132
Views
15
CrossRef citations to date
0
Altmetric
Review

Hypoxia-activated anticancer drugs

Pages 635-646 | Published online: 14 Jun 2005

Bibliography

  • HARRIS AL: Hypoxia - a key regulatory factor in tumour growth. Nat. Rev. Cancer (2002) 2:38–47.
  • • Excellent review of tumour hypoxia.
  • BROWN JM, WILSON WR: Exploiting tumor hypoxia in cancer treatment. Nat. Rev Cancer (2004) 4:437–447.
  • •• Excellent and recent review of hypoxia andhypoxia-activated prodrugs.
  • EVANS SM, JUDY KD, DUNPHY I et al: Comparative measurements of hypoxia in human brain tumors using needle electrodes and EF5 binding. Cancer Res. (2004) 64:1886–1892.
  • BARTHEL H, WILSON H, COLLINGRIDGE DR et al.: LI vivo evaluation of [18F]fluoroetanidazole as a new marker for imaging tumour hypoxia with positron emission tomography. BE J. Cancer (2004) 90:2232–2242.
  • VAUPEL P, SCHLENGER K, KNOOP C, HOCKEL M: Oxygenation of human tumors: evaluation of tissue oxygen distribution in breast cancers by computerized 02 tension measurements. Cancer Res. (1991) 51:3316–3322.
  • MOVSAS B, CHAPMAN JD, HORWITZ EM et al: Hypoxic regions exist in human prostate carcinoma. Urology (1999) 53:11–18.
  • TANNOCK IF, LEE CM, TUNGGAL JK, COWAN DS, EGORIN MG: Limited penetration of anticancer drugs through tumor tissue: a potential cause of resistance of solid tumors to chemotherapy. Clin. Cancer Res. (2002) 8:878–884.
  • • Comment on the importance of the extravascular diffusion of drugs.
  • BROWN JM, GIACCIA AJ: The unique physiology of solid tumors: opportunities (and problems) for cancer therapy. Cancer Res. (1998) 58:1405–1416.
  • DENNY WA, WILSON WR, HAY MP: Recent developments in the design of bioreductive drugs. Br. .1 Cancer (1996) 74\(Supp1.27):32–38.
  • DENNY WA: Prodrug strategies in cancer therapy. Eur. I Med. Chem. (2001) 36:577–595.
  • • General review of prodrugs in cancer therapy, including hypoxia.
  • PRUIJN FB, STURMAN JR, LIYANAGE HDS, HICKS KO, HAY MP, WILSON WR: Extravascular transport of drugs in tumor tissue: effect of lipophilicity on diffusion of tirapazamine analogues in multicellular layer cultures. J. Med. Chem. (2005) 48:1079–1087.
  • • Describes an experimental model for the quantitative measurement of drug extravascular diffusion.
  • DENNY WA, WILSON WR: Considerations for the design of nitrophenyl mustards as drugs selectively toxic for hypoxic mammalian cells. ./. Med. Chem. (1986) 29:879–887.
  • PALMER BD, WILSON WR, PULLEN SM, DENNY WA: Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines. J. Med. Chem. (1990) 33:112–121.
  • MAUGER AB, BURKE PJ, SOMANI HH, FRIEDLOS F, KNOX RJ: Self-immolative prodrugs: candidates for antibody-directed enzyme prodrug therapy in conjunction with a nitroreductase enzyme. J. Med. Chem. (1994) 37:3452–3458.
  • TERCEL M, LEE AE, HOGG A et al.: Hypoxia-selective antitumor agents. 16. Nitroarylmethyl quaternary salts as bioreductive prodrugs of the alkylating agent mechlorethamine. I Med. Chem. (2001) 44:3511–3522.
  • PATTERSON LH: Rationale for the use of aliphatic N-oxides of cytotoxic anthraquinones as prodrug DNA binding agents: a new class of bioreductive agent. Cancer Met. Rev (1993) 12:119–134.
