Synthesis, characterization, and cytotoxicity of a series of estrogen-tethered platinum(IV) complexes

Chemistry and Biology

Volumn 11, Issue 4, 2004, Pages 557-564

  Barnes, Katie R ^a   Kutikov, Alexander ^a   Lippard, Stephen J ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTRADIOL; ESTROGEN; ESTROGEN RECEPTOR; HIGH MOBILITY GROUP B1 PROTEIN; PLATINUM COMPLEX;

ARTICLE; BREAST TUMOR; CELL SURVIVAL; CHEMISTRY; DOSE RESPONSE; DRUG DESIGN; DRUG EFFECT; DRUG SCREENING; GENE EXPRESSION; GENETICS; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

BREAST NEOPLASMS; CELL LINE, TUMOR; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; ESTRADIOL; ESTROGENS; GENE EXPRESSION; HMGB1 PROTEIN; HUMANS; ORGANOPLATINUM COMPOUNDS; RECEPTORS, ESTROGEN; STRUCTURE-ACTIVITY RELATIONSHIP;

MINK CELL FOCUS-FORMING VIRUS;

EID: 1942522066     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2004.03.024     Document Type: Article

References (39)

1. Rosenberg B., Van Camp L., Krigas T. Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode. Nature. 205:1965;698-699.
2. Wong E., Giandomenico C.M. Current status of platinum-based antitumor drugs. Chem. Rev. 99:1999;2451-2466.
3. Trimmer E.E., Essigmann J.M. Cisplatin. Essays Biochem. 34:1999;191-211.
4. Loehrer P.J., Einhorn L.H. Cisplatin. Ann. Intern. Med. 100:1984;704-713.
5. Reedijk J. The mechanism of action of platinum anti-tumor drugs. Pure Appl. Chem. 59:1987;181-192.
6. Jamieson E.R., Lippard S.J. Structure, recognition, and processing of cisplatin-DNA adducts. Chem. Rev. 99:1999;2467-2498.
7. Cohen S.M., Lippard S.J. Cisplatin. from DNA damage to cancer chemotherapy Prog. Nucleic Acid Res. Mol. Biol. 67:2001;93-130.
8. Pil P., Lippard S.J. Cisplatin and Related Drugs. Bertino J.R. Encyclopedia of Cancer, Vol. 1. 1997;392-410 Academic Press, San Diego.
9. Takahara P.M., Frederick C.A., Lippard S.J. Crystal structure of the anticancer drug cisplatin bound to duplex DNA. J. Am. Chem. Soc. 118:1996;12309-12321.
10. Kartalou M., Essigmann J.M. Recognition of cisplatin adducts by cellular proteins. Mutat. Res. 478:2001;1-21.
11. Huang J.-C., Zamble D.B., Reardon J.T., Lippard S.J., Sancar A. HMG-domain proteins specifically inhibit the repair of the major DNA adduct of the anticancer drug cisplatin by human excision nuclease. Proc. Natl. Acad. Sci. USA. 91:1994;10394-10398.
12. Brown S.J., Kellett P.J., Lippard S.J. Ixr1, a yeast protein that binds to platinated DNA and confers sensitivity to cisplatin. Science. 261:1993;603-605.
13. Cohen S.M., Jamieson E.R., Lippard S.J. Enhanced binding of the TATA-binding protein to TATA boxes containing flanking cisplatin 1,2-cross-links. Biochemistry. 39:2000;8259-8265.
14. Barnes K.R., Lippard S.J. Cisplatin and related anticancer drugs. recent advances and insights Met. Ions Biol. Syst. in press:2003.
15. He Q., Liang C.H., Lippard S.J. Steroid hormones induce HMG1 overexpression and sensitize breast cancer cells to cisplatin and carboplatin. Proc. Natl. Acad. Sci. USA. 97:2000;5768-5772.
16. Chau K.Y., Lam H.Y.P., Lee K.L.D. Estrogen treatment induces elevated expression of HMG1 in MCF-7 cells. Exp. Cell Res. 241:1998;269-272.
17. Altman J., Castrillo T., Beck W., Bernhardt G., Schonenberger H. Metal complexes with biologically important ligands. 62. Platinum(II) complexes of 3-(2-aminoethoxy)estrone and -estradiol. Inorg. Chem. 30:1991;4085-4088.
18. Jackson A., Davis J., Pither R.J., Rodger A., Hannon M.J. Estrogen-derived steroidal metal complexes. agents for cellular delivery of metal centers to estrogen receptor-positive cells Inorg. Chem. 40:2001;3964-3973.
19. Gandolfi O., Apfelbaum H.C., Migron Y., Blum J. Syntheses of cis-dichlorodiammineplatinum analogs having steroidal hormones bound to the metal atom via malonato bridges. Inorg. Chim. Acta. 161:1989;113-123.
20. Ehrenstorfer-Schafers E.-M., Steiner N., Altman J., Beck W. Metal complexes of biologically important ligands, LV. Binding of steroidal hormones through α-amino acid ligands to platinum(II) and palladium(II). Z. Naturforsch. 45b:1990;817-827.
