photodynamic therapy Biochim. Biophys. Acta - Rev. Cancer 2007 1776 86 107
20. J. C. Reed Cytochrome c: can't live with it - can't live without it Cell 1997 91 559 562
21. A. C. E. Moor Signaling pathways in cell death and survival after photodynamic therapy J. Photochem. Photobiol., B 2000 57 1 13
22. P. Pasetto X. Chen C. M. Drain R. W. Franck Synthesis of hydrolytically stable porphyrin C- and S-glycoconjugates in high yields Chem. Commun. 2001 81 82
23. X. Chen C. M. Drain Photodynamic therapy using carbohydrate conjugated porphyrins Drug Design Rev. Online 2004 1 215 234
24. C. Xu B. Bailly-Maitre J. C. Reed Endoplasmic reticulum stress: cell life and death decisions J. Clin. Invest. 2005 115 2656 2664
25. E. A. Slee C. Adrain S. J. Martin Serial killers: ordering caspase activation events in apoptosis Cell Death Differentiation 1999 6 1067 1074
26. S. Kothakota T. Azuma C. Reinhard A. Klippel J. Tang K. Chu T. J. McGarry M. W. Kirschner K. Koths D. J. Kwiatkowski L. T. Williams Caspase-3-generated fragment of gelsolin: effector of morphological change in apoptosis Science 1997 278 294 298
27. S.-W. Yu H. Wang M. F. Poitras C. Coombs W. J. Bowers H. J. Federoff G. G. Poirier T. M. Dawson V. L. Dawson Mediation of poly(ADP-ribose) polymerase-1-dependent cell death by apoptosis-inducing factor Science 2002 297 259 263
28. G. de Murcia J. M. de Murcia Poly(ADP-ribose) polymerase: a molecular nick-sensor Trends Biochem. Sci. 1994 19 172 176
29. B. S. P. Reddy S. M. Sondhi J. W. Lown Synthetic DNA minor groove-binding drugs Pharm. Therap. 1999 84 1 111
30. C. M. Drain X. Gong Synthesis of meso substituted porphyrins in air without solvents or catalysts Chem. Commun. 1997 2117 2118
31. J. S. Lindsey I. C. Schreiman H. C. Hsu P. C. Kearney A. M. Marguerettaz Rothemund and Adler-Longo reactions revisited: Synthesis of tetraphenylporphyrins under equilibrium conditions J. Org. Chem. 1987 52 827 836
32. A. D. Adler F. R. Longo J. D. Finarelli J. Goldmacher J. Assour L. Korsakoff A simplified synthesis for meso-tetraphenylporphine J. Org. Chem. 1967 32 476 476
33. J. Caramelo A. J. Parodi How sugars convey information on protein conformation in the endoplasmic reticulum Seminars Cell Developmental Biol. 2007 18 732 742
34. C. M. Drain X. Gong V. Ruta C. E. Soll P. F. Chicoineau Combinatorial synthesis and modification of functional porphyrin libraries: identification of new, amphipathic motifs for biomolecule binding J. Comb. Chem. 1999 1 286 290
35. M. W. Grinstaff M. G. Hill J. A. Labinger H. B. Gray Mechanism of catalytic oxygenation of alkanes by halogenated iron porphyrins Science 264 1311 1313
36. D. Samaroo M. Vinodu X. Chen C. M. Drain 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
37. K. Fujimoto T. Miyata Y. Aoyama Saccharide-directed cell recognition and molecular delivery using macrocyclic saccharide clusters: Masking of hydrophobicity to enhance the saccharide specificity J. Am. Chem. Soc. 2000 122 3558 3559
38. M. Lam N. L. Oleinick A.-L. Nieminen Photodynamic therapy-induced apoptosis in epidermoid carcinoma cells. Reactive oxygen species and mitochondrial inner membrane permeabilization J. Biol. Chem. 2001 276 47379 47386
39. R. K. Pandey Recent advances in photodynamic therapy J. Porphyrins Phthalocyanines 2000 4 368 373
40. M. Srivastava N. Ahmad S. Gupta H. Mukhtar Involvement of Bcl-2 and Bax in photodynamic therapy-mediated apoptosis. Antisense Bcl-2 oligonucleotide sensitizes RIF 1 cells to photodynamic therapy apoptosis J. Biol. Chem. 2001 276 15481 15488
41. Y. Luo D. Kessel Initiation of apoptosis versus necrosis by photodynamic therapy with chloroaluminum phthalocyanine Photochem. Photobiol. 1997 66 479 483
42. A. C. E. Moor Signaling pathways in cell death and survival after photodynamic therapy J. Photochem. Photobiol., B 2000 57 1 13