Superoxide dismutase mimics: chemistry, pharmacology, and therapeutic potential.
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Journal: 2010/October - Antioxidants and Redox Signaling
ISSN: 1557-7716
Abstract:
Oxidative stress has become widely viewed as an underlying condition in a number of diseases, such as ischemia-reperfusion disorders, central nervous system disorders, cardiovascular conditions, cancer, and diabetes. Thus, natural and synthetic antioxidants have been actively sought. Superoxide dismutase is a first line of defense against oxidative stress under physiological and pathological conditions. Therefore, the development of therapeutics aimed at mimicking superoxide dismutase was a natural maneuver. Metalloporphyrins, as well as Mn cyclic polyamines, Mn salen derivatives and nitroxides were all originally developed as SOD mimics. The same thermodynamic and electrostatic properties that make them potent SOD mimics may allow them to reduce other reactive species such as peroxynitrite, peroxynitrite-derived CO(3)(*-), peroxyl radical, and less efficiently H(2)O(2). By doing so SOD mimics can decrease both primary and secondary oxidative events, the latter arising from the inhibition of cellular transcriptional activity. To better judge the therapeutic potential and the advantage of one over the other type of compound, comparative studies of different classes of drugs in the same cellular and/or animal models are needed. We here provide a comprehensive overview of the chemical properties and some in vivo effects observed with various classes of compounds with a special emphasis on porphyrin-based compounds.
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Antioxid Redox Signal 13(6): 877-918
PMID: 20095865

Superoxide Dismutase Mimics: Chemistry, Pharmacology, and Therapeutic Potential

Department of Radiation Oncology, Duke University Medical School, Durham, North Carolina.
Departamento de Química, CCEN, Universidade Federal da Paraíba, João Pessoa, Brazil.
Department of Medicine, Duke University Medical School, Durham, North Carolina.
Corresponding author.
Address correspondence to: Ines Batinić-Haberle, Ph.D., Department of Radiation Oncology–Cancer Biology, Duke University Medical Center, Research Drive, 281b/285 MSRB I, Box 3455, Durham, NC 27710. E-mail:ude.ekud@cinitabi
Address correspondence to: Ines Batinić-Haberle, Ph.D., Department of Radiation Oncology–Cancer Biology, Duke University Medical Center, Research Drive, 281b/285 MSRB I, Box 3455, Durham, NC 27710. E-mail:ude.ekud@cinitabi
Received 2009 Sep 3; Revised 2010 Jan 17; Accepted 2010 Jan 22.
Copyright 2010, Mary Ann Liebert, Inc.

Abstract

Oxidative stress has become widely viewed as an underlying condition in a number of diseases, such as ischemia–reperfusion disorders, central nervous system disorders, cardiovascular conditions, cancer, and diabetes. Thus, natural and synthetic antioxidants have been actively sought. Superoxide dismutase is a first line of defense against oxidative stress under physiological and pathological conditions. Therefore, the development of therapeutics aimed at mimicking superoxide dismutase was a natural maneuver. Metalloporphyrins, as well as Mn cyclic polyamines, Mn salen derivatives and nitroxides were all originally developed as SOD mimics. The same thermodynamic and electrostatic properties that make them potent SOD mimics may allow them to reduce other reactive species such as peroxynitrite, peroxynitrite-derived CO3, peroxyl radical, and less efficiently H2O2. By doing so SOD mimics can decrease both primary and secondary oxidative events, the latter arising from the inhibition of cellular transcriptional activity. To better judge the therapeutic potential and the advantage of one over the other type of compound, comparative studies of different classes of drugs in the same cellular and/or animal models are needed. We here provide a comprehensive overview of the chemical properties and some in vivo effects observed with various classes of compounds with a special emphasis on porphyrin-based compounds. Antioxid. Redox Signal. 13, 877–918.

