Synthesis, spectral characterization, and in vitro cellular activities of metapristone, a potential cancer metastatic chemopreventive agent derived from mifepristone (RU486)

AAPS Journal

Volumn 16, Issue 2, 2014, Pages 289-298

  Wang, Jichuang ^a   Chen, Jianzhong ^a,b   Wan, Liyuan ^a   Shao, Jingwei ^a   Lu, Yusheng ^a   Zhu, Yewei ^a   Ou, Minrui ^a   Yu, Suhong ^a   Chen, Haijun ^a   Jia, Lee ^a  

^a FUZHOU UNIVERSITY   (China)

^b FUJIAN UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

cancer metastasis chemoprevention; in vitro cellular activities; metapristone; mifepristone; spectral properties

Indexed keywords

ANTIMETASTATIC AGENT; CASPASE 3; DRUG METABOLITE; METAPRISTONE; MIFEPRISTONE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL ACTIVITY; CELL ADHESION; CELL CYCLE ARREST; CELL INVASION; CELL MIGRATION; CELLULAR DISTRIBUTION; CIRCULATING TUMOR CELL; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG EFFECT; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IN VITRO STUDY; METASTASIS INHIBITION; MOLECULAR DOCKING; MOLECULAR DYNAMICS; SPECTROSCOPY; TUMOR INVASION;

ANNEXIN A5; ANTICARCINOGENIC AGENTS; CASPASE 3; CELL ADHESION; CELL CYCLE; CELL LINE, TUMOR; CHROMATOGRAPHY, LIQUID; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MEMBRANE POTENTIAL, MITOCHONDRIAL; MIFEPRISTONE; NEOPLASM METASTASIS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84895886667     PISSN: 15507416     EISSN: None     Source Type: Journal    
DOI: 10.1208/s12248-013-9559-2     Document Type: Article

References (39)

