Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway

BMC Cancer

Volumn 6, Issue , 2006, Pages

  Habermehl, Daniel ^a   Kammerer, Bernd ^a   Handrick, René ^a   Eldh, Therese ^a   Gruber, Charlotte ^a   Cordes, Nils ^c   Daniel, Peter T ^d   Plasswilm, Ludwig ^b   Bamberg, Michael ^a   Belka, Claus ^a   Jendrossek, Verena ^a  

^a UNIVERSITY HOSPITAL TÜBINGEN   (Germany)

^b UNIVERSITY HOSPITAL BASEL   (Switzerland)

^c DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^d CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALLOCRYPTOPINE; BENZYLOXYCARBONYLVALYLALANYLASPARTYL FLUOROMETHYL KETONE; CASPASE; CASPASE 8; CASPASE 9; CHELERYTHRINE; CHELIDONINE; CHELIDONIUM EXTRACT; DEATH RECEPTOR; FAS ASSOCIATED DEATH DOMAIN PROTEIN; FLICE INHIBITORY PROTEIN; LIGAND; NSC 631570; PROTEIN BCL 2; PROTEIN BCL XL; PROTOPINE; SANGUINARINE; UKRAIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL DEATH; CELL NUCLEUS; CHEMICAL COMPOSITION; CHROMATIN CONDENSATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ANALYSIS; DRUG CYTOTOXICITY; DRUG MECHANISM; ENZYME ACTIVATION; FLOW CYTOMETRY; FLUORESCENCE MICROSCOPY; GENE OVEREXPRESSION; HUMAN; HUMAN CELL; LIQUID CHROMATOGRAPHY; LYMPHOMA CELL LINE; MASS SPECTROMETRY; MEMBRANE DEPOLARIZATION; MEMBRANE POTENTIAL; MITOCHONDRIAL MEMBRANE; MITOCHONDRION; PROTEIN EXPRESSION; PROTEIN PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION; SYNTHESIS; T CELL LYMPHOMA; WESTERN BLOTTING;

EID: 33644505182     PISSN: 14712407     EISSN: 14712407     Source Type: Journal    
DOI: 10.1186/1471-2407-6-14     Document Type: Article

References (62)

