Skip to main content
SpringerLink
Log in

Gold

  • Chapter
Metal Compounds in Cancer Therapy

Abstract

Gold, the noblest of elements, has a medicinal history that can be traced through the written history of every culture and far into prehistory by means of archaeological records. The early medicinal properties of gold were assigned on the basis of its mystical importance and its association with the sun (Higby, 1982). Modern medicine dismisses such uses for lack of plausible mechanisms. Yet, one can still obtain a modern descendant of such treatments. ‘Goldwasser’ is a liqueur containing particles of elemental gold foil (about 10 cents’ worth of gold in a litre) and reputed to have medicinal properties.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Agrawal, K. C., Bears, K. B., Marcus, D. and Jonassen, H. B. (1978) Gold triphenylphosphine complexes as a new class of potential antitumor agents. Proc. Am. Assoc. Cancer Res., 69, 110.

    Google Scholar 

  • Amagai, T., Miyamoto, T. K., Ichida, H. and Sasaki, Y. (1989) Preparation and crystal structure of new gold(I) complexes linked to pyrimidines. Bull Chem. Soc. Japan, 62, 1078–1080.

    Article  CAS  Google Scholar 

  • Arizti, M. P., Garcia-Orad, A., Sommer, F. et al. (1991) Intracellular accumulation and cytotoxic effect of (8-thiotheophyllinate)(triphenylphosphine) gold(I) in Friend leukemia cells. Anticancer Res., 11, 625–628.

    PubMed  CAS  Google Scholar 

  • Bakka, A., Endresen, L., Johnsen, A. B. S. et al. (1981) Resistance against cis-dichlorodiammineplatinum in cultured cells with a high content of metallothionein. Toxicol. Appl Pharmacol, 61, 215–226.

    Article  PubMed  CAS  Google Scholar 

  • Berners-Price, S. J., Jarrett, P. S. and Sadler, P. J. (1987) 31P NMR studies of [Au2(-(x-DPPE)+2] anti-tumor complexes. Conversion into [Au(DPPE)2 +] induced by thiols and blood plasma. Inorg. Chem., 26, 3074–3077.

    Article  CAS  Google Scholar 

  • Berners-Price, S. J., Mirabelli, C. K., Johnson, R. K. et al. (1986) In vivo antitumor activity and in vitro cytotoxic properties of bis[l,2-bis (diphenylphosphi-no) ethane]gold(I) chloride. Cancer Res., 46, 5486–5493.

    PubMed  CAS  Google Scholar 

  • Berners-Price, S. J., Girard, G. R., Hill, D. T. et al. (1990) Cytotoxicity and antitumour activity of some tetrahedral bis(diphosphino)gold(I) chelates. J. Med.Chem., 33, 1386–1392.

    Article  PubMed  CAS  Google Scholar 

  • Beverly, B. and Couri, D. (1987) Role of myeloperoxidase (MPO) in aurothio-malate metabolism. Fed. Proc, 46, 854.

    Google Scholar 

  • Brown, D.H. and Smith, W. E. (1980) The chemistry of the gold drugs used in the treatment of rheumatoid arthritis. Chem. Soc. Rev., 9, 217–239.

    Article  CAS  Google Scholar 

  • Crooke, S. T., Snyder, R. M., Butt, T. R. et al. (1986) Cellular and molecular pharmacology of auranofin and related gold complexes. Biochem. Pharmacol, 35, 3423–3431.

    Article  PubMed  CAS  Google Scholar 

  • De Pancorbo, M. M., Garcia-Orad, A., Arizti, M. P. et al. (1990) 8-(Thiotheophylli-nato) (triphenylphosphine) Gold(I), (tTPAu): a new complex of therapeutic gold ion, in Metal Ions in Biology and Medicine (eds Ph. Collery, L. A. Porier, M. Marfait and J. C. Eitenne), John Libbey Eurotext, Paris, pp. 385–389.

    Google Scholar 

  • Dhubhghaill, O. M. N., Sadler, P. J. and Kuroda, R. (1990) Gold(I) complexes of 1-diphenylarsino-2-diphenylphosphinoethane (dadpe): solution studies, X-ray crystal structures and cytotoxicity of [(AuCl)2dadpe].0.5dma (dma = dimethylacetamide) and [Au(dadpe)2]Cl.H2O. J. Chem. Soc. Dalton Trans, 2913-19.

