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Promise and challenges in drug discovery and development of hybrid anticancer drugs

, PhD & , PhD
Pages 1099-1111 | Published online: 30 Oct 2009

Bibliography

  • Dunham W. Report sees 7.6 million global 2007 cancer deaths. American Cancer Society; 2007
  • Miller A, Hoogstraten B, Staquet M, Winkler A. Reporting results of cancer treatment. Cancer 1981;47:207-14
  • Brown SB, Brown EA, Walker I. The present and future role of photodynamic therapy in cancer treatment. Lancet Oncol 2004;5:497-508
  • Madhani M, Patra AK, Miller TW, Biological activity of designed photolabile metal nitrosyls: light-dependent activation of soluble guanylate cyclase and vasorelaxant properties in rat aorta. J Med Chem 2006;49:7325-30
  • van Lier JE, Tian H, Ali H, Trisulfonated porphyrazines: new photosensitizers for the treatment of retinal and subretinal edema. J Med Chem 2009;52:889-905
  • Gottesman MM. Mechanisms of cancer drug resistance. Annu Rev Med 2002;53:615-27
  • Marx JL. Drug resistance of cancer cells probed. Science 1986;234:818-20
  • Zimmermann GR, Lehár J, Keith CT. Multi-target therapeutics: when the whole is greater than the sum of the parts. Drug Discov Today 2007;12:34-42
  • Eymard JC, Priou F, Zannetti A, Randomized phase II study of docetaxel plus estramustine and single-agent docetaxel in patients with metastatic hormone-refractory prostate cancer. Ann Oncol 2007;18:1064-70
  • Fizazi K, Le Maitre A, Hudes G, Meta-analysis of Estramustine in Prostate Cancer (MECaP) Trialists' Collaborative Group: addition of estramustine to chemotherapy and survival of patients with castration-refractory prostate cancer: a meta-analysis of individual patient data. Lancet Oncol 2007;8:994-1000
  • Machiels JP, Mazzeo F, Clausse M, Prospective randomized study comparing docetaxel, estramustine, and prednisone with docetaxel and prednisone in metastatic hormone-refractory prostate cancer. J Clin Oncol 2008;26:5261-8
  • Sporn MB. Dichotomies in cancer research: some suggestions for a new synthesis. Nat Clin Pract Oncol 2006;3:364-73
  • Sporn MB, Suh N. Chemoprevention: an essential approach to controlling cancer. Nat Rev Cancer 2002;2:537-43
  • Morphy R, Rankovic Z. Designed multiple ligands. An emerging drug discovery paradigm. J Med Chem 2005;48:6523-43
  • Frantz S. The trouble with making combination drugs. Nat Rev Drug Discov 2006;5:881-2
  • Morphy R, Kay C, Rankovic Z. From magic bullets to designed multiple ligands. Drug Discov Today 2004;9:641-51
  • Meunier B. Hybrid molecules with a dual mode of action: dream or reality? Acc Chem Res 2008;41:69-77
  • Tew KD, Stearns ME. Hormone-independent, non-alkylating mechanism of cytotoxicity for estramustine. Urol Res 1987;15:155-60
  • Trafalis DT. Hybrid aza-steroid alkylators in the treatment of colon cancer. Cancer Lett 2006;243:202-10
  • Cline SD, Macdonald TL, Osheroff N. Azatoxin is a mechanistic hybrid of the topoisomerase II-targeted anticancer drugs etoposide and ellipticine. Biochemistry 1997;36:13095-101
  • Viegas-Junior C, Danuello A, da Silva Bolzani V, Molecular hybridization: a useful tool in the design of new drug prototypes. Curr Med Chem 2007;14:1829-52