1. Danilos J, Zbroja-Sontag W, Baran E, Kurylcio L, Kondratowicz L, Jusiak L: Preliminary studies on the effect of Ukrain (Tris(2-([5bS-(5ba,6b,12ba)]- 5b,6,7,12b,13,14-hexahydro-13-methyl[1,3] benzodioxolo[5,6-v]-1-3- dioxolo[4,5-i]phenanthridinium-6-ol] -Ethaneaminyl)Phosphinesulfide.6HCl ) on the immunological response in patients with malignant tumours. Drugs Exp Clin Res 1992, 18(Suppl):55-62.
2. Pengsaa P, Wongpratoom W, Vatanasapt V, Udomthavornsuk B, Mairieng E, Tangvorapongchai V, Pesi M, Krusan S, Boonvisoot V, Nowicky JW: The effects of thiophosphoric acid (Ukrain) on cervical cancer, stage IB bulky. Drugs Exp Clin Res 1992, 18(Suppl):69-72.
3. Sotomayor EM, Rao K, Lopez DM, Liepins A. Enhancement of macrophage turmouricidal activity by the alkaloid derivative Ukrain. In vitro and in vivo studies. Drugs Exp Clin Res 1992, 18(Suppl):5-11.
4. Hohenwarter O, Strutzenberger K, Katinger H, Liepins A, Nowicky JW: Selective inhibition of in vitro cell growth by the anti-tumour drug Ukrain. Drugs Exp Clin Res 1992, 18(Suppl):1-4.
5. Grinevich Y, Shalimov S, Bendyuh G, Zahriychuk O, Hodysh Y: Effect of Ukrain on the growth and metastasizing of Lewis carcinoma in C57BL/6 mice. Drugs Exp Clin Res 2005, 31(2):59-70.
6. Cordes N, Plasswilm L, Bamberg M, Rodemann HP: Ukrain, an alkaloid thiophosphoric acid derivative of Chelidonium majus L. protects human fibroblasts but not human tumour cells in vitro against ionizing radiation. Int J Radiat Biol 2002, 78(1):17-27.
7. Panzer A, Hamel E, Joubert AM, Bianchi PC, Seegers JC: Ukrain(TM), a semisynthetic Chelidonium majus alkaloid derivative, acts by inhibition of tubulin polymerization in normal and malignant cell lines. Cancer Lett 2000, 160(2):149-157.
8. Ernst E, Schmidt K: Ukrain - a new cancer cure? A systematic review of randomised clinical trials. BMC Cancer 2005, 5(1):69.
9. Liepins A, Nowicky JW, Bustamante JO, Lam E: Induction of bimodal programmed cell death in malignant cells by the derivative Ukrain (NSC-631570). Drugs Exp Clin Res 1996, 22(35): 73-79.
10. Kurochkin SN, Kolobkov SL, Votrin II, Voltchek IV: Induction of apoptosis in cultured Chinese hamster ovary cells by Ukrain and its synergistic action With etoposide. Drugs Exp Clin Res 2000, 26(5-6):275-278.
11. Nowicky JW, Hiesmayr W, Nowicky W, Liepins A: Influence of Ukrain on human xenografts in vitro. Drugs Exp Clin Res 1996, 22(3-5):93-97.
12. Roublevskaia IN, Haake AR, Ludlow JW, Polevoda BV: Induced apoptosis in human prostate cancer cell line LNCaP by Ukrain. Drugs Exp Clin Res 2000, 26(5-6):141-147.
13. Roublevskaia IN, Polevoda BV, Ludlow JW, Haake AR: Induced G2/M arrest and apoptosis in human epidermoid carcinoma cell lines by semisynthetic drug Ukrain. Anticancer Res 2000, 20(5A):3163-3167.
14. Fischer U, Janicke RU, Schulze-Osthoff K: Many cuts to ruin: a comprehensive update of caspase substrates. Cell Death Differ 2003, 10(1):76-100.
15. Thorburn A: Death receptor-induced cell killing. Cell Signal 2004, 16(2):139-144.
16. Scholz C, Wieder T, Starck L, Essmann F, Schulze-Osthoff K, Dorken B, Daniel PT: Arsenic trioxide triggers a regulated form of caspase-independent necrotic cell death via the mitochondrial death pathway. Oncogene 2005, 24(11):1904-1913.
17. Orrenius S: Mitochondrial regulation of apoptotic cell death. Toxicol Lett 2004, 149(1-3):19-23.
18. Weinmann M, Jendrossek V, Handrick R, Guner D, Goecke B, Belka C: Molecular ordering of hypoxia-induced apoptosis: critical involvement of the mitochondrial death pathway in a FADD/caspase-8 independent manner. Oncogene 2004, 23(21):3757-3769.
19. Belka C, Rudner J, Wesselborg S, Stepczynska A, Marini P, Lepple-Wienhues A, Faltin H, Bamberg M, Budach W, Schulze-Osthoff K: Differential role of caspase-8 and BID activation during radiation- and CD95-induced apoptosis. Oncogene 2000, 19(9):1181-1190.
20. Rudner J, Jendrossek V, Lauber K, Daniel PT, Wesselborg S, Belka C: Type I and type II reactions in TRAIL-induced apoptosis -- results from dose-response studies. Oncogene 2005, 24(1):130-140.
21. von Haefen C, Wieder T, Essmann F, Schulze-Osthoff K, Dorken B, Daniel PT: Paclitaxel-induced apoptosis in BJAB cells proceeds via a death receptor-independent, caspases-3/-8-driven mitochondrial amplification loop. Oncogene 2003, 22(15):2236-2247.