    Google Scholar 

  • Elder, R. C. and Eidsness, M. K. (1987) Synchrotron X-ray studies of metal-based drugs and metabolites. Chem. Rev., 87, 1027–1046.

    Article  CAS  Google Scholar 

  • Elder, R. C., Tepperman, K. G., Eidsness, M. K. et al. (1983) EXAFSandXANESof gold-based anti-arthritic drugs and metabolites. ACS Symp. Ser., 209, 385–400.

    Article  CAS  Google Scholar 

  • Endresen, L., Bakka, A. and Rugstad, H. E. (1983) Increased resistance to chlorambucil in cultured cells with a high concentration of cytoplasmic metallothionein. Cancer Res., 43, 2918–2926.

    PubMed  CAS  Google Scholar 

  • Finkelstein, A. E., Burrone, O. R., Walz, D. T. and Misher, A. (1977) Effect of auranofin on DNA and protein synthesis in human lymphocytes. J. Rheumatol, 4, 245–251.

    PubMed  CAS  Google Scholar 

  • Garcia-Orad, A., Aritzi, P., Sommer, F. et al. (1993) The (8-theopyllinate) (triphenyllphosphine) Gold(I), ETAuP: a new gold complex as an anti-tumor agent. Biomed. Pharmacother., 47, 363–370.

    Article  PubMed  CAS  Google Scholar 

  • Grootveld, M. C., Razi, M. T. and Sadler, P. J. (1983) Progress in the characterization of gold drugs. Clin. Rheumatol, 3 (Suppl. 1), 5–16.

    Google Scholar 

  • Haiduc, I. and Silvestru, C. (1989) Rhodium, iridium, copper and gold antitumor organometallic compounds. In Vivo, 3, 285–294.

    PubMed  CAS  Google Scholar 

  • Hill, D. T., Girard, G. R., McCabe, F. L. et al. (1989) [μ-l,l′-Bis (diphenyl-phosphino) ferrocene]bis(chlorogold(I)): synthesis, iron-57 and gold-197 Mössbauer spectroscopy, X-ray crystal structure and antitumor activity. Inorg.Chem., 28, 3529–3533.

    Article  CAS  Google Scholar 

  • Higby, G. J. (1982) Gold in medicine. Gold Bull, 15, 130–140.

    Article  PubMed  CAS  Google Scholar 

  • Hoke, G. D., Macia, R. A., Meunier, P. C. et al. (1989) In vivo and in vitro cardiotoxicity of a gold-containing antineoplastic drug candidate in the rabbit. Toxicol. Appl. Pharmacol, 100, 293–306.

    Article  PubMed  CAS  Google Scholar 

  • Isab, A. A. and Sadler, P. J. (1977) Reactions of gold(III) ions with ribonuclease A and methionine derivatives in aqueous solution. Biochim. Biophys. Acta, 492, 322–330.

    Article  PubMed  CAS  Google Scholar 

  • Isab, A. A., Hormann, A. L., Coffer, M. T. and Shaw, C. F. III (1988) Reversibly and irreversibly formed products from the reactions of mercaptalbumin (AlbSH) with Et3PAuCN and of AlbSAuPEt3 with HCN. J. Am. Chem. Soc., 110, 3278–3284.

    Article  CAS  Google Scholar 

  • Johnson, R. K., Mirabelli, C. K., Faucette, L. F. et al. (1985) Antitumor activity of compounds related to bis(diphenylphosphine)ethane and its chlorogold(I) coordination complex. Proc. Am. Assoc. Cancer Res., 26, 254.

    Google Scholar 

  • Jones, P. G. (1981a) X-ray structural investigations of gold compounds. Gold Bull, 14, 102–118.

    Article  CAS  Google Scholar 

  • Jones, P. G. (1981b) X-ray structural investigations of gold compounds. Gold Bull, 14, 159–166.

    Article  CAS  Google Scholar 

  • Jones, P. G. (1983) X-ray structural investigations of gold compounds. Gold Bull, 16, 114–125.