  • Hulsman N, Medema JP, Bos C, Chemical insights in the concept of hybrid drugs: the antitumor effect of nitric oxide-donating aspirin involves a quinone methide but not nitric oxide nor aspirin. J Med Chem 2007;50:2424-31
  • Nudelman A, Rephaeli A. novel mutual prodrug of retinoic and butyric acids with enhanced anticancer activity. J Med Chem 2000;43:2962-6
  • Daehne W, Frederiksen E, Gundersen E, Acyloxymethyl esters of ampicillin. J Med Chem 1970;13:607-12
  • Alexander J, Cargill R, Michelson SR, Schwam H. (Acyloxy) alkyl carbamates as novel bioreversible prodrugs for amines: increased permeation through biological membranes. J Med Chem 1988;31:318-22
  • Greenwald RB, Pendri A, Conover CD, Drug delivery systems employing 1, 4-or 1, 6-elimination: poly (ethylene glycol) prodrugs of amine-containing compounds. J Med Chem 1999;42:3657-67
  • Barnes KR, Kutikov A, Lippard SJ. Synthesis, characterization, and cytotoxicity of a series of estrogen-tethered platinum(IV) complexes. Chem Biol 2004;11:557-64
  • Guzzo PR, Dinn SR, Lu J, Oettinger-Loomis S. Preparation of optically active (acyloxy) alkyl esters from optically active O-acyl-alpha-hydroxy acids. Tetrahedron Lett 2002;43:5685-9
  • Kantoff P. Recent progress in management of advanced prostate cancer. Oncology (Williston) 2005;19:631-6
  • Hulsman N, Medema JP, Bos C, Chemical insights in the concept of hybrid drugs: the antitumor effect of nitric oxide-donating aspirin involves a quinone methide but not nitric oxide nor aspirin. J Med Chem 2007;50:2424-31
  • Altucci L, Gronemeyer H. The promise of retinoids to fight against cancer. Nat Rev Cancer 2001;1:181-93
  • Miller AA, Kurschel E, Osieka R, Schmidt CG. Clinical pharmacology of sodium butyrate in patients with acute leukemia. Eur J Cancer Clin Oncol 1987;23:1283-7
  • Candido E, Reeves R, Davie JR. Sodium butyrate inhibits histone deacetylation in cultured cells. Cell 1978;14:105-13
  • Chen TA, Allfrey VG. Rapid and reversible changes in nucleosome structure accompany the activation, repression, and superinduction of murine fibroblast protooncogenes c-fos and c-myc. Proc Natl Acad Sci 1987;84:5252-6
  • Thorne AW, Kmiciek D, Mitchelson K, Patterns of histone acetylation. Eur J Biochem 1990;193:701-13
  • Ogryzko VV, Schiltz RL, Russanova V, The transcriptional coactivators p300 and CBP are histone acetyltransferases. Cell 1996;87:953
  • Wolffe AP. Sinful repression. Nature 1997;387:16-7
  • Lin RJ, Nagy L, Inoue S, Role of the histone deacetylase complex in acute promyelocytic leukaemia. Nature 1998;391:811-14
  • Grignani F, De Matteis S, Nervi C, Fusion proteins of the retinoic acid receptor-alpha recruit histone deacetylase in promyelocytic leukaemia. Nature 1998;391:815-18
  • He LZ, Guidez F, Tribioli C, Distinct interactions of PML-RARalpha and PLZF-RARalpha with co-repressors determine differential responses to RA in APL. Nat Genet 1998;18:126-35
  • Warrell RP, He LZ, Richon V, Therapeutic targeting of transcription in acute promyelocytic leukemia by use of an inhibitor of histone deacetylase. J Natl Cancer Inst 1998;90:1621-5
  • Mann KK, Rephaeli A, Colosimo AL, A retinoid/butyric acid prodrug overcomes retinoic acid resistance in leukemias by induction of apoptosis. Mol Cancer Res 2003;1:903-12
  • Altucci L, Leibowitz MD, Ogilvie KM, RAR and RXR modulation in cancer and metabolic disease. Nat Rev Drug Discov 2007;6:793-810
