Design, synthesis and antitumor properties of glycosylated antitumor ether lipid (GAEL)- chlorambucil-hybrids

Chemistry and Physics of Lipids

Volumn 194, Issue , 2016, Pages 139-148

  Idowu, Temilolu ^a   Samadder, Pranati ^a   Arthur, Gilbert ^a   Schweizer, Frank ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

Author keywords

Antitumor agent; Cationic lipid; Chlorambucil linked hybrid; Cytotoxic lipid; Glycolipid; Hybrid drug

Indexed keywords

CHLORAMBUCIL; ETHER LIPID; GLUCOSAMINE; GLYCEROLIPID; GLYCOSYLATED ANTITUMOR ETHER LIPID; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; ETHER DERIVATIVE; GLYCOLIPID;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL LINE; CELL VIABILITY; CONTROLLED STUDY; COVALENT BOND; CYTOTOXICITY; DEACETYLATION; DRUG DESIGN; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROGENATION; IN VITRO STUDY; MTS ASSAY; PRIORITY JOURNAL; CELL PROLIFERATION; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; GLYCOSYLATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL CULTURE;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; CELL SURVIVAL; CHLORAMBUCIL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; ETHERS; GLYCOLIPIDS; GLYCOSYLATION; HUMANS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 84954386847     PISSN: 00093084     EISSN: 18732941     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2015.07.003     Document Type: Article

References (49)