  • WARE DC, PALMER BD, WILSON WR, DENNY WA: Hypoxia-selective antitumor agents. 7. Metal complexes of aliphatic mustards are a new class of hypoxia-selective cytotoxins. Synthesis and evaluation of cobalt(III) complexes of bidentate mustards. J. Med. Chem. (1993) 36:1839–1846.
  • TOMASZ M, Y. PALOM Y: The mitomycin bioreductive antitumor agents: cross-linking and alkylation of DNA as the molecular basis of their activity. Pharmacol Ther. (1997) 76:73–87.
  • SEOW HA, PENKETH PG, BELCOURT ME TOMASZ M, ROCKWELL S, SARTORELLI AC: Nuclear overexpression of NAD(P)H:quinone oxidoreductase 1 in Chinese hamster ovary cells increases the cytotoxicity of mitomycin C under aerobic and hypoxic conditions. j. Biol. Chem. (2004) 279:31606–31612.
  • SARTORELLI AC: Therapeutic attack of hypoxic cells of solid tumors: presidential address. Cancer Res. (1988) 48:775–778.
  • HAFFTY BG, WILSON LD, SON YH et al.: Concurrent chemo-radiotherapy with mitomycin C compared with porfiromycin in squamous cell cancer of the head and neck: Final results of a randomized clinical trial. Int. Radiat. Oncol Biol. Phys. (2005) 61:119–128.
  • CUMMINGS J, SPANSWICK VJ, GARDINER J, RITCHIE A, SMYTH JF: Pharmacological and biochemical determinants of the antitumor activity of the indoloquinone E09. Biochem. Pharmacol (1998) 55:253–260.
  • WINSKI SL, SWANN E, HARGREAVES RH et al: Relationship between NAD(P)H:quinone oxidoreductase 1 (NQ01) levels in a series of stably transfected cell lines and susceptibility to antitumor quinones. Biochem. Pharmacol (2001) 61:1509–1516.
  • JAFFAR M, PHILLIPS RM, WILLIAMS KJ et al: 3-Substituted-5-aziridiny1-1-methylindole-4,7-diones as NQ01-directed antitumour agents: mechanism of activation and cytotoxicity in vitro. Biochem. Pharmacol (2003) 66:1199–1206.
  • PHILLIPS RM, JAFFAR M, MAITLAND DJ et al: Pharmacological and biological evaluation of a series of substituted 1,4-naphthoquinone bioreductive drugs. Biochem. Pharmacol (2004) 68:2107–2116.
  • BREIDER MA, PILCHER GD, GRAZIANO MJ, GOUGH AW: Retinal degeneration in rats induced by CI-1010, a 2-nitroimidazole radiosensitizer. Toxicol Patna (1988) 26:234–239.
  • DENNY WA, ROBERTS PB, ANDERSON RF, BROWN JM, WILSON WR: NLA-1: a 2-nitroimidazole radiosensitizer targeted to DNA by intercalation. Int. J. Radiat. Oncol Biol. Phys. (1992) 22:553–556.
  • PAPADOPOULOU MV, EPPERLY MW SHIELDS DS, BLOOMER WD: Radiosensitization and hypoxic cell toxicity of NLA-1 and NLA-2, two new bioreductive compounds. Jan. Cancer Res. (1992) 83:410–414.
  • PAPADOPOULOU MV, BLOOMER WD: NLCQ-1 (NSC 709257): Exploiting hypoxia with a weak DNA-intercalating bioreductive drug. Clin. Cancer Res. (2003) 9:5714–5720.
  • PALMER BD, WILSON WR, ANDERSON RF, BOYD M, DENNY WA: Hypoxia-selective antitumor agents. 14. Synthesis and hypoxic cell cytotoxicity of regioisomers of the hypmda-selective cytotmdn 5-I/V,Nbis(2-chloroethyl)amino1-2,4-dinitrobenzamide. I Med. Chem. (1996) 39:2518–2528.
