Targeting and treatment of tumor hypoxia by newly designed prodrug possessing high permeability in solid tumors

Molecular Pharmaceutics

Volumn 13, Issue 7, 2016, Pages 2283-2289

  Ikeda, Yutaka ^a   Hisano, Hikaru ^a   Nishikawa, Yuji ^b   Nagasaki, Yukio ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b ASAHIKAWA MEDICAL COLLEGE   (Japan)

Author keywords

drug penetration; prodrug; solid tumor; tumor hypoxia

Indexed keywords

DOXORUBICIN; GEMCITABINE; ANTINEOPLASTIC AGENT; NITROIMIDAZOLE DERIVATIVE; PRODRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG DISTRIBUTION; DRUG RELEASE; DRUG SELECTIVITY; HUMAN; HUMAN CELL; HYPOXIA; IMMUNOFLUORESCENCE; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; SOLID TUMOR; SURVIVAL RATE; ANIMAL; BAGG ALBINO MOUSE; DRUG EFFECTS; NEOPLASMS; PERMEABILITY; TUMOR CELL LINE; TUMOR HYPOXIA;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; HUMANS; MALE; MICE; MICE, INBRED BALB C; NEOPLASMS; NITROIMIDAZOLES; PERMEABILITY; PRODRUGS; TUMOR HYPOXIA;

EID: 84979018810     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/acs.molpharmaceut.6b00011     Document Type: Article

References (23)

