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From 5-fluorouracil acyclonucleosides to benzo-fused six- and seven-membered rings linked to pyrimidine and purine bases: the shift from differentiating anticancer agents to apoptotic inducers

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Pages 1223-1235 | Published online: 28 Sep 2008

Bibliography

  • Malet-Martino M, Jolimaitre P, Martino R. The prodrugs of 5-fluorouracil. Curr Med Chem Anticancer Agents 2002;2:267-310
  • Ajmera S, Bapat AR, Stephanian E, et al. Synthesis and interaction with uridine phosphorylase of 5′-deoxy-4′,5-difluorouridine, a new prodrug of 5-fluorouracil. J Med Chem 1988;31:1094-8
  • Campos J, Pineda MJ, Gómez JA, et al. 5-Fluorouracil derivatives. 1. Acyclonucleosides through a Tin (IV) chloride-mediated regiospecific ring opening of alkoxy-1,4-diheteroepanes. Tetrahedron 1996;52:8907-24
  • D'Amore ESG, Tollot M, Stracca-Panca V, et al. Therapy associated differentiation in rhabdomyosarcomas. Modern Pathol 1994;7:69-75
  • Crouch GD, Kalebic T, Tsokos M, et al. Ara-C treatment leads to differentiation and reverses the transformed phenotype in a human rhabdomyosarcoma cell line. J Exp Cell Res 1993;204:210-6
  • Melguizo C, Prados J, Fernández JE, et al. Actinomycin D causes multidrug resistance and differentiation in a human rhabdomyosarcoma cell line. Cell Mol Biol 1994;40:137-45
  • Shimada H, Newton WA, Soule EH, et al. Pathology of fatal rhabdomyosarcoma. Report from intergroup rhabdomyosarcoma study (IRS-I and IRS-II). Cancer 1987;59:459-65
  • Altmannsberger M, Weber K, Droste R, et al. Desmin is a specific marker for rhabdomyosarcomas of human and rat origin. Am J Pathol 1985;118:85-95
  • Vélez C, Muros MA, Aránega AE, et al. Coexpression of intermediate filament proteins in the chick embryo heart. Acta Anat 1990;139:226-33
  • Prados J, Melguizo C, Fernández JE, et al. Actin, tropomyosin and α-actinin as markers of differentiation in human rhabdomyosarcoma cell lines induced with dimethyl sulfoxide. Cell Mol Biol 1993;39:525-36
  • Gómez JA, Campos J, Marchal JA, et al. Chemical modifications on the acyclic moiety of [3-(2-hydroxyethoxy)-1-alkoxy]-propylnucleobases. 2. Differentiation and growth inhibition in rhabdomyosarcoma cells after exposure to a novel 5-fluorouracil acyclonucleoside. Tetrahedron 1997;53:7319-34
  • Marchal JA, Melguizo C, Prados J, et al. Modulation of myogenic differentiation in a human rhabdomyosarcoma cell Line by a new derivative of 5-fluorouracil (QF-3602). Jpn J Cancer Res 2000;91:934-40
  • Saniger E, Campos JM, Entrena E, et al. Medium benzene-fused oxacycles with the 5-fluorouracil moiety: synthesis, antiproliferative activities and apoptosis induction in breast cancer cells. Tetrahedron 2003;59:5457-67
  • Harris JR, Lippman ME, Morrow M, et al. Diseases of the breast. Lippincott-Raven: New York; 1996. p. 159
  • Hickman JA. Apoptosis induced by anticancer drugs. Cancer Metastasis Rev 1992;11:121-39
  • Rasbridge SA, Gillet CE, Seymour AM, et al. The effects of chemotherapy on morphology, cellular proliferation, apoptosis and oncoprotein expression in primary breast carcinoma. Br J Cancer 1994;70:335-41
  • Lundberg AS, Weinberg RA. Control of the cell cycle and apoptosis. Eur J Cancer 1999;35:531-9