  • WILSON WR, PULLEN SM, HOGG A, HELSBY NA, HICKS KO, DENNY WA: Quantitation of bystander effects in nitroreductase suicide gene therapy using three-dimensional cell cultures. Cancer Res. (2002) 62:1425–1432.
  • • Quantitation of bystander effects.
  • HELSBY NA, FERRY DM, PATTERSON AV, PULLEN SM, WILSON WR: 2-Amino metabolites are key mediators of CB 1954 and SN 23862 bystander effects in nitroreductase GDEPT. Br. J. Cancer (2004) 90:1084–1092.
  • BOGER DL, JOHNSON DS: CC-1065 and the duocarmycins: understanding their biological function through mechanistic studies. Angew Chem. Int. Ed. (1996) 35:1438–1474.
  • • Useful general review on the duocarmycin class of potent cytotoxins.
  • GIESEG MA, MATEJOVIC J, DENNY WA: Comparison of the patterns of DNA alkylation by phenol and amino seco-CBI-TMI compounds: use of a PCR method for the facile preparation of single end-labelled double stranded DNA. Anticancer Drug Des. (1999) 14:77–84.
  • HAY MP, ATWELL GJ, WILSON WR, PULLEN SM, DENNY WA: Structure-activity relationships for 4-nitrobenzyl carbamates of 5-aminobenz[e]indoline minor groove alkylating agents as prodrugs for gene therapy in conjunction with E. coil nitroreductase. I Med. Chem. (2003) 46:2456–2466.
  • ATWELL G.J, WILSON WR, DENNY WA: Synthesis and cytotoxicity of amino analogues of the potent DNA alkylating agent seco-CBI-TMI. Bioorg. Med. Chem. Lett. (1997) 7:1493–1496.
  • YANG S, DENNY WA: A new short synthesis of 3-substituted-1-(chloromethyll-2,3-dihydro-(1Ii-benzo [e] indo1-5-ylamines (amino-CBIs). I Org. Chem. (2002) 67:8958–8961.
  • HAY MP, SYKES BM, O'CONNOR CJ, DENNY WA: Substituent effects on the kinetics of reductively-initiated fragmentation of nitrobenzyl carbamates designed as triggers for bioreductive drugs. I Chem. Soc. Perkin Trans. /(1999) 2759–2770.
  • SHYAM K, PENKETH PG, SHAPIRO M, et al.: Hypoxia-selective nitrobenzyloxycarbonyl derivatives of 1,2-his(methylsulfonyll 1 (2 chloroethyl)hydrazines. I Med. Chem. (1999) 42:941–946.
  • MULCAHY RT, GIPP JJ, SCHMIDT JP, JOSWIG C, BORCH RT. Nitrobenzyl phosphoramidates as potential hypoxia-selective alkylating agents. J. Med. Chem. (1994) 37:1610–1615.
  • HAY MP, SYKES BM, DENNY WA et al: A 2-nitroimidazole carbamate prodrug of 5-amino-1-(chloromethyl)-3-1(5,6,7-trimethoxyindo1-2-yl)carbony11-1,2-dihydro-3H-benzlelindole (amino-sew-CBI-TMI) for use with ADEPT and GDEPT. Bioorg. Med. Chem. Lett. (1999) 15:2237–2242.
  • TERCEL M, WILSON WR, ANDERSON RF, DENNY WA: Hypoxia-selective antitumor agents. 12. Nitrobenzyl quaternary salts as bioreductive prodrugs of the alkylating agent mechlorethamine. I Med. Chem. (1996) 39:1084–1094.
  • WILSON WR, FERRY DM, TERCEL M, ANDERSON RF, DENNY WA: Reduction of nitroarylmethyl quaternary ammonium prodrugs of mechlorethamine by radiation. Radiat. Res. (1998) 149:237–245.
  • WILSON WR, DENNY WA, PULLEN SM, et al: Tertiary amine N-oxides as bioreductive drugs: DACA N-oxide, nitracrine Noxide and AQ4N. Br. J. Cancer (1996) 74 (Supp1.27):43–47.
