Comprehensive pharmacokinetic studies and oral bioavailability of two Mn porphyrin-based SOD mimics, MnTE-2-PyP5+ and MnTnHex-2-PyP 5+

Free Radical Biology and Medicine

Volumn 58, Issue , 2013, Pages 73-80

  Weitner, Tin ^a,b   Kos, Ivan ^a   Sheng, Huaxin ^a   Tovmasyan, Artak ^a   Reboucas, Julio S ^a,c   Fan, Ping ^a   Warner, David S ^a   Vujaskovic, Zeljko ^a,d   Batinic Haberle, Ines ^a   Spasojevic, Ivan ^a  

^a DUKE UNIVERSITY MEDICAL CENTER   (United States)

^b UNIVERSITY OF ZAGREB   (Croatia)

^c FEDERAL UNIVERSITY OF PARAÍBA   (Brazil)

^d UNIVERSITY OF MARYLAND SCHOOL OF MEDICINE   (United States)

Author keywords

Free radicals; LC MS MS; Mn porphyrins; MnTE 2 PyP5+; MnTnHex 2 PyP5+; Mouse organs; Mouse plasma; Oral availability; Pharmacokinetics; SOD mimic

Indexed keywords

MANGANESE DERIVATIVE; MANGANESE SUPEROXIDE DISMUTASE; N ALKYLPYRIDYLPORPHYRIN; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; BLOOD BRAIN BARRIER; BRAIN; CATALYSIS; CONTROLLED STUDY; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG EFFICACY; FEMALE; HEART; HYDROPHILICITY; IN VIVO STUDY; INTRACELLULAR SPACE; KIDNEY; LIPOPHILICITY; LIVER; LUNG; MAXIMUM PLASMA CONCENTRATION; MITOCHONDRION; MOLECULAR MIMICRY; MOUSE; NONHUMAN; PRIORITY JOURNAL; SIGNAL TRANSDUCTION; SINGLE DRUG DOSE; SOLUBILITY; SPLEEN; STATIC ELECTRICITY; TIME TO MAXIMUM PLASMA CONCENTRATION; TISSUE DISTRIBUTION;

ANIMALS; BIOMIMETICS; BLOOD-BRAIN BARRIER; CATALYSIS; CHROMATOGRAPHY, LIQUID; HUMANS; METALLOPORPHYRINS; MICE; MITOCHONDRIA; OXIDATIVE STRESS; OXYGEN; REACTIVE OXYGEN SPECIES; SIGNAL TRANSDUCTION; SUPEROXIDE DISMUTASE; TANDEM MASS SPECTROMETRY;

ANIMALIA;

EID: 84876006120     PISSN: 08915849     EISSN: 18734596     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2013.01.006     Document Type: Article

References (50)

