A mechanism for the proapoptic activity of ursodeoxycholic acid: Effects on Bcl-2 conformation

Cell Death and Differentiation

Volumn 11, Issue 8, 2004, Pages 906-914

  Castelli, M ^a   Reiners, Jr ^b   Kessel, D ^a  

^a WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b WAYNE STATE UNIVERSITY   (United States)

Author keywords

Apoptosis; Bcl 2; CPO; NPe6; Photodynamic therapy (PDT); SnET2

Indexed keywords

BH3 PROTEIN; LIPOSOME; PHOTOSENSITIZING AGENT; PROTEIN BCL 2; PROTEIN BCL XL; URSODEOXYCHOLIC ACID; 2 AMINO 6 BROMO 4 (1 CYANO 2 ETHOXY 2 OXOETHYL) 4H CHROMENE 3 CARBOXYLIC ACID ETHYL ESTER; BCL2 PROTEIN, MOUSE; BENZOPYRAN DERIVATIVE; BILE ACID; ENZYME INHIBITOR; HA14-1; NITRILE; ONCOPROTEIN;

ANIMAL CELL; APOPTOSIS; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG POTENTIATION; DRUG PROTEIN BINDING; ENDOPLASMIC RETICULUM; FLUORESCENCE POLARIZATION; FLUORESCENCE RESONANCE ENERGY TRANSFER; HYDROPHOBICITY; HYPOTHESIS; LIGHT DAMAGE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN DOMAIN; PROTEIN LOCALIZATION; REGULATORY MECHANISM; STRUCTURE ACTIVITY RELATION; TUMOR CELL; ANIMAL; CELL CULTURE; CHEMISTRY; CONFORMATION; DRUG EFFECT; METABOLISM; PHYSIOLOGY;

ANIMALS; APOPTOSIS; BENZOPYRANS; BILE ACIDS AND SALTS; ENDOPLASMIC RETICULUM; ENZYME INHIBITORS; FLUORESCENCE POLARIZATION; FLUORESCENCE RESONANCE ENERGY TRANSFER; LIPOSOMES; MICE; MOLECULAR CONFORMATION; NITRILES; PHOTOSENSITIZING AGENTS; PROTO-ONCOGENE PROTEINS; TUMOR CELLS, CULTURED; URSODEOXYCHOLIC ACID;

EID: 4344618200     PISSN: 13509047     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.cdd.4401433     Document Type: Article

References (42)

