Development of cytarabine prodrugs and delivery systems for leukemia treatment

Bibliography

• Meeker ND, Yang JJ, Schiffman JD. Pharmacogenomics of pediatric acute lymphoblastic leukemia. Expert Opin Pharmacother 2010;11(10):1621-32
   PubMed Web of Science ®Google Scholar
• Faderl S, Talpaz M, Estrov Z, The biology of chronic myeloid leukemia. N Engl J Med 1999;341:164-72
   PubMed Web of Science ®Google Scholar
• The Leukemia and Lymphoma Society, Facts 2009-2010. Available from: http://www.leukemia-lymphoma.org/attachments/National/br_1247234696.pdf [Last accessed 15 July 2010]
   Google Scholar
• Fullmer A, O'Brien S, Kantarjian H, Jabbour E. Emerging therapy for the treatment of acute lymphoblastic leukemia. Expert Opin Emerg Drugs 2010;15(1):1-11
   PubMed Web of Science ®Google Scholar
• Cilloni D, Messa E, Rotolo A, Saglio G. Emerging drugs for chronic myeloid leukemia. Expert Opin Emerg Drugs 2010;15(2):175-84
   PubMed Web of Science ®Google Scholar
• Harris TJR, McCormick F. The molecular pathology of cancer. Nat Rev Clin Oncol 2010;7(5):251-65
   PubMed Web of Science ®Google Scholar
• Kumar L, Vikram P, Kochupilla V. Recent advances in the management of multiple myeloma. Nat Med J Ind 2006;19(2):80-9
   PubMed Web of Science ®Google Scholar
• Das M, Mohanty C, Sahoo SK. Ligand-based targeted therapy for cancer tissue. Expert Opin Drug Deliv 2009;6(3):285-304
   PubMed Web of Science ®Google Scholar
• Fernandez HF, Rowe JM. Induction therapy in acute myeloid leukemia: intensifying and targeting the approach. Cur Opin Hematol 2010;17(2):79-84
   PubMed Web of Science ®Google Scholar
• Arya LS. Acute lymphoblastic leukemia: current treatment concepts. Ind Pediatrics 2000;37(4):397-406
   PubMedGoogle Scholar
• Hoogstraten B, Glidewell O, Holland JF, Long term follow-up of combination chemotherapy-radiotherapy of stage III Hodgkin's disease: a Cancer and Acute Leukemia Group B study. Cancer 1979;43(4):1234-44
   PubMed Web of Science ®Google Scholar
• Kumar R, Shandal V, Shamim SA, Clinical applications of PET and PET/CT in pediatric malignancies. Expert Rev Anticancer Ther 2010;10(5):755-68
   PubMed Web of Science ®Google Scholar
• Jabbour E, Cortes JE, Giles FJ, Current and emerging treatment options in chronic myeloid leukemia. Cancer 2007;109(11):2171-81
   PubMed Web of Science ®Google Scholar
• Shah M, Agarwal B. Recent advances in management of acute myeloid leukemia (AML). Ind J Pediat 2008;75(8):831-37
   PubMed Web of Science ®Google Scholar
• Pinilla-Ibarz J, Bello C. Modern approaches to treating chronic myelogenous leukemia. Cur Oncol Rep 2008;10(5):365-71
   PubMedGoogle Scholar
• Matsumura I. Standard therapies for acute myeloid leukemia. Rinsho Ketsueki 2009;50(10):1389-400
   PubMedGoogle Scholar
• Mayer RJ, Davis RB, Schiffer CA. Intensive postremission chemotherapy in adults with acute myeloid leukemia. N Engl J Med 1994;331:896-903
   PubMed Web of Science ®Google Scholar
• Robak T, Wierzbowska A. Current and emerging therapies for acute myeloid leukemia. Clin Ther 2009;31(2):2349-70
   PubMedGoogle Scholar
• Abali H, Urun Y, Oksuzoglu B, Comparison of ICE (ifosfamide-carboplatin-etoposide) versus DHAP (cytosine arabinoside-cisplatin-dexamethasone) as salvage chemotherapy in patients with relapsed or refractory lymphoma. Cancer Invest 2008;26(4):401-6
