Melanoma-specific ferrocene esters of the fungal cytotoxin illudin M

Anti-Cancer Drugs

Volumn 20, Issue 8, 2009, Pages 676-681

  Knauer, Sebastian ^a   Biersack, Bernhard ^a   Zoldakova, Miroslava ^a   Effenberger, Katharina ^a   Milius, Wolfgang ^a   Schobert, Rainer ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

Anti cancer drug; Apoptosis; Conjugates; Ferrocene; Illudin M; Melanoma

Indexed keywords

1,1' FERROCENEDIOIC ACID; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; BENZENE DERIVATIVE; BIS(ILLUDINYL M) 1,1,' FERROCENEDIOATE; CASPASE 9; CYTOTOXIN; FERROCENE DERIVATIVE; ILLUDIN M; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CELL SPECIFICITY; COVALENT BOND; DRUG STRUCTURE; GENE TARGETING; HUMAN; HUMAN CELL; IC 50; LEUKEMIA; MELANOMA; NICK END LABELING; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; SKIN FIBROBLAST; WESTERN BLOTTING;

ANTIBIOTICS, ANTINEOPLASTIC; APOPTOSIS; CASPASE 9; CELL LINE, TUMOR; CELL SURVIVAL; ESTERS; FERROUS COMPOUNDS; FIBROBLASTS; GLUTATHIONE; HUMANS; MELANOMA; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SESQUITERPENES; SPECTROPHOTOMETRY, ULTRAVIOLET; SUBSTRATE SPECIFICITY;

EID: 70349311735     PISSN: 09594973     EISSN: None     Source Type: Journal    
DOI: 10.1097/CAD.0b013e32832e056a     Document Type: Article

References (33)