  • Qin LF, Ng IO. Induction of apoptosis by cisplatin and its effect on cell cycle-related proteins and cell cycle changes in hepatoma cells. Cancer Lett 2002;175:27-38
  • Matsuo S, Tanako S, Yamashita J, et al. Synergistic cytotoxic effects of tumour necrosis factor, interferon-gamma and tamoxifen on breast cancer cell lines. Anticancer Res 2000;12:1575-9
  • Trouet A, Pasioukov A, Derpooten KV, et al. Extracellulary tumour-activated prodrugs for the selective chemotherapy of cancer: application to doxorubicin and preliminary in vitro and in vivo studies. Cancer Res 2001;61:2843-6
  • Trujillo MA, Gómez JA, Campos J, et al. Cis and trans-1-[3-Hydroxymethyl)-1,4-Dioxepan-5-yl]pyrimidines: a new nucleoside prototype with a seven-membered moiety. Tetrahedron 2001;57:3951-61
  • Campos J, Gómez JA, Trujillo MA, et al. Diheterocyclanes as synthons for the preparation of novel series of nucleoside and Acyclonucleoside analogues. Il Farmaco 1997;52:263-9
  • Saniger E, Campos JM, Entrena A, et al. Neighbouring group participation as the key step in the reactivity of acyclic and cyclic salicyl-derived O,O-acetals with 5-fluorouracil. Antiproliferative activity, cell cycle dysregulation and apoptotic induction of new O,N-acetals against breast cancer cells. Tetrahedron 2003;59:8017-26
  • Marchal JA, Núñez MC, Suárez I, et al. A synthetic uracil derivative with antitumor activity through decreasing cyclin D1 and CDK1, and increasing p21 and p27 in MCF-7 cells. Breast Cancer Res Ther 2007;105:237-46
  • Meyn RE, Stephens LC, Hunter NR, et al. Kinetics of cisplatin-induced apoptosis in murine mammary and ovarian adenocarcinomas. Int J Cancer 1995;60:725-9
  • Milas L, Hunter NR, Kurdoglu B, et al. Kinetics of mitotic arrest and apoptosis in murine mammary and ovarian tumors treated with taxol. Cancer Chemother Pharm 1995;35:297-303
  • Chadderton A, Villeneuve DJ, Gluck S, et al. Role of specific apoptotic pathways in the restoration of paclitaxel-induced apoptosis by valspodar in doxorubicin-resistant MCF-7 breast cancer cells. Breast Cancer Res Ther 2000;59:231-44
  • Saunders DE, Lawrence WD, Christensen C, et al. Paclitaxel-induced apoptosis in MCF-7 breast-cancer cells. Int J Cancer 1997;70:214-20
  • Campos J, Saniger E, Marchal JA, et al. New médium oacyclic O,N-acetals and related open analogues: biological activities. Curr Med Chem 2005;12:1423-38
  • Sherr CJ. The Pezcoller lecture: cancer cell cycles revisited. Cancer Res 2000;60:3689-95
  • Sherr CJ. Mammalian G1 cyclins. Cell 1993;73:1059-65
  • Shi L, Nishioka WK, Th'ng J, et al. Premature p34cdc2 activation required for apoptosis. Science 1994;263:1143-5
  • Gillett C, Fantl V, Smith R, et al. Amplification and overexpression of cyclin D1 in breast cancer detected by immunohistochemical staining. Cancer Res 1994;54:1812-7
  • Oyama T, Kashiwabara K, Yoshimoto K, et al. Overexpression of the cyclin D1 oncogene in invasive lobular carcinoma of the breast. Cancer Res 1998;58:2876-80
  • Keum JS, Kong G, Yang SC, et al. Cyclin D1 overexpression is an indicator of poor prognosis in resectable non-small cell lung cancer. Br J Cancer 1999;81:127-32
  • Deng CX. Tumor formation in Brca1 conditional mutant mice. Environ Mol Mutagen 2002;39:171-7