   PubMed Web of Science ®Google Scholar
• Petit J, Boque C, Cancelas JA, Feasibility of ESHAP + G-CSF as peripheral blood hematopoietic progenitor cell mobilisation regimen in resistant and relapsed lymphoma: a single-center study of 22 patients. Leuk Lymphoma 1999;34(1-2):119-27
   PubMed Web of Science ®Google Scholar
• Weigert O, Weidmann E, Mueck R, A novel regimen combining high dose cytarabine and bortezomib has activity in multiply relapsed and refractory mantle cell lymphoma – long-term results of a multicenter observation study. Leuk Lymphoma 2009;50(5):716-22
   PubMed Web of Science ®Google Scholar
• Suzuki K, Nakazato T, Sanada Y, Successful treatment with hyper-CVAD and highly active anti-retroviral therapy (HAART) for AIDS-related Burkitt lymphoma. Rinsho Ketsueki 2010;51(3):207-12
   PubMedGoogle Scholar
• Kantarjian HM, O'Brien S, Smith TL, Results of treatment with hyper-CVAD, a dose-intensive regimen, in adult acute lymphocytic leukemia. J Clin Oncol 2000;18(3):547-61
   PubMed Web of Science ®Google Scholar
• Plunkett W, Liliemark JO, Estey E, Keating MJ. Saturation of ara-CTP accumulation during high-dose ara-C therapy: pharmacologic rationale for intermediate-dose ara-C. Semin Oncol 1987;14:159-66
   PubMed Web of Science ®Google Scholar
• Cohen SS. The lethality of aranucleotides. Med Biol 1976;54(5):299-326
   PubMedGoogle Scholar
• Capizzi RL, White JC, Powell BL, Perrino F. Effect of dose on the pharmacokinetic and pharmacodynamic effects of cytarabine. Semin Hematol 1991;28(4):54-69
   PubMedGoogle Scholar
• Slevin ML, Piall EM, Aherne GW, Subcutaneous infusion of cytosine arabinoside. A practical alternative to intravenous infusion. Cancer Chemother Pharmacol 1983;10(2):112-14
   PubMed Web of Science ®Google Scholar
• Stella VJ, Charman WN, Naringrekar VH. Prodrugs. Do they have advantages in clinical practice? Drugs 1985;29:455-73
   PubMed Web of Science ®Google Scholar
• Harper NJ. Drug latentiation. Prog Drug Res 1962;4:221-94
   Google Scholar
• Sinkula AA, Yalkowsky SH. Rationale for design of biologically reversible drug derivatives: prodrugs. J Pharm Sci 1975;64:181-210
   PubMed Web of Science ®Google Scholar
• Peterson LW, McKenna CE. Prodrug approaches to improving the oral absorption of antiviral nucleotide analogues. Expert Opin Drug Deliv 2009;6(4):405-20
   PubMed Web of Science ®Google Scholar
• Ali M, Hariharan AG, Mishra N, Jain S. Catalytic antibodies as potential therapeutics. Ind J Biotech 2009;8(3):253-58
   Web of Science ®Google Scholar
• Jin MJ, Hong JH, Han HK. Synthesis and in vivo evaluation of N4-amino acid derivatives of cytarabine for improving the oral delivery of cytarabine. J Korean Pharm Sci 2008;38(4):255-9
   Google Scholar
• Sun Y, Sun J, Shi L, Synthesis, transport and pharmacokinetics of 5-amino acid ester prodrugs of 1-beta-D-arabinofuranosylcytosine. Mol Pharm 2009;6(1):315-25
   PubMedGoogle Scholar
• Li F, Maag J, Alfredson H. Prodrugs of nucleoside analogues for improved oral absorption and tissue targeting. J Pharm Sci 2008;97(3):1109-34
   PubMed Web of Science ®Google Scholar