  • PATTERSON, LH: Bioreductively activated antitumor Noxides: the case of AQ4N, a unique approach to hypoxia-activated cancer chemotherapy. Drug Met. Rev (2002) 34:581–592.
  • PATTERSON LH, MCKEOWN SR, RUPARELIA K, et al: Enhancement of chemotherapy and radiotherapy of murine tumors by AQ4N, a bioreductively activated anti-tumor agent. BE I Cancer (2000) 82: 1984-1990.
  • GALLAGHER R, HUGHES CM, MURRAY MM et al: The chemopotentiation of cisplatin by the novel bioreductive drug AQ4N. BE Cancer (2001) 85:625–629.
  • McCARTHY HO, YAKKUNDI A, McERLANE et al: Bioreductive GDEPT using cytochrome P450 3A4 in combination with AQ4N. Cancer Gene Ther. (2003) 10:40–48.
  • WELSH S, WILLIAMS R, KIRKPATRICK L, PAINE-MURRIETA G, POWIS G: Antitumor activity and pharmacodynamic properties of PX-478, an inhibitor of hypoxia-inducible factor-1a. Mol. Cancer Ther. (2004) 3:233–244.
  • RISCHIN D, PETERS L, FISHER R et al: Tirapazamine, cisplatin, and radiation versus fluorouracil, cisplatin, and radiation in patients with locally advanced head and neck cancer: a randomized Phase II trial of the Trans-Tasman Radiation Oncology Group (TROG 98.02). I Clin. Oncol (2005) 23:79–87.
  • •• Data on the most advanced trial oftirapazamine with radiation.
  • VON PAWEL J, VON ROEMELING R, GATZEMEIER U et al: Tirapazamine plus cisplatin versus cisplatin in advanced non-small-cell lung cancer: A report of the international CATAPULT I study group. Clin. Oncol (2000) 18:1351–1359.
  • • Detailed review of clinical data, concluding that tirapazamine significantly enhances the activity of cisplatin in non-small-cell lung cancer.
  • PATTERSON AV, SAUNDERS MP, CHINJE EC, PATTERSON LH, STRATFORD IJ: Enzymology of tirapazamine metabolism: a review. Anticancer Drug Des. (1998) 13:541–573.
  • ANDERSON RF, SHINDE SS, HAY MP, GAMAGE SA, DENNY WA: Activation of 3-amino-1,2,4-benzotriazine 1,4-dioxide antitumor agents to oxidizing species following their one-electron reduction. Am. Chem. Soc. (2003) 125:748–756.
  • •• An important advance in the understanding of the mechanism of action of tirapazamine.
  • SHINDE S, ANDERSON RF, HAY MP, GAMAGE SA, DENNY WA: Oxidation of 2-deoxyribose by benzotriazinyl radicals of antitumor 3-aminobenzotriazine 1,4-dioxides. J. Am. Chem. Soc. (2004) 126:7865–7874.
  • HWANG JT, GREENBERG MM, FUCHS T, GATES KS: Reaction of the hypoxia-selective antitumor agent tirapazamine with a C r-radical in single-stranded and double-stranded DNA: The drug and its metabolites can serve as surrogates for molecular oxygen in radical-mediated DNA damage reactions. Biochemistry (1999) 38:14248–14255.
  • KOCH CJ: Unusual concentration dependence of toxicity of SR-4233, a hypoxic cell toxin. Cancer Res. (1993) 53:3992–3997.
  • HICKS KO, PRUIJN FB, STURMAN JR, DENNY WA, WILSON WR: Multicellular resistance to tirapazamine is due to restricted extravascular transport: a pharmacokinetic/pharmacodynamic study using multicellular layer cultures. Cancer Res. (2003) 63:5970–5977.
  • HAY MP, DENNY WA: New and versatile syntheses of 3-alky1-1,2,4-benzotriazine-1,4-dioxides: preparation of the bioreductive cytotoxins 5R4895 and 5R4941. TeL Lett. (2002) 43:9569–9571.
