Cytotoxic activity and structure activity relationship of ceramide analogues in Caki-2 and HL-60 cells

Korean Journal of Physiology and Pharmacology

Volumn 14, Issue 6, 2010, Pages 441-447

  Kim, Yong Jin ^a   Kim, Eun Ae ^a   Sohn, Uy Dong ^a   Yim, Chul Bu ^a   Im, Chaeuk ^a  

^a Chung Ang University   (South Korea)

Author keywords

B13; Ceramide; CoMFA; CoMSIA; Cytotoxicity

Indexed keywords

B 13; CERAMIDE DERIVATIVE; DEXTRO THREO 2 (N MYRISTOYLAMINO) 1 (4' NITROPHENYL) 1,3 PROPANEDIOL; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CELL STRAIN HL 60; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG STRUCTURE; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; KIDNEY CANCER; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RELIABILITY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 79251525201     PISSN: 12264512     EISSN: None     Source Type: Journal    
DOI: 10.4196/kjpp.2010.14.6.441     Document Type: Article

References (32)

1. Kolesnick RN, Goni FM, Alonso A. Compartmentalization of ceramide signaling: physical foundations and biological effects. J Cell Physiol. 2000;184:285-300.
2. Merrill AH Jr, Sullards MC, Allegood JC, Kelly S, Wang E. Sphingolipidomics: high-throughput, structure-specific, and quantitative analysis of sphingolipids by liquid chromatography tandem mass spectrometry. Methods. 2005;36:207-224. (Pubitemid 40726151)
3. Merrill AH Jr. De novo sphingolipid biosynthesis: a necessary, but dangerous, pathway. J Biol Chem. 2002;277:25843-25846.
4. Hannun YA, Obeid LM. The ceramide-centric universe of lipid-mediated cell regulation: stress encounters of the lipid kind. J Biol Chem. 2002;277:25847-25850.
5. Kolesnick RN. The therapeutic potential of modulating the ceramide sphingomyelin pathway. J Clin Invest. 2002;110:3-8.
6. Hanada K, Kumagai K, Yasuda S, Miura Y, Kawano M, Fukasawa M, Nishijima M. Molecular machinery for non-vesicular trafficking of ceramide. Nature. 2003;426:803-809.
7. Lee DW, Park SY, Ryu JS, Kim SH, Im C, Choi SH, Lee SE, Ko SK, Sohn UD. Relaxation effect of synthetic ceramide analogues in cat esophageal smooth muscle cells. Korean J Physiol Pharmacol. 2008;12:137-142.
8. Kanto T, Kalinski P, Hunter OC, Lotze MT, Amoscatto AA. Ceramide mediates tumor-induced dendritic cell apoptosis. J Immunol. 2001;167:3773-3784.
9. Noda S, Yoshimura S, Sawada M, Naganawa T, Iwama T, Nakashima S, Sakai N. Role of ceramide during cisplatin-induced apoptosis in C6 glioma cells. J Neurooncol. 2001;52: 11-21. (Pubitemid 32544656)
10. Selzner M, Bielawska A, Morse MA, Rudiger HA, Sindram D, Hannun YA, Clavien PA. Induction of apoptotic cell death and prevention of tumor growth by ceramide analogues in metastatic human colon cancer. Cancer Res. 2001;61:1233-1240.
11. Zheng W, Kollmeyer J, Symolon H, Momin A, Munter E, Wang E, Kelly S, Allegood JC, Liu Y, Peng Q. Ceramides and other bioactive sphingolipid backbones in health and disease: lipidomic analysis, metabolism and roles in membrane structure, dynamics, signaling and autophagy. Biochim Biophys Acta. 2006;1758:1864-1884.
12. Liu X, Elojeimy S, El-Zawahry AM, Holman DH, Bielawska A, Bielawski J, Rubinchik S, Guo GW, Dong JY, Keane T, Hannun YA, Tavassoli M, Norris JS. Modulation of ceramide metabolism enhances viral protein apoptin's cytotoxicity in prostate cancer. Mol Ther. 2006;14:637-646.
13. Michael JM, Lavin MF, Watters DJ. Resistance to radiation-induced apoptosis in burkitt's lymphoma cells is associated with defective ceramide signaling. Cancer Res. 1997;57:3600-3605.