• Nam NH, Sardari S, Selecky M, Parang K. Carboxylic acid and phosphate ester derivatives of fluconazole: Synthesis and antifungal activities. Bioorg Med Chem 2004;12(23):6255-69
   PubMed Web of Science ®Google Scholar
• Liu B, Cui C, Duan W, Synthesis and evaluation of anti-tumor activities of N4 fatty acyl amino acid derivatives of 1-beta-arabinofuranosylcytosine. Eur J Med Chem 2009;44:3596-600
   PubMed Web of Science ®Google Scholar
• Bergman AM, Kuiper CM, Voorn DA, Antiproliferative activity and mechanism of action of fatty acid derivatives of arabinofuranosylcytosine in leukaemia and solid tumour cell lines. Biochem Pharmacol 2004;67:503-11
   PubMed Web of Science ®Google Scholar
• Breistol K, Balzarini J, Sandvold ML, Antitumour activity of P-4055 (Elaidic Acid-Cytarabine) compared to cytarabine in metastatic and s.c. human tumour xenograft models. Cancer Res 1999;59:2944-9
   PubMed Web of Science ®Google Scholar
• Ross DD, Chen SR, Cuddy DP. Effects of 1-beta-D-arabinofuranosylcytosine on DNA replication intermediates monitored by PH-step alkaline elution. Cancer Res 1990;50:2658-66
   PubMed Web of Science ®Google Scholar
• Bergman AM, Kuiper CM, Myhren F, Antiproliferative activity and mechanism of action of fatty acid derivatives of arabinosylcytosine (ara-C) in leukaemia and solid tumour cell lines. Nucleosides Nucleotides Nucleic Acids 2004;23:1523-6
   PubMed Web of Science ®Google Scholar
• Galmarini CM, Myhren F, Sandvold ML. CP-4055 and CP-4126 are active in ara-C and gemcitabine-resistant lymphoma cell lines. Br J Haematol 2009;144(2):273-5
   PubMed Web of Science ®Google Scholar
• Adams DJ, Sandvold ML, Myhren F, Anti proliferative activity of ELACY (CP-4055) in combination with cloretazine (VNP40101M), idarubicin, gemcitabine, irinotecan and topotecan in human leukemia and lymphoma cells. Leuk Lymphoma 2008;49(4):786-97
   PubMed Web of Science ®Google Scholar
• Dueland S, Aamdal S, Lind MJ, Intravenous administration of CP-4055 (ElacytTM) in patients with solid tumours. A phase 1 study. Acta Oncol 2009;48:137-45
   PubMed Web of Science ®Google Scholar
• Chhikara BS, Mandal D, Parang K. Synthesis and evaluation of fatty acyl ester derivatives of cytarabine as anti-leukemia agents. Eur J Med Chem 2010;45(10):4601-8
   Google Scholar
• Peterson LW, McKenna CE. Prodrug approaches to improving the oral absorption of antiviral nucleotide analogues. Expert Opin Drug Deliv 2009;6(4):405-20
   PubMed Web of Science ®Google Scholar
• Hong CI, Nechaev A, West CR. Nucleoside conjugates as potential antitumor agents. 2. Synthesis and biological activity of 1-b-D-arabinofuranosylcytosine conjugates of prednisolone and prednisone. J Med Chem 1979;22:1428-32
   PubMed Web of Science ®Google Scholar
• Raetz CRH, Chu MY, Srivastava SP, Turcotte JG. A phospholipid derivative of cytosine arabinoside and its conversion to phosphatidylinositol by animal tissue. Science 1977;196:303-5
   PubMed Web of Science ®Google Scholar
• Rosowsky A, Kim SH, Ross J, Wick MM. Lipophilic 5′-alkyl phosphate esters of 1-beta-D-arabinofuranosylcytosine and its N4-acyl and 2,2′-anhydro-3′-O-acyl derivatives as potential prodrugs. J Med Chem 1982;25:171-8
   PubMed Web of Science ®Google Scholar
