Cellular Redox Modulator, ortho Mn(III) meso-tetrakis(N-n-Hexylpyridinium-2- yl)porphyrin, MnTnHex-2-PyP5+ in the Treatment of Brain Tumors

Anti-Cancer Agents in Medicinal Chemistry

Volumn 11, Issue 2, 2011, Pages 202-212

  Keir, Stephen T ^a,b   Dewhirst, Mark W ^c   Kirkpatrick, John P ^c   Bigner, Darell D ^a,b   Batinic Haberle, Ines ^c  

^a DUKE CANCER INSTITUTE   (United States)

^b DUKE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

Brain tumors; Glioma; Novel anticancer therapeutic strategy; Peroxynitrite scavenger; Porphyrins; SOD mimic

Indexed keywords

ANTINEOPLASTIC AGENT; MANGANESE SUPEROXIDE DISMUTASE; MANGANESE TETRAKIS(N HEXYLPYRIDINIUM 2 YL)PORPHYRIN; METAL COMPLEX; PEROXYNITRITE; PORPHYRIN DERIVATIVE; PYRIDINIUM DERIVATIVE; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN METABOLITE; SCAVENGER; SUPEROXIDE; SUPEROXIDE DISMUTASE; TRANSCRIPTION FACTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BLOOD BRAIN BARRIER; CANCER INHIBITION; CANCER SURVIVAL; CENTRAL NERVOUS SYSTEM; CONTROLLED STUDY; CYTOSOL; FEMALE; GLIOBLASTOMA; GLIOMA; IMMUNE RESPONSE; INFLAMMATION; LIPOPHILICITY; MEDULLOBLASTOMA; MITOCHONDRION; MOUSE; NONHUMAN; OXIDATION REDUCTION REACTION; PROTEIN EXPRESSION; TUMOR MODEL; TUMOR XENOGRAFT;

EID: 79953791901     PISSN: 18715206     EISSN: None     Source Type: Journal    
DOI: 10.2174/187152011795255957     Document Type: Article

References (106)

1. Wen, P. Y.; Kesari S. Malignant gliomas in adults. N. Engl. J. Med., 2008, 359, 492-507.
2. Stupp, R.; Mason, W. P.; van den Bent, M. J.; Weller, M.; Fisher, B.; Taphoorn, M. J.; Belanger, K.; Brandes, A. A.; Marosi, C.; Bogdahn, U.; Curschmann, J.; Janzer, R. C.; Ludwin, S. K.; Gorlia, T.; Allgeier, A.; Lacombe, D.; Cairncross, J. G.; Eisenhauer, E.; Mirimanoff, R. O. Radiotherapy plus concomitant and adjuvant temozolomide for glioblastoma. N. Engl. J. Med., 2005. 352, 987-996.
3. Lamborn, K. R.; Yung, W. K.; Chang, S. M.; Wen, P. Y.; Cloughesy, T. F.; DeAngelis, L. M.; Robins, H. I.; Lieberman, F. S.; Fine, H. A.; Fink, K. L.; Junck, L.; Abrey, L.; Gilbert, M. R.; Mehta, M.; Kuhn, J. G.; Aldape, K. D.; Hibberts, J.; Peterson, P. M.; Prados, M. D. Progression-free survival: an important end point in evaluating therapy for recurrent high-grade gliomas. Neuro Oncol., 2008, 10, 162-170.
4. Wong, E. T.; Hess, K. R.; Gleason, M. J.; Jaeckle, K. A.; Kyritsis, A. P.; Prados, M. D.; Levin, V. A.; Yung, W. K. Outcomes and prognostic factors in recurrent glioma patients enrolled onto phase II clinical trials. J. Clin. Oncol., 1999, 17, 2572-2578.
5. Grill, J.; Kieffer, V.; Kalifa, C. Measuring the neuro-cognitive sideeffects of irradiation in children with brain tumors. Pediatr. Blood Cancer., 2004, 42, 452-456.