    Article  CAS  Google Scholar 

  • Kägi, J. H. R. and Kojima, Y. (1985) Metallothionein II. Birkhäuser Verlag, Basel.

    Google Scholar 

  • Kubicka-Muranyi, M., Goebel, C., Griem, P. et al. (1993) Adverse immune reactions to drugs (gold, procainamide) and environmental chemicals (mercury, platinum): the role of phagocytic cells in generating immunogenic metabolites, in Symposium in Immunology I and II (eds M. Eibel, C. Huber and U. Wahn), Springer-Verlag, pp. 189-210.

    Google Scholar 

  • Laib, J. E., Shaw, C. F. III, Petering, D. H. et al. (1985) Formation and characterization of aurothioneins: Au, Zn, Cd-thionein, Au, Cd-thionein, and (thiomalato-Au) x-thionein. Biochemistry, 24, 1977–1986.

    Article  PubMed  CAS  Google Scholar 

  • Mirabelli, C. K., Johnson, R. K., Sung, C. M. et al. (1985) Evaluation of the in vivo anti-tumor activity and in vitro cytotoxic properties of auranofin, a coordinated gold compound, in murine tumor models. Cancer Res., 45, 32–39.

    PubMed  CAS  Google Scholar 

  • Mirabelli, C. K., Johnson, R. K., Hill, D. T. et al. (1986a) Correlation of the in vitro cytotoxic and in vivo anti-tumor activities of gold(I) coordination complexes. J.Med.Chem., 29, 218–223.

    Article  PubMed  CAS  Google Scholar 

  • Mirabelli, C. K., Jensen, B. D., Mattern, M. R. et al. (1986b) x-[l,2-bis (diphenylphosphino) ethane]bis (l-thio-β-D-glucopyranosato-S) gold(I): a novel antitumor agent. Anti-Cancer Drug Des., 1, 223–234.

    CAS  Google Scholar 

  • Mogilnicka, E. M. and Webb, M. (1983) Time-dependent uptake and metallothionein binding of gold, copper and zinc in the rat kidney. Biochem. Pharmacol, 32, 1341–1346.

    Article  PubMed  CAS  Google Scholar 

  • Moustatih, A. and Garnier-Suillerot, A. (1989) Bifunctional antitumor compounds: synthesis and characterization of a Au(III)-streptonigrin complex with thiol-modulating properties. J. Med. Chem., 32, 1426–1431.

    Article  PubMed  CAS  Google Scholar 

  • Parish, R. V. and Cottrill, S. M. (1987) Medicinal gold compounds. Gold Bull, 20, 3–12.

    Article  CAS  Google Scholar 

  • Puddephatt, R. J. (1978) The Chemistry of Gold. Elsevier, Amsterdam.

    Google Scholar 

  • Sadler, P. J. (1976) The biological chemistry of gold. A metallo-drug and heavy atom label with variable valency. Struct. Bonding, 29, 171–219.

    Article  CAS  Google Scholar 

  • Sadler, P. J., Nasr, M. and Narayanan, V. L. (1984) The design of metal complexes as anticancer drugs, in Platinum Coordination Complexes in Cancer Chemotherapy (eds M. P. Hacker, E. B. Douple and I. H. Krakoff), Martinus Nijhoff Publishing, Boston, pp. 290–304.

    Chapter  Google Scholar 

  • Schmitz, G., Minkel, D. T., Gingrich, D. and Shaw, C. F. III (1980) The binding of gold(I) to metallothionein. J. Inorg. Biochem., 12, 293–306.

    Article  PubMed  CAS  Google Scholar 

  • Schuhmann, D., Kubicka-Muranyi, M., Mirtcheva, J. et al. (1990) Adverse immune reactions to gold: chronic treatment with an Au(I) drug sensitizes mouse T cells not to Au(I) but to Au(III) and induces autoantibody formation. J.Immunol, 145, 2132–2139.

    PubMed  CAS  Google Scholar 

  • Shaw, C. F. III (1979) The mammalian biochemistry of gold: an inorganic perspective of chrysotherapy. Inorg. Persp. Biol. Med., 2, 278–355.

    Google Scholar 

  • Shaw, C. F. III (1989) The protein chemistry of anti-arthritic gold(I) thiolates and related complexes. Comments Inorg Chem., 8, 233–267.

