Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells

Journal of Medicinal Chemistry

Volumn 52, Issue 18, 2009, Pages 5748-5752

  Antoon, James W ^a   Liu, Jiawang ^b   Gestaut, Matthew M ^a   Burow, Matthew E ^a   Beckman, Barbara S ^a   Foroozesh, Maryam ^b  

^a TULANE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b XAVIER UNIVERSITY OF LOUISIANA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (BENZYLIDENEAMINO) 3 HYDROXY N TETRADECYLPROPANAMIDE; ANTINEOPLASTIC AGENT; CERAMIDE; CERAMIDE DERIVATIVE; PROPIONAMIDE DERIVATIVE; SPHINGANINE; SPHINGOSINE 1 PHOSPHATE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CANCER CELL; CANCER CELL MCF 7TN R; CANCER CELL MDA MB 231; CELL PROLIFERATION; CELL STRAIN MCF 7; CELL SURVIVAL; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG MECHANISM; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; HUMAN CELL; IC 50; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; APOPTOSIS; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; CERAMIDES; DRUG DESIGN; DRUG RESISTANCE, NEOPLASM; HORMONES; HUMANS; INHIBITORY CONCENTRATION 50; LYSOPHOSPHOLIPIDS; SPHINGOSINE;

EID: 70349205553     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9009668     Document Type: Article

References (13)

1. Simstein, R.; Burow, M.; Parker, A.; Weldon, C.; Beckman, B. Apoptosis, chemoresistance, and breast cancer: insights from the MCF-7 cell model system. Exp. Biol. Med. (Maywood, NJ, U. S.) 2003, 228, 995-1003.
2. Shabbits, J. A.; Mayer, L. D. P-Glycoprotein modulates ceramide-mediated sensitivity of human breast cancer cells to tubulin-binding anticancer drugs. Mol. Cancer Ther. 2002, 1, 205-213.
3. Gouaze-Andersson, V.; Yu, J. Y.; Kreitenberg, A. J.; Bielawska, A.; Giuliano, A. E.; Cabot, M. C. Ceramide and glucosylceramide upregulate expression of the multidrug resistance gene MDR1 in cancer cells. Biochim. Biophys. Acta 2007, 1771, 1407-1417.
4. Liu, Y. Y.; Yu, J. Y.; Yin, D.; Patwardhan, G. A.; Gupta, V.; Hirabayashi, Y.; Holleran, W. M.; Giuliano, A. E.; Jazwinski, S. M.; Gouaze-Andersson, V.; Consoli, D. P.; Cabot, M. C. A role for ceramide in driving cancer cell resistance to doxorubicin. FASEB J. 2008, 22, 2541-2551.
5. Schiffmann, S.; Sandner, J.; Birod, K.; Wobst, I.; Angioni, C.; Ruckhaberle, E.; Kaufmann, M.; Ackermann, H.; Lotsch, J.; Schmidt, H.; Geisslinger, G.; Grosch, S. Ceramide synthases and ceramide levels are increased in breast cancer tissue. Carcinogenesis 2009, 30, 745-752.
6. Qiu, L.; Zhou, C.; Sun, Y.; Di, W.; Scheffler, E.; Healey, S.; Wanebo, H.; Kouttab, N.; Chu, W.; Wan, Y. Paclitaxel and ceramide synergistically induce cell death with transient activation of EGFR and ERK pathway in pancreatic cancer cells. Oncol. Rep. 2006, 16, 907-913.
7. Lucci, A.; Giuliano, A. E.; Han, T. Y.; Dinur, T.; Liu, Y. Y.; Senchenkov, A.; Cabot, M. C. Ceramide toxicity and metabolism differ in wild-type and multidrug-resistant cancer cells. Int. J. Oncol. 1999, 15, 535-540.
8. Liu, Y. Y.; Han, T. Y.; Giuliano, A. E.; Cabot, M. C. Expression of glucosylceramide synthase, converting ceramide to glucosylceramide, confers adriamycin resistance in human breast cancer cells. J. Biol. Chem. 1999, 274, 1140-1146.
9. Ameyar, M.; Atfi, A.; Cai, Z.; Stancou, R.; Shatrov, V.; Bettaieb, A.; Chouaib, S. Analysis of human breast adenocarcinoma MCF7 resistance to tumor necrosis factor-induced cell death. Lack of correlation between JNK activation and ceramide pathway. J. Biol. Chem. 1998, 273, 29002-29008.
10. Struckhoff, A. P.; Bittman, R.; Burow, M. E.; Clejan, S.; Elliott, S.; Hammond, T.; Tang, Y.; Beckman, B. S. Novel ceramide analogs as potential chemotherapeutic agents in breast cancer. J. Pharmacol. Exp. Ther. 2004, 309, 523-532.
11. Weldon, C. B.; Parker, A. P.; Patten, D.; Elliott, S.; Tang, Y.; Frigo, D. E.; Dugan, C. M.; Coakley, E. L.; Butler, N. N.; Clayton, J. L.; Alam, J.; Curiel, T. J.; Beckman, B. S.; Jaffe, B. M.; Burow, M. E. Sensitization of apoptotically-resistant breast carcinoma cells to TNF and TRAIL by inhibition of p38 mitogen-activated protein kinase signaling. Int. J. Oncol. 2004, 24, 1473-1480.
12. Yacoub, A.; Mitchell, C.; Brannon, J.; Rosenberg, E.; Qiao, L.; McKinstry, R.; Linehan, W. M.; Su, Z. S.; Sarkar, D.; Lebedeva, I. V.; Valerie, K.; Gopalkrishnan, R. V.; Grant, S.; Fisher, P. B.; Dent, P. MDA-7 (interleukin-24) inhibits the proliferation of renal carcinoma cells and interacts with free radicals to promote cell death and loss of reproductive capacity. Mol. Cancer Ther 2003, 2, 623-632.
13. Meeran, S. M.; Katiyar, S.; Elmets, C. A.; Katiyar, S. K. Interleukin- 12 deficiency is permissive for angiogenesis in UV radiation-induced skin tumors. Cancer Res. 2007, 67, 3785-3793.