1. Dougherty TJ, Gomer CJ, Henderson BW, Jori G, Kessel D, Korbelik M, Moan J and Peng Q (1998) Photodynamic therapy. J. Natl. Cancer Inst. 90: 889-905
2. Kim HR, Luo Y, Li G and Kessel D (1999) Enhanced apoptotic response to photodynamic therapy after Bcl-2 transfection. Cancer Res. 59: 3429-3432
3. Kessel D, Luo Y, Deng Y and Chang CK (1997) The role of subcellular localization in initiation of apoptosis by photodynamic therapy. Photochem. Photobiol. 65: 422-426
4. Xue LY, Chiu SM and Oleinick NL (2001) Photochemical destruction of the Bcl-2 oncoprotein during photodynamic therapy with the phthalocyanine photosensitizer Pc 4. Oncogene 20: 3420-3427
5. Kessel D, Castelli M and Reiners Jr JJ (2002) Apoptotic response to photodynamic therapy versus the Bcl-2 antagonist HA14-1. Photochem. Photobiol. 76: 314-319
6. Kessel D and Castelli M (2001) Evidence that Bcl-2 is the target of three photosensitizers that induce a rapid apoptotic response. Photochem. Photobiol. 74: 318-322
7. Usuda J, Chiu SM, Murphy ES, Lam M, Nieminen A and Oleinick NL (2003) Domain-dependent photodamage to Bcl-2: a membrane-anchorage region is needed to form the target of phthalocyanine photosensitization. J. Biol. Chem. 278: 2021-2029
8. Ljubuncie P, Fuhrman B, Oiknine J, Aviram M and Bomzon A (1996) Effect of deoxycholic acid and ursodeoxycholic acid on lipid peroxidation in cultured macrophages. Gut 39: 475-478
9. Mitsuyoshi H, Nakashima T, Sumida Y, Yoh T, Nakajima Y, Ishikawa H, Inaba K, Sakamoto Y, Okanoue T and Kashima K (1999) Ursodeoxycholic acid protects hepatocytes against oxidative injury via induction of antioxidants. Biochem. Biophys. Res. Commun. 263: 537-542
10. Nguyen TD, Oliva L, Villard PH, Puyoou F, Sauze C, Montet AM, Lacarelle B, Durand A and Montet JC (1999) CYP2E1 and CYP3A1/2 gene expression is not associated with the ursodeoxycholate effect on ethanol-induced lipoperoxidation. Life Sci. 65: 1103-1113
11. Rodrigues CM, Fan G, Wong PY, Kren BT and Steer CJ (1998) Ursodeoxycholic acid may inhibit deoxycholic acid-induced apoptosis by modulating mitochondrial transmembrane potential and reactive oxygen species production. Mol. Med. 4: 165-178
12. Rodrigues CM, Ma X, Linehan-Stieers C, Fan G, Kren BT and Steer CJ (1999) Ursodeoxycholic acid prevents cytochrome c release in apoptosis by inhibiting mitochondrial membrane depolarization and channel formation. Cell Death Differ. 6: 842-854
13. Rodrigues CM, Fan G, Ma X, Kren BT and Steer CJ (1998) A novel role for ursodeoxycholic acid in inhibiting apoptosis by modulating mitochondrial membrane perturbation. J. Clin. Invest. 101: 2790-2799
14. Rodrigues CM and Steer CJ (2001) The therapeutic effects of ursodeoxycholic acid as an anti-apoptotic agent. Expert Opin. Invest. Drugs 10: 1243-1253
15. Botla R, Spivey JR, Aguilar H, Bronk SF and Gores GJ (1995) Ursodeoxycholate (UDCA) inhibits the mitochondrial membrane permeability transition induced by glycochenodeoxycholate: a mechanism of UDCA cytoprotection. J. Pharmacol. Exp. Ther. 272: 930-938
16. Rolo AP, Palmeira CM and Wallace KB (2002) Interactions of combined bile acids on hepatocyte viability: cytoprotection or synergism. Toxicol. Lett. 126: 197-203
17. Schlottman K, Wachs FP, Krieg RC, Kullmann F, Scholmerich J and Rogler G (2000) Characterization of bile salt-induced apoptosis in colon cancer cell lines. Cancer Res. 60: 4270-4276
18. Kessel D, Caruso JA and Reiners Jr JJ (2000) Potentiation of photodynamic therapy by ursodeoxycholic acid. Cancer Res. 60: 6985-6988
19. Wang JL, Liu D, Zhang ZJ, Shan S, Han X, Srinivasula SM, Croce CM, Alnemri ES and Huang Z (2000) Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proc. Natl. Acad. Sci. USA 97: 7124-7129
20. Liu D and Huang Z (2001) Synthetic peptides and non-peptidic molecules as probes of structure and function of Bcl-2 family proteins and modulators of apoptosis. Apoptosis 6: 453-462