22. Guner D, Belka C, Daniel PT: Disruption of cell death signaling in cancer: impact on disease prognosis and response to therapy. Curr Med Chem Anti-Canc Agents 2003, 3(5):319-326.
23. Sturm I, Bosanquet AG, Hermann S, Guner D, Dorken B, Daniel PT: Mutation of p53 and consecutive selective drug resistance in B-CLL occurs as a consequence of prior DNA-damaging chemotherapy. Cell Death Differ 2003, 10(4):477-484.
24. Mrozek A, Petrowsky H, Sturm I, Kraus J, Hermann S, Hauptmann S, Lorenz M, Dorken B, Daniel PT: Combined p53/Bax mutation results in extremely poor prognosis in gastric carcinoma with low microsatellite instability. Cell Death Differ 2003, 10(4):461-467.
25. Fischer U, Schulze-Osthoff K: New approaches and therapeutics targeting apoptosis in disease. Pharmacol Rev 2005, 57(2):187-215.
26. Belka C, Jendrossek V, Pruschy M, Vink S, Verheij M, Budach W: Apoptosis-modulating agents in combination with radio-therapy-current status and outlook. Int J Radiat Oncol Biol Phys 2004, 58(2):542-554.
27. Weinmann M, Jendrossek V, Guner D, Goecke B, Belka C: Cyclic exposure to hypoxia and reoxygenation selects for tumor cells with defects in mitochondrial apoptotic pathways. Faseb J 2004, 18(15):1906-8 Epub 2004 Sep 28.
28. Marini P, Schmid A, Jendrossek V, Faltin H, Daniel PT, Budach W, Belka C: Irradiation specifically sensitises solid tumour cell lines to TRAIL mediated apoptosis. BMC Cancer 2005, 5(1):5.
29. McLaughlin F, La Thangue NB: Histone deacetylase inhibitors open new doors in cancer therapy. Biochem Pharmacol 2004, 68(6):1139-1144.
30. El-Zawahry A, McKillop J, Voelkel-Johnson C: Doxorubicin increases the effectiveness of Apo2L/TRAIL for tumor growth inhibition of prostate cancer xenografts. BMC Cancer 2005, 5(1):2.
31. Jendrossek V, Handrick R, Belka C: Celecoxib activates a novel mitochondrial apoptosis signaling pathway. Faseb J 2003, 17(11):1547-9 Epub 2003 Jun 17.
32. Scholz C, Richter A, Lehmann M, Schulze-Osthoff K, Dorken B, Daniel PT: Arsenic trioxide induces regulated, death receptor-independent cell death through a Bcl-2-controlled pathway. Oncogene 2005, 24(47):7031-42.
33. Schmelz K, Wieder T, Tamm I, Muller A, Essmann F, Geilen CC, Schulze-Osthoff K, Dorken B, Daniel PT: Tumor necrosis factor alpha sensitizes malignant cells to chemotherapeutic drugs via the mitochondrial apoptosis pathway independently of caspase-8 and NF-kappaB. Oncogene 2004, 23(40):6743-6759.
34. Eberle J, Fecker LF, Hossini AM, Wieder T, Daniel PT, Orfanos CE, Geilen CC: CD95/Fas signaling in human melanoma cells: conditional expression of CD95L/FasL overcomes the intrinsic apoptosis resistance of malignant melanoma and inhibits growth and progression of human melanoma xenotransplants. Oncogene 2003, 22(57):9131-9141.
35. Panzer A, Joubert AM, Eloff JN, Albrecht CF, Erasmus E, Seegers JC: Chemical analyses of Ukrain, a semi-synthetic Chelidonium majus alkaloid derivative, fail to confirm its trimeric structure. Cancer Lett 2000, 160(2):237-241.
36. Jendrossek V, Muller I, Eibl H, Belka C: Intracellular mediators of erucylphosphocholine-induced apoptosis. Oncogene 2003, 22(17):2621-2631.
37. Rudner J, Belka C, Marini P, Wagner RJ, Faltin H, Lepple-Wienhues A, Bamberg M, Budach W: Radiation sensitivity and apoptosis in human lymphoma cells. Int J Radiat Biol 2001, 77(1):1-11.
38. Kataoka T, Schroter M, Hahne M, Schneider P, Irmler M, Thome M, Froelich CJ, Tschopp J: FLIP prevents apoptosis induced by death receptors but not by perforin/granzyme B, chemotherapeutic drugs, and gamma irradiation. J Immunol 1998, 161(8):3936-3942.
39. von Haefen C, Gillissen B, Hemmati PG, Wendt J, Guner D, Mrozek A, Belka C, Dorken B, Daniel PT: Multidomain Bcl-2 homolog Bax but not Bak mediates synergistic induction of apoptosis by TRAIL and 5-FU through the mitochondrial apoptosis pathway. Oncogene 2004, 23(50):8320-8332.
40. Daniel PT, Schulze-Osthoff K, Belka C, Guner D: Guardians of cell death: the Bcl-2 family proteins. Essays Biochem 2003, 39:73-88.
41. Roublevskaia IN, Haake AR, Polevoda BV: Bcl-2 overexpression protects human keratinocyte cells from Ukrain-induced apoptosis but not from G2/M arrest. Drugs Exp Clin Res 2000, 26(5-6):149-156.