• MacCoss M, Ryu EK, Matsushita T. The synthesis, characterization, and preliminary biological evaluation of 1-beta-D-arabinofuranosylcytosine-5′-diphosphate-L-1,2-dipalmitin. Biochem Biophys Res Commun 1978;85:714-23
   PubMed Web of Science ®Google Scholar
• Yoshida Y, Yamada J, Watanabe T, Participation of the peroxisomal beta-oxidation system in the chain shortening of PCA16, a metabolite of the cytosine arabinoside prodrug, YNKO1, in rat liver. Biochem Pharmacol 1990;39:1505-12
   PubMed Web of Science ®Google Scholar
• Saneyoshi M, Morozumi M, Kodama K, Synthetic nucleosides and nucleotides. XVI. Synthesis and biological evaluations of a series of 1-beta-D-arabinofuranosylcytosine 5′-alkyl or arylphosphates. Chem Pharm Bull 1980;28:2915-23
   PubMed Web of Science ®Google Scholar
• Schleyer E, Braess J, Ramsauer B, Pharmacokinetics of Ara-CMP-stearate (YNK01): phase I study of the oral Ara-C derivative. Leukemia 1995;9:1085-90
   PubMed Web of Science ®Google Scholar
• Ueda T, Kamiya K, Urasaki Y, Clinical pharmacology of 1-beta-D-arabinofuranosylcytosine-5′-stearylphosphate, an orally administered long-acting derivative of low-dose 1-beta-D-arabinofuranosylcytosine. Cancer Res 1994;54:109-13
   PubMed Web of Science ®Google Scholar
• Braess J, Freund M, Hanauske A, Oral cytarabine ocfosfate in acute myeloid leukemia and non-Hodgkin's lymphoma phase I/II studies and pharmacokinetics. Leukemia 1998;12:1618-26
   PubMed Web of Science ®Google Scholar
• Heussner P, Willemze R, Ganser A, YNK01, an oral cytosine arabinoside derivative in acute myeloid leukemia and chronic myeloid leukemia. Haematol Blood Transfus 1997;38:882-5
   Google Scholar
• Snow B. Drug information: a guide to current resources. 1999, Chapter 15. 2nd edition. Maryland: Scarecrow Press, Inc. pp. 456-64
   Google Scholar
• Gouy MH, Jordheim LP, Lefebvre I, Special features of mixed phosphotriester derivatives of cytarabine. Bioorg Med Chem 2009;17:6340-47
   PubMed Web of Science ®Google Scholar
• Tobias SC, Borch RF. Synthesis and biological evaluation of a cytarabine phosphoramidate prodrug. Mol Pharma 2004;1(2):112-6
   PubMed Web of Science ®Google Scholar
• Mehellou Y, Valente R, Mottram H, Phophoramidates of 2′-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism. Bioorg Med Chem 2010;18:2439-46
   PubMed Web of Science ®Google Scholar
• Utreja P, Jain S, Tiwary AK. Novel drug delivery systems for sustained and targeted delivery of anti-cancer drugs: current status and future prospects. Curr Drug Deliv 2010;7(2):152-61
   PubMedGoogle Scholar
• Diab R, Degobert G, Hamoudeh M, Nucleoside analogue delivery systems in cancer therapy. Expert Opin Drug Deliv 2007;4(5):513-31
   PubMed Web of Science ®Google Scholar
• Dubey SK, Pandey A, Mishra R, Site directed drug delivery by non-viral mode. Ind J Biotech 2007;6(2):159-74
   Google Scholar
• Kripp M, Hofheinz RD. Treatment of lymphomatous and leukemic meningitis with liposomal encapsulated cytarabine. Int J Nanomedicine 2008;3(4):397-401
   PubMed Web of Science ®Google Scholar
• Manjanna KM, Kumar TMP, Shivakumar B. Natural polysaccharide hydrogels as novel excipients for modified drug delivery systems: a review. Int J ChemTech Res 2010;2(1):509-25
   Google Scholar