21. Wilton JC, Matthews GM, Burgoyne RD, Mills CO, Chipman JK and Coleman R (1994) Fluorescent choleretic and cholestatic bile salts take different paths across the hepatocyte:transcytosis of glycolithocholate leads to an extensive redistribution of annexin II. J. Cell Biol. 127: 401-410
22. Heyduk T (2002) Measuring protein conformational changes by FRET/LRET. Curr. Opin. Biotechnol. 3: 292-296
23. Toledano H, Edrei R and Kimel S (1998) Photodynamic damage by liposomebound porphycenes: comparison between in vitro and in vivo models. J. Photochem. Photobiol. B 42: 20-27
24. Conus S, Kaufmann T, Fellay I, Otter I, Rosse T and Borner C (2000) Bcl-2 is a monomeric protein: prevention of homodimerization by structural constraints. EMBO J. 19: 1534-1544
25. Budihardjo I, Oliver H, Lutter M, Luo X and Wang X (1999) Biochemical pathways of caspase activation during apoptosis. Annu. Rev. Cell Dev. Biol. 15: 269-290
26. Kessel D, Luo Y, Mathieu P and Reiners Jr JJ (2000) Determinants of the apoptotic response to lysosomal photodamage. Photochem. Photobiol. 71: 196-200
27. Reiners Jr JJ, Caruso JA, Mathieu P, Chelladurai B, Yin XM and Kessel D (2002) Release of cytochrome c and activation of pro-caspase-9 following lysosomal photodamage involves Bid cleavage. Cell Death Differ. 9: 934-944
28. Usuda J, Xue L-Y, Chio S-M, Azizuddin K, Morris RL, Mulvihill J and Oleinick NO (2003) From molecular PDT damage to cell and tumor responses: attempts at bridging the gap on the role of Bcl-2. Proc. SPIE 4952: 1-9
29. Xue L, Chiu S-M, Fiebig A, Andrews DW and Oleinick NO (2003) Photodamage to multiple Bcl-xL isoforms by photodynamic therapy with the phthalocyanine photosensitizer Pc 4. Oncogene 22: 9197-9204
30. Grebenova D, Kuzelova K, Smetana K, Pluskalova M, Cajthamlova H, Marinov I, Fuchs O, Soucek J, Jarolim P and Hrkal Z (2003) Mitochondrial and endoplasmic reticulum stress-induced apoptotic pathways are activated by 5-aminolevulinic acid-based photodynamic therapy in HL60 leukemia cells. J. Photochem. Photobiol. B 69: 71-85
31. Hanada M, Aime-Sempe C, Sato T and Reed JC (1995) Structure-function analysis of Bcl-2 protein. Identification of conserved domains important for homodimerization with Bcl-2 and heterodimerization with Bax. J. Biol. Chem. 270: 11962-11969
32. Xie Z, Schendel S, Matsuyama S and Reed JC (1998) Acidic pH promotes dimerization of Bcl-2 family proteins. Biochemistry 37: 6410-6418
33. Rodrigues CMP, Sola S, Sharpe JC, Moura JJG and Steer CJ (2003) Tauroursodeoxycholic acid prevents Bax-induced membrane perturbation and cytochrome c release in isolated mitochondria. Biochemistry 42: 3070-3080
34. Hsu YT and Youle RJ (1998) Bax in murine thymus is a soluble monomeric protein that displays differential detergent-induced conformations. J. Biol. Chem. 273: 10777-10783
35. Garbo GM, Vicente MGH, Fingar V and Kessel D (2003) Effects of ursodeoxycholic acid on photodynamic therapy in a murine tumor model. Photochem. Photobiol. 78: 407-410
36. Morgan AR, Garbo GM, Keck RW and Selman SH (1988) New photosensitizers for photodynamic therapy: combined effect of metallopurpurin derivatives and light on transplantable bladder tumors. Cancer Res. 48: 194-198
37. Roberts WG, Shiau FY, Nelson JS, Smith KM and Berns MW (1988) In vitro characterization of monoaspartyl chlorin e6 and diaspartyl chlorin e6 for photodynamic therapy. J. Natl. Cancer Inst. 80: 330-336
38. 13C-labeled chenodeoxycholic, hyodeoxycholic, and ursodeoxycholic acids for the study of bile acid metabolism in liver disease. Clin. Chim. Acta 203: 77-89
39. 13C-labeled bile acids using formyl esters and a modified lead tetraacetate procedure. J. Lipid Res. 18: 400-403
40. Kochi J (1965) Formation of alkyl halides from acids by decarboxylation with lead (IV) acetate and halide salts. J. Org. Chem. 30: 3265-3271
41. Lee ST, Hoeflich KP, Wasfy GW, Woodgett JR, Leber B, Andrews DW, Hedley DW and Penn LZ (1999) Bcl-2 targeted to the endoplasmic reticulum can inhibit apoptosis induced by Myc but not etoposide in Rat-1 fibroblasts. Oncogene 18: 3520-3528
42. Schendel SL and Reed JC (2000) Measuring pore formation by Bcl-2 family proteins. Methods Enzymol. 322: 274-282