Evaluation of cancer-preventive activity and structure-activity relationships of 3-demethylubiquinone Q2, isolated from the ascidian Aplidium glabrum, and its synthetic analogs

Pharmaceutical Research

Volumn 23, Issue 1, 2006, Pages 70-81

  Fedorov, Sergey N ^a,b   Radchenko, Oleg S ^a   Shubina, Larisa K ^a   Balaneva, Nadezhda N ^a   Bode, Ann M ^b   Stonik, Valentin A ^a   Dong, Zigang ^b  

^a UNIVERSITY OF MINNESOTA   (United States)

^b PACIFIC INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Apoptosis; Cancer prevention; Marine prenylated quinones; Nuclear factor; Structure activity relationship

Indexed keywords

2 (3',7' DIMETHYL OCTA 2',6' DIENYL) [1,4]BENZOQUINONE; 2 METHOXY 3 (3',7' DIMETHYL OCTA 2',6' DIENYL) [1,4]BENZOQUINONE; 2 METHOXY 3 (3',7',11' TRIMETHYL DODECA 2',6',10' TRIENYL) [1,4]BENZOQUINONE; 2 METHOXY 3,5 (3',7',11' DIMETHYL OCTA 2',6' DIENYL) [1,4]BENZENE 1,4 DIOL; 2 METHOXY 5 (3',7' DIMETHYL OCTA 2',6' DIENYL) [1,4]BENZOQUINONE; 2 METHOXY 5 (3',7',11' TRIMETHYL DODECA 2',6',10' TRIENYL) [1,4]BENZOQUINONE; 2 METHOXY 5,6 (3',7',11' DIMETHYL OCTA 2',6' DIENYL) [1,4]BENZENE 1,4 DIOL; 2 METHOXY 6 (3',7' DIMETHYL OCTA 2',6' DIENYL) [1,4]BENZOQUINONE; 2 METHOXY 6 (3',7',11' TRIMETHYL DODECA 2',6',10' TRIENYL) [1,4]BENZOQUINONE; 2,3 DIMETHOXY 5 (3',7',11' TRIMETHYL DODECA 2',6',10' TRIENYL) [1,4]BENZOQUINONE; 2,3 DIMETHOXY 5 (3',7',11' TRIMETHYL DODECA 2',6',10' TRIENYL)BENZENE 1,4 DIOL; 2,3 DIMETHOXY 5,6 (3',7',11' DIMETHYL OCTA 2',6' DIENYL) [1,4]BENZENE 1,4 DIOL; 3 DEMETHYLUBIQUINONE Q2; AGAR; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; ISOPRENE; METHANETHIOSULFONATE; PROTEIN P53; QUINONE DERIVATIVE; SULFONIC ACID DERIVATIVE; THIOMESYLIC ACID METHYL ESTER; UNCLASSIFIED DRUG;

ANIMAL CELL; APLIDIUM GLABRUM; APOPTOSIS; ARTICLE; ASCIDIACEA; ASSAY; CANCER PREVENTION; CELL TRANSFORMATION; DRUG ACTIVITY; DRUG EFFECT; DRUG ISOLATION; DRUG SCREENING; FLOW CYTOMETRY; MEDICINAL PLANT; MOUSE; NONHUMAN; NONPARAMETRIC TEST; PRIORITY JOURNAL; PROTEIN FUNCTION; SKIN CELL; STATISTICAL ANALYSIS; STATISTICAL SIGNIFICANCE; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL SURVIVAL; DNA; FLOW CYTOMETRY; GENES, P53; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; NF-KAPPA B; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSCRIPTION FACTOR AP-1; UBIQUINONE; UROCHORDATA;

EID: 32244442128     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11095-005-8813-4     Document Type: Article

References (59)