• Trigo RM, Blanco MD, Teijon JM, Sastre R. Anti-cancer drug, Ara-C, release from pHEMA hydrogels. Biomater 1994;15(14):1181-6
   PubMed Web of Science ®Google Scholar
• Sastre RL, Blanco MD, Gomez C, Cytarabine trapping in poly(2-hydroxyethyl methacrylate-co-acrylamide) hydrogels: drug delivery studies. Polym Int 1999;48:843-50
   Web of Science ®Google Scholar
• Kaasgaard T, Andresen TL. Liposomal cancer therapy: exploiting tumor characteristics. Expert Opin Drug Deliv 2010;7(2):225-43
   PubMed Web of Science ®Google Scholar
• Alam MI, Beg S, Samad A, Strategy for effective brain drug delivery. Eur J Pharm Sci 2010;40(5):385-403
   PubMed Web of Science ®Google Scholar
• Bhattacharya S, Bajaj A. Advances in gene delivery through molecular design of cationic lipids. Chem Commun 2009;31:4632-56
   PubMedGoogle Scholar
• Rao NM. Cationic lipid-mediated nucleic acid delivery: beyond being cationic. Chem Phys Lipids 2010;163(3):245-52
   PubMed Web of Science ®Google Scholar
• Maeda H, Wu J, Sawa T, Tumour vascular permeability and the EPR effect in macromolecular therapeutics: a review. J Control Release 2000;65:271-84
   PubMed Web of Science ®Google Scholar
• Abu Lila AS, Ishida T, Kiwada H. Targeting anticancer drugs to tumor vasculature using cationic liposomes. Pharma Res 2010;27(7):1171-83
   Google Scholar
• Dhamecha DL, Rathi AA, Saifee M, Drug vehicle based approaches of penetration enhancement. Int J Pharm Pharm Sci 2009;1:24-46
   Google Scholar
• Benesch M, Urban C. Liposomal cytarabine for leukemic and lymphomatous meningitis: recent developments. Expert Opin Pharm 2008;9(2):301-9
   PubMed Web of Science ®Google Scholar
• Mulik R, Kulkarni V, Murthy RSR. Chitosan-based thermosensitive hydrogel containing liposomes for sustained delivery of cytarabine. Drug Devel Ind Pharm 2009;35(1):49-56
   PubMed Web of Science ®Google Scholar
• Benesch M, Urban C. Liposomal cytarabine for leukemic and lymphomatous meningitis: recent developments. Expert Opin Pharmacother 2008;9(2):301-9
   PubMed Web of Science ®Google Scholar
• Phuphanich S, Maria B, Braeckman R, Chamberlain M. A pharmacokinetic study of intra-CSF administered encapsulated cytarabine (DepoCyt®) for the treatment of neoplastic meningitis in patients with leukemia, lymphoma, or solid tumors as part of a phase III study. J NeuroOncol 2007;81(2):201-8
   PubMed Web of Science ®Google Scholar
• Jaeckle KA, Batchelor T, O'Day SJ. An open label trial of sustained-release cytarabine (DepoCyt™) for the intrathecal treatment of solid tumor neoplastic meningitis. J Neuro Oncol 2002;57(3):231-39
   PubMed Web of Science ®Google Scholar
• Bayne WF, Mayer LD, Swenson CE. Pharmacokinetics of CPX-351 (cytarabine/daunorubicin HCl) liposome injection in the mouse. J Pharm Sci 2009;98(7):2540-48
   PubMed Web of Science ®Google Scholar
• Tardi P, Johnstone S, Harasym N, In vivo maintenance of synergistic cytarabine: daunorubicin ratios greatly enhances therapeutic efficacy. Leuk Res 2009;33:129-39
   PubMed Web of Science ®Google Scholar
• Feldman E, Lancet J, Kolitz JE, Phase I study of a liposomal carrier (CPX-351) containing an optimized, synergistic, fixed molar ratio of cytarabine and daunorubicin in advanced leukemias and myelodysplastic syndromes. Am Soc Hematol Ann Meet Blood 2007;110:900