1. I. Batinic-Haberle, Z. Rajic, A. Tovmasyan, J.S. Reboucas, X. Ye, K.W. Leong, M.W. Dewhirst, Z. Vujaskovic, L. Benov, and I. Spasojevic Diverse functions of cationic Mn(III) N-substituted pyridylporphyrins, recognized as SOD mimics Free Radic. Biol. Med. 51 2011 1035 1053
2. I. Batinic-Haberle, J.S. Reboucas, L. Benov, and I. Spasojevic Chemistry, biology and medical effects of water soluble metalloporphyrins K.M. Kadish, K.M. Smith, R. Guillard, Handbook of Porphyrin Science 2011 World Scientific Singapore 291 393
3. I. Batinic-Haberle, J.S. Reboucas, and I. Spasojevic Superoxide dismutase mimics: chemistry, pharmacology, and therapeutic potential Antioxid. Redox Signaling 13 2010 877 918
4. Tovmasyan, A.; Sheng, H.; Weitner, T.; Arulpragasam, A.; Lu, M.; Warner, D. S.; Spasojevic, I.; Batinic-Haberle, I. Design, mechanism of action, bioavailability and therapeutic effects of Mn porphyrin-based redox modulators. Med. Princ. Pract. (in press); 2012. 10.1159/000341715
5. I. Batinic-Haberle, M.M. Ndengele, S. Cuzzocrea, J.S. Reboucas, I. Spasojevic, and D. Salvemini Lipophilicity is a critical parameter that dominates the efficacy of metalloporphyrins in blocking the development of morphine antinociceptive tolerance through peroxynitrite-mediated pathways Free Radic. Biol. Med. 46 2009 212 219
6. I. Batinic-Haberle, L. Benov, I. Spasojevic, and I. Fridovich The ortho effect makes manganese(III) meso-tetrakis(N-methylpyridinium-2-yl)porphyrin a powerful and potentially useful superoxide dismutase mimic J. Biol. Chem 273 1998 24521 24528
7. G. Ferrer-Sueta, I. Batinic-Haberle, I. Spasojevic, I. Fridovich, and R. Radi Catalytic scavenging of peroxynitrite by isomeric Mn(III) N-methylpyridylporphyrins in the presence of reductants Chem. Res. Toxicol. 12 1999 442 449
8. G. Ferrer-Sueta, C. Quijano, B. Alvarez, and R. Radi Reactions of manganese porphyrins and manganese-superoxide dismutase with peroxynitrite Methods Enzymol. 349 2002 23 37
9. G. Ferrer-Sueta, D. Vitturi, I. Batinic-Haberle, I. Fridovich, S. Goldstein, G. Czapski, and R. Radi Reactions of manganese porphyrins with peroxynitrite and carbonate radical anion J. Biol. Chem. 278 2003 27432 27438
10. J.S. Reboucas, I. Spasojevic, D.H. Tjahjono, A. Richaud, F. Mendez, L. Benov, and I. Batinic-Haberle Redox modulation of oxidative stress by Mn porphyrin-based therapeutics: the effect of charge distribution Dalton Trans. 9 2008 1233 1242
11. T.P. Umile, and J.T. Groves Catalytic generation of chlorine dioxide from chlorite using a water-soluble manganese porphyrin Angew. Chem. Int. Ed. Engl. 50 2011 695 698
12. I. Batinic-Haberle, I. Spasojevic, H.M. Tse, A. Tovmasyan, Z. Rajic St, D.K. Clair, Z. Vujaskovic, M.W. Dewhirst, and J.D. Piganelli Design of Mn porphyrins for treating oxidative stress injuries and their redox-based regulation of cellular transcriptional activities Amino Acids 42 2012 95 113
13. M.C. Jaramillo, M.M. Briehl, and M.E. Tome Manganese porphyrin glutathionylates the p65 subunit of NF-κB to potentiate glucocorticoid-induced apoptosis in lymphoma Free Radic. Biol. Med. 49 2010 S63
14. •- dismutation J. Chem. Soc. Dalton Trans. 2002 2689 2696
15. Z. Rajic, A. Tovmasyan, I. Spasojevic, H. Sheng, M. Lu, A.M. Li, E.B. Gralla, D.S. Warner, L. Benov, and I. Batinic-Haberle A new SOD mimic, Mn(III) ortho N-butoxyethylpyridylporphyrin, combines superb potency and lipophilicity with low toxicity Free Radic. Biol. Med. 52 2012 1828 1834
16. S. Miriyala, I. Spasojevic, A. Tovmasyan, D. Salvemini, Z. Vujaskovic St, D. Clair, and I. Batinic-Haberle Manganese superoxide dismutase, MnSOD and its mimics Biochim. Biophys. Acta 794-814 1822 2012
17. I. Spasojevic, A.M. Li, A. Tovmasyan, Z. Rajic, D. Salvemini St., D. Clair, J.S. Valentine, Z. Vujaskovic, E.B. Gralla, and I. Batinic-Haberle Accumulation of porphyrin-based SOD mimics in mitochondria is proportional to their lipophilicity Free Radic. Biol. Med. 49 2010 S199