  • Reynolds CP, Matthay KK, Villablanca JG, Maurer BJ. Retinoid therapy of high-risk neuroblastoma. Cancer Lett 2003;197:185-92
  • Freemantle SJ, Spinella MJ, Dmitrovsky E. Retinoids in cancer therapy and chemoprevention: promise meets resistance. Oncogene 2003;22:7305-15
  • Sun SY, Wan H, Yue P, Evidence that retinoic acid receptor beta induction by retinoids is important for tumor cell growth inhibition. J Biol Chem 2000;275:17149-53
  • Sirchia SM, Ferguson AT, Sironi E, Evidence of epigenetic changes affecting the chromatin state of the retinoic acid receptor beta2 promoter in breast cancer cells. Oncogene 2000;19:1556-63
  • Widschwendter M, Berger J, Hermann M, Methylation and silencing of the retinoic acid receptor-beta2 gene in breast cancer. J Natl Cancer Inst 2000;92:826-32
  • Gediya LK, Belosay A, Khandelwal A, Improved synthesis of histone deacetylase inhibitors (HDIs) (MS-275 and CI-994) and inhibitory effects of HDIs alone or in combination with RAMBAs or retinoids on growth of human LNCaP prostate cancer cells and tumor xenografts. Bioorg Med Chem 2008;16:3352-60
  • Gediya LK, Chopra P, Purushottamachar P, A new simple and high-yield synthesis of suberoylanilide hydroxamic acid and its inhibitory effect alone or in combination with retinoids on proliferation of human prostate cancer cells. J Med Chem 2005;48:5047-51
  • Hess-Stumpp H, Bracker TU, Henderson D, Politz O. MS-275, a potent orally available inhibitor of histone deacetylases–the development of an anticancer agent. Int J Biochem Cell Biol 2007;39:1388-405
  • Verheul HMW, Qian DZ, Carducci MA, Pili R. Sequence-dependent antitumor effects of differentiation agents in combination with cell cycle-dependent cytotoxic drugs. Cancer Chemother Pharmacol 2007;60:329-39
  • Gediya LK, Khandelwal A, Patel J, Design, synthesis, and evaluation of novel mutual prodrugs (hybrid drugs) of all-trans-retinoic acid and histone deacetylase inhibitors with enhanced anticancer activities in breast and prostate cancer cells in vitro. J Med Chem 2008;51:3895-904
  • Longley DB, Harkin DP, Johnston PG. 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer 2003;3:330-8
  • Lennard L. Therapeutic drug monitoring of antimetabolic cytotoxic drugs. Br J Clin Pharmacol 1999;47:131
  • Menger FM, Rourk MJ. Synthesis and reactivity of 5-fluorouracil/cytarabine mutual prodrugs. J Org Chem 1997;62:9083-8
  • Shirao K, Hoff P, Ohtsu A, Comparison of the efficacy, toxicity, and pharmacokinetics of a uracil/tegafur (UFT) plus oral leucovorin (LV) regimen between Japanese and American patients with advanced colorectal cancer: joint United States and Japan study of UFT/LV. J Clin Oncol 2004;22:3466
  • Engel D, Nudelman A, Tarasenko N, Novel prodrugs of tegafur that display improved anticancer activity and antiangiogenic properties. J Med Chem 2008;51:314-23
  • Ohtsu H, Nakanishi Y, Bastow KF, Antitumor agents 216. Synthesis and evaluation of paclitaxel-camptothecin conjugates as novel cytotoxic agents. Bioorg Med Chem 2003;11:1851-7
  • Shi Q, Wang HK, Bastow KF, Antitumor agents 210. Synthesis and evaluation of taxoid-epipodophyllotoxin conjugates as novel cytotoxic agents. Bioorg Med Chem 2001;9:2999-3004