  • HAY MP, GAMAGE SA, KOVACS MS et al.: Structure-activity relationships of 1,2,4-benzotriazine 1,4-dioxides as hypoxia-selective analogues of tirapazamine. J. Med. Chem. (2003), 46:169–182.
  • DELAHOUSSAYE YM, HAY MP, PRUIJN FB, DENNY WA, BROWN JM: Improved potency of the hypoxic cytotoxin tirapazamine by DNA-targeting. Biochem. Pharmacol (2003) 65:1807–1815.
  • HAY MP, PRUIJN FB, GAMAGE SA et al: DNA-targeted 1,2,4-benzotriazine 1,4-dioxides: potent analogues of the hypoxia-selective cytotoxin tirapazamine. J. Med. Chem. (2004) 47:475–488.
  • SIIM BG, PRUIJN FB, STURMAN JR et al.: Selective potentiation of the hypoxic cytotoxicity of tirapazamine by its 1-Noxide metabolite SR 4317. Cancer Res. (2004) 64:736–742.
  • SIMIC M, LILIE J: Kinetics of ammonia detachment from reduced cobalt(III) complexes based on conductometric pulse radiolysis. J. Am. Chem. Soc. (1974) 96:291–292.
  • ANDERSON RE DENNY WA, WARE DC, WILSON WR: Pulse radiolysis studies on the mechanism of hypoxia-selective cytotoxicity of the cobalt(III)-nitrogen mustard complex SN 24771. Br. J. Cancer (1996) 74\(Supp1.27):48–51.
  • PARKER LL, LACY SM, FARRUGIA LJ et al: A novel design strategy for stable metal complexes of nitrogen mustards as bioreductive prodrugs. J. Med. Chem. (2004) 47:5683–5689.
  • AHN G-0, WARE DC, DENNY WA, WILSON WR: Optimization of the auxiliary ligand shell of cobalt(III) (8-hydroxyquinoline) complexes as model hypoxia-selective radiation-activated prodrugs. Radiat. Res. (2004) 162:315–325.
  • WILSON WR, TERCEL M, ANDERSON RE DENNY WA: Radiation-activated prodrugs as hypoxia-selective cytotoxins: model studies with nitroarylmethyl quaternary salts. Anticancer Drug Des. (1998) 13:663–685.
  • SHIBAMOTO Y, SUGIE C, ITO M, OGINO H: The Japanese experiences with hypoxia-targeting pharmacoradiotherapy from hypoxic cell sensitizers to radiation-activated prodrugs. Expert Opin. Pharmacother. (2004) 5:2459–2467.
  • SHIBAMOTO Y, ZHOU L, HATTA H, MORI M, NISHMOTO S: In vivo evaluation of a novel antitumor prodrug, 1-(2'-oxopropy0-5-fluorouracil (OFU001), which releases 5-fluorouracil upon hypoxic irradiation. Int. I Radiat. Oncol Biol. Phys. (2001) 49:407–413.
  • HEPPNER F, MOSE JR: The liquefaction(oncolysis) of malignant gliomas by a non pathogenic Clostridium. Acta Neurochir. (1978) 42:123–125.
  • FOX ME. LEMMON MJ, MAUCHLINE ML et al: Anaerobic bacteria as a delivery system for cancer gene therapy: in vitro activation of 5-fluorocytosine by genetically engineered Clostridia. Gene Ther. (1996) 3:173–178.
  • LEMMON MJ, VAN ZIJL P, FOX ME et al: Anaerobic bacteria as a gene delivery system that is controlled by the tumor microenvironment. Gene Ther. (1997) 4:791–796.
  • LIU SC, MINTON NP, GIACCIA AJ, BROWN JM: Anticancer efficacy of systemically delivered anaerobic bacteria as gene therapy vectors targeting tumor hypoxia/necrosis. Gene Ther. (2002) 9:291–296.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.