1. Al-Abd, A. M.; Aljehani, Z. K.; Gazzaz, R. W.; Fakhri, S. H.; Jabbad, A. H.; Alahdal, A. M.; Torchilin, V. P. Pharmacokinetic strategies to improve drug penetration and entrapment within solid tumors J. Controlled Release 2015, 219, 269-277 10.1016/j.jconrel.2015.08.055
2. Vaupel, P.; Mayer, A. Hypoxia in cancer: significance and impact on clinical outcome Cancer Metastasis Rev. 2007, 26, 225-239 10.1007/s10555-007-9055-1
3. Wilson, W. R.; Hay, M. P. Targeting hypoxia in cancer therapy Nat. Rev. Cancer 2011, 11, 393-410 10.1038/nrc3064
4. Minchinton, A. I.; Tannock, I. F. Drug penetration in solid tumours Nat. Rev. Cancer 2006, 6, 583-592 10.1038/nrc1893
5. Ruoslahti, E.; Bhatia, S. N.; Sailor, M. J. Targeting of drugs and nanoparticles to tumors J. Cell Biol. 2010, 188, 759-768 10.1083/jcb.200910104
6. Chen, Y.; Hu, L. Design of anticancer prodrugs for reductive activation Med. Res. Rev. 2009, 29, 29-64 10.1002/med.20137
7. Ljungkvist, A. S.; Bussink, J.; Kaanders, J. H.; van der Kogel, A. J. Dynamics of tumor hypoxia measured with bioreductive hypoxic cell markers Radiat. Res. 2007, 167, 127-145 10.1667/RR0719.1
8. Varia, M. A.; Calkins-Adams, D. P.; Rinker, L. H.; Kennedy, A. S.; Novotny, D. B.; Fowler, W. C., Jr; Raleigh, J. A. Pimonidazole: a novel hypoxia marker for complementary study of tumor hypoxia and cell proliferation in cervical carcinoma Gynecol. Oncol. 1998, 71, 270-277 10.1006/gyno.1998.5163
9. Hay, M. P.; Denny, W. A.; Wilson, W. R. Nitroimidazole-based ″extruded mustards' designed as reductively activated hypoxia-selective cytotoxins Anti-Cancer Drug Des. 1996, 11, 383-402
10. Hay, M. P.; Wilson, W. R.; Denny, W. A. Nitroarylmethylcarbamate prodrugs of doxorubicin for use with nitroreductase gene-directed enzyme prodrug therapy Bioorg. Med. Chem. 2005, 13, 4043-4055 10.1016/j.bmc.2005.03.055
11. Yoshitomi, T.; Ozaki, Y.; Thangavel, S.; Nagasaki, Y. Redox nanoparticle therapeutics to cancer-increase in therapeutic effect of doxorubicin, suppressing its adverse effect J. Controlled Release 2013, 172, 137-143 10.1016/j.jconrel.2013.08.011
12. Weiss, J. T.; Dawson, J. C.; Fraser, C.; Rybski, W.; Torres-Sánchez, C.; Bradley, M.; Patton, E. E.; Carragher, N. O.; Unciti-Broceta, A. Development and Bioorthogonal Activation of Palladium-Labile Prodrugs of Gemcitabine J. Med. Chem. 2014, 57, 5395-5404 10.1021/jm500531z
13. Grantab, R.; Sivananthan, S.; Tannock, I. F. The penetration of anticancer drugs through tumor tissue as a function of cellular adhesion and packing density of tumor cells Cancer Res. 2006, 66, 1033-1039 10.1158/0008-5472.CAN-05-3077
14. Primeau, A. J.; Rendon, A.; Hedley, D.; Lilge, L.; Tannock, I. F. The distribution of the anticancer drug doxorubicin in relation to blood vessels in solid tumors Clin. Cancer Res. 2005, 11, 8782-8788 10.1158/1078-0432.CCR-05-1664
15. Maeda, H.; Wu, H. J.; Sawa, T.; Matsumura, Y.; Hori, K. Tumor vascular permeability and the EPR effect in macromolecular therapeutics J. Controlled Release 2000, 65, 271-284 10.1016/S0168-3659(99)00248-5
16. Cabral, H.; Matsumoto, Y.; Mizuno, K.; Chen, Q.; Murakami, M.; Kimura, M.; Terada, Y.; Kano, M. R.; Miyazono, K.; Uesaka, M.; Nishiyama, N.; Kataoka, K. Accumulation of sub-100 nm polymeric micelles in poorly permeable tumours depends on size Nat. Nanotechnol. 2011, 6, 815-823 10.1038/nnano.2011.166
17. Denny, W. A.; Wilson, W. R. Bioreducible mustards: a paradigm for hypoxia- selective prodrugs of diffusible cytotoxins (HPDCs) Cancer Metastasis Rev. 1993, 12, 135-151 10.1007/BF00689806
18. Duan, J. X.; Jiao, H.; Kaizerman, J.; Stanton, T.; Evans, J. W.; Lan, L.; Lorente, G.; Banica, M.; Jung, D.; Wang, J.; Ma, H.; Li, X.; Yang, Z.; Hoffman, R. M.; Ammons, W. S.; Hart, C. P.; Matteucci, M. Potent and highly selective hypoxia-activated achiral phosphoramidate mustards as anticancer drugs. J J. Med. Chem. 2008, 51, 2412-2420 10.1021/jm701028q
19. Everett, S. A.; Naylor, M. A.; Patel, K. B.; Stratford, M. R.; Wardman, P. Bioreductively-activated prodrugs for targeting hypoxic tissues: elimination of aspirin from 2-nitroimidazole derivatives Bioorg. Med. Chem. Lett. 1999, 9, 1267-1272 10.1016/S0960-894X(99)00171-7
20. Hicks, K. O.; Pruijn, F. B.; Sturman, J. R.; Denny, W. A.; Wilson, W. R. Multicellular resistance to tirapazamine is due to restricted extravascular transport: a pharmacokinetic/ pharmacodynamic study in HT29 multicellular layer cultures Cancer Res. 2003, 63, 5970-5977
21. Sutherland, R. M.; Eddy, H. A.; Bareham, B.; Reich, K.; Vanantwerp, D. Resistance to Adriamycin inmulticellular spheroids Int. J. Radiat. Oncol., Biol., Phys. 1979, 5, 1225-1230 10.1016/0360-3016(79)90643-6
22. Tannock, I. F.; Lee, C. M.; Tunggal, J. K.; Cowan, D. S.; Egorin, M. J. 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
23. Pruijn, F. B.; Sturman, J. R.; Liyanage, H. D.; Hicks, K. O.; Hay, M. P.; Wilson, W. R. 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 10.1021/jm049549p