  • Bastow KF, Wang HK, Cheng YC, Lee KH. Antitumor agents–CLXXIII. Synthesis and evaluation of camptothecin-4 beta-amino-4′-O-demethyl epipodophyllotoxin conjugates as inhibitors of mammalian DNA topoisomerases and as cytotoxic agents. Bioorg Med Chem 1997;5:1481-8
  • Nakagawa-Goto K, Nakamura S, Bastow KF, Antitumor agents. 256. Conjugation of paclitaxel with other antitumor agents: evaluation of novel conjugates as cytotoxic agents. Bioorg Med Chem Lett 2007;17:2894-8
  • Rink SM, Yarema KJ, Solomon MS, Synthesis and biological activity of DNA damaging agents that form decoy binding sites for the estrogen receptor. Proc Natl Acad Sci USA 1996;93:15063-8
  • Mitra K, Marquis JC, Hillier SM, A rationally designed genotoxin that selectively destroys estrogen receptor-positive breast cancer cells. J Am Chem Soc 2002;124:1862-3
  • Sharma U, Marquis JC, Nicole Dinaut A, Design, synthesis, and evaluation of estradiol-linked genotoxicants as anti-cancer agents. Bioorg Med Chem Lett 2004;14:3829-33
  • Barnard C. Platinum anti-cancer agents. Platinum Metals Rev 1989;33:162-7
  • Hess SM, Anderson JG, Bierbach U. A non-crosslinking platinum–acridine hybrid agent shows enhanced cytotoxicity compared to clinical BCNU and cisplatin in glioblastoma cells. Bioorg Med Chem Lett 2005;15:443-6
  • Kelland LR, Farrell N. Platinum-based drugs in cancer therapy. Humana Pr, Inc.; 2000
  • Provencher-Mandeville J, Descoteaux C, Mandal SK, Synthesis of 17beta-estradiol-platinum(II) hybrid molecules showing cytotoxic activity on breast cancer cell lines. Bioorg Med Chem Lett 2008;18:2282-7
  • Marquis JC, Hillier SM, Dinaut AN, Disruption of gene expression and induction of apoptosis in prostate cancer cells by a DNA-damaging agent tethered to an androgen receptor ligand. Chem Biol 2005;12:779-87
  • Lipinski CA. Drug-like properties and the causes of poor solubility and poor permeability. J Pharmacol Toxicol Methods 2000;44:235-49
  • Veber DF, Johnson SR, Cheng HY, . Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 2005;45(12):2615-23
  • Bradshaw TD, Westwell AD. The development of the antitumour benzothiazole prodrug, Phortress, as a clinical candidate. Curr Med Chem 2004;11:1009-21
  • Sinko PJ, Balimane PV. Carrier-mediated intestinal absorption of valacyclovir, the L-valyl ester prodrug of acyclovir: 1. Interactions with peptides, organic anions and organic cations in rats. Biopharm Drug Dispos 1998;19(4):209-17
  • Lorenzi PL, Landowski CP, Song X, Amino acid ester prodrugs of 2-bromo-5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole enhance metabolic stability in vitro and in vivo. J Pharmacol Exp Ther 2005;314:883-90
  • Berenbaum MC. What is synergy? Pharmacol Rev 1989;41:93-141
  • Greco WR, Bravo G, Parsons JC. The search for synergy: a critical review from a response surface perspective. Pharmacol Rev 1995;47:331-85
  • Zhao L, Wientjes MG, Au JL. Evaluation of combination chemotherapy: integration of nonlinear regression, curve shift, isobologram, and combination index analyses. Clin Cancer Res 2004;10:7994-8004
  • Chou TC. Theoretical basis, experimental design, and computerized simulation of synergism and antagonism in drug combination studies. Pharmacol Rev 2006;58:621
  • Gunnarsson P, Andersson SB, Johansson SÅ, Pharmacokinetics of estramustine phosphate (Estracyt®) in prostatic cancer patients. Eur J Clin Pharmacol 1984;26(1):113-19

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