Thiols and the chemoprevention of cancer

Current Opinion in Pharmacology

Volumn 7, Issue 4, 2007, Pages 404-409

  Huber, Wolfgang W ^a   Parzefall, Wolfram ^a  

^a MEDICAL UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCYSTEINE; BENZYL SELENOCYANATE; BUCILLAMINE; CAPTOPRIL; CARCINOGEN; CYCLOPHOSPHAMIDE; GLUTATHIONE; ISOTHIOCYANIC ACID; PROTEIN; SELENIUM DERIVATIVE; THIOL;

ANTIOXIDANT ACTIVITY; CANCER; CANCER CHEMOTHERAPY; CANCER PREVENTION; CARCINOGENESIS; CHEMOPROPHYLAXIS; ENZYME INDUCTION; GLUTATHIONE METABOLISM; HUMAN; OXIDATION; OXIDATION REDUCTION STATE; OXIDATIVE STRESS; PRIORITY JOURNAL; REVIEW; SIGNAL TRANSDUCTION;

ANIMALS; ANTICARCINOGENIC AGENTS; ANTIOXIDANTS; CARCINOGENS; CYSTEINE; DRUG DELIVERY SYSTEMS; GLUTATHIONE; HUMANS; NEOPLASMS; OXIDATION-REDUCTION; OXIDATIVE STRESS; SIGNAL TRANSDUCTION; SULFHYDRYL COMPOUNDS;

EID: 34548066349     PISSN: 14714892     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.coph.2007.05.005     Document Type: Review

References (54)