21. Descoteaux C., Provencher-Mandeville J., Mathieu I., Perron V., Mandal S.K., Asselin E., Berube G. Synthesis of 17β-estradiol platinum(II) complexes. biological evaluation on breast cancer cell lines Bioorg. Med. Chem. Lett. 13:2003;3927-3931.
22. Hambley T.W., Battle A.R., Deacon G.B., Lawrenz E.T., Fallon G.D., Gatehouse B.M., Webster L.K., Rainone S. Modifying the properties of platinum(IV) complexes in order to increase biological effectiveness. J. Inorg. Biochem. 77:1999;3-12.
23. Giandomenico C.M., Abrams M.J., Murrer B.A., Vollano J.F., Rheinheimer M.I., Wyer S.B., Bossard G.E., Higgins J.D. Carboxylation of kinetically inert platinum(IV) hydroxy complexes. An entree into orally active platinum(IV) antitumor agents. Inorg. Chem. 34:1995;1015-1021.
24. Choi S., Filotto C., Bisanzo M., Delaney S., Lagasee D., Whitworth J., Jusko A., Li C., Wood N.A., Willingham J.et al. Reduction and anticancer activity of platinum(IV) complexes. Inorg. Chem. 37:1998;2500-2504.
25. Lemma K., Sargeson A.M., Elding L.I. Kinetics and mechanism for reduction of oral anticancer platinum(IV) dicarboxylate compounds by L-ascorbate ions. J. Chem. Soc. Dalton Trans. 1167-1172:2000.
26. 3)] (JM335) by thiols. Inorg. Chem. 39:2000;1728-1734.
27. Larner J.M., MacLusky N.J., Hochberg R.B. The naturally occurring C-17 fatty acid esters of estradiol are long-acting estrogens. J. Steroid Biochem. 22:1985;407-413.
28. MacLusky N.J., Larner J.M., Hochberg R.B. Actions of an estradiol-17-fatty acid ester in estrogen target tissues of the rat. comparison with other C-17 metabolites and a pharmacological C-17 ester Endocrinology. 124:1989;318-324.
29. Orme M.W., Labroo V.M. Synthesis of β-estradiol-3-benzoate-17- (succinyl-12A-tetracycline). a potential bone-seeking estrogen Bioorg. Med. Chem. Lett. 4:1994;1375-1380.
30. Alvarez-Valdes A., Perez J.M., Lopez-Solera I., Lannegrand R., Continente J.M., Amo-Ochoa P., Camazon M.J., Solans X., Font-Bardia M., Navarro-Ranninger C. Preparation and characterization of platinum(II) and (IV) complexes of 1,3-diaminepropane and 1,4-diaminebutane. circumvention of cisplatin resistance and DNA interstrand cross-link formation in CH1cisR ovarian tumor cells J. Med. Chem. 45:2002;1835-1844.
31. Khan S.R.A., Huang S., Shamsuddin S., Inutsuka S., Whitmire K.H., Siddik Z.H., Khokhar A.R. Synthesis, characterization and cytotoxicity of new platinum(IV) axial carboxylate complexes. crystal structure of potential antitumor agent Bioorg. Med. Chem. 8:2000;515-521.
32. Khokhar A.R., Deng Y., Kido Y., Siddik Z.H. Preparation, characterization, and antitumor activity of new ethylenediamine platinum(IV) complexes containing mixed carboxylate ligands. J. Inorg. Biochem. 50:1993;79-87.
33. Salmon-Chemin L., Buisine E., Yardley V., Kohler S., Debreu M.-A., Landry V., Sergheraert C., Croft S.L., Krauth-Siegel R.L., Davioud-Charvet E. 2- and 3-substituted 1,4-napthoquinone derivatives as subversive substrates of trypanothione reductase and lipoamide dehydrogenase from Trypanosoma cruzi. synthesis and correlation between redox cycling activities and in vitro cytotoxicity J. Med. Chem. 44:2001;548-565.
34. II30 affect estrogen receptor-mediated transcriptional activation. Mol. Endocrinol. 11:1997;1009-1019.
35. Romine L.E., Wood J.R., Lamia L.A., Prendergast P., Edwards D.P., Nardulli A.M. The high mobility group protein 1 enhances binding of the estrogen receptor DNA binding domain to the estrogen response element. Mol. Endocrinol. 12:1998;664-674.
36. Zhang C.C., Krieg S., Shapiro D.J. HMG-1 stimulated estrogen response element binding by estrogen receptor from stably transfected HeLa cells. Mol. Endocrinol. 13:1999;632-643.
37. Boonyaratanakornkit V., Melvin V., Prendergast P., Altmann M., Ronfani L., Bianchi M.E., Taraseviciene L., Nordeen S.K., Allegretto E.A., Edwards D.P. High-mobility group chromatin proteins 1 and 2 functionally interact with steroid hormone receptors to enhance their DNA binding in vitro and transcriptional activity in mammalian cells. Mol. Cell. Biol. 18:1998;4471-4487.
38. Brezniceanu M.-L., Volp K., Bosser S., Solbach C., Lichter P., Joos S., Zornig M. HMGB1 inhibits cell death in yeast and mammalian cells and is abundantly expressed in human breast carcinoma. FASEB J. 17:2003;1295-1297.
39. 2]. Indian J. Chem. 8:1970;193-194.