42. Chung HS, An HJ, Jeong HJ, Won JH, Hong SH, Kim HM: Water extract isolated from Chelidonium majus enhances nitric oxide and tumour necrosis factor-alpha production via nuclear factor-kappaB activation in mouse peritoneal macrophages. J Pharm Pharmacol 2004, 56(1):129-134.
43. Chaturvedi MM, Kumar A, Darnay BG, Chainy GB, Agarwal S, Aggarwal BB: Sanguinarine (pseudochelerythrine) is a potent inhibitor of NIF-kappaB activation, IkappaBalpha phosphorylation, and degradation. J Biol Chem 1997, 272(48):30129-30134.
44. Barreto MC, Pinto RE, Arrabaca JD, Pavao ML: Inhibition of mouse liver respiration by Chelidonium majus isoquinoline alkaloids. Toxicol Lett 2003, 146(1):37-47.
45. Hiller KO, Ghorbani M, Schilcher H: Antispasmodic and relaxant activity of chelidonine, protopine, coptisine, and Chelidonium majus extracts on isolated guinea-pig ileum. Planta Med 1998, 64(8):758-760.
46. Saeed SA, Gilani AH, Majoo RU, Shah BH: Anti-thrombotic and anti-inflammatory activities of protopine. Pharmacol Res 1997, 36(1):1-7.
47. Vavreckova C, Gawlik I, Muller K: Benzophenanthridine alkaloids of Chelidonium majus; I. Inhibition of 5- and 12-lipoxygenase by a non-redox mechanism. Planta Med 1996, 62(5):397-401.
48. Vavreckova C, Gawlik I, Muller K: Benzophenanthridine alkaloids of Cheildonium majus; II. Potent inhibitory action against the growth of human keratinocytes. Planta Med 1996, 62(6):491-494.
49. Panzer A, Joubert AM, Bianchi PC, Hamel E, Seegers JC: The effects of chelidonine on tubulin polymerisation, cell cycle progression and selected signal transmission pathways. Eur J Cell Biol 2001, 80(1):111-118.
50. Ahmad N, Gupta S, Husain MM, Heiskanen KM, Mukhtar H: Differential antiproliferative and apoptotic response of sanguinarine for cancer cells versus normal cells. Clin Cancer Res 2000, 6(4):1524-1528.
51. Kemeny-Beke A, Aradi J, Damjanovich J, Beck Z, Facsko A, Berta A, Bodnar A: Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine.
52. Hoffmann TK, Leenen K, Hafner D, Balz V, Gerharz CD, Grund A, Ballo H, Hauser U, Bier H: Antitumor activity of protein kinase C inhibitors and cisplatin in human head and neck squamous cell carcinoma lines. Anticancer Drugs 2002, 13(1):93-100.
53. Ding Z, Tang SC, Weerasinghe P, Yang X, Pater A, Liepins A. The alkaloid sanguinarine is effective against multidrug resistance in human cervical cells via bimodal cell death. Biochem Pharmacol 2002, 63(8):1415-1421.
54. Debiton E, Madelmont JC, Legault J, Barthomeuf C: Sanguinarine-induced apoptosis is associated with an early and severe cellular glutathione depletion. Cancer Chemother Pharmacol 2003, 51(6):474-82 Epub 2003 Apr 17.
55. Wolff J, Knipling L: Antimicrotubule properties of benzophenanthridine alkaloids. Biochemistry 1993, 32(48):13334-13339.
56. Chan SL, Lee MC, Tan KO Yang LK, Lee AS, Flotow H, Fu NY, Butler MS, Soejarto DD, Buss AD, Yu VC: Identification of chelerythrine as an inhibitor of BclXL function. J Biol Chem 2003, 278(23):20453-6 Epub 2003 Apr 17.
57. Vogt A, Tamewitz A, Skoko J, Sikorski RP, Giuliano KA, Lazo JS: The benzo[c]phenanthridine alkaloid, sanguinarine, is a selective, cell-active inhibitor of mitogen-activated protein kinase phosphatase-I. J Biol Chem 2005, 280(19):19078-86 Epub 2005 Mar 7.
58. Nakajima. T, Yukawa O, Azuma C, Ohyama H, Wang B, Kojima S, Hayata I, Hama-Inaba H: Involvement of protein kinase C-related anti-apoptosis signaling in radiation-induced apoptosis in murine thymic lymphoma(3SBH5) cells. Radiat Res 2004, 161(5):528-534.
59. Chmura SJ, Mauceri HJ, Advani S, Heimann R, Beckett MA, Nodzenski E, Quintans J, Kufe DW, Weichselbaum RR: Decreasing the apoptotic threshold of tumor cells through protein kinase C inhibition and sphingomyelinase activation increases tumor killing by ionizing radiation. Cancer Res 1997, 57(19):4340-4347.
60. Adhami VM, Aziz MH, Mukhtar H, Ahmad N: Activation of prodeath Bcl-2 family proteins and mitochondrial apoptosis pathway by sanguinarine in immortalized human HaCaT keratinocytes. Clin Cancer Res 2003, 9(8):3176-3182.
61. Benninger J, Schneider HT, Schuppan D, Kirchner T, Hahn EG: Acute hepatitis induced by greater celandine (Chelidonium majus). Gastroenterology 1999, 117(5):1234-1237.
62. Stickel F, Poschl G, Seitz HK, Waldherr P, Hahn EG, Schuppan D: Acute hepatitis induced by Greater Celandine (Chelidonium majus). Scand J Gastroenterol 2003, 38(5):565-568.