6. Onvani, S.; Etame, A. B.; Smith, C. A.; Rutka, J. T. Genetics of medulloblastoma: clues for novel therapies. Expert Rev. Neurother., 2010, 10, 811-823.
7. Dougherty, T. J.; Gomer, C. J.; Henderson, B. W.; Jori, G.; Kessel, D.; Korbelik, M.; Moan, J.; Peng, Q. Photodynamic therapy. J. Natl. Cancer Inst., 1998, 90, 889-905.
8. Nakajima, S.; Hayashi, H.; Omote, Y.; Yamazaki, Y.; Hirata, S.; Maeda, T.; Kubo, Y.; Takemura, T.; Kakiuchi, Y.; Shindo, Y.; et al. The tumour-localizing properties of porphyrin derivatives. J. Photochem. Photobiol. B., 1990, 7, 189-198.
9. Nakajima, S.; Sakata, I.; Omote, Y.; Yamazaki, K.; Maeda, T.; Kubo, Y.; Samejima, N.; Takemura, T.; Shindo, Y.; Yamauchi, H.; et al. Detection and quantitative estimation of metalloporphyrins in vivo. J. Photochem. Photobiol. B., 1991, 8, 409-417.
10. 111 In-labeled Mn-metalloporphyrin for tumor imaging. Nucl. Med. Biol., 1993, 20, 231-237.
11. Nakajima, S.; Shigemi, N.; Murakami, N.; Aburano, T.; Sakata, I.; Maruyama, I.; Inoue, M.; Takemura, T. Therapeutic and imaging capacity of tumor-localizing radiosensitive Mn-porphyrin on SCCVII tumor-bearing C3H/He mice. Anticancer Drugs, 1997, 8, 386-390.
12. Nakajima, S.; Sakata, I.; Hirano, T.; Takemura, T. Therapeutic effect of interstitial photodynamic therapy using ATX-S10(Na) and a diode laser on radio-resistant SCCVII tumors of C3H/He mice. Anticancer Drugs, 1998, 9, 539-543.
13. Nakajima, S.; Fujii, T.; Murakami, N.; Aburano, T.; Sakata, I.; Nakae, Y.; Takemura, T. Therapeutic and imaging capacity of tumor-localizing radiosensitive Mn-porphyrin KADT-F10 for SCCVII tumors in C3H /He mice. Cancer Lett., 2002, 181, 173-178.
14. Benov, L.; Craik, J.; Batinic-Haberle, I. Protein damage by photoactivated Zn(II) N-alkylpyridylporphyrins. Amino Acids, 2010.
15. Arambula, J. F.; Preihs, C.; Brothwick, D.; Magda, D.; Jonathan L. Sessler, J. L. Texaphyrins: Tumor Localizing Redox Active Expanded Porphyrins. Submitted to Anticancer Agents Med. Chem.
16. Batinic-Haberle, I.; Reboucas, J. S.; Spasojevic, I. Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential. Antioxid. Redox Signal., 2010.
17. Batinic-Haberle, I.; Reboucas, J. S.; Benov, L.; Spasojevic, I. Chemistry, biology and medical effects of water-soluble metalloporphyrins, in Handbook of Porphyrin Science, K. M. Kadish, K. M. Smith, R. Guilard, Eds. World Scientific, 2010, Vol 11, (in press).
18. Batinic-Haberle, I.; Spasojevic, I.; Tse, H. M.; Tovmasyan, A.; Rajic, Z.; St. Clair D. K.; Vujaskovic, Z.; Dewhirst, M. W.; Piganelli, J. D. Design of Mn porhyrins for treating oxidative stress injuries and their redox-based regulation of cellular transcriptional activities. Amino Acids, 2010, doi: 10.1007/s726-010-0603-06.