1. A. Anel, and et al. Cytotoxicity of chlorambucil and chlorambucil-fatty acid conjugates against human lymphomas and normal human peripheral blood lymphocytes Biochem. Pharmacol. 40 1990 1193 1200
2. R. Bittman, H.S. Byun, B. Mercier, and H. Salari 2′-(Trimethylammonio) ethyl 4-(hexadecyloxy)-3(S)-methoxybutane phosphonate: a novel potent antineoplastic agent J. Med. Chem. 36 1993 297 299
3. R. Bittman, H.S. Byun, and B.H. Mercier Salari Isosteric phosphonate analogs of ET-16-OMe. Synthesis and biological evaluation of the enantiomers of 2′-(trimethylammonio) ethyl 4-(hexadecyloxy)-3-methoxybutanephosphonate and 2′-(trimethylammonio) ethyl 4-(hexadecylthio)-3-methoxybutanephosphonate J. Med. Chem. 37 1994 425 430
4. R. Bittman, H.S. Byun, K.C. Reddy, P. Samadder, and G. Arthur Enantioselective synthesis and antiproliferative properties of an ilmofosine analog, 2′-(trimethylammonio) ethyl 3-(hexadecyloxy)-2-(methoxymethyl) propyl phosphate, on epithelial cancer cell growth J. Med. Chem. 40 1997 1391 1395
5. U.S. Chowdhury Synthesis of a versatile tetrasaccharide of sialyl Le(x) and Le(x) antigens Tetrahedron 52 12 1996 775 12782
6. M. Daker, M. Ahmad, and A.S. Khoo Quercetin-induced inhibition and synergistic activity with cisplatin - a chemotherapeutic strategy for nasopharyngeal carcinoma cells Cancer Cell Int. 12 2012 34
7. M. Dean, T. Fojo, and S. Bates Tumour stem cells and drug resistance Nat. Rev. Cancer 5 2005 275 284
8. P.B. Deming, and et al. Bcr-Abl-mediated protection from apoptosis downstream of mitochondrial cytochrome c release Mol. Cell. Biol. 24 2004 10289 10299
9. M. Diehn, and M.F. Clarke Cancer stem cells and radiotherapy: new insights into tumor radioresistance J. Natl. Cancer Inst. 98 2006 1755 1757
10. F. Drabløs, and et al. Alkylation damage in DNA and RNA - repair mechanisms and medical significance DNA Repair (Amst.) 3 2004 1389 1407
11. Early Breast Cancer Trialists' Collaborative Group Polychemotherapy for early breast cancer: an overview of the randomised trials. Early Breast Cancer Trialists' Collaborative Group Lancet 352 1998 930 934
12. Early Breast Cancer Trialists' Collaborative Group Effects of chemotherapy and hormonal therapy for early breast cancer on recurrence and 15-year survival: an overview of the randomised trials Lancet 365 2005 1687 1717
13. R.K. Erukulla, X. Zhou, P. Samadder, G. Arthur, and R. Bittman Synthesis and evaluation of the antiproliferative effects of 1-O-hexadecyl-2-O-methyl-3-O-(2′-acetamido-2′-deoxy-beta-d- glucopyranosyl)-sn-glycerol and 1-O-hexadecyl-2-O-methyl-3-0- (2'-amino-2'-deoxy-beta-d-glucopyranosyl)-sn-glycerol on epithelial canc J. Med. Chem. 39 1996 1545 1548
14. C.E. Eyler, and J.N. Rich Survival of the fittest: cancer stem cells in therapeutic resistance and angiogenesis J. Clin. Oncol. 26 2008 2839 2845
15. S. Fortin, and G. Bérubé Advances in the development of hybrid anticancer drugs Exp. Opin. Drug Discov. 8 2013 1029 1047
16. C. Gajate, M. Santos-Beneit a Modolell, and F. Mollinedo Involvement of c-Jun NH2-terminal kinase activation and c-Jun in the induction of apoptosis by the ether phospholipid 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine Mol. Pharmacol. 53 1998 602 612
17. L.K. Gediya, and V.C. Njar Promise and challenges in drug discovery and development of hybrid anticancer drugs Exp. Opin. Drug Discov. 4 2009 1099 1111
18. M.M. Gottesman, T. Fojo, and S.E. Bates Multidrug resistance in cancer: role of ATP-dependent transporters Nat. Rev. Cancer 2 2002 48 58
19. M.M. Gottesman Mechanism of cancer resistance Annu. Rev. Med. 53 2002 615 627
20. P.N. Guivisdalsky, and et al. Synthesis and antineoplastic properties of ether-linked thioglycolipids J. Med. Chem. 33 1990 2614 2621
21. P.O. Gunnarsson, S.B. Andersson, S.A. Johansson, T. Nilsson, and G. Plym-Forshell Pharmacokinetics of estramustine phosphate (Estracyt) in prostatic cancer patients Eur. J. Clin. Pharmacol. 26 1984 113-9
22. A. Gupta, and et al. Design, synthesis and biological evaluation of estradiol-chlorambucil hybrids as anticancer agents Bioorg. Med. Chem. Lett. 20 2010 1614 1618
23. D. Hanahan, and R.A. Weinberg Hallmarks of cancer: the next generation Cell 144 2011 646 674