14. Norris JS, Bielawska A, Day T, El-Zawahry A, Elojeimy S, Hannun YA, Holman D, Hyer M, Landon C, Lowe S, Dong JY, McKillop J, Norris K, Obeid L, Rubinchik S, Tavassoli M, Tomlinson S, Voelkel-Johnson C, Liu X. Combined therapeutic use of AdGFPFasL and small molecule inhibitors of ceramide metabolism in prostate and head and neck cancers: a status report. Cencer Gene Ther. 2006;13:1045-1051.
15. Senchenkov A, Litvak DA, Cabot MC. Targeting ceramide metabolism a strategy for overcoming drug resistance. J Natl Cancer Inst. 2001;93:347-357. (Pubitemid 32229379)
16. Mathias S, Pena LA, Kolensnick RA. Signal transduction of stress via ceramide. Biochem J. 1998;335:465-480.
17. Eto M, Bennouna J, Hunter OC. C16-ceramide accumulates following androgen ablation in LNCaP prostate cancer cells. Prostate. 2003;57:66-79.
18. Pettus BJ, Chalfant CE, Hannun YA. Ceramide in apoptosis: an overview and current perspectives. Biochim Biophys Acta. 2002;1585:114-125.
19. Bose R, Verheij M, Haimovitz FA, Scotto K, Fuks Z, Kolesnick R. Ceramide synthase mediates daunorubicin-induced apoptosis: an alternative mechanism for generating death signals. Cell. 1995;82:405-414.
20. Hannun YA, Luberto C. Ceramide in the eukaryotic stress response. Trends Cell Biol. 2000;10:73-80.
21. Nam EJ, Lee HS, Lee YJ, Joo WS, Maeng S, Im HI, Park CW, Kim YS. Ceramide is involved in MPP + -induced cytotoxicity in human neuroblastoma cells. Korean J Physiol Pharmacol. 2002;6:281-286. (Pubitemid 36181864)
22. Bieberich E, Hu B, Silva J, Mackinnon S, Yu RK, Fillmore H, Broaddus WC, Ottenbrite RM. Synthesis and characterization of novel ceramide analogs for induction of apoptosis in human cancer cells. Cancer Letters. 2002;181:55-64.
23. Radin NS. Killing cancer cells by poly-drug elevation of ceramide levels: a hypothesis whose time has come? Eur J Biochem. 2001;268:193-204.
24. Bielawska A, Greenberg MS, Perry D, Jayadev S, Shayman JA, McKay C, Hannun YA. (1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol as an inhibitor of ceramidase. J Biol Chem. 1996;271:12646-12654.
25. Raisova M, Goltz G, Bektas M, Bielawska A, Riebeling C, Hossini AM, Eberle J, Hannun YA, Orfanos CE, Geilen CC. Bcl-2 overexpression prevents apoptosis induced by ceramidase inhibitors in malignant melanoma and hacat keratinocytes. FEBS Lett. 2002;516:47-52.
26. Samsel L, Zaidel G, Drumgoole HM, Jelovac D, Drachenberg C, Rhee JG, Brodie AM, Bielawska A, Smyth MJ. The ceramide analog, B13, induces apoptosis in prostate cancer cell lines and inhibits tumor growth in prostate cancer xenografts. Prostate. 2004;58:382-393.
27. Holman DH, Turner LS, El-Zawahry A, Elojeimy S, Liu X, Bielawski J, Szulc ZM, Norris K, Zeidan Y, Hannun YA. Lysosomotropic acid ceramidase inhibitor induces apoptosis in prostate cancer cells. Cancer Chemther Pharmacol. 2008;61: 231-242.
28. Kwon OH. Synthesis and anticancer activity of Aryl-1,3-propanediol thiourea derivatives. Chung-Ang Graduate School Master Thesis. 2002.
29. Park JG, Kramer BS, Steinberg SM, Carmichael J, Collins JM, Minna JD, Gazdar AF. Chemosensitivity testing of human colorectal carcinoma cell lines using a tetrazolium-based colorimetric assay. Cancer Research. 1987;47:5875-5879.
30. Manthey JA, Guthrie N. Antiproliferative activities of citrus flavonoids against six human cancer cell lines. J Agric Food Chem. 2002;50:5837-5843.
31. SYBYL Molecular Modeling Software. Tripos Inc., St. Louis, USA. 2010.
32. Chang YT, Choi J, Ding S, Prieschl EE, Baumruker T, Lee JM, Chung SK, Schultz PG. The synthesis and biological characterization of a ceramide library. J Am Chem Soc. 2002;124: 1856-1857. (Pubitemid 34215294)