19. Rabbani, Z. N.; Salahuddin, F. K.; Yarmolenko, P.; Batinic-Haberle, I.; Thrasher, B. A.; Gauter-Fleckenstein, B.; Dewhirst, M. W.; Anscher, M. S.; Vujaskovic, Z. Low molecular weight catalytic metalloporphyrin antioxidant AEOL 10150 protects lungs from fractionated radiation. Free Radic. Res., 2007, 41, 1273-1282.
20. Gauter-Fleckenstein, B.; Fleckenstein, K.; Owzar, K.; Jiang, C.; Batinic-Haberle, I.; Vujaskovic, Z. Comparison of two Mn porphyrin-based mimics of superoxide dismutase in pulmonary radioprotection. Free Radic. Biol. Med., 2008, 44, 982-989.
21. 5+, via suppression of oxidative stress in a mouse model of breast tumor. Free Radic. Biol. Med. 2009, 47, 992-1004.
22. Moeller, B. J.; Batinic-Haberle, I.; Spasojevic, I.; Rabbani, Z. N.; Anscher, M. S.; Vujaskovic, Z.; Dewhirst, M. W. A manganese porphyrin superoxide dismutase mimetic enhances tumor radioresponsiveness. Int. J. Radiat. Oncol. Biol. Phys. 2005, 63, 545-552.
23. Moeller, B. J.; Cao, Y.; Li, C. Y.; Dewhirst, M. W. Radiation activates HIF-1 to regulate vascular radiosensitivity in tumors: role of oxygenation, free radicals and stress granules. Cancer Cell, 2004, 5, 429-441.
24. Zhao, Y.; Chaiswing, L.; Oberley, T. D.; Batinic-Haberle, I.; St. Clair, W.; Epstein, C. J.; St, Clair, D. A mechanism-based antioxidant approach for the reduction of skin carcinogenesis. Cancer Res., 2005, 65, 1401-1405.
25. Jaramillo, M. C.; Frye, J. B.; Crapo, J. D.; Briehl, M. M.; Tome, M. E. Increased manganese superoxide dismutase expression or treatment with manganese porphyrin potentiates dexamethasoneinduced apoptosis in lymphoma cells. Cancer Res., 2009, 69, 5450-5457.
26. Jaramillo, M. C.; Briehl, M. M.; Tome, M. E. Manganese porphyrin glutathionylates the p65 subunit of NF-κB to potentiate glucocorticoid-induced apoptosis in lymphoma. Free Radic. Biol. Med., 2010, 49, S63.
27. Makinde, A. Y.; Luo-Owen, X.; Rizvi, A.; Crapo, J. D.; Pearlstein, R. D.; Slater, J. M.; Gridley, D. S. Effect of a metalloporphyrin antioxidant (MnTE-2-PyP) on the response of a mouse prostate cancer model to radiation. Anticancer Res., 2009, 29, 107-118.
28. Kos, I.; Rebouças, J. S.; DeFreitas-Silva, G.; Salvemini, D.; Vujaskovic, Z.; Dewhirst, M. W.; Spasojevic, I.; Batinic-Haberle, I. The effect of lipophilicity of porphyrin-based antioxidants. Comparison of ortho and meta isomers of Mn(III) N-alkylpyridylporphyrins. Free Radic. Biol. Med., 2009, 47, 72-78.
29. Sheng, H.; Tse, H.M.; Jung, J.Y.; Zhang, Z.; Spasojevic, I.; Piganelli, J.D.; Batinic-Haberle, I.; Warner, D. Neuroprotective efficacy from a lipophilic redox-modulating Mn porphyrin: rodent models of ischemic stroke and subarachnoid hemorrhage. J. Pharmacol. Exp. Ther., 2011, (under revision).
30. Doyle, T.; Bryant, L.; Batinic-Haberle, I.; Little, J.; Cuzzocrea, S.; Masini, E.; Spasojevic, I.; Salvemini, D. Supraspinal inactivation of mitochondrial superoxide dismutase is a source of peroxynitrite in the development of morphine antinociceptive tolerance. Neuroscience, 2009, 164, 702-710.