1. Na H.K., and Surh Y.J. Transcriptional regulation via cysteine thiol modification: a novel molecular strategy for chemoprevention and cytoprotection. Mol Carcinogen 45 (2006) 368-380. This up-to-date review gives a detailed summary of thiol-related signalling mechanisms, particularly of individual chemoprotective substances that function via modification of these mechanisms.
2. Cross J.V., and Templeton D.J. Regulation of signal transduction through protein cysteine oxidation. Antioxid Redox Signal 8 (2006) 1819-1827
3. Giles G.I. The redox regulation of thiol dependent signaling pathways in cancer. Curr Pharm Des 12 (2006) 4427-4443
4. Jones D.P. Redefining oxidative stress. Antioxid Redox Signal 8 (2006) 1865-1879
5. Pullar J.M., Thomson S.J., King M.J., Turnbull C.I., Midwinter R.G., and Hampton M.B. The chemopreventive agent phenethyl isothiocyanate sensitizes cells to Fas-mediated apoptosis. Carcinogenesis 25 (2004) 765-772
6. Lillig C.H., and Holmgren A. Thioredoxin and related molecules-from biology to health and disease. Antioxid Redox Signal 9 (2007) 25-47. This study is an up-to-date and comprehensive review on thioredoxin and glutaredoxin, providing various illustrations of thioredoxin functions and discussing the relation with several disease conditions.
7. Haendeler J. Thioredoxin-1 and posttranslational modifications. Antioxid Redox Signal 8 (2006) 1723-1728
8. Trosko J.E. Dietary modulation of the multistage, multimechanisms of human carcinogenesis: effects on initiated stem cells and cell-cell communication. Nutr Cancer 54 (2006) 102-110
9. Kwiecien I., Michalska M., and Wlodek L. The selective effect of cystathionine on doxorubicin hepatotoxicity in tumor-bearing mice. Eur J Pharmacol 550 (2006) 39-46
10. Neuwelt E.A., Pagel M.A., Kraemer D.F., Peterson D.R., and Muldoon L.L. Bone marrow chemoprotection without compromise of chemotherapy efficacy in a rat brain tumor model. J Pharmacol Exp Ther 309 (2004) 594-599
11. Block K.I., Koch A.C., Mead M.N., Tothy P.K., Newman R.A., and Gyllenhaal C. Impact of antioxidant supplementation on chemotherapeutic efficacy: a systematic review of the evidence from randomized controlled trials. Cancer Treat Rev (2007) 10.1016/j.ctrv.2007.01.005. In this paper, various antioxidants including GSH and NAC are discussed with regard to possible interactions with the effects of anticancer chemotherapy. A total of 845 articles were considered leading to the selection of 19 trials that met the inclusion criteria. As a result, none of the trials reported decreased therapy efficiency by antioxidants whereas there was an improvement of therapy in several of the trials.
12. Hayes J.D., Flanagan J.U., and Jowsey I.R. Glutathione transferases. Annu Rev Pharmacol Toxicol 45 (2005) 51-88
13. Guengerich F.P. Activation of dihaloalkanes by thiol-dependent mechanisms. J Biochem Mol Biol 36 (2003) 20-27
14. Hayes J.D., and McLellan L.I. Glutathione and glutathione-dependent enzymes represent a co-ordinately regulated defence against oxidative stress. Free Radic Res 31 (1999) 273-300
15. Klaunig J.E., and Kamendulis L.M. The role of oxidative stress in carcinogenesis. Annu Rev Pharmacol Toxicol 44 (2004) 239-267
16. Valko M., Rhodes C.J., Moncol J., Izakovic M., and Mazur M. Free radicals, metals and antioxidants in oxidative stress-induced cancer. Chem Biol Interact 160 (2006) 1-40
17. Michelet L., Zaffagnini M., Massot V., Keryer E., Vanacker H., Miginiac-Maslow M., Issakidis-Bourguet E., and Lemaire S.D. Thioredoxins, glutaredoxins, and glutathionylation: new crosstalks to explore. Photosynth Res 89 (2006) 225-245
18. Fratelli M., Gianazza E., and Ghezzi P. Redox proteomics: identification and functional role of glutathionylated proteins. Expert Rev Proteomics 1 (2004) 365-376
19. Kim E.H., and Surh Y.J. 15-Deoxy-Delta12,14-prostaglandin J2 as a potential endogenous regulator of redox-sensitive transcription factors. Biochem Pharmacol 72 (2006) 1516-1528
20. Drake E.N. Cancer chemoprevention: selenium as a prooxidant, not an antioxidant. Med Hypotheses 67 (2006) 318-322