24. J.K. Jackson, and et al. The antineoplastic ether lipid, s-phosphonate, selectively induces apoptosis in human leukemic cells and exhibits antiangiogenic and apoptotic activity on the chorioallantoic membrane of the chick embryo Cancer Chemother. Pharmacol. 41 1998 326 332
25. L. Jahreiss, M. Renna, R. Bittman, and G.D.C. Arthur Rubinsztein 1-O-Hexadecyl-2-O-methyl-3-O-(2′-acetamido-2′-deoxy-beta-d-glucopyranosyl)-sn-glycerol (Gln) induces cell death with more autophagosomes which is autophagy-independent Autophagy 5 2009 835 846
26. F. Li, B. Tiede, J. Massagué, and Y. Kang Beyond tumorigenesis: cancer stem cells in metastasis Cell Res. 17 2007 3 14
27. D.B. Longley, and P.G. Johnston Molecular mechanisms of drug resistance J. Pathol. 205 2005 275 292
28. M. MacFarlane Cell death pathways-potential therapeutic targets Xenobiotica 39 2009 616 624
29. F. Mollinedo, C. Gajate, S. Martín-Santamaría, and F. Gago ET-18-OCH3 (edelfosine): a selective antitumour lipid targeting apoptosis through intracellular activation of Fas/CD95 death receptor Curr. Med. Chem. 11 2004 3163 3184
30. R. Morphy, C. Kay, and Z. Rankovic From magic bullets to designed multiple ligands Drug Discov. Today 9 2004 641 651
31. J. O'shaughnessy, and et al. Superior survival with capecitabine plus docetaxel combination therapy in anthracycline-pretreated patients with advanced breast cancer: phase iii trial results J. Clin. Oncol. 20 2002 2812 2823
32. N.H.T. Petersen, and et al. Transformation-associated changes in sphingolipid metabolism sensitize cells to lysosomal cell death induced by inhibitors of acid sphingomyelinase Cancer Cell 24 2013 379 393
33. B. Reux, and et al. Synthesis and cytotoxic properties of new fluorodeoxyglucose-coupled chlorambucil derivatives Bioorg. Med. Chem. 16 2008 5004 5020
34. P. Saftig, and K. Sandhoff Killing from the inside Nature 502 2013 2 3
35. H. Salari, S. Howard, and R. Bittman Synthesis and antineoplastic properties of an ether glycerophosphonocholine, and analog of ET-18-OCH3-GPC Biochem. Biophys. Res. Commun. 187 1992 603 608
36. P. Samadder, R. Bittman, H.-S. Byun, and G. Arthur Synthesis and use of novel ether phospholipid enantiomers to probe the molecular basis of the antitumor effects of alkyllysophospholipids: correlation of differential activation of c-Jun NH(2)-terminal protein kinase with antiproliferative effects in neur J. Med. Chem. 47 2004 2710-3
37. P. Samadder, R. Bittman, H. Byun, and G. Arthur A glycosylated antitumor ether lipid kills cells via paraptosis-like cell death Biochem. Cell Biol. 414 2009 401 414
38. P. Samadder, H.S. Byun, R. Bittman, and G. Arthur An active endocytosis pathway is required for the cytotoxic effects of glycosylated antitumor ether lipids Anticancer Res. 31 2011 3809 3818
39. P. Samadder, Y. Xu, F. Schweizer, and G. Arthur Cytotoxic properties of -gluco-, -galacto- and -manno-configured 2-amino-2-deoxy-glycerolipids against epithelial cancer cell lines and BT-474 breast cancer stem cells Eur. J. Med. Chem. 78 2014 225 235
40. M. Smalley, and A. Ashworth Stem cells and breast cancer: a field in transit Nat. Rev. Cancer 3 2003 832 844
41. L.A. Smets, H. Van Rooij, and G.S. Salomons Signalling steps in apoptosis by ether lipids Apoptosis 4 1999 419 427
42. M.S. Soengas, and et al. Inactivation of the apoptosis effector Apaf-1 in malignant melanoma Nature 409 2001 207 211
43. M.B. Sporn, and N. Suh Chemoprevention an essential approach to controlling cancer Nat. Rev. Cancer 2 2002 537 543
44. M.B. Sporn Dichotomies in cancer research: some suggestions for a new synthesis Nat. Clin. Pract. Oncol. 3 2006 364 373
45. WHO Cancer. (2014) at http://www.who.int/mediacentre/factsheets/fs297/en/.
46. C.R. Willis, and et al. A phase I/II study examining pentostatin, chlorambucil, and theophylline in patients with relapsed chronic lymphocytic leukemia and non-Hodgkin's lymphoma Ann. Hematol. 85 2006 301-7
47. S.T. Wong, and S. Goodin Overcoming drug resistance in patients with metastatic breast cancer Pharmacotherapy 29 2009 954 965
48. Y. Xu, M. Ogunsina, P. Samadder, G. Arthur, and F. Schweizer Structural-activity relationships of glucosamine-derived glycerolipids ChemMedChem 8 2013 511 520
49. G. Zhang, Z. Guan, L. Zhang, J. Min, and L. Zhang Synthesis of 2-amino-2-deoxy-β-glycosyl-(1 → 5)-nucleosides and the interaction with RNA Bioorg. Med. Chem. 11 2003 3273 3278