  • Hosokawa Y, Papanikolau A, Cardiff RD, et al. In vivo analysis of mammary and non-mammary tumorigenesis in MMTV-Cyclin D1 transgenic mice deficient in p53. Transgenic Res 2001;10:471-8
  • Arnold A, Papanikolaou A. Cyclin D1 in breast cancer pathogenesis. J Clin Oncol 2005;23:4215-24
  • Núñez MC, Entrena A, Rodríguez-Serrano F, et al. Synthesis of novel 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-uracil and – thymine, and their corresponding S-oxidized derivatives. Tetrahedron 2005;61:10363-9
  • Nomura M, Endo K, Shuto S, et al. Ring expansion reaction of 1-[2,3,5-tri-O-TBS-4α-formyl-β-D-ribofuranosyl]uracil by treating with (methylene)triphenylphosphorane to give a new nucleoside containing dihydrooxepine ring at the sugar moiety. Tetrahedron 1999;55:14847-54
  • Núñez MC, Rodríguez-Serrano F, Marchal JA, et al. 6′-Chloro-7- or 9-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)- 7H- or 9H-purines and their corresponding sulfones as a new family of cytotoxic drugs. Tetrahedron 2007;63:183-90
  • Núñez MC, Pavani MG, Díaz-Gavilán M, et al. Synthesis and anticancer activity studies of novel 1-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)uracil and (6′-substituted)-7 or 9-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-7H-or 9H-purines. Tetrahedron 2006;62:11724-33
  • Díaz-Gavilán M, Gómez-Vidal JA, Rodríguez-Serrano F, et al. Anticancer activity of (1,2,3,5-tetrahydro-4,1-benzoxazepine-3-yl)-pyrimidines and -purines against the MCF-7 cell line: preliminary cDNA microarray studies. Bioorg Med Chem Lett 2008;18:1457-60
  • Schnall S, MacDonald JS. Manual of oncologic therapeutics. In: MacDonald JS, Haller DG, Mayer RJ, editors. JB Lippincott: Philadelphia, PA; 1995. pp 170-84
  • Palomer A, Cabré F, Pascual J, et al. Identification of novel cyclooxygenase-2 selective inhibitors using pharmacophore models. J Med Chem 2002;45:1402-11
  • Díaz-Gavilán M, Conejo-García A, Cruz-López O, et al. Synthesis and anticancer activity of (RS)-9-(2,3-dihydro-1,4-benzoxathiin-3-ylmethyl)-9H-purines. ChemMedChem 2008;3:127-35
  • Marchal JA, Boulaiz H, Suárez I, et al. Growth inhibition, G1-arrest, and apoptosis in MCF-7 human breast cancer cells by novel highly lipophilic 5-fluorouracil derivatives. Invest New Drugs 2004;22:379-89
  • Rekker RF, de Kort HM. The hydrophobic fragmental constant; an extension to a 1000 data point set. Eur J Med Chem 1979;14:479-88
  • Campos J, Núñez MC, Rodríguez V, et al. QSAR of 1,1′-(1,2-ethylenebisbenzyl)bis(4-substitutedpyridinium) dibromides as choline kinase inhibitors: a different approach for antiproliferative drug design. Bioorg Med Chem Lett 2000;10:767-70
  • Burr A, Bundgaard H, Falch E. Prodrugs as drug delivery systems. Part 37. Prodrugs of 5-fluorouracil. IV. Hydrolysis kinetics, bioactivation and physicochemical properties of various N-acyloxymethyl derivatives of 5-fluorouracil. Int J Pharm 1985;24:43-60
  • Gulyaeva N, Zaslavsky A, Lechner P, et al. Relative hydrophobicity and lipophilicity of drugs measured by aqueous two-phase partitioning, octanol-buffer partitioning and HPLC. A simple model for predicting blood-brain distribution. Eur J Med Chem 2003;38:391-6

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