18. I. Spasojevic, S. Miryala, A. Tovmasyan, D. Salvemini, Z. Vujaskovic, I. Batinic-Haberle St., and D. Clair Lipophilicity of Mn(III) N- alkylpyridylporphyrins dominates their accumulation within mitochondria and therefore in vivo efficacy: a mouse study Free Radic. Biol. Med. 51 2011 S98
19. H. Sheng, I. Spasojevic, H.M. Tse, J.Y. Jung, J. Hong, Z. Zhang, J.D. Piganelli, I. Batinic-Haberle, and D.S. Warner Neuroprotective efficacy from a lipophilic redox-modulating Mn(III) N-hexylpyridylporphyrin, MnTnHex-2-PyP: rodent models of ischemic stroke and subarachnoid hemorrhage J. Pharmacol. Exp. Ther. 338 2011 906 916
20. 5+, in plasma and major organs of B6C3F1 mice Free Radic. Biol. Med. 45 2008 943 949
21. I. Kos, J.S. Reboucas, G. DeFreitas-Silva, D. Salvemini, Z. Vujaskovic, M.W. Dewhirst, I. Spasojevic, and I. Batinic-Haberle Lipophilicity of potent porphyrin-based antioxidants: comparison of ortho and meta isomers of Mn(III) N-alkylpyridylporphyrins Free Radic. Biol. Med. 47 2009 72 78
22. B. Gauter-Fleckenstein, K. Fleckenstein, K. Owzar, C. Jiang, I. Batinic-Haberle, and Z. Vujaskovic Comparison of two Mn porphyrin-based mimics of superoxide dismutase in pulmonary radioprotection Free Radic. Biol. Med. 44 2008 982 989
23. B. Gauter-Fleckenstein, K. Fleckenstein, K. Owzar, C. Jiang, J.S. Reboucas, I. Batinic-Haberle, and Z. Vujaskovic Early and late administration of MnTE-2-PyP5+ in mitigation and treatment of radiation-induced lung damage Free Radic. Biol. Med. 48 2010 1034 1043
24. B.J. Moeller, I. Batinic-Haberle, I. Spasojevic, Z.N. Rabbani, M.S. Anscher, Z. Vujaskovic, and M.W. Dewhirst A manganese porphyrin superoxide dismutase mimetic enhances tumor radioresponsiveness Int. J. Radiat. Oncol. Biol. Phys. 63 2005 545 552
25. 5+, via suppression of oxidative stress in a mouse model of breast tumor Free Radic. Biol. Med. 47 2009 992 1004
26. J.D. Piganelli, S.C. Flores, C. Cruz, J. Koepp, I. Batinic-Haberle, J. Crapo, B. Day, R. Kachadourian, R. Young, B. Bradley, and K. Haskins A metalloporphyrin-based superoxide dismutase mimic inhibits adoptive transfer of autoimmune diabetes by a diabetogenic T-cell clone Diabetes 51 2002 347 355
27. I. Batinic-Haberle, S.T. Keir, Z. Rajic, A. Tovmasyan, and D.D. Bigner Lipophilic Mn porphyrins in the treatment of brain tumors Free Radic. Biol. Med. 51 2011 S119
28. Batinic-Haberle, I.; Keir, S. T.; Rajic, Z.; Tovmasyan, A.; Spasojevic, I.; Dewhirst, M. W.; Bigner, D. D. Glioma growth suppression via modulation of cellular redox status by a lipophilic Mn porphyrin. Presented at the Mid-Winter SPORE Meeting. San Francisco, USA; 2011:31-32.
29. H. Saba, I. Batinic-Haberle, S. Munusamy, T. Mitchell, C. Lichti, J. Megyesi, and L.A. MacMillan-Crow Manganese porphyrin reduces renal injury and mitochondrial damage during ischemia/reperfusion Free Radic. Biol. Med. 42 2007 1571 1578
30. A. Drobyshevsky, K. Luo, M. Derrick, L. Yu, H. Du, P.V. Prasad, J. Vasquez-Vivar, I. Batinic-Haberle, and S. Tan Motor deficits are triggered by reperfusion-reoxygenation injury as diagnosed by MRI and by a mechanism involving oxidants J. Neurosci. 32 2012 5500 5509
31. •- disproportionation Inorg. Chem. 41 2002 5874 5881
32. A.J. Bailer Testing for the equality of area under the curves when using destructive measurement techniques J. Pharmacokinet. Biopharm 16 1988 303 309
33. M.P. Murphy, and R.A. Smith Targeting antioxidants to mitochondria by conjugation to lipophilic cations Annu. Rev. Pharmacol. Toxicol. 47 2007 629 656
34. H. Saitoh, S. Kawai, K. Miyazaki, and T. Arita Transport characteristics of propantheline across rat intestinal brush border membrane J. Pharm. Pharmacol. 40 1988 176 180