1. C. Herskind K. Fleckenstein J. Lohr C. Y. Li F. Wenz F. Lohr 2004 Antitumoral action of interferons and interleukins in combination with radiotherapy. Part I: immunologic basis Strahlenther. Onkol. 180 187 193
2. E. A. Rogozin L. N. Urazova V. Yu Serebrov 2003 Influence of vaccines of Venezuelan equine encephalitis, influenza and mumps viruses on morphological pattern and vitality of human tumor cells in vitro J. BUON 8 39 43
3. P. Hersey 1993 Evaluation of vaccinia viral lysates as therapeutic vaccines in the treatment of melanoma Ann. N.Y. Acad. Sci. 690 167 177
4. I. D. Davis M. Jefford P. Parente J. Cebon 2003 Rational approaches to human cancer immunotherapy J. Leukoc. Biol. 73 3 29
5. K. L. Rinehart 2000 Antitumor compounds from tunicates Med. Res. Rev. 20 1 27
6. B. Haefner 2003 Drugs from the deep: marine natural products as drug candidates Drug Discov. Today 8 536 544
7. A. M. Mayer V. K. Lehmann 2001 Marine pharmacology in 1999: antitumor and cytotoxic compounds Anticancer Res 21 2489 2500
8. R. H. Thomson 1971 Naturally Occurring Quinones Academic Press London
9. J. F. Pennock 1967 The chemistry of isoprenoid quinones J. B. Pridham Terpenoids in Plants Academic Press London 129 146
10. D. J. Faulkner 1986 Marine natural products Nat. Prod. Rep. 3 1 33
11. M. Ochi, H. Kotsuki, S. Inoue, M. Taniguchi, and T. Tokoroyama. Isolation of 2-(3,7,11-trimethyl-2,6,10-dodecatrienyl) hydroquinone from the brown seaweed Dictyopteris unulata. Chem. Lett. 831-832 (1979).
12. R. J. Capon E. L. Ghisalberti P. R. Jefferies 1981 Isoprenoid dihydroquinones from a brown alga, Cystophora sp Phytochemistry 20 2598 2600
13. W. H. Gerwick W. Fenical 1981 Ichthyotoxic and cytotoxic metabolites of the tropical brown alga Stypopodium zonale (Lamouroux) Papenfuss J. Org. Chem. 46 22 27
14. W. Fenical 1978 Diterpenoids P. J. Scheuer Marine Natural Products, Chemical and Biological Perspectives, Vol. 2 Academic Press New York 238 245
15. L. Minale 1978 Terpenoids from marine sponges P. J. Scheuer Marine Natural Products, Chemical and Biological Perspectives, Vol. 1 Academic Press New York 220 240
16. S. De Rosa A. Crispino A. De Giulio C. Iodice A. Milone 1995 Sulfated polyprenylhydroquinones from the sponge Ircinia spinulosa J. Nat. Prod. 58 1450 1454
17. G. Bifulco I. Bruno L. Minale R. Riccio 1995 Bioactive prenylhydroquinone sulfates and a novel, C31 furanoterpene alcohol sulfate from the marine sponge, Ircinia sp J. Nat. Prod. 58 1444 1449
18. B. F. Bowden J. C. Coll 1981 Studies of Australian soft corals. XXVI tetraprenylbenzoquinone derivatives from a Nephthea species of soft coral (Octocorallia, Alcyonacea) Aust. J. Chem. 34 2677 2681
19. B. N. Ravi R. J. Wells 1982 Lipid and terpenoid metabolites of the gorgonian Plexaura flava Aust. J. Chem. 35 105 112
20. B. M. Howard K. Clarkson R. L. Bernstein 1979 Simple prenylated hydroquinone derivatives from the marine urochordate Aplidium californicum Tetrahedron Lett. 20 4449 4452
21. N. M. Targett W. S. Keeran 1984 A terpenehydroquinone from the marine ascidian Aplidium constellatum J. Nat. Prod. 47 556 557
22. G. Guella I. Mancini F. Pietra 1987 Verapliquinones: novel diprenylquinones from an Aplidium sp. (Ascidiacea) of the Ile-Verte waters, Brittany Helv. Chim. Acta 70 621 626
23. D. J. Faulkner 1993 Marine natural products Nat. Prod. Rep. 10 497 539
24. X. Fu M. Bilayet Hossain D. van der Helm F. Schmitz 1994 Longithorone A: unprecedented dimeric prenylated quinone from the tunicate Aplidium longithorax J. Am. Chem. Soc. 116 12125 12126