   Google Scholar
• Lima WS, Tardia PG, Santos ND. Leukemia-selective uptake and cytotoxicity of CPX-351, a synergistic fixed-ratio cytarabine:daunorubicin formulation, in bone marrow xenografts. Leuk Res 2010;34(9):1214-23
   PubMed Web of Science ®Google Scholar
• Schwendener R, Schott H. Lipophilic arabinofuranosyl cytosine derivatives in liposomes. Methods Enzymol 2005;391:58-70
   PubMed Web of Science ®Google Scholar
• Horber DH, Von Ballmoos P, Schott H, Schwendener RA. Cell cycle-dependent cytotoxicity and induction of apoptosis by liposomal N4-hexadecyl-1-beta-D-arabinofuranosylcytosine. Br J Cancer 1995;72(5):1067-73
   PubMed Web of Science ®Google Scholar
• Horber DH, Schott H, Schwendener RA. Cellular pharmacology of a liposomal preparation of N4-hexadecyl-1-beta-D-arabinofuranosylcytosine, a lipophilic derivative of 1-beta-D-arabinofuranosylcytosine. Br J Cancer 1995;71(5):957-62
   PubMed Web of Science ®Google Scholar
• Rentsch KM, Schwendener RA, Schott H, Hanseler E. Pharmacokinetics of N4-octadecyl-1-beta-D-arabinofuranosylcytosine in plasma and whole blood after intravenous and oral administration to mice. J Pharm Pharmacol 1997;49(11):1076-81
   PubMed Web of Science ®Google Scholar
• Koller-Lucae SKM, Schott H, Schwendener RA. Interactions with human blood in vitro and pharmacokinetic properties in mice of liposomal N4-octadecyl-1-beta-D-arabinofuranosylcytosine, a new anticancer drug. J Pharmacol Exp Ther 1997;282(3):1572-80
   PubMed Web of Science ®Google Scholar
• Jancar J, Douglas JF, Starr FW, Current issues in research on structure-property relationships in polymer nanocomposites. Polymer 2010;51(15):3321-43
   Web of Science ®Google Scholar
• Sandhiya S, Dkhar SA, Surendiran A. Emerging trends of nanomedicine – an overview. Fundam Clin Pharmacol 2009;23(3):263-9
   PubMed Web of Science ®Google Scholar
• Kumari A, Yadav SK, Yadav SC. Biodegradable polymeric nanoparticles based drug delivery systems. Colloids Surf B Biointerfaces 2010;75(1):1-18
   PubMed Web of Science ®Google Scholar
• Surendiran A, Sandhiya S, Pradhan SC, Adithan C. Novel applications of nanotechnology in medicine. Ind J Med Res 2009;130(6):689-701
   PubMed Web of Science ®Google Scholar
• Rukmani K, Sivakumar M, Kumar SS. Nanoparticular drug delivery system of cytarabine hydrochloride (CTH) for improved treatment of Lymphoma. J Biomed Nanotech 2007;3(1):90-6
   Web of Science ®Google Scholar
• Blanco MD, Gomez C, Olmo R, Chitosan microspheres in PLG films as devices for cytarabine release. Intern J Pharma 2000;202:29-39
   PubMed Web of Science ®Google Scholar
• Azeem A, Anwer MK, Talegaonkar S. Niosomes in sustained and targeted drug delivery: some recent advances. J Drug Target 2009;17(9):671-89
   PubMed Web of Science ®Google Scholar
• Sagar GH, Arunagirinathan MA, Bellare JR. Self assembled surfactant nano-structures important in drug delivery: a review. Ind J Exp Biol 2007;45:133-59
   PubMed Web of Science ®Google Scholar
• Ruckmani K, Ghosal SK. The efficacy of 1-beta-D-arabinofuranosylcytosine entrapped in niosomes against leukaemia in mice. STP Pharma Sci 2001;11(4):301-3
   Google Scholar