31. Spasojevic, I.; Kos, I.; Benov, L. T.; Rajic, Z.; Fels, D.; Dedeugd, C.; Ye, X.; Vujaskovic, Z.; Reboucas, J. S.; Leong, K. W.; Dewhirst, M. W.; Batinic-Haberle, I. Bioavailability of metalloporphyrin-based SOD mimics is greatly influenced by a single charge residing on a Mn site, Free Radic. Res. 2010, 45, 188-200.
32. Pollard, J. M.; Rebouças, J. S.; Durazo, A.; Kos, I.; Fike, F.; Panni, M.; Gralla, E. B.; Valentine, J. S.; Batinic-Haberle, I.; Gatti, R. A. Radioprotective effects of manganese-containing superoxide dismutase mimics on ataxia telangiectasia cells. Free Radic. Biol. Med., 2009, 47, 250-260.
33. Yu, L.; Drobyshevsky, A.; Derricka, M.; Luo, T.; Batinic-Haberle, I.; Tan, S. Efferct of Mn porphyrins and antioxidants on MRI predictors and behavior in an animal model of cerebral palsy. Free Radic. Biol. Med., 2010, 49, S159.
34. Murphy, M. P.; Smith, R. A. J. Targeting antioxidants to mitochondria by conjugation to lipophilic cations. Annu. Rev. Pharmacol. Toxicol., 2007, 47, 629-656.
35. Murphy, M. P. Targeting lipophilic cations to mitochondria. Biochim. Biophys. Acta, 2008, 177, 1028-1031.
36. Spasojevic, I.; Li, A. M.; Tovmasyan, A.; Rajic, Z.; Salvemini, D.; St. Clair, D.; Valentine, J. S.; Vujaskovic, Z.; Gralla, E. B.; Batinic-Haberle, I. Accumulation of porphyrin-based SOD mimics in mitochondria is proportional to their lipophilicity. S. cerevisiae study of ortho Mn(III) N-alkylpyridylporphyrins. Free Radic. Biol. Med., 2010, 49, S199.
37. 5+ targets mouse heart mitochondria. Free Radic. Biol. Med., 2007, 42, 1193-1200.
38. Miriyala, S.; Holley, A. K.; St Clair, D. K. MnSOD-Signals of distinction (SOD). Submitted to Anticancer Agents Med. Chem.
39. Friedman, H. S.; Colvin, O. M.; Skapek, S. X.; Ludeman, S. M.; Elion, G. B.; Schold, S. C. Jr.; Jacobsen, P. F.; Muhlbaier, L. H.; Bigner, D. D. Experimental chemotherapy of human medulloblastoma cell lines and transplantable xenografts with bifunctional alkylating agents. Cancer Res., 1988, 48, 4189-4195.
40. Sathornsumetee, S.; Hjelmeland, A. B.; Keir, S. T.; McLendon, R. E.; Batt, D.; Ramsey, T.; Yusuff, N.; Rasheed, B. K.; Kieran, M. W.; Laforme, A.; Bigner, D. D.; Friedman, H. S.; Rich, J. N. AAL881, a novel small molecule inhibitor of RAF and vascular endothelial growth factor receptor activities, blocks the growth of malignant glioma. Cancer Res., 2006, 66, 8722-8730.
41. Gamez, I.; Ryan, R. P.; Keir, S. T. Corticorelin Acetate, a Synthetic Corticotropin-releasing Factor with Preclinical Antitumor Activity, alone and with Bevacizumab, against Human Brain Tumor Models. Anticancer Res., 2010, 30, 5037-5042.
42. Friedman, H. S.; Schold, S. C. Jr.; Bigner, D. D. Chemotherapy of Subcutaneous and Intracranial Human Medulloblastoma Xenografts in Athymic Nude Mice. Cancer Res., 1986, 46, 224-228.