35. R.A. Rosenthal, K.D. Huffman, L.W. Fisette, C.A. Damphousse, W.B. Callaway, B. Malfroy, and S.R. Doctrow Orally available Mn porphyrins with superoxide dismutase and catalase activities J. Biol. Inorg. Chem. 14 2009 979 991
36. H.C. O'Neill, C.W. White, L.A. Veress, T.B. Hendry-Hofer, J.E. Loader, E. Min, J. Huang, R.C. Rancourt, and B.J. Day Treatment with the catalytic metalloporphyrin AEOL 10150 reduces inflammation and oxidative stress due to inhalation of the sulfur mustard analog 2-chloroethyl ethyl sulfide Free Radic. Biol. Med. 48 2010 1188 1196
37. R.A. Rosenthal, B. Fish, R.P. Hill, K.D. Huffman, Z. Lazarova, J. Mahmood, M. Medhora, R. Molthen, J.E. Moulder, S.T. Sonis, P.J. Tofilon, and S.R. Doctrow Salen Mn complexes mitigate radiation injury in normal tissues Anticancer Agents Med. Chem 11 2011 359 372
38. L.P. Liang, J. Huang, R. Fulton, B.J. Day, and M. Patel An orally active catalytic metalloporphyrin protects against 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine neurotoxicity in vivo J. Neurosci. 27 2007 4326 4333
39. R.A. Smith, and M.P. Murphy Animal and human studies with the mitochondria-targeted antioxidant MitoQ Ann. N. Y. Acad. Sci. 1201 2010 96 103
40. I. Spasojevic, Y. Chen, T.J. Noel, Y. Yu, M.P. Cole, L. Zhang, Y. Zhao St, D.K. Clair, and I. Batinic-Haberle Mn porphyrin-based superoxide dismutase (SOD) mimic, MnIIITE-2-PyP5+, targets mouse heart mitochondria Free Radic. Biol. Med. 42 2007 1193 1200
41. R.A. Smith, C.M. Porteous, A.M. Gane, and M.P. Murphy Delivery of bioactive molecules to mitochondria in vivo Proc. Natl. Acad. Sci. USA 100 2003 5407 5412
42. H. Sheng, J.J. Enghild, R. Bowler, M. Patel, I. Batinić-Haberle, C.L. Calvi, B.J. Day, R.D. Pearlstein, J.D. Crapo, and D.S. Warner Effects of metalloporphyrin catalytic antioxidants in experimental brain ischemia Free Radic. Biol. Med. 33 2002 947 961
43. R.M. Davis, J.B. Mitchell, and M.C. Krishna Nitroxides as cancer imaging agents Anti-Cancer Agents Med. Chem. 11 2011 347 358
44. P. Anand, A.B. Kunnumakkara, R.A. Newman, and B.B. Aggarwal Bioavailability of curcumin: problems and promises Mol. Pharm. 4 2007 807 818
45. L. Baum, C.W. Lam, S.K. Cheung, T. Kwok, V. Lui, J. Tsoh, L. Lam, V. Leung, E. Hui, C. Ng, J. Woo, H.F. Chiu, W.B. Goggins, B.C. Zee, K.F. Cheng, C.Y. Fong, A. Wong, H. Mok, M.S. Chow, P.C. Ho, S.P. Ip, C.S. Ho, X.W. Yu, C.Y. Lai, M.H. Chan, S. Szeto, I.H. Chan, and V. Mok Six-month randomized, placebo-controlled, double-blind, pilot clinical trial of curcumin in patients with Alzheimer disease J. Clin. Psychopharmacol. 28 2008 110 113
46. Q.Y. Li, C. Pedersen, B.J. Day, and M. Patel Dependence of excitotoxic neurodegeneration on mitochondrial aconitase inactivation J. Neurochem. 78 2001 746 755
47. H. Sheng, J.J. Enghild, R. Bowler, M. Patel, I. Batinic-Haberle, C.L. Calvi, B.J. Day, R.D. Pearlstein, J.D. Crapo, and D.S. Warner Effects of metalloporphyrin catalytic antioxidants in experimental brain ischemia Free Radic. Biol. Med. 33 2002 947 961
48. A.M. James, H.M. Cocheme, R.A. Smith, and M.P. Murphy Interactions of mitochondria-targeted and untargeted ubiquinones with the mitochondrial respiratory chain and reactive oxygen species: implications for the use of exogenous ubiquinones as therapies and experimental tools J. Biol. Chem 280 2005 21295 21312
49. S. Rausaria, M.M. Ghaffari, A. Kamadulski, K. Rodgers, L. Bryant, Z. Chen, T. Doyle, M.J. Shaw, D. Salvemini, and W.L. Neumann Retooling manganese(III) porphyrin-based peroxynitrite decomposition catalysts for selectivity and oral activity: a potential new strategy for treating chronic pain J. Med. Chem. 54 2011 8658 8669
50. S. Rausaria, A. Kamadulski, N.P. Rath, L. Bryant, Z. Chen, D. Salvemini, and W.L. Neumann Manganese(III) complexes of bis(hydroxyphenyl)dipyrromethenes are potent orally active peroxynitrite scavengers J. Am. Chem. Soc. 133 2011 4200 4203