1. Fleseriu M, Biller BM, Findling JW, Molitch ME, Schteingart DE, Gross C, et al. Mifepristone, a glucocorticoid receptor antagonist, produces clinical and metabolic benefits in patients with Cushing's syndrome. J Clin Endocr Metab. 2012;97(6):2039-49.
2. El Etreby MF, Liang YY, Wrenn RW, Schoenlein PV. Additive effect of mifepristone and tamoxifen on apoptotic pathways in MCF-7 human breast cancer cells. Breast Cancer Res Tr. 1998;51(2):149-68. (Pubitemid 28561420)
3. Fiscella J, Bonfiglio T, Winters P, Eisinger SH, Fiscella K. Distinguishing features of endometrial pathology after exposure to the progesterone receptor modulator mifepristone. Hum Pathol. 2011;42(7):947-53.
4. Fried G, Meister B, Râdestad A. Peptide-containing nerves in the human pregnant uterine cervix: an immunohistochemical study exploring the effect of RU 486 (mifepristone). Hum Reprod. 1990;5(7):870-6. (Pubitemid 20357682)
5. Ligr M, Li Y, Logan SK, Taneja S, Melamed J, Lepor H, et al. Mifepristone inhibits GRβ coupled prostate cancer cell proliferation. J Urol. 2012;188(3):981-8.
6. Goel N, Malik R, Rathi B, Bhaskaran S, Rajaram S, Mehta S, et al. Pregnancy with metastatic gastrointestinal stromal tumor (GIST) on imatinib chemotherapy: an oncologist's nightmare and obstetrician's dilemma. J Gastroint Cancer. 2013;44(1):115-7.
7. Wang Y, Yang D, Song L, Li T, Yang J, Zhang X, et al. Mifepristone-inducible caspase-1 expression in mouse embryonic stem cells eliminates tumor formation but spares differentiated cells in vitro and in vivo. Stem Cells. 2012;30(2):169-79.
8. Cher ML, Towler DA, Rafii S, Rowley D, Donahue HJ, Keller E, et al. Cancer interaction with the bone microenvironment: a workshop of the National Institutes of Health Tumor Microenvironment Study Section. Am J Pathol. 2006;168(5):1405-12.
9. Wempe SL, Gamarra-Luques CD, Telleria CM. Synergistic lethality of mifepristone and LY294002 in ovarian cancer cells. Cancer Growth Metast. 2013;6:1-13.
10. Chen JZ, Wang JC, Xu JG, Shao JW, Jia L. Pharmaceutical characteristics of mifepristone: from terminating pregnancy to preventing cancer metastasis. Med Res Rev 2013 (in press).
11. de Moor JS, Mariotto AB, Parry C, Alfano CM, Padgett L, Kent EE, et al. Cancer survivors in the United States: prevalence across the survivorship trajectory and implications for care. Cancer Epidem Biomar. 2013;22(4):561-70.
12. Heikinheimo O, Haukkamaa M, Lahteenmaki P. Distribution of RU 486 and its demethylated metabolites in humans. J Clin Endocrinol Metab. 1989;68(2):270-5. (Pubitemid 19052863)
13. Shi YE, Ye ZH, He CH, Zhang GQ, Xu JQ, Van Look PF, et al. Pharmacokinetic study of RU 486 and its metabolites after oral administration of single doses to pregnant and non-pregnant women. Contraception. 1993;48(2):133-49. (Pubitemid 23259097)
14. Teng YN, Dong RQ, Wang BJ, Liu HJ, Jiang ZM, Wei CM, et al. Determinations of mifepristone and its metabolites and their pharmacokinetics in healthy female Chinese subjects. Acta Pharm Sin. 2011;46(10):1241-5.
15. Heikinheimo O, Kontula K, Croxatto H, Spitz I, Luukkainen T, Lahteenmaki P. Plasma concentrations and receptor binding of RU 486 and its metabolites in humans. J Steroid Biochem. 1987;26(2):279-84. (Pubitemid 17040134)
16. Haier J, Nasralla M, Nicolson GL. Cell surface molecules and their prognostic values in assessing colorectal carcinomas. Ann Surg. 2000;231(1):11-24. (Pubitemid 30043934)
17. Permezel JM, Lenton EA, Roberts I, Cooke ID. Acute effects of progesterone and the antiprogestin RU 486 on gonadotropin secretion in the follicular phase of the menstrual cycle. J Clin Endocrinol Metab. 1989;68(5):960-5. (Pubitemid 19127416)
18. Lash GE, Fitzpatrick TE, Graham CH. Effect of hypoxia on cellular adhesion to vitronectin and fibronectin. Biochem Bioph Res Co. 2001;287(3):622-9. (Pubitemid 32912759)
19. Arck P, Hagen E, Hildebrandt M, Klapp B, Hertwig K. Pregnancy as a model of controlled invasion might be attributed to the ratio of CD3/CD8 to CD56. Am J Reprod Immunol. 2000;44(1):1-8. (Pubitemid 30462142)
20. Murray MJ, Lessey BA. Embryo implantation and tumor metastasis: common pathways of invasion and angiogenesis. Semin Reprod Endocrinol. 1999;17(3):275-90.