Abstract

Abbreviations Used

ACNacetonitrile
AEOL11207Mn(III) 5,15-bis(methylcarboxylato)-10,20-bis(trifluoromethyl)porphyrin
AEOL11209Mn(III) 5,15-bis(4-carboxylatophenyl)-10, 20-bis(formyl)porphyrin
AP-1activator protein-1
CAT-14-trimethylammonium-tempo iodide
CO3·−carbonate radical
CuBr8TM-4-PyP4+Cu(II) β-octabromo-meso-tetrakis(N-methylpyridinium-4-yl)porphyrin
CuTM-4-PyP4+Cu(II) meso-tetrakis (N-methylpyridinium-4-yl)porphyrin
E1/2half-wave reduction potential
EBAMEbis-(5-aminosalicylic acid) methyl ester
EDTAethylenediaminetetraacetic acid
EGTAethylenebis(oxyethylenenitrilo)tetraaceticacid
EHPGethylenebis(hydroxyphenylglycine)
FeTM-4-PyP5+Fe(III) meso-tetrakis(N-methylpyridinum-4-yl) porphyrin; the axial ligation is not indicated but at pH∼7 monohydroxo species is present in solution
HIF-1αhypoxia inducible factor-1
ICVintracerebroventricularly
MCAOmiddle cerebral artery occlusion
MnBr8TM-3-PyP4+Mn(II) β-octabromo-meso-tetrakis(N-methylpyridinium-3-yl)porphyrin
[MnBV]2Mn(III) biliverdin IX
[MnBVDME]2Mn(II) biliverdin IX dimethylester
[MnBVDT]2Mn(III) biliverdin IX ditaurate
MnBr8TM-4-PyP4+Mn(II) β-octabromo-meso-tetrakis(N-methylpyridinium-4-yl)porphyrin
Mn(III) salenEUK-8
MnBr8TCPP3−Mn(III) β-octabromo-meso-tetrakis(4-carboxylatophenyl)porphyrin (also MnBr8TBAP)
MnBr8TSPP3−Mn(III) β-octabromo-meso-tetrakis(4-sulfonatophenyl)porphyrin
MnTCPP3−Mn(III) meso-tetrakis(4-carboxylatophenyl)porphyrin (also MnTBAP, also abbreviated as MnTBAP), AEOL10201
MnTSPP3−Mn(III) meso-tetrakis(4-sulfonatophenyl)porphyrin
[MnMBVDME]2Mn(III) mesobiliverdin IX dimethylester
MnPMn porphyrin
MnT-2-PyP+Mn(III) meso-tetrakis(2-pyridyl)porphyrin
MnTalkyl-2,3,4-PyP5+Mn(III) meso-tetrakis(N-alkylyridinium-2 or 3 or 4-yl)porphyrin, alkyl being methyl (M, AEOL10112), ethyl (E, AEOL10113), n-propyl (nPr), n-butyl (nBu), n-hexyl (nHex), n-heptyl (nHep), n-octyl (nOct); 2 and 3 relate to ortho and meta isomers, respectively
MnTDE(or M or nPr)-2-ImP5+Mn(III) tetrakis[N,N'-diethyl(or dimethyl or di-n-propyl)imidazolium-2-yl)porphyrin; diethyl analogue is AEOL10150
MnTDM-4-PzP5+Mn(III) meso-tetrakis(N,N'-dimethylpyrazolium-4-yl)porphyrin
MnTDMOE-2-ImP5+Mn(III) tetrakis[N,N'-di(2-methoxethyl)imidazolium-2-yl)porphyrin
MnTrM-2-corrole3+Mn(III) meso-tris(N-methylpyridinium-2-yl)corrole
MnTTEG-2-PyP5+Mn (III) 5,10,15,20-tetrakis(N-(1-(2-(2(-2-methoxyethoxy)ethoxy)ethyl)pyridinium-2-yl) porphyrin
NBTnitrobluetetrazolium
NF-κBnuclear factor κB
NHEnormal hydrogen electrode
NOnitric oxide
O2·−superoxide
PNperoxynitrite
POWpartition coefficient between n-octanol and water
Rfthin-layer chromatographic retention factor that presents the ratio between the solvent and compound path in 10:10:80 = satKNO3(aq):H2O:acetonitrile
RNSreactive nitrogen species
ROSreactive oxygen species
SalenN,N'-bis-(salicylideneamino)ethane
SODsuperoxide dismutase
Tempo2,2,6,6,-tetramethylpiperidine-1-oxyl
Tempol4-OH-2,2,6,6,-tetramethylpiperidine-1-oxyl
TFtranscription factor
TLCthin-layer chromatography
TPA12-O-tetradecanoylphorbol-13-acetate
Xxanthine
XOxanthine oxidase
Abbreviations Used

Footnotes

Reviewing Editors: Maria T. Carri, David Harrison, Carlos C. Lopes de Jesus, Ronald P. Mason, Juan J. Poderoso, and Naoyuki Taniguchi

Footnotes

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