1. Anchel M, Hervey A, Robbins WJ. Antibiotic substances from Basidiomycetes. VII. Clitocybe illudens. Proc Natl Acad Sci U S A 1950; 36:300-305.
2. Anchel M, Hervey A, Robbins WJ. Production of illudin M and of a fourth crystalline product by Clitocybe illudens. Proc Natl Acad Sci U S A 1952; 38:927-928.
3. Walser J, Heinstein PF. Mode of action of illudin S. Antimicrob Agents Chemother 1973; 3:357-363.
4. Tanaka K, Inoue T, Kadota S, Kikuchi T. Metabolism by rat liver cytosol of illudin S, a toxic substance of Lampteromyces japonicus. II. Characterization of illudin S-metabolizing enzyme. Xenobiotica 1992; 22:33-39.
5. Dick RA, Yu X, Kensler TW. NADPH alkenal/one oxidoreductase activity determines sensitivity of cancer cells to the chemotherapeutic alkylating agent irofulven. Clin Cancer Res 2004; 10:1492-1499.
6. Jaspers NGJ, Raams A, Kelner MJ, Ng JMY, Yamashita YM, Takeda S, et al. Anti-tumour compounds illudin S and irofulven induce DNA lesions ignored by global repair and exclusively processed by transcription-and replication-coupled repair pathways. DNA Repair 2002; 1:1027-1038.
7. Kelner MJ, McMorris TC, Beck WT, Zamora JM, Taetle R. Preclinical evaluation of illudins as anticancer agents. Cancer Res 1987; 47:3186-3189.
8. Kelner MJ, McMorris TC, Taetle R. Preclinical evaluation of illudins as anticancer agents: basis for selective cytotoxicity. J Natl Cancer Instit 1990; 82:1562-1656.
9. Kelner MJ, McMorris TC, Montoya MA, Estes L, Rutherford M, Samson KM, Taetle R. Characterization of cellular accumulation and toxicity of illudin S in sensitive and nonsensitive tumor cells. Cancer Chemother Pharmacol 1997; 40:65-71.
10. Kinder FR, Wang R-M, Bauta WE, Bair KW. Design, synthesis, and antitumor activity of bicyclic and isomeric analogues of illudin M. Bioorg Med Chem Lett 1996; 6:1029-1034.
11. McMorris TC, Kelner MJ, Wang W, Estes LA, Montoya MA, Taetle R. Structure-activity relationships of illudins: analogs with improved therapeutic index. J Org Chem 1992; 57:6876-6883.
12. Kelner MJ, McMorris TC, Estes L, Starr RJ, Rutherford M, Montoya M, et al. Efficacy of acylfulvene illudin analogues against a metastatic lung carcinoma MV522 xenograft nonresponsive to traditional anticancer agents: retention of activity against various mdr phenotypes and unusual cytotoxicity against ERCC2 and ERCC3 DNA helicase-deficient cells. Cancer Res 1995; 55:4936-4940.
13. Kelner MJ, McMorris TC, Estes L, Wnag W, Samson KM, Taetle R. Efficacy of HMAF (MGI-114) in the MV522 metastatic lung carcinoma xenograft model nonresponsive to traditional anticancer agents. Invest New Drugs 1996; 14:161-167.
14. Senzer N, Arsenau J, Richards D, Berman B, MacDonald JR, Smith S. Irofulven demonstrates clinical activity against metastatic hormone-refractory prostate cancer in a phase 2 single-agent trial. Am J Clin Oncol 2005; 28:36-42.
15. Eckhardt SG, Baker SD, Britten CD, Hidalgo M, Siu L, Hammond LA, et al. Phase I and pharmacokinetic study of irofulven, a novel mushroom-derived cytotoxin, administered for five consecutive days every four weeks in patients with advanced solid malignancies. J Clin Oncol 2000; 18:4086-4097.
16. Berg WJ, Schwartz L, Yu R, Mazumdar M, Motzer RJ. Phase II trial of irofulven (6-hydroxymethylacylfulvene) for patients with advanced renal cell carcinoma. Invest New Drugs 2001; 19:317-320. (Pubitemid 32782972)
17. Yeo W, Boyer M, Chung HC, Ong SYK, Kim R, Zee B, et al. Irofulven as first line therapy in recurrent or metastatic gastric cancer: a phase II multicenter study by the Cancer Therapeutics Research Group (CTRG). Cancer Chemother Pharmacol 2007; 59:295-300.
18. Seiden MV, Gordon AN, Bodurka DC, Matulonis UA, Penson RT, Reed E, et al. A phase II study of irofulven in women with recurrent and heavily pretreated ovarian cancer. Gyn Oncol 2006; 101:55-61.
19. Schilder RJ, Blessing JA, Pearl ML, Rose PG. Evaluation of irofulven (MGI-114) in the treatment of recurrent or persistent endometrial carcinoma: a phase II study of the Gynecologic Oncology Group. Invest New Drugs 2004; 22:343-349.
20. Dowell JE, Johnson DH, Rogers JS, Shyr Y, McCullough N, Krozely P, et al. A phase II trial of 6-hydroxymethylacylfulvene (MGI-114, irofulven) in patients with advanced non-small cell lung cancer previously treated with chemotherapy. Invest New Drugs 2001; 19:85-88.
21. Lee MS, Gupta N, Penson RT, Loewenstein J, Wepner MS, Seiden MV, et al. Cone damage in patients receiving high-dose irofulven treatment. Arch Ophthalmol 2005; 123:29-34.
22. Schobert R, Biersack B, Knauer S, Ocker M. Conjugates of the fungal cytotoxin illudin M with improved tumour specificity. Bioorg Med Chem 2008; 16:8592-8597.
23. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65:55-63.
24. Farnaud S, Amini M, Rapisarda C, Cammack R, Bui T, Drake A, et al. Biochemical and spectroscopic studies of human melanotransferrin (MTf): electron-paramagnetic resonance evidence for a difference between the iron-binding site of MTf and other transferrins. Int J Biochem Cell Biol 2008; 40:2739-2745.
25. Dunn LL, Sekyere EO, Rahmanto YS, Richardson DR. The function of melanotransferrin: a role in melanoma cell proliferation and tumorigenesis. Carcinogenesis 2006; 27:2157-2169.
26. Fouda MFR, Abd-Elzaher MM, Abdelsamaia RA, Labib AA. On the medicinal chemistry of ferrocene. Appl Organomet Chem 2007; 21:613-625.
27. Kovjazin R, Eldar T, Patya M, Vanichkin A, Lander HM, Novogrodsky A. Ferrocene-induced lymphocyte activation and antitumor activity is mediated by redox-sensitive signaling. FASEB J 2003; 17:467-469.
28. Spencer J, Mendham AP, Kotha AK, Richardson SCW, Hillard EA, Jaouen G, et al. Structural and biological investigation of ferrocene-substituted 3-methylidene-1,3-dihydro-2H-indol-2-ones. Dalton Trans 2009; 918-921.
29. Selzer E, Schlagbauer-Wadl H, Okamoto I, Pehamberger H, Potter R, Jansen B. Expression of Bcl-2 family members in human melanocytes, in melanoma metastases and in melanoma cell lines. Melanoma Res 1998; 8:197-203.
30. Thallinger C, Skorjanec S, Soleiman A, Tzaneva S, Griss J, Rous W, et al. Orally administered rapamycin, dacarbazine or both for treatment of human melanoma evaluated in severe combined immunodeficiency mice. Pharmacology 2008; 82:233-238.
31. Gavrieli Y, Sherman Y, Ben-Sasson SA. Identification of programmed cell death in situ via specific labeling of nuclear DNA fragmentation. J Cell Biol 1992; 119:493-501.
32. Herzig MC, Trevino AV, Liang H, Salinas R, Waters SJ, MacDonald JR, et al. Apoptosis induction by the dual-action DNA-and protein-reactive antitumor drug irofulven is largely Bcl-2-independent. Biochem Pharmacol 2003; 65:503-513.
33. Wang W, Waters SJ, MacDonald JR, Roth C, Shentu S, Freeman J, et al. Irofulven (6-hydroxymethylacylfulvene, MGI-114)-induced apoptosis in human pancreatic cancer cells is mediated by ERK and JNK kinases. Anticancer Res 2002; 22:559-564.