43. Pollack, I. F.; Bredel, M.; Erff, M.; Hamilton, A. D.; Sebti, S. M. Inhibition of Ras and related guanosine triphosphate-dependent proteins as a therapeutic strategy for blocking malignant glioma growth: II--preclinical studies in a nude mouse model. Neurosurgery, 1999, 45, 1208-14; discussion 1214-1215.
44. Gehan, E. A. A Generalized Wilcoxon Test for Comparing Arbitrarily Singly-Censored Samples. Biometrika, 1965, 52, 203-223.
45. Liou, G. Y.; Storz, P. Reactive oxygen species in cancer. Free Radic. Res., 2010, 44, 479-496.
46. Storz, P. Reactive oxygen species in tumor progression. Front Biosci., 2005, 10, 1881-1896.
47. Halliwell, B.; Gutteridge, J. Free radicals in biology and medicine. 4th edition ed. 2007, New York: Oxford Press.
48. Ridnour, L. A.; Oberley, T. D.; Oberley, L. W. Tumor suppressive effects of MnSOD overexpression may involve imbalance in peroxide generation versus peroxide removal. Antioxid. Redox Signal., 2004, 6, 501-512.
49. Hernandez-Garcia, D.; Wood, C. D.; Castro-Obregon, S.; Covarrubias, L. Reactive oxygen species: a radical role in development? Free Radic. Biol. Med., 2010, 49, 130-143.
50. Chan, S. C.; Hui, L.; Chen, H. M. Enhancement of the cytolytic effect of anti-bacterial peptide cecropin by the microvilli of cancer cells. Anticancer Res., 1998, 18, 4467-4474.
51. Zwaal, R. F.; Schroit, A. J. Pathophysiologic implications of membrane phospholipid asymmetry in blood cells. Blood, 1997, 89, 1121-1132.
52. Hoskin, D. W.; Ramamoorthy, A. Studies on anticancer activities of antimicrobial peptides. Biochim. Biophys. Acta, 2008, 1778, 357-375.
53. Schweizer, F. Cationic amphiphilic peptides with cancer-selective toxicity. Eur. J. Pharmacol., 2009, 625, 190-194.
54. Kornguth, S. E.; Kalianke, T.; Robins, H. I.; Cohen, J. D.; Turski, P. Preferential binding of radiolabeled poly-L-lysine to C6 and U87 MG glioblastomas compared to endothelial cells in vitro. Cancer Res., 1989, 49, 6390-6395.
55. Jensen, T. J.; Vicente, M. G. H.; Luguya, R.; Norton, J.; Fronczek, F. R.; Smith, K. M. Effect of overall charge and charge distribution on cellular uptake, distribution and phototoxicity of cationic porphyrins in Hep2 cells. J. Photochem. Photobiol. B: Biol., 2010, 100, 100-111.
56. Merchant, T. E.; Pollack, I. F.; Loeffler, J. S. Brain tumors across the age spectrum: biology, therapy, and late effects. Semin. Radiat. Oncol., 2010, 20, 58-66.
57. Padovani, L.; André, N.; Carrie, C.; Muracciole, X. Childhood and adult medulloblastoma: what difference? Cancer Radiother., 2009, 13, 530-535.
58. Prados, M. D.; Russo, C. Chemotherapy of brain tumors. Semin. Surg. Oncol., 1998, 14, 88-95.
59. Karajannis, M.; Allen, J. C.; Newcomb, E. W. Treatment of pediatric brain tumors. J. Cell Physiol., 2008, 217, 584-589.
60. Fan, Q. W.; Weiss, W. A. Targeting the RTK-PI3K-mTOR axis in malignant glioma: overcoming resistance. Curr. Top. Microbiol. Immunol., 2010, 347, 279-296.
61. Quant, E. C.; Wen, P. Y. Novel medical therapeutics in glioblastomas, including targeted molecular therapies, current and future clinical trials. Neuroimaging Clin. N. Am., 2010, 20, 425-448.
62. Gogvadze, V.; Orrenius, S.; Zhivotovsky, B. Mitochondria as targets for chemotherapy. Apoptosis, 2009, 14, 624-640.
63. Kanu, O. O.; Mehta, A.; Di, C.; Lin, N.; Bortoff, K.; Bigner, D. D.; Yan, H.; Adamson, D. C. Glioblastoma multiforme: a review of therapeutic targets Expert Opin. Ther. Targets, 2009, 13, 701-718.
64. 5+ in mitigation and treatment of radiation-induced lung damage. Free Radic. Biol. Med., 2010, 48, 1034-1043.
65. 5+) mitigates total body irradiation-induced long-term bone marrow suppression. Free. Radic. Biol. Med., 2010, (under revision).
66. Pearlstein, R. D.; Higuchi, Y.; Moldovan, M.; Johnson, K.; Fukuda, S.; Gridley, D. S.; Crapo, J. D.; Warner, D. S.; Slater, J. M. Metalloporphyrin antioxidants ameliorate normal tissue radiation damage in rat brain. Int. J. Radiat. Biol., 2010, 86, 145-163.
67. Makinde, A. Y.; Rizvi, A.; Crapo, J. D.; Pearlstein, R. D.; Slater, J. M.; Gridley, D. S. A metalloporphyrin antioxidant alters cytokine responses after irradiation in a prostate tumor model. Radiat. Res., 2010, 173, 441-452.
68. Pazhanisamy, S. K.; Li, H; Batinic-Haberle, I.; Zhou, D. NADPH oxidase inhibition attenuates total body-irrradiation-induced hematopoietic genomic instability, Mutagenesis, 2010, (in press).
69. Mao, X. W.; Crapo, J. D.; Mekonnen, T.; Lindsey, N.; Martinez, P.; Gridley, D. S.; Slater, J. M. Radioprotective effect of a metalloporphyrin compound in rat eye model. Curr. Eye Res., 2009, 34, 62-72.
70. Lee, J. H., Park, J. W. A manganese porphyrin complex is a novel radiation protector. Free Radic. Biol. Med., 2004, 37, 272-283.
71. Nebert, D. W.; Mason, H. S. An Electron Spin Resonance Study of Neoplasms. Cancer Res., 1963, 23, 833-840.
72. Reuter, S.; Gupta, S. C.; Chaturvedi, M. M.; Aggrawal, B. B. Oxidative stress, inflammation, and cancer: how are they linked? Free Radic. Biol. Med., 2010, 49, 1603-1616.
73. Grek, C. L.; Tew, K. D. Redox metabolism and malignancy. Curr. Opin. Pharmacol., 2010, 10, 362-368.
74. Bell, E. L.; Klimova, T. A.; Eisenbart, J.; Moraes, C. T.; Murphy, M. P.; Budinger, G. R.; Chandel, N. S. The Qo site of the mitochondrial complex III is required for the transduction of hypoxic signaling via reactive oxygen species production. J. Cell Biol., 2007, 177, 1029-1036.
75. 2 sensing. J. Bol. Chem., 2000, 275, 25130-25138.
76. Dewhirst, M. W. Relationships between cycling hypoxia, HIF-1, angiogenesis and oxidative stress. Rad. Res., 2009, 172, 653-665.
77. Dewhirst, M. W.; Cao, Y.; Moeller, B. Cycling hypoxia and free radicals regulate angiogenesis and radiotherapy response. Nat. Rev., 2008, 8, 425-437.
78. Bristow, R. G.; Hill, R. P. Hypoxia and metabolism. Hypoxia, DNA repair and genetic instability. Nat. Rev., 2008, 8, 180-192.
79. Bulut, A. S.; Erden, E.; Sak, S. D.; Doruk, H.; Kursun, N.; Dincol, D. Significance of inducible nitric oxide synthase expression in benign and malignant breast epithelium: an immunohistochemical study of 151 cases. Virchows Arch., 2005, 447, 24-30.
