Design and synthesis of glycoside inhibitors of glioma and melanoma growth

Journal of Medicinal Chemistry

Volumn 50, Issue 2, 2007, Pages 364-373

  García Álvarez, Isabel ^a   Corrales, Guillermo ^a   Doncel Pérez, Ernesto ^b,c   Mũoz, Ana ^d   Nieto Sampedro, Manuel ^b,c   Fernández Mayoralas, Alfonso ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b HOSPITAL NACIONAL DE PARAPLÉJICOS   (Spain)

^c INSTITUTO CAJAL   (Spain)

^d FAES FARMA SA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL 2 N ACETYL 2 AMINO 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; CERAMIDE GLUCOSYLTRANSFERASE; GLYCOSIDE; OCTYL 2 AMINO 2 DEOXY 2 N (OLEOYL) ALPHA DEXTRO GLUCOPYRANOSIDE; OCTYL 2 AMINO 2 N BENZOYL 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; OGT 2378; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CELL PROLIFERATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; GLIOMA CELL; HUMAN; HUMAN CELL; MELANOMA CELL; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; GLIOMA; GLYCOSIDES; HUMANS; MELANOMA; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33846406055     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0611556     Document Type: Article

References (22)

1. Friedman HS, S. M. What is "hope" for a patient with a deadly brain tumor? Cerebrum: The DANA Forum on Brain Science 2003, 5, 7-18.
2. McWilliams, R. R.; Rao, R. D.; Brown, P. D.; Link, M. J.; Buckner, J. C. Treatment options for brain metastases from melanoma. Expert Rev. Anticancer Ther. 2005, 5, 809-820.
3. Nieto-Sampedro, M. Astrocyte mitogen inhibitor related to epidermal growth factor receptor. Science 1988, 240, 1784-1786.
4. Abad-Rodriguez, J.; Vallejo-Cremades, M.; Nieto-Sampedro, M. Control of glial number: Purification from mammalian brain extracts of an inhibitor of astrocyte division. Glia 1998, 23, 156-168.
5. Abad-Rodriguez, J.; Bernabe, M.; Romero-Ramirez, L.; Vallejo-Cremades, M.; Fernandez-Mayoralas, A.; Nieto-Sampedro, M. Purification and structure of neurostatin, an inhibitor of astrocyte division of mammalian brain. J. Neurochem. 2000, 74, 2547-2556.
6. Santos-Benito, F. F.; Fernández-Mayoralas, A.; Martín-Lomas, M.; Nieto-Sampedro, M. Inhibition of proliferation of normal and transformed cells by blood group-related oligosaccharides. J. Exp. Med. 1992, 176, 915-918.
7. Coterón, J. M.; Kamaljit, S.; Asensio, J. L.; Domínguez- Dalda, M.; Fernández-Mayoralas, A.; Jiménez-Barbero, J.; Martín-Lomas, M.; Abad-Rodríguez, J.; Nieto-Sampedro, M. Oligosaccharides structurally related to E-selectin ligands are inhibitors of neural cell division: Synthesis, conformational analysis, and biological activity. J. Org. Chem. 1995, 60, 1502-1519.
8. Nieto-Sampedro, M.; Bailon, C.; Fernandez-Mayoralas, A.; Martin-Lomas, M.; Mellstrom, B.; Naranjo, J. R. Experimental brain glioma: Growth arrest and destruction by a blood-group-related tetrasaccharide. J Neuropathol. Exp. Neurol. 1996, 55, 169-177.
9. Aguilera, B.; Romero-Ramirez, L.; Abad-Rodriguez, J.; Corrales, G.; Nieto-Sampedro, M.; Fernández-Mayoralas, A. Novel disaccharide inhibitors of human glioma cell division. J. Med. Chem. 1998, 41, 4599-4606.
10. Fernandez-Mayoralas, A.; De La Figuera, N.; Zurita, M.; Vaquero, J.; Abraham, G. A.; San Roman, J.; Nieto-Sampedro, M. Central neural tumor destruction by controlled release of a synthetic glycoside dispersed in a biodegradable polymeric matrix. J. Med. Chem. 2003, 46, 1286-1288.
11. Bai, Y.; Boons, G.-J.; Burton, A.; Johnson, M.; Haller, M. Vinyl glycosides in oligosaccharide synthesis (part 6): 3-Buten-2-yl 2-azido-2-deoxy glycosides and 3-buten-2-yl 2-phthalimido-2-deoxy glycosides as novel glycosyl donors. J. Carbohydr. Chem. 2000, 19, 939-958.
12. Madsen, R.; Roberts, C.; Fraser-Reid, B. The pent-4-enoyl group: A novel amine-protecting group that is readily cleaved under mild conditions. J. Org. Chem. 1995, 60, 7920-7926.
13. Li, Y.; Li, C.; Wang, P.; Chu, S.; Guan, H.; Yu, B. An unprecedented N-transacylation reaction on 2-acetamido-2-deoxy-α-D-glucopyranosides. Tetrahedron Lett. 2004, 45, 611-613.
14. Hanessian, S.; Zhan, L.; Bovey, R.; Saavedra, O. M.; Juillerat-Jeanneret, L. Functionalized glycomers as growth inhibitors and inducers of apoptosis in human glioblastoma cells. J. Med. Chem. 2003, 46, 3600-3611.
15. Nieto-Sampedro, M.; Doncel-Pérez, E.; Fernández-Mayoralas, A. Natural, synthetic and semisynthetic glycolipid inhibitors of glioma growth. Expert Opin. Ther. Pat. 2004, 14, 487-497.
16. Birkle, S.; Zeng, G.; Gao, L.; Yu, R. K.; Aubry, J. Role of tumor-associated gangliosides in cancer progression. Biochimie 2003, 85, 455-463.
17. Guerrera, M.; Ladisch, S. N-Butyldeoxynojirimycin inhibits murine melanoma cell ganglioside metabolism and delays tumor onset. Cancer Lett. 2003, 201, 31-40.
18. Weiss, M.; Hettmer, S.; Smith, P.; Ladisch, S. Inhibition of melanoma tumor growth by a novel inhibitor of glucosylceramide synthase. Cancer Res. 2003, 63, 3654-3658.
19. Seyfried, T. N.; Smith, P. D.; Platt, F. M. WO0168093, 2001.
20. Fiaux, H.; Popowycz, F.; Favre, S.; Schütz, C.; Vogel, P.; Gerber-Lemaire, S.; Juillerat-Jeanneret, L. Functionalized pyrrolidines inhibit α-mannosidase activity and growth of human glioblastoma and melanoma cells. J. Med. Chem. 2005, 48, 4237-4246.
21. Benda, P.; Lightbody, J.; Sato, G.; Levine, L.; Sweet, W. Differentiated rat glial cell strain in tissue culture. Science 1968, 161, 370-371.
22. Ponten, J.; Macintyre, E. H. Long term culture of normal and neoplastic human glia. Acta Pathol. Microbiol. Scand. 1968, 74, 465-486.