25. X. Fu M. Bilayet Hossain F. Schmitz D. van der Helm 1997 Longithorones, unique prenylated para- and metacyclopropane type quinones from the tunicate Aplidium longithorax J. Org. Chem. 62 3810 3819
26. 2 from the Far-eastern ascidian Aplidium glabrum: structure and synthesis Tetrahedron Lett. 46 559 562
27. S. De Rosa A. De Giulio C. Iodice 1994 Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays J. Nat. Prod. 57 1711 1716
28. D. Misiti H. W. Moore K. Folkers 1965 Identification of plastoquionone-2 from chloroplasts J. Am. Chem. Soc. 87 1402 1403
29. K. Sakamoto H. Miyoshi K. Takegami T. Mogi Y. Anraku H. Iwamura 1996 Probing substrate binding site of the Escherichia coli quinol oxidases using synthetic ubiquinol analogues J. Biol. Chem. 271 29897 29902
30. N. H. Colburn B. F. Former K. A. Nelson S. H. Yuspa 1979 Tumour promoter induces anchorage independence irreversibly Nature 281 589 591
31. N. H. Colburn E. J. Wendel G. Abruzzo 1981 Dissociation of mitogenesis and late-stage promotion of tumor cell phenotype by phorbol esters: mitogen-resistant variants are sensitive to promotion Proc. Natl. Acad. Sci. USA 78 6912 6916
32. Z. Dong J. L. Cmarik E. J. Wendel N. H. Colburn 1994 Differential transformation efficiency but not AP-1 induction under anchorage-dependent and -independent conditions Carcinogenesis 15 1001 1004
33. Z. Dong M. J. Birrer R. G. Watts L. M. Matrisian N. H. Colburn 1994 Blocking of tumor promoter-induced AP-1 activity inhibits induced transformation in JB6 mouse epidermal cells Proc. Natl. Acad. Sci. USA 91 609 613
34. Z. Dong S. G. Watts Y. Sun N. H. Colburn 1995 Progressive elevation of AP-1 activity during preneoplastic-to neoplastic progression as modeled in mouse JB6 cell variants Int. J. Oncol. 7 359 364
35. Z. Dong V. Lavrovsky N. H. Colburn 1995 Transformation reversion induced in JB6 RT101 cells by AP-1 inhibitors Carcinogenesis 16 749 756
36. Z. Dong J. L. Cmarik 2002 Harvesting cells under anchorage-independent cell transformation conditions for biochemical analyses Sci. STKE 2002 PL7
37. V. Lavrovsky Z. Dong W. Y. Ma N. Colburn 1996 Drug-induced reversion of progression phenotype is accompanied by reversion of AP-1 phenotype in JB6 cells In Vitro Cell. Dev. Biol., Anim. 32 234 237
38. J. Strickland Y. Sun Z. Dong N. H. Colburn 1997 Grafting assay distinguishes promotion sensitive from promotion resistant JB6 cells Carcinogenesis 18 1135 1138
39. Y. Sun K. Nakamura G. Hegamyer Z. Dong N. Colburn 1993 No point mutation of Ha-ras or p53 genes expressed in preneoplastic-to-neoplastic progression as modeled in mouse JB6 cell variants Mol Carcinog 8 49 57
40. B. N. Ames J. [tmp] McCann E. Yamasaki 1975 Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test Mutat. Res. 31 347 364
41. S. N. Fedorov A. M. Bode V. A. Stonik I. A. Gorshkova P. C. Schmid O. S. Radchenko E. V. Berdyshev Z. Dong 2004 Marine alkaloid polycarpine and its synthetic derivative dimethylpolycarpine induce apoptosis in JB6 cells through p53- and caspase 3-dependent pathways Pharm. Res. 21 2307 2319
42. C. Huang W. Y. Ma A. Goranson Z. Dong 1999 Resveratrol suppresses cell transformation and induces apoptosis through a p53-dependent pathway Carcinogenesis 20 237 242
43. M. Nomura A. Kaji W. Ma K. Miyamoto Z. Dong 2001 Suppression of cell transformation and induction of apoptosis by caffeic acid phenethyl ester Mol. Carcinog. 31 83 89
