Parallel syntheses of disulfide inhibitors of the thioredoxin redox system as potential antitumor agents

Anti-Cancer Drug Design

Volumn 14, Issue 5, 1999, Pages 421-432

  Kirkpatrick, D Lynn ^a,b   Watson, Shawndra ^a   Kunkel, Mark ^c   Fletcher, Susan ^a   Ulhaq, Saraj ^a   Powis, Garth ^c  

^a UNIVERSITY OF REGINA   (Canada)

^b ProlX Pharmaceuticals Inc   (United States)

^c UNIVERSITY OF ARIZONA   (United States)

Author keywords

Antitumor; Combinatorial; Disulfide; Thioredoxin redox system

Indexed keywords

1 PHENYLETHYL 2 IMIDAZOLYL DISULFIDE; ANTINEOPLASTIC AGENT; CYSTEINE; DISULFIDE; THIOREDOXIN; THIOREDOXIN REDUCTASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CELL STRAIN HL 60; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG PURITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; HUMAN; HUMAN CELL; LEUKEMIA CELL; MOUSE; NONHUMAN; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMBINATORIAL CHEMISTRY TECHNIQUES; DISULFIDES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICE; MICE, SCID; STRUCTURE-ACTIVITY RELATIONSHIP; THIOREDOXIN; TUMOR CELLS, CULTURED;

ANIMALIA; MINK CELL FOCUS-FORMING VIRUS;