    Article  CAS  Google Scholar 

  • Shaw, C. F. III and Savas, M. M. (1992) Aurothioneins, in Metallothioneins: Synthesis, Structure and Properties of Metallothioneins, Phytochelatins, and Metal-Thiolate Complexes (eds M. J. Stillman, C. F. Shaw III and K. T. Suzuki), VCH Publishers, New York, pp. 144–163.

    Google Scholar 

  • Shaw, C. F. III, Beery, A. and Stocco, G. C. (1986) Anti-tumor activity of two binuclear gold(I) complexes with bridging dithiolate ligands. Inorg. Chim. Acta, 123, 213–216.

    Article  CAS  Google Scholar 

  • Shaw, C. F. III, Cancro, M. P., Witkiewicz, P. L. and Eldridge, J. (1980) Gold(III) oxidation of disulfides in aqueous solution. Inorg. Chem., 19, 3198–3201.

    Article  CAS  Google Scholar 

  • Shaw, C. F. III, Isab, A. A., Coffer, M. T. and Mirabelli, C. K. (1990) Gold(I) efflux from auranofin-treated red blood cells. Evidence for a glutathione-gold-albumin metabolite. Biochem. Pharmacol, 40, 1227–1234.

    Article  PubMed  CAS  Google Scholar 

  • Simon, T. M., Kunishima, D. H., Vibert, G. J. and Lorber, A. (1979a) Inhibitory effects of a new oral gold compound on HeLa cells. Cancer, 44, 1965–1975.

    Article  PubMed  CAS  Google Scholar 

  • Simon, T. M., Kunishima, D. H., Vibert, G. J. and Lorber, A. (1979b) Cellular antiproliferative action exerted by auranofin. J. Rheumatol (Suppl. 5), 91–97.

    Google Scholar 

  • Simon, T. M., Kunishima, D. H., Vibert, G. J. and Lorber, A. (1981) Screening trial with the coordinated gold compound auranofin using mouse lymphocytic leukemia P388. Cancer Res., 41, 94–97.

    PubMed  CAS  Google Scholar 

  • Smith, W. E. and Reglinski, J. (1991) Gold drugs used in the treatment of rheumatoid arthritis. Persp. Bioinorg. Chem., 1, 183–208.

    CAS  Google Scholar 

  • Snyder, R. M., Mirabelli, C. K. and Crooke, S. T. (1986) Cellular association, intracellular distribution, and efflux of auranofin via sequential ligand exchange reactions. Biochem. Pharmacol, 35, 923–932.

    Article  PubMed  CAS  Google Scholar 

  • Snyder, R. M., Mirabelli, C. K., Johnson, R. K. et al. (1986) Modulation of the antitumor and biochemical properties of bis(diphenylphosphine)ethane with metals. Cancer Res., 46, 5054–5060.

    PubMed  CAS  Google Scholar 

  • Stillman, M. J., Shaw, C. F. III and Suzuki, K. T. (eds) (1992) Metallothioneins: Synthesis, Structure and Properties of Metallothioneins, Phytochelatins and Metal Thiolate Complexes. VCH Publishers, New York.

    Google Scholar 

  • Verwilghen, J., Kingsley, G. H., Gambling, L. and Panayi, G. S. (1992) Activation of gold-reactive T lymphocytes in rheumatoid arthritis patients treated with gold. Arthr. Rheum., 35, 1413–1418.

    Article  CAS  Google Scholar 

  • Witkiewicz, P. L. and Shaw, C. F. III (1981) The oxidative cleavage of peptide and protein disulfide bonds by gold(III): a possible mechanism for gold(III) toxicity. JCS Chem. Commun., 1111–1114.

    Google Scholar 

Download references

Authors
  1. C. Frank Shaw III
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Johnson Matthey Technology Centre, Reading, UK

    Simon P. Fricker

Rights and permissions

Reprints and permissions

Copyright information

© 1994 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Shaw, C.F. (1994). Gold. In: Fricker, S.P. (eds) Metal Compounds in Cancer Therapy. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-1252-9_3

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-1252-9_3

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-4545-2

  • Online ISBN: 978-94-011-1252-9

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation