A new SOD mimic, Mn(III) ortho N-butoxyethylpyridylporphyrin, combines superb potency and lipophilicity with low toxicity

Free Radical Biology and Medicine

Volumn 52, Issue 9, 2012, Pages 1828-1834

  Rajic, Zrinka ^a,e   Tovmasyan, Artak ^a   Spasojevic, Ivan ^a   Sheng, Huaxin ^a   Lu, Miaomiao ^a,b   Li, Alice M ^c,f   Gralla, Edith B ^c   Warner, David S ^a   Benov, Ludmil ^d   Batinic Haberle, Ines ^a  

^a DUKE UNIVERSITY MEDICAL CENTER   (United States)

^b ZHENGZHOU UNIVERSITY   (China)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d KUWAIT UNIVERSITY   (Kuwait)

^e UNIVERSITY OF ZAGREB   (Croatia)

^f YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Drug toxicity; MnTnBuOE 2 PyP 5+; MnTnHex 2 PyP 5+; SOD mimic

Indexed keywords

ALKYL GROUP; HEPTANE; MANGANASE MESO TETRAKIS(N N BUTOXYETHYLPYRIDINIUM 2 YL)PORPHYRIN; MANGANASE ORTHO N BUTOXYETHYLPYRIDYLPORPHYRIN; MANGANESE SUPEROXIDE DISMUTASE; OXYGEN; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVITY; FUNGUS GROWTH; IN VIVO STUDY; LIPOPHILICITY; MALE; MOUSE; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SACCHAROMYCES CEREVISIAE; SOLVATION;

ANIMALS; CATALYSIS; ELECTROCHEMICAL TECHNIQUES; MALE; METALLOPORPHYRINS; MICE; MICE, INBRED C57BL; MICELLES; MOLECULAR MIMICRY; OXIDATIVE STRESS; SACCHAROMYCES CEREVISIAE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; SUPEROXIDE DISMUTASE;

ANIMALIA; SACCHAROMYCES CEREVISIAE;

EID: 84859088996     PISSN: 08915849     EISSN: 18734596     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2012.02.006     Document Type: Article

References (34)