80. Nakamura, Y.; Yasuoka, H.; Tsujimoto, M.; Yoshidome, K.; Nakahara, M.; Nakao, K.; Nakamura, M.; Kakudo, K. Nitric oxide in breast cancer: induction of vascular endothelial growth factor-C and correlation with metastasis and poor prognosis. Clin. Cancer Res., 2006, 12, 1201-1207.
81. Szabó, C.; Ischiropoulos, H.; Radi, R. Peroxynitrite: biochemistry, pathophysiology and development of therapeutics. Nat. Rev. Drug Discov., 2007, 6, 662-680.
82. Tse, H. M.; Milton, M. J.; Piganelli, J. D. Mechanistic analysis of the immunomodulatory effects of a catalytic antioxidant on antigen-presenting cells: implication for their use in targeting oxidation-reduction reactions in innate immunity. Free Radic. Biol. Med., 2004, 36, 233-247.
83. - dismutation. Mn(III) methoxyethylpyridyl-and methoxyethylimidazolylporphyrins. J. Chem. Soc. Dalton Trans., 2004, 11, 1696-1702.
84. Verrax, J.; Curi Pedrosa, R.; Beck, R.; Dejeans, N.; Taper, H.; Buc Calderon, P. In situ modulation of oxidative stress: a novel and efficient strategy to kill cancer cells. Curr. Med. Chem., 2009, 16, 1821-1830.
85. Harrison, F. R.; May, J. M. Vitamin C function in the brain: vital role of the ascorbate transporter SVCT2. Free Radic. Biol. Med., 2009, 46, 719-730.
86. Verrax, J.; Calderon, P. B. The controversial place of vitamin C in cancer treatment. Biochem. Pharmacol., 2008, 76, 1644-1652.
87. Batinic-Haberle, I.; Rajic, Z.; Benov, L. A combination of two antioxidants produces a prooxidative effect forcing Escherichia coli to adapt via induction of oxyR regulon. Anticancer Agents Med. Chem., submitted
88. Williams, N. H.; Yandell, J. K. Outer-sphere Electron-Transfer Reactions of Ascorbate Anions. Aust. J. Chem., 1982, 35, 1133-1144.
89. Imlay, J. A. Cellular defenses against superoxide and hydrogen peroxide. Annu. Rev. Biochem., 2008, 77, 755-776.
90. Jang, S.; Imlay, J. A. Micromolar intracellular hydrogen peroxide disrupts metabolism by damaging iron-sulfur enzymes. J. Biol. Chem., 2007, 282, 929-937.
91. Shan, W.; Zhong, W., Zhao, R.; Oberley, T.D. Thioredoxin 1 as a subcellular biomarker of redox imbalance in human prostate cancer progression. Free Rad. Biol. Med., 2010, 49, 2078-2087.
92. Sessler, J. L.; Miller, R. A. Texaphyrins: new drugs with diverse clinical applications in radiation and photodynamic therapy. Biochem. Pharmacol., 2000, 59, 733-739.
93. Viani, G. A.; Manta, G. B.; Fonseca, E. C.; De Fendi, L. I.; Afonso, S. L.; Stefano, E. J. Whole brain radiotherapy with radiosensitizer for brain metastases. J. Exp. Clin. Cancer Res., 2009. 28, 1.
94. Crow, J. P.; Calinasan, N. Y.; Chen, J.; Hill, J. L.; Beal, M. F. Manganese porphyrin given at symptom onset markedly extends survival of ALS mice. Ann. Neurol., 2005, 58, 258-265.
95. Ye, X.; Fels, D.; Dedeugd, C.; Dewhirst, M. W.; Leong, K.; Batinic-Haberle, I. The in vitro cytotoxic effects of Mn(III) alkylpyridylporphyrin/ ascorbate system on four tumor cell lines. Free Radic. Biol. Med., 2009, 47, S136.
