Human polymerase α inhibitors for skin tumors. Part 2. Modeling, synthesis and influence on normal and transformed keratinocytes of new thymidine and purine derivatives

References

• Jorizzo J. Topical treatment of actinic keratosis with fluorouracil: is irritation associated with efficacy? J Drugs Dermatol 2004;3:21–6.
   PubMedGoogle Scholar
• Rhodes LE, de Rie M, Enstrom Y, Groves R, Morken T, Goulden V, et al. Photodynamic therapy using topical methyl aminolevulinate vs surgery for nodular basal cell carcinoma: results of a multicenter randomized prospective trial. Arch Dermatol 2004;140:17–23.
   PubMed Web of Science ®Google Scholar
• Rivers JK, Arlette J, Shear N, Guenther L, Carey W, Poulin Y. Topical treatment of actinic keratoses with 3.0% diclofenac in 2.5% hyaluronan gel. Br J Dermatol 2002;146:94–100.
   PubMed Web of Science ®Google Scholar
• Lebwohl M, Dinehart S, Whiting D, Lee PK, Tawfik N, Jorizzo J, et al. Imiquimod 5% cream for the treatment of actinic keratosis: results from two phase III, randomized, double-blind, parallel group, vehicle-controlled trials. J Am Acad Dermatol 2004; 50:714–21.
   PubMed Web of Science ®Google Scholar
• Maeda N, Kokai Y, Ohtani S, Sahara H, Kuriyama I, Kamisuki S, et al. Anti-tumor effects of dehydroaltenusin, a specific inhibitor of mammalian DNA polymerase alpha. Biochem Biophys Res Commun 2007;352:390–6.
   PubMed Web of Science ®Google Scholar
• Kuriyama I, Musumi K, Yonezawa Y, Takemura M, Maeda N, Iijima H, et al. Inhibitory effects of glycolipids fraction from spinach on mammalian DNA polymerase activity and human cancer cell proliferation. J Nutr Biochem 2005;16:594–601.
   PubMed Web of Science ®Google Scholar
• Maeda N, Kokai Y, Ohtani S, Sahara H, Hada T, Ishimaru C, et al. Anti-tumor effects of the glycolipids fraction from spinach which inhibited DNA polymerase activity. Nutr Cancer 2007;57:216–23.
   PubMed Web of Science ®Google Scholar
• Matsubara K, Saito A, Tanaka A, Nakajima N, Akagi R, Mori M, Mizushina Y. Catechin conjugated with fatty acid inhibits DNA polymerase and angiogenesis. DNA Cell Biol 2006;25:95–103.
   PubMed Web of Science ®Google Scholar
• Matsubara K, Saito A, Tanaka A, Nakajima N, Akagi R, Mori M, et al. Epicatechin conjugated with fatty acid is a potent inhibitor of DNA polymerase and angiogenesis. Life Sci 2007;80:1578–5.
   PubMed Web of Science ®Google Scholar
• Gandhi V, Huang P, Chapman AJ, Chen F, Plunkett W. Incorporation of fludarabine and 1-beta-D-arabinofuranosylcytosine 5’-triphosphates by DNA polymerase alpha: affinity, interaction, and consequences. Clin Cancer Res 1997;3:1347–55.
   PubMed Web of Science ®Google Scholar
• Jiang HY, Hickey RJ, Abdel-Aziz W, Malkas LH. Effects of gemcitabine and araC on in vitro DNA synthesis mediated by the human breast cell DNA synthesome. Cancer Chemother Pharmacol 2000;45:320–8.
   PubMed Web of Science ®Google Scholar
• Richartz A, Höltje M, Brandt B, Schäfer-Korting M, Höltje HD. Targeting human DNA polymerase alpha for the inhibition of keratinocyte proliferation. Part 1.Homology model, active site architecture and ligand binding. J Enzyme Inhib Med Chem 2008;23:94–100.
   PubMed Web of Science ®Google Scholar
• O’Dwyer PJ, Moyer JD, Suffness M, Harrison SD Jr, Cysyk R, Hamilton TC, et al. Antitumor activity and biochemical effects of aphidicolin glycinate (NSC 303812) alone and in combination with cisplatin in vivo. Cancer Res 1994;54:724–9.
   PubMed Web of Science ®Google Scholar
• Julia M, Baillarge M.Keto derivs. of aminophenols by the Friedel-Crafts and the Fries reactions. Bull Chim Soc Fr 1952:639–42.
   Google Scholar
• Hoffer M. Alpha-thymidine. Chem Ber 1960;93:2777–81.
   Google Scholar
• Lan T, McLaughlin LW. Minor groove hydration is critical to the stability of DNA duplexes. J Am Chem Soc 2000;122:6512–13.
   Web of Science ®Google Scholar
• Vogler R, Sauer B, Kim DS, Schäfer-Korting M, Kleuser B. Sphingosine-1-phosphate and its potentially paradoxical effects on critical parameters of cutaneous wound healing. J Invest Dermatol 2003;120:693–700.
   PubMed Web of Science ®Google Scholar
• Gysler A, Lange K, Korting HC, Schafer-Korting M. Prednicarbate biotransformation in human foreskin keratinocytes and fibroblasts. Pharm Res 1997;14:793–7.
   PubMed Web of Science ®Google Scholar
• Liebsch M, Spielmann H. 3T3 NRU Phototoxicity Assay. Available at http://ecvam-dbalmjrcceceuint/public_view_doccfm?id=736F27E9E9F7A9D869FB48087878D2497180BB0BC12CB10496CDA74B54630A05A3291B895581F634, 1998.
