Structure activity relationships of N-linked and diglycosylated glucosamine-based antitumor glycerolipids

Molecules

Volumn 18, Issue 12, 2013, Pages 15288-15304

  Ogunsina, Makanjuola ^a   Pan, Hangyi ^a   Samadder, Pranati ^a   Arthur, Gilbert ^a   Schweizer, Frank ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

Author keywords

Anticancer agents; Antitumor ether lipids; Carbohydrates; Glycolipids

Indexed keywords

ANTINEOPLASTIC AGENT; GLUCOSAMINE; GLYCOLIPID;

ARTICLE; CELL SURVIVAL; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG EFFECT; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; COMBINATORIAL CHEMISTRY TECHNIQUES; GLUCOSAMINE; GLYCOLIPIDS; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84890948458     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181215288     Document Type: Article

References (24)

1. Canadian Cancer Society's Advisory Committee on Cancer Statistics. Canadian Cancer Statistics 2013; Canadian Cancer Society: Toronto, ON, Canada, 2013; pp. 1-114
2. World Health Organization. Fact Sheet 2007, N° 310; WHO Media Centre: Geneva, Switzerland, 2007.
3. Tan, D.S.-W.; Gerlinger, M.; Teh, B.-T.; Swanton, C. Anti-cancer drug resistance: Understanding the mechanisms through the use of integrative genomics and functional RNA interference. Eur. J. Cancer 2010, 46, 2166-2177.
4. Tanner, M.; Kapanen, A.I.; Junttila, T.; Raheem, O.; Grenman, S.; Elo, J.; Elenius, K.; Isola, J. Characterization of a novel cell line established from a patient with Herceptin-resistant breast cancer. Mol. Cancer Ther. 2004, 3, 1585-1592.
5. Erukulla, R.V.; Zhou, X.; Samadder, P.; Arthur, G.; Bittman, R. Synthesis and evaluation of the antiproliferative effects of 1-O-hexadecyl-2-Omethyl-3-O- (2-acetamido-2-deoxy-β-Dglucopyranosyl)-sn-glycerol and 1-O-hexadecyl-2-O-methyl-3-O-(2-amino-2-deoxy-β-Dglucopyranosyl) -sn-glycerol on epithelial cancer cell growth. J. Med. Chem. 1996, 39, 1545-1548.
6. Samadder, P.; Bittman, R.; Byun, H.S.; Arthur, G. A glycosylated antitumor ether lipid kills cells via paraptosis-like cell death. Biochem. Cell Biol. 2009, 87, 401-414.
7. Samadder, P.; Byun, H.S.; Bittman, R.; Arthur, G. An active endocytosis pathway is required for the cytotoxic effects of glycosylated antitumor ether lipids. Anticancer Res. 2011, 31, 3809-3818.
8. Samadder, P.; Byun, H.; Bittman, R.; Arthur, G. Glycosylated antitumor ether lipids are more effective against oncogene-transformed fibroblasts than alkyllysophospholipids. Anticancer Res. 1998, 18, 465-470.
9. Arthur, G. Tolerability of Rag2M mice to 1-O-Hexadecyl-2-O-methyl-3-O- (2′-amino-2′-deoxy-β-D-glucopyranosyl)-sn-glycerol. Department of Biochemistry and Medical Genetics, University of Manitoba, Winnipeg, MB, Canada. Unpublished work, 2012.
10. Yang, G.; Franck, R.W.; Bittman, R.; Samadder, P.; Arthur, G. Synthesis and growth inhibitory properties of glucosamine-derived glycerolipids. Org. Lett. 2001, 3, 197-200.
11. Rempel, B.P.; Withers, S.G. Covalent inhibitors of glycosidases and their applications in biochemistry and biology. Glycobiology 2008, 18, 570-586.
12. Guoa, W.; Hiratakea, H.; Ogawab, K.; Yamamotob, M.; Maa, S.; Sakataa, K. β-d-Glycosylamidines: Potent, selective, and easily accessible β-glycosidase inhibitors. Bioorg. Med. Chem. Lett. 2001, 11, 467-470.
13. Spevak, W.; Tropper, F.D. β-Glycosylamide glycopolymers: Synthesis, physical properties, chemical and enzymatic stability. MRS Proc. 1995, 394, doi:10.1557/PROC-394-187.
14. Fjelde, E.; Sorkin, E.; Rhodes, J.M. The effect of glucosamine on human epidermoid carcinoma cells in tissue culture. Exp. Cell Res. 1956, 10, 88-98.
15. Jung, C.W.; Jo, J.R.; Lee, S.H.; Park, Y.K.; Jung, N.K.; Song, D.K.; Bae, J.; Nam, K.Y.; Ha, J.S.; Park, I.S.; et al. Anti-cancer properties of glucosamine-hydrochloride in YD-8 human oral cancer cells: Induction of the caspase-dependent apoptosis and down-regulation of HIF-1α. Toxicol In Vitro 2012, 26, 42-50.
16. Adibekian, A.; Martin, B.R.; Wang, C.; Hsu, K.L.; Bachovchin, D.A.; Niessen, S.; Hoover, H.; Cravatt, B.F. Click-generated triazole ureas as ultrapotent in vivo-active serine hydrolase inhibitors. Nat. Chem. Biol. 2011, 7, 469-478.
17. Salunke, S.; Babuzb, N.S.; Chen, C. Iron (III) chloride as an efficient catalyst or stereoselective synthesis of glycosyl azides and a cocatalyst with Cu(0) for the subsequent click chemistry. Chem. Commun. 2011, 47, 10440-10442.
18. Ibatullin, F.M.; Selivanov, S.I. Reaction of 1,2-trans-glycosyl acetates with phosphorus pentachloride: New efficient approach to 1,2-trans-glycosyl chlorides. Tetrahedron Lett. 2002, 43, 9577-9580.
19. Bowden, K.; Heilbron, I.M.; Jones, E.R.H. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols. J. Chem. Soc. 1946, 39-45, doi:10.1039/JR9460000039.
20. Bera, S.; Dhondikubeer, R.; Findlay, B.; Zhanel, G.G.; Schweizer, F. Synthesis and antibacterial activities of Neomycin B-based lipids. Molecules 2012, 17, 9129-9141.
21. Paul, K.J.; Loganathan, D. Synthesis of novel glycolipids derived from glycopyranosyl azides and N-(β-glycopyranosyl) azidoacetamides. Tetrahedron Lett. 2008, 49, 6356-6359.
22. Xu, Y.; Ogunsina, M.; Samadder, P.; Arthur, G.; Schweizer, F. Structure-Activity Relationships of glucosamine derived Glycerolipids: The role of the anomeric linkage, the cationic charge and the glycerol moiety on the antitumor activity. ChemMedChem 2013, 8, 511-520.
23. Bednarczyk, D.; Walczewska, A.; Grzywacz, D.; Sikorski, A.; Liberek, B.; Myszka, H. Differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-D- glucopyranosyl chlorides and their application in the synthesis of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside. Carbohyd. Res. 2012, 367, 10-17.
24. Miao, C.; Zhi, J.; Sun, S.; Yang, X.; Hu, A. Formation of conjugated polynaphthalene via Bergman cyclization. J. Polym. Sci. A Polym. Chem. 2010, 48, 2187-2193.