96. Chen, Q.; Espey, M. G.; Sun, A. Y.; Pooput, C.; Kirk, K. L.; Krishna, M. C.; Khosh, D. B.; Drisko, J.; Levine M. Pharmacologic doses of ascorbate act as a pro-oxidant and desrease growth of aggressive tumor xenografts in mice. Proc. Natl. Acad. Sci. U.S.A., 2008, 105, 11105-11109.
97. Verrax, J.; Beck, R.; Dejeans, N.; Glorieux, C.; Sid, B.; Curi Pedrosa, R.; Benites, J.; Vásquez, D.; Valderrama, J.A.; Buc Calderon, P. Redox-active quinones and ascorbate: an innovative cancer therapy that exploits the vulnerability of cancer cells to oxidative stress. Anticancer Agents Med. Chem., 2011, (this Issue, submitted).
98. Ohno, S.; Ohno, Y.; Suzuki, N.; Soma, G.; Inoue, M. High-dose vitamin C (ascorbic acid) therapy in the treatment of patients with advanced cancer. Anticancer Res., 2009, 29, 809-815.
99. Chen, Q.; Espey, M. G.; Sun, A. Y.; Lee, J.-H.; Krishna, M. C.; Shacter, E.; Choyke, P. L.; Pooput, C.; Kirk, K. L.; Buettner, G. R.; Levine, M. Ascorbate in pharmacologic concentrations selectively generates ascorbate radical and hydrogen peroxide in extracellular fluid in vivo. Proc. Natl. Acad. Sci. USA, 2007, 104, 8749-8754.
100. Piganelli, J. D., Flores, S. C., Cruz, C., Koepp, J., Young, R., Bradley, B., Kachadourian, R., Batinić-Haberle, I., Haskins, K. A Metalloporphyrin Superoxide Dismutase Mimetic (SOD Mimetic) Inhibits Autoimune Diabetes. Diabetes, 2002, 51, 347-355.
101. Rajic, Z.; Benov, L.; Kos, I.; Tovmasyan, A.; Batinic-Haberle, I. Cationic Mn porphyrins change their action from anti-to prooxidative in the presence of cellular reductants. Relevance to understanding the beneficial therapeutic effects of SOD mimics in mammalian systems. Free Radic. Biol. Med., 2010, 49, S194.
102. Kim, A.; Joseph, S.; Khan, A.; Epstein, C. J.; Sobel, R.; Huang, T.-T. Enhanced expression of mitochondrial superoxide dismutase leads to prolonged in vivo cell cycle progression and up-regulation of mitochondrial thioredoxin. Free Radic. Biol. Med., 2010, 48, 1501-1512.
103. Hempel, N.; Carrico, P. M.; Melendez, J. A. Manganese superoxide dismutase (Sod2) and redox-control of signaling events that drive metastasis. Submitted to Anticancer Agents Med. Chem. This Issue, 2011.
104. MacMillan-Crow, L. A.; Crow, J. Does More MnSOD Mean More Hydrogen Peroxide? Anticancer Agents Med. Chem., 2011, (this Issue, in press).
105. Tovmasyan, A.; Rajic, Z.; Spasojevic, I.; Reboucas, J. S.; Chen, X.; Sheng, H.; Warner, D. S.; Benov, L.; Batinic-Haberle, I. Methoxy-derivatization of alkyl chains increases the efficacy of cationic Mn porphyrins. Synthesis, characterization, SODlike activity, and SOD-deficient E. coli study of meta Mn(III) N-methoxyalkylpyridylporphyrins. Dalton Trans., 2011, DOI:10. 1039/C0DT01321H.
106. Batinic-Haberle, I.; Rajic, Z.; Tovmasyan, A.; Dewhirst, M.; Spasojevic, I. Diverse functions of cationic Mn(III) substituted N-pyridylporphyrins, known as SOD mimics. Free Radic. Biol. Med., (under revision).