   Google Scholar
• Vermes I, Haanen C, Richel DJ, Schaafsma MR, Kalsbeek-Batenburg E, Reutelingsperger CP. Apoptosis and secondary necrosis of lymphocytes in culture. Acta Haematol 1997;98:8–13.
   PubMed Web of Science ®Google Scholar
• Manggau M, Kim DS, Ruwisch L, Vogler R, Korting HC, Schäfer-Korting M, et al. 1Alpha,25-dihydroxyvitamin D3 protects human keratinocytes from apoptosis by the formation of sphingosine-1-phosphate. J Invest Dermatol 2001;117:1241–9.
   PubMed Web of Science ®Google Scholar
• Zdrazil B, Höltje M, Schwanke A, Schmitz B, Schäfer-Korting M, Höltje H-D.Molecular modeling studies of new potential human DNA polymerase alpha inhibitors. 2009; submitted.
   Google Scholar
• Hansske F, Madej D, Robins MJ. 2’ and 3’-Ketonucleosides and their arabino and xylo reduction products: convenient access via selective protection and oxidation of ribonucleosides. Tetrahedron 1984;40:125–35.
   Web of Science ®Google Scholar
• Sharma M, Bobek M. Synthesis of 2′,3′-dideoxy-3′-methylene pyrimine nucleosides as potential anti-AIDS agents. Tetrahedron Lett 1990;31:5839–42.
   Web of Science ®Google Scholar
• Samano V, Robins MJ. Nucleic acid related compounds. 60. Mild periodinane oxidation of protected nucleosides to give 2’-,and 3’-ketonucleosides. The first isolation of a purine 2’-deoxy-3’-ketonucleoside derivative. J Org Chem 1990;55:5186–8.
   Web of Science ®Google Scholar
• Wright GE, Dudycz LW, Kazimierczuk Z, Brown NC, Khan NN. Synthesis, cell growth inhibition, and antitumor screening of 2-(p-n-butylanilino)purines and their nucleoside analogues. J Med Chem 1987;30:109–16.
   PubMed Web of Science ®Google Scholar
• Frieden M, Avino A, Eritja R. Convenient synthesis of 8-amino-2’-deoxyadenosine. Nucleosides Nucleotides Nucleic Acids 2003;22:193–202.
   PubMed Web of Science ®Google Scholar
• Koshkin AA. Syntheses and base-pairing properties of locked nucleic acid nucleotides containing hypoxanthine, 2,6-diaminopurine, and 2-aminopurine nucleobases. J Org Chem 2004;69:3711–18.
   PubMed Web of Science ®Google Scholar
• Fedorocko P, Hoferova Z, Hofer M, Brezani P. Administration of liposomal muramyl tripeptide phosphatidylethanolamine (MTP-PE) and diclofenac in the combination attenuates their anti-tumor activities. Neoplasma 2003;50:176–84.
   PubMed Web of Science ®Google Scholar
• Hoferova Z, Fedorocko P, Hofmanova J, Hofer M, Znojil V, Minksova K, et al. The effect of nonsteroidal antiinflammatory drugs ibuprofen, flurbiprofen, and diclofenac on in vitro and in vivo growth of mouse fibrosarcoma. Cancer Invest 2002;20:490–8.
   PubMed Web of Science ®Google Scholar
• Boucher PD, Im MM, Freytag SO, Shewach DS. A novel mechanism of synergistic cytotoxicity with 5-fluorocytosine and ganciclovir in double suicide gene therapy. Cancer Res 2006;66:3230–7.
   PubMed Web of Science ®Google Scholar
• Haberland A, Schreiber S, Maia CS, Rübbelke MK, Schaller M, Korting HC, et al. The impact of skin viability on drug metabolism and permeation — BSA toxicity on primary keratinocytes. Toxicol In Vitro 2006;20:347–54.
   PubMed Web of Science ®Google Scholar
• Edelson RE, Gorycki PD, MacDonald TL. The mechanism of aphidicolin bioinactivation by rat liver in vitro systems. Xenobiotica 1990;20:273–87.
   PubMed Web of Science ®Google Scholar
• Vogt T, McClelland M, Jung B, Popova S, Bogenriede T, Becker B, et al. Progression and NSAID-induced apoptosis in malignant melanomas are independent of cyclooxygenase II. Melanoma Res 2001;11:587–99.
   PubMed Web of Science ®Google Scholar
• Rodriguez CO Jr, Mitchell BS, Ayres M, Eriksson S, Gandhi V. Arabinosylguanine is phosphorylated by both cytoplasmic deoxycytidine kinase and mitochondrial deoxyguanosine kinase. Cancer Res 2002;62:3100–5.
   PubMed Web of Science ®Google Scholar
• Baron JM, Holler D, Schiffer R, Frankenberg S, Neis M, Merk HF, et al. Expression of multiple cytochrome p450 enzymes and multidrug resistance-associated transport proteins in human skin keratinocytes. J Invest Dermatol 2001;116:541–8.
   PubMed Web of Science ®Google Scholar
• Schiffer R, Neis M, Holler D, Rodriguez F, Geier A, Gartung C, et al. Active influx transport is mediated by members of the organic anion transporting polypeptide family in human epidermal keratinocytes. J Invest Dermatol 2003;120:285–91.
   PubMed Web of Science ®Google Scholar