44. C. Huang W. Y. Ma J. Li S. S. Hecht Z. Dong 1998 Essential role of p53 in phenethyl isothiocyanate-induced apoptosis Cancer Res. 58 4102 4106
45. Z. He W. Y. Ma T. Hashimoto A. M. Bode C. S. Yang Z. Dong 2003 Induction of apoptosis by caffeine is mediated by the p53, Bax, and caspase 3 pathways Cancer Res. 63 4396 4401
46. L. R. Bernstein N. H. Colburn 1989 AP1/jun function is differentially induced in promotion-sensitive and resistant JB6 cells Science 244 566 569
47. M. R. Young J. J. Li M. Rincon R. A. Flavell B. K. Sathyanarayana R. Hunziker N. Colburn 1999 Transgenic mice demonstrate AP-1 (activator protein-1) transactivation is required for tumor promotion Proc. Natl. Acad. Sci. USA 96 9827 9832
48. R. Chiu P. Angel M. Karin 1989 Jun-B differs in its biological properties from, and is a negative regulator of, c-Jun Cell 59 979 986
49. E. Passegue W. Jochum M. Schorpp-Kistner U. Mohle-Steinlein E. F. Wagner 2001 Chronic myeloid leukemia with increased granulocyte progenitors in mice lacking junB expression in the myeloid lineage Cell 104 21 32
50. H. Le-Niculescu E. Bonfoco Y. Kasuya F. X. Claret D. R. Green M. Karin 1999 Withdrawal of survival factors results in activation of the JNK pathway in neuronal cells leading to Fas ligand induction and cell death Mol. Cell. Biol. 19 751 763
51. T. Kondo T. Matsuda T. Kitano A. Takahashi M. Tashima H. Ishikura H. Umehara N. Domae T. Uchiyama T. Okazaki 2000 Role of c-jun expression increased by heat shock- and ceramide-activated caspase-3 in HL-60 cell apoptosis. Possible involvement of ceramide in heat shock-induced apoptosis J. Biol. Chem. 275 7668 7676
52. S. Kasibhatla T. Brunner L. Genestier F. Echeverri A. Mahboubi D. R. Green 1998 DNA damaging agents induce expression of Fas ligand and subsequent apoptosis in T lymphocytes via the activation of NF-kappa B and AP-1 Mol. Cell 1 543 551
53. S. K. Manna N. K. Sah B. B. Aggarwal 2000 Protein tyrosine kinase p56lck is required for ceramide-induced but not tumor necrosis factor-induced activation of NF-kappa B, AP-1, JNK, and apoptosis J. Biol. Chem. 275 13297 13306
54. S. Leppa M. Eriksson R. Saffrich W. Ansorge D. Bohmann 2001 Complex functions of AP-1 transcription factors in differentiation and survival of PC12 cells Mol. Cell. Biol. 21 4369 4378
55. A. Berry M. Goodwin C. L. Moran T. C. Chambers 2001 AP-1 activation and altered AP-1 composition in association with increased phosphorylation and expression of specific Jun and Fos family proteins induced by vinblastine in KB-3 cells Biochem. Pharmacol. 62 581 591
56. M. Fan M. E. Goodwin M. J. Birrer T. C. Chambers 2001 The c-Jun NH(2)-terminal protein kinase/AP-1 pathway is required for efficient apoptosis induced by vinblastine Cancer Res. 61 4450 4458
57. R. Bessho K. Matsubara M. Kubota K. Kuwakado H. Hirota Y. Wakazono Y. W. Lin A. Okuda M. Kawai R. Nishikomori 1994 Pyrrolidine dithiocarbamate, a potent inhibitor of nuclear factor kappa B (NF-kappa B) activation, prevents apoptosis in human promyelocytic leukemia HL-60 cells and thymocytes Biochem. Pharmacol. 48 1883 1889
58. L. Garcia-Bermejo C. Perez N. E. Vilaboa E. de Blas P. Aller 1998 cAMP increasing agents attenuate the generation of apoptosis by etoposide in promonocytic leukemia cells J. Cell. Sci. 111Pt 5 637 644
59. A. A. Beg D. Baltimore 1996 An essential role for NF-kappaB in preventing TNF-alpha-induced cell death Science 274 782 784