21. Fitzpatrick TE, Lash GE, Yanaihara A, Charnock-Jones DS, Macdonald-Goodfellow SK, Graham CH. Inhibition of breast carcinoma and trophoblast cell invasiveness by vascular endothelial growth factor. Exp Cell Res. 2003;283(2):247-55. (Pubitemid 36269030)
22. Janneau JL, Maldonado-Estrada J, Tachdjian G, Miran I, Motté N, Saulnier P, et al. Transcriptional expression of genes involved in cell invasion and migration by normal and tumoral trophoblast cells. J Clin Endocrinol Metab. 2002;87(11):5336-9. (Pubitemid 35316382)
23. Hödl C, Raunegger K, Strommer R, Ecker GF, Kunert O, Sturm S, et al. Syntheses and antigestagenic activity of Mifepristone derivatives. J Med Chem. 2009;52(5):1268-74.
24. Hödl C, Strauss WS, Sailer R, Seger C, Steiner R, Haslinger E, et al. A novel, high-affi nity, fluorescent progesterone receptor antagonist. Synthesis and in vitro studies. Bioconjug Chem. 2004;15(2):359-65. (Pubitemid 38365196)
25. Shao J, Dai Y, Zhao W, Xie J, Xue J, Ye J, et al. Intracellular distribution and mechanisms of actions of photosensitizer zinc(II)- phthalocyanine solubilized in Cremophor EL against human hepatocellular carcinoma HepG2 cells. Cancer Lett. 2013;330(1):49-56.
26. Jaffe EA, Nachman RL, Becker CG, Minick CR. Culture of human endothelial cells derived from umbilical veins. Identification by morphologic and immunologic criteria. J Clin Invest. 1973;52(11):2745-56.
27. Zamzami N, Marchetti P, Castedo M, Decaudin D, Macho A, Hirsch T, et al. Sequential reduction of mitochondrial transmembrane potential and generation of reactive oxygen species in early programmed cell death. J Exp Med. 1995;182(2):367-77.
28. Shao J, Xue J, Dai Y, Liu H, Chen N, Jia L, et al. Inhibition of human hepatocellular carcinoma HepG2 by phthalocyanine photosensitiser PHOTOCYANINE: ROS production, apoptosis, cell cycle arrest. Eur J Cancer. 2012;48(13):2086-96.
29. Schoch GA, D'Arcy B, Stihle M, Burger D, Bär D, Benz J, et al. Molecular switch in the glucocorticoid receptor: active and passive antagonist conformations. J Mol Biol. 2010;395(3):568-77.
30. Honer C, Nam K, Fink C, Marshall P, Ksander G, Chatelain RE, et al. Glucocorticoid receptor antagonism by cyproterone acetate and RU486. Mol Pharmacol. 2003;63(5):1012-20. (Pubitemid 36529919)
31. von Geldern TW, Tu N, Kym PR, Link JT, Jae HS, Lai C, et al. Liver-selective glucocorticoid antagonists: a novel treatment for type 2 diabetes. J Med Chem. 2004;47(17):4213-30. (Pubitemid 39056076)
32. Macindoe G, Mavridis L, Venkatraman V, Devignes MD, Ritchie DW. HexServer: an FFT-based protein docking server powered by graphics processors. Nucleic Acids Res. 2010;38(Web Server issue):W445-9.
33. Li DQ, Wang ZB, Bai J, Zhao J, Wang Y, Hu K, et al. Effects of mifepristone on invasive and metastatic potential of human gastric adenocarcinoma cell line MKN-45 in vitro and in vivo. World J Gastroenterol. 2004;10(12):1726-9. (Pubitemid 38931194)
34. Saha P, Hödl C, Strauss WS, Steiner R, Goessler W, Kunert O, et al. Synthesis, in vitro progesterone receptors affinity of gadolinium containing mifepristone conjugates and estimation of binding sites in human breast cancer cells. Bioorgan Med Chem. 2010;18(5):1891-8.
35. Ma Y, Katiyar P, Jones LP, Fan S, Zhang Y, Furth PA, et al. The breast cancer susceptibility gene BRCA1 regulates progesterone receptor signaling in mammary epithelial cells. Mol Endocrinol. 2006;20(1):14-34. (Pubitemid 43011667)
36. Zhang L, Wang XM, Jiao XM, Liu SS. The effect of superoxide ainon on transmembrane potential and proton transfer of myocardial mitochondria. Chinese J Pathophysiol. 1996;12(2):181-4.
37. Vermes I, Haanen C, Steffens-Nakken H, Reutellingsperger C. A novel assay for apoptosis flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled annexin V. J Immunol Methods. 1995;184(1):39-51.
38. Ferretti C, Bruni L, Dangles-Marie V, Pecking A, Bellet D. Molecular circuits shared by placental and cancer cells, and their implications in the proliferative, invasive and migratory capacities of trophoblasts. Hum Reprod Update. 2007;13(2):121-41. (Pubitemid 46323191)
39. Ellis LM, Radinsky R, Fidler IJ. Recent advances in the biology of cancer invasion and metastasis. Surgical Oncology: Contemporary Principles and Practice. 2001. p. 101-22.