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 Signal. 13 2010 877 918
4. I. Batinic-Haberle, I. Spasojevic, R.D. Stevens, P. Hambright, P. Neta, A. Okado-Matsumoto, and I. Fridovich New class of potent catalysts of O2.-dismutation. Mn(III) ortho-methoxyethylpyridyl- and di-ortho- methoxyethylimidazolylporphyrins Dalton Trans. 2004 1696 1702
5. 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
6. 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. 8 2011 906 916
7. S. Miriyala, I. Spasojevic, A. Tovmasyan, D. Salvemini, Z. Vujaskovic, D. St. Clair, and I. Batinic-Haberle Manganese superoxide dismutase, MnSOD and its mimics Biochim. Biophys. Acta. 1822 2012 794 814
8. 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
9. T. Doyle, L. Bryant, I. Batinic-Haberle, J. Little, S. Cuzzocrea, E. Masini, I. Spasojevic, and D. Salvemini Supraspinal inactivation of mitochondrial superoxide dismutase is a source of peroxynitrite in the development of morphine antinociceptive tolerance Neuroscience 164 2009 702 710
10. Drobyshevsky, A.; Luo, K.; Derrick, M.; Yu, L.; Prasad, P.V.; Vasquez-Vivar, J.; Batinic-Haberle, I.; Tan, S. Oxidants in fetal brain reperfusion-reoxygenation injury trigger motor deficits. J. Neurosci. Under revision.
11. I. Kos, L. Benov, I. Spasojevic, J.S. Reboucas, and I. Batinic-Haberle High lipophilicity of meta Mn(III) N-alkylpyridylporphyrin-based superoxide dismutase mimics compensates for their lower antioxidant potency and makes them as effective as ortho analogues in protecting superoxide dismutase-deficient Escherichia coli J. Med. Chem. 52 2009 7868 7872
12. A. Okado-Matsumoto, I. Batinic-Haberle, and I. Fridovich Complementation of SOD-deficient Escherichia coli by manganese porphyrin mimics of superoxide dismutase activity Free Radic. Biol. Med. 37 2004 401 410
13. A. Tovmasyan, Z. Rajic, I. Spasojevic, H. Sheng, D. Warner, A. Li, E.B. Gralla, L. Benov, and I. Batinic-Haberle Structural modification diminishes toxicity of lipophilic longer Mn(III) N-alkylpyridylporphyrin based powerful SOD mimics. Synthesis, characterization and SOD-deficient E. coli and S. cerevisiae studies Free Radic. Biol. Med. 49 2010 S201
14. J.S. Reboucas, I. Spasojevic, and I. Batinic-Haberle Quality of potent Mn porphyrin-based SOD mimics and peroxynitrite scavengers for pre-clinical mechanistic/therapeutic purposes J. Pharm. Biomed. Anal. 48 2008 1046 1049
15. 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
16. R.S. Tipson On esters of p-toluenesulfonic acid J. Org. Chem. 9 1944 235 241
17. ̇- dismutation J. Chem. Soc., Dalton Trans. 2002 2689 2696
18. D. Lahaye, K. Muthukumaran, C.H. Hung, D. Gryko, J.S. Reboucas, I. Spasojevic, I. Batinic-Haberle, and J.S. Lindsey Design and synthesis of manganese porphyrins with tailored lipophilicity: investigation of redox properties and superoxide dismutase activity Bioorg. Med. Chem. 15 2007 7066 7086
19. I. Spasojevic, I. Batinic-Haberle, R.D. Stevens, P. Hambright, A.N. Thorpe, J. Grodkowski, P. Neta, and I. Fridovich Manganese(III) biliverdin IX dimethyl ester: a powerful catalytic scavenger of superoxide employing the Mn(III)/Mn(IV) redox couple Inorg. Chem. 40 2001 726 739
20. M. Eckshtain, I. Zilbermann, A. Mahammed, A. Saltsman, Z. Okun, E. Maimon, H. Cohen, D. Meyerstein, and Z. Gross Superoxide dismutase activity of corrole metal complexes Dalton Trans. 2009 7879 7882
21. J. Lee, J.A. Hunt, and J.T. Groves Mechanisms of iron porphyrin reactions with peroxynitrite J. Am. Chem. Soc. 120 1998 7493 7501
22. J. Lee, J.A. Hunt, and J.T. Groves Manganese porphyrins as redox-coupled peroxynitrite reductases J. Am. Chem. Soc. 120 1998 6053 6061
23. E.B. Gralla, and J.S. Valentine Null mutants of Saccharomyces cerevisiae Cu, Zn superoxide dismutase: characterization and spontaneous mutation rates J. Bacteriol. 173 1991 5918 5920
24. C. Kaiser, S. Michaelis, and A. Mitchell Methods in yeast genetics 1994 Cold Spring Harbor Laboratory Press Cold Spring Harbor
25. 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
26. H. Sheng, W. Yang, S. Fukuda, H.M. Tse, W. Paschen, K. Johnson, I. Batinic-Haberle, J.D. Crapo, R.D. Pearlstein, J. Piganelli, and D.S. Warner Long-term neuroprotection from a potent redox-modulating metalloporphyrin in the rat Free Rad. Biol. Med. 47 2009 917 923
27. 5+ Free Radic. Biol. Med. 51 2011 S148
28. S. Goldstein, I. Fridovich, and G. Czapski Kinetic properties of Cu, Zn-superoxide dismutase as a function of metal content-order restored Free Radic. Biol. Med. 41 2006 937 941
29. C.K. Vance, and A.F. Miller A simple proposal that can explain the inactivity of metal-substituted superoxide dismutases J. Am. Chem. Soc. 120 1998 461 467
30. R.M. Ellerby, D.E. Cabelli, J.A. Graden, and J.S. Valentine Copper-zinc superoxide dismutase: why not pH-dependent? J. Am. Chem. Soc. 118 1996 6556 6561
31. A.G. Tovmasyan, Z. Rajic, I. Spasojevic, J.S. Reboucas, X. Chen, D. Salvemini, H. Sheng, D.S. Warner, L. Benov, and I. Batinic-Haberle Methoxy-derivatization of alkyl chains increases the in vivo efficacy of cationic Mn porphyrins. Synthesis, characterization, SOD-like activity, and SOD-deficient E. coli study of meta Mn(III) N-methoxyalkylpyridylporphyrins Dalton Trans. 40 2011 4111 4121
32. 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
33. X. Ye, D. Fels, A. Tovmasyan, K.M. Aird, C. de Deugd, J.L. Allensworth, I. Kos, W. Park, I. Spasojevic, G.R. Devi, M.W. Dewhirst, K.W. Leong, and I. Batinic-Haberle Cytotoxic effects of Mn(III) N-alkylpyridylporphyrins in the presence of cellular reductant, ascorbate Free. Radic. Res. 45 2011 1289 1306
34. I. Spasojevic, A.M. Li, A. Tovmasyan, Z. Rajic, D. Salvemini, D. St. 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. 2010 S199