EID: 0033497080     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. Alley M.C., Scudiero D.A., Monks A., Hursey M.L., Czerwinski M.J., Fine D.L., Abbott B.J., Mayo J.G., Shoemaker R.H., Boyd M.R. (1988) Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Research, 48, 589.
2. Baker A., Payne C.M., Briehl M.M., Powis G. (1997) Thioredoxin, a gene found overexpressed in human cancer, inhibits apoptosis in vitro and in vivo. Cancer Research, 57, 5162.
3. Berggren M., Gallegos A., Gasdaska J.R., Gasdaska P.Y., Warneke J., Powis G. (1996) Thioredoxin and thioredoxin reductase gene expression in human tumors and cell lines, and the effects of serum stimulation and hypoxia. Anti-cancer Research, 16, 3459.
4. Cromlish J.A., Roeder R.G. (1989) Human transcription factor IIIC (TFIIIC). Purification, polypeptide structure, and the involvement of thiol groups in specific DNA binding. Journal of Biological Chemistry, 265, 18100.
5. Fountoulakis M. (1992) Unfolding intermediates of the extra-cellular domain of the interferon γ receptor. Journal of Biological Chemistry, 267, 7095.
6. Gallegos A., Gasdaska J.R., Goodman D., Gasdaska P.Y., Berggren M., Briehl M.M., Powis G. (1996) Transfection with human thioredoxin increases cell proliferation and a dominant negative mutant thioredoxin reverses the transformed phenotype of breast cancer cells. Cancer Research, 56, 5765.
7. Galter D., Mihm S., Dröge W. (1994) Distinct effects of glutathione disulphide on the nuclear transcription factor KB and the activator protein1. European Journal of Biochemistry, 221, 639.
8. Gasdaska P.Y., Oblong J.E., Cotgreave I.A., Powis G. (1994) The predicted amino acid sequence of human thioredoxin is identical to that of the autocrine growth factor human adult T-cell derived factor (ADF): thioredoxin mRNA is elevated in some human tumors. Biochimica et Biophysica Acta, 1218, 292.
9. Gasdaska J.R., Berggren M., Powis G. (1995) Cell growth stimulation by the redox protein thioredoxin occurs by a novel helper mechanism. Cell Growth and Differentiation, 6, 1642.
10. 73→Ser mutation. Biochemical Pharmacology, 52, 1741.
11. Grippo J.F., Tienrungroj W., Dahmer M.K., Housley P.R., Pratt W.B. (1983) Evidence that the endogenous heat-stable glucocorticoid receptor-activating factor is thioredoxin. Journal of Biological Chemistry, 258, 13658.
12. Hayashi T., Ueno Y., Okamoto T. (1993) Oxidoreductive regulation of nuclear factor KκB: involvement of a cellular reducing catalyst thioredoxin. Journal of Biological Chemistry, 268, 11380.
13. Holmgren A. (1985) Thioredoxin. Annual Reviews in Biochemistry, 54, 237.
14. Kauver L.M., Laborde E. (1998) The diversity challenge in combinatorial chemistry. Current Opinion in Drug Discovery and Development, 1, 67.
15. Kirkpatrick D.L., Jimale M.L., King K.M., Chen T. (1992) Synthesis and evaluation of imidazolyl disulfides for selective cytotoxicity to hypoxic EMT6 tumor cells in vitro. European Journal of Medicinal Chemistry, 27, 33.
16. Kirkpatrick D.L., Abu Sa'da I., Chernoff W., Kuperus M. (1994) Disulfide cytotoxicity under hypoxia. Oncology Research, 3, 545.
17. Kirkpatrick D.L., Kuperus M., Dowdeswell M., Potier N., Donald L.J., Kunkel M., Berggren M., Angulo M., Powis, G. (1998) Mechanism of inhibition of the thioredoxin growth factor system by antitumor 2-imidazolyl disulfides. Biochemical Pharmacology, 55, 987.
18. Kunkel M.W., Kirkpatrick D.L., Johnson J.I., Powis G. (1997) Cell-line directed screening assay for inhibitors of thioredoxin reductase signalling as potential anti-cancer drugs. Anti-Cancer Drug Design, 12, 659.
19. Laurent T.C., Moore B.C., Reichard P. (1964) Enzymatic synthesis of deoxyribonucleotides. VI. Isolation and characterization of thioredoxin, the hydrogen donor from Esoherichia coil B. Journal of Biological Chemistry, 239, 3436.
20. Nakamura H., Masutani H., Tagaya Y., Yamauchi A., Inamoto T., Nanbu Y., Fujii S., Ozawa K., Yodi J. (1992) Expression and growth-promoting effect of adult T-cell leukemia-derived factor. A human thioredoxin homologue in hepatocellular carcinoma. Cancer, 69, 2091.
21. Oblong J.E., Berggren M., Gasdaska P.Y., Powis G. (1994a) Site-directed mutagenesis of active site cysteines in human thioredoxin produces competitive inhibitors of human thioredoxin reductase and elimination of mitogenic properties of thioredoxin. Journal of Biological Chemistry, 269, 11714.
22. Oblong J.E., Chantler E.L., Gallegos A., Kirkpatrick D.L., Chen T., Marshall, Powis G. (1994b) Reversible inhibition of human thioredoxin reductase activity by cytotoxic alkyl 2-imidazolyl disulfide analogues. Cancer Chemotherapy Pharmacology, 34, 434.
23. Oblong J.E., Gasdaska P.Y., Sherrill K., Powis G. (1993) Purification of human thioredoxin reductase; properties and characterization by absorption and circular dichroism spectroscopy. Biochemistry, 32, 7271.
24. Powis G., Kirkpatrick D.L., Angulo M., Gasdaska J.R., Broome Powell M., Salmon S.E., Montfort W.R. (1996) Thioredoxin redox signalling: a novel target for anti-cancer drug development. Anti-Cancer Drugs, 7(S3), 121.
25. Rubartelli A., Bajetto A., Allavena G., Wollman E., Sitia R. (1992) Secretion of thioredoxin by normal and neoplastic cells through a leaderless secretory pathway. Journal of Biological Chemistry, 267, 24161.
26. Sasada T., Iwata S., Sato N., Kitaoka Y, Hirota K., Nakamura K., Nishiyama A., Taniguchi Y., Takabayashi A., Yodoi J. (1996) Redox control of resistance to cisdiamminedichloroplatinum (II) (COOP): protective effect of human thioredoxin against COOP-induced cytotoxicity. Journal of Clinical Investigation, 97, 2268.
27. Silverman R.B., Nandi O.L. (1988) Reduced thioredoxin: a possible physiological cofactor for vitamin K epoxide reductase. Further support for an active site disulfide. Biochemical and Biophysical Research Communications, 155, 1248.
28. Takai Y., Kikkawa U., Kaibuchi K., Nishizuka Y. (1984) Membrane phospholipid metabolism and signal transduction for protein phosphorylation. Advances in Cyclic Nucleotide Protein Phosphorylation Research, 18, 119.
29. Weichsel A., Gasdaska J.R., Powis G., Montfort W.R. (1996) Crystal structure of reduced, oxidized, and mutated human thioredoxins: evidence for a regulatory homodimer. Structure, 4, 735.
30. Yamada M., Tomida A., Yoshikawa H., Taketani Y., Tsuruo T. (1996) Increased expression of thioredoxin/adult T-cell leukemia-derived factor in cisplatin-resistant human cancer cell lines. Clinical Cancer Research, 2, 427.
31. Yamada M., Tomida A., Yoshikawa H., Taketani Y., Tsuruo T. (1997) Overexpression of thioredoxin does not confer resistance to cisplatin in transfected human avarian and colon cancer cell lines. Cancer Chemotherapy and Pharmacology, 40, 31.