21. Heiss E., Herhaus C., Klimo K., Bartsch H., and Gerhauser C. Nuclear factor kappa B is a molecular target for sulforaphane-mediated anti-inflammatory mechanisms. J Biol Chem 276 (2001) 32008-32015
22. Pei P., Horan M.P., Hille R., Hemann C.F., Schwendeman S.P., and Mallery S.R. Reduced nonprotein thiols inhibit activation and function of MMP-9: implications for chemoprevention. Free Radic Biol Med 41 (2006) 1315-1324
23. Blakytny R., Erkell L.J., and Brunner G. Inactivation of active and latent transforming growth factor beta by free thiols: potential redox regulation of biological action. Int J Biochem Cell Biol 38 (2006) 1363-1373
24. Iciek M., Chwatko G., Rokita H., Bald E., and Wlodek L. The effects of modulation of gamma-glutamyl transpeptidase activity in HepG2 cells on thiol homeostasis and caspase-3-activity. Biochim Biophys Acta 1773 (2007) 201-208
25. Albini A., Morini M., D'Agostini F., Ferrari N., Campelli F., Arena G., Noonan D.M., Pesce C., and De Flora S. Inhibition of angiogenesis-driven Kaposi's sarcoma tumor growth in nude mice by oral N-acetylcysteine. Cancer Res 61 (2001) 8171-8178
26. Cat B., Stuhlmann D., Steinbrenner H., Alili L., Holtkotter O., Sies H., and Brenneisen P. Enhancement of tumor invasion depends on transdifferentiation of skin fibroblasts mediated by reactive oxygen species. J Cell Sci 119 (2006) 2727-2738. The authors show that N-acetylcysteine, selenium-containing compounds, and other antioxidants inhibit the transdifferentiation of skin fibroblasts to myofibroblasts, a phenomenon that facilitates tumor invasion. The data support the concept of stromal therapy as a means of chemoprevention of cancer progression.
27. Brown K.E., Meleah Mathahs M., Broadhurst K.A., Coleman M.C., Ridnour L.A., Schmidt W.N., and Spitz D.R. Increased hepatic telomerase activity in a rat model of iron overload: a role for altered thiol redox state?. Free Radic Biol Med 42 (2007) 228-235. This paper, employing a rat liver model, provides in vivo evidence that increased telomerase activity is associated with thiol alterations.
28. del Bello B., Paolicchi A., Comporti M., Pompella A., and Maellaro E. Hydrogen peroxide produced during gamma-glutamyl transpeptidase activity is involved in prevention of apoptosis and maintenance of proliferation in U937 cells. Faseb J 13 (1999) 69-79
29. Urig S., Becker K., Lieske J., Fritz-Wolf K., Irmler A., Ahmadi R., Hartmann M., Helmke B.M., Koncarevic S., Allenberger B., et al. On the potential of thioredoxin reductase inhibitors for cancer therapy. Semin Cancer Biol 16 (2006) 452-465. A comprehensive review on the perspectives of cancer therapy based on thioredoxin reductase inhibition, which is a fairly novel concept in cancer chemotherapy/chemoprevention.
30. Biaglow J.E., and Miller R.A. The thioredoxin reductase/thioredoxin system: novel redox targets for cancer therapy. Cancer Biol Ther 4 (2005) 6-13
31. Heiss E., and Gerhauser C. Time-dependent modulation of thioredoxin reductase activity might contribute to sulforaphane-mediated inhibition of NF-kappaB binding to DNA. Antioxid Redox Signal 7 (2005) 1601-1611
32. Dinkova-Kostova A.T., Holtzclaw W.D., Cole R.N., Itoh K., Wakabayashi N., Katoh Y., Yamamoto M., and Talalay P. Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants. Proc Natl Acad Sci USA 99 (2002) 11908-11913
33. Hong F., Freeman M.L., and Liebler D.C. Identification of sensor cysteines in human Keap1 modified by the cancer chemopreventive agent sulforaphane. Chem Res Toxicol 18 (2005) 1917-1926
34. Zhang Y., Li J., and Tang L. Cancer-preventive isothiocyanates: dichotomous modulators of oxidative stress. Free Radic Biol Med 38 (2005) 70-77
35. Cho H.Y., Reddy S.P., and Kleeberger S.R. Nrf2 defends the lung from oxidative stress. Antioxid Redox Signal 8 (2006) 76-87
36. Dinkova-Kostova A.T., Massiah M.A., Bozak R.E., Hicks R.J., and Talalay P. Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups. Proc Natl Acad Sci USA 98 (2001) 3404-3409
37. Huber W.W., Scharf G., Rossmanith W., Prustomersky S., Grasl-Kraupp B., Peter B., Turesky R.J., and Schulte-Hermann R. The coffee components Kahweol and Cafestol induce γ-glutamylcysteine synthetase, the rate limiting enzyme of chemoprotective glutathione synthesis, in several organs of the rat. Arch Toxicol 75 (2002) 685-694
38. McMahon M., Itoh K., Yamamoto M., Chanas S.A., Henderson C.J., McLellan L.I., Wolf C.R., Cavin C., and Hayes J.D. The Cap'n'Collar basic leucine zipper transcription factor Nrf2 (NF-E2 p45-related factor 2) controls both constitutive and inducible expression of intestinal detoxification and glutathione biosynthetic enzymes. Cancer Res 61 (2001) 3299-3307
39. De Flora S., Izzotti A., D'Agostini F., and Balansky R.M. Mechanisms of N-acetylcysteine in the prevention of DNA damage and cancer, with special reference to smoking-related end-points. Carcinogenesis 22 (2001) 999-1013
40. Reliene R., and Schiestl R.H. Antioxidant N-acetyl cysteine reduces incidence and multiplicity of lymphoma in Atm deficient mice. DNA Rep (Amst) 5 (2006) 852-859. In a 2-year study on ROS-sensitive atm-deficient mice, dietary N-acetylcysteine reduced both incidence and multiplicity of lymphoma by ca. 50% while increasing the lifespan of these animals by ca. one-third.
41. Izzotti A., Bagnasco M., Cartiglia C., Longobardi M., Camoirano A., Tampa E., Lubet R.A., and De Flora S. Modulation of multigene expression and proteome profiles by chemopreventive agents. Mutat Res 591 (2005) 212-223
42. Niture S.K., Velu C.S., Smith Q.R., Bhat G.J., and Srivenugopal K.S. Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines. Carcinogenesis 28 (2007) 378-389
43. Hosseinimehr S.J., and Karami M. Chemoprotective effects of captopril against cyclophosphamide-induced genotoxicity in mouse bone marrow cells. Arch Toxicol 79 (2005) 482-486
44. Wielandt A.M., Vollrath V., Farias M., and Chianale J. Bucillamine induces glutathione biosynthesis via activation of the transcription factor Nrf2. Biochem Pharmacol 72 (2006) 455-462
45. Kassie F., Uhl M., Rabot S., Grasl-Kraupp B., Verkerk R., Kundi M., Chabicovsky M., Schulte-Hermann R., and Knasmuller S. Chemoprevention of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)-induced colonic and hepatic preneoplastic lesions in the F344 rat by cruciferous vegetables administered simultaneously with the carcinogen. Carcinogenesis 24 (2003) 255-261
46. Kim T.S., Yun B.Y., and Kim I.Y. Induction of the mitochondrial permeability transition by selenium compounds mediated by oxidation of the protein thiol groups and generation of the superoxide. Biochem Pharmacol 66 (2003) 2301-2311
47. Spallholz J.E., Palace V.P., and Reid T.W. Methioninase and selenomethionine but not Se-methylselenocysteine generate methylselenol and superoxide in an in vitro chemiluminescent assay: implications for the nutritional carcinostatic activity of selenoamino acids. Biochem Pharmacol 67 (2004) 547-554
48. Kim T.S., Jeong D.W., Yun B.Y., and Kim I.Y. Dysfunction of rat liver mitochondria by selenite: induction of mitochondrial permeability transition through thiol-oxidation. Biochem Biophys Res Commun 294 (2002) 1130-1137
49. Richie Jr. J.P., Kleinman W., Desai D.H., Das A., Amin S.G., Pinto J.T., and El-Bayoumy K. The organoselenium compound 1,4-phenylenebis(methylene)selenocyanate inhibits 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced tumorgenesis and enhances glutathione-related antioxidant levels in A/J mouse lung. Chem Biol Interact 161 (2006) 93-103
50. Pinto J.T., Krasnikov B.F., and Cooper A.J. Redox-sensitive proteins are potential targets of garlic-derived mercaptocysteine derivatives. J Nutr 136 (2006) 835S-841S
51. Huber W.W., and Parzefall W. Modification of N-acetyltransferases and glutathione S-transferases by coffee components: possible relevance for cancer risk. Meth Enzymol 401 (2005) 307-341
52. Khan S.M., Sobti R.C., and Kataria L. Pesticide-induced alteration in mice hepato-oxidative status and protective effects of black tea extract. Clin Chim Acta 358 (2005) 131-138
53. Nakamura Y., Yoshida C., Murakami A., Ohigashi H., Osawa T., and Uchida K. Zerumbone, a tropical ginger sesquiterpene, activates phase II drug metabolizing enzymes. FEBS Lett 572 (2004) 245-250
54. 2. Carcinogenesis 27 (2006) 2383-2391