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. 2010 Sep 15;13(6):877–918. doi: 10.1089/ars.2009.2876

Table 1.

Selected Physicochemical Properties of Some SOD Mimics

 
  
  
  
 Lipophilicity
  
Compound MnIII/II potential,E½/mV vs. NHEa SOD activitylog kcat(O2•–)b PN red. activitylog kred(ONOO–)c Rel. Rfd log Pow Ref.
Cationic porphyrins
MnTM-2-PyP5+ +220 7.79 7.28 0.5 −7.86 29, 179
MnTE-2-PyP5+ +228 7.76 (cyt c) 7.73 (p.r.) 7.53 1 −6.89 30, 179, 302
MnTnPr-2-PyP5+ +238 7.38 7.15 1.8 −5.93 37, 179
MnTnBu-2-PyP5+ +254 7.25 7.11 3.2 −5.11 37, 179
MnTnHex-2-PyP5+ +314 7.48 7.11 6.3 −2.76 37, 179
MnTnHep-2-PyP5+ +342 7.65   7.7 −2.10 178, 179
MnTnOct-2-PyP5+ +367 7.71 7.15 8.2 −1.24 179
MnTMOE-2-PyP5+ +251 8.04 (p.r.)   1.2   38
MnTTEG-2-PyP5+ +250 8.11   1.0   36
MnTrM-2-PyP4+ +118 6.63   1.1   30, 265
MnBM-2-PyP3+  +53 6.52   2.3   30, 265
MnTrE-2-PyP4+       2.2   30, 265
MnBE-2-PyP3+       4.4   30, 265
MnTDM-2-ImP5+ +320 8.11   0.5   266
MnTDE-2-ImP5+ +346 7.83 (p.r.)   2.3 −6.48 38
MnTDnPr-2-ImP5+ +320 8.11       167
MnTM,MOE-2-ImP5+ +356 7.98 (p.r.)   1.2   38
MnTDMOE-2-ImP5+ +365 7.59 (p.r.)   1.6   38
MnTDTEG-2-ImP5+ +412 8.55   2.0   36
MnTM-3-PyP5+  +52 6.61 6.62 0.8 −6.96 29, 179
MnTE-3-PyP5+  +54 6.65   1.7 −5.98 178, 179
MnTnPr-3-PyP5+  +62 6.69   3.7 −5.00 178, 179
MnTnBu-3-PyP5+  +64 6.69   6.7 −4.03 178, 179
MnTnHex-3-PyP5+  +64 6.64   9.2 −2.06 178, 179
MnTM-4-PyP5+  +60 6.58 6.63 0.5   29, 266
MnTE-4-PyP5+  +70 6.86       299
MnTDM-4-PzP5+  −4 5.83   0.6   266
MnT(TriMA)P5+ −100 5.11   1.8   266
MnT(TFTriMA)P5+  +58 6.02       30
MnCl1TE-2-PyP5+ +293 7.75   1.1   166
MnCl2TE-2-PyP5+ +343 8.11   1.2   166
MnCl3TE-2-PyP5+ +408 8.41   1.3   166
MnCl4TE-2-PyP5+ +448 8.60   1.3   165
MnCl5TE-2-PyP5+ +560 8.41       165
MnBr8TM-3-PyP4+ +468 ≥8.85       85
MnBr8TM-4-PyP4+ +480 ≥8.67       33, 85
CuTM-4-PyP4+   <3.7       33
CuBr8TM-4-PyP4+   6.46       33
Neutral porphyrins
MnT-2-PyP+ −280 4.29   10.2   301
MnBr8T-2-PyP+ +219 5.63       261, 301
MnT-4-PyP+ −200 4.53       299
MnTPP+ −270 4.83       299
MnTPFPP+ −120 5.00       299
MnTBzP+  +88 5.20       182
Anionic porphyrins
MnTBAP3– (pure form) −194 3.16 5.02     264
MnTSPP3– −160 3.93 5.53     30
MnT(2,6-Cl2-3-SO3-P)P3–  +88 6.00       30
MnT(2,6-F2-3-SO3-P)P3–  +7 5.51       30
MnBr8TSPP3– +209 5.56       262
MnBr8TCPP3– +213 5.07       262
Salens
Mn(salen)+, EUK-8 −130 5.78e   12   255, 302
EUK-134   5.78       255
EUK-189   5.78       255
Cyclic polyamines
M40403 +525 (ACN) 7.08, 6.55   13   204, 255, 269
M40404(2R,21R-Me2-M40403) +452 (ACN) Inactive   12   204, 269, 255
2S,21S-Me2-M40403 +464 (ACN) 8.37, 9.20       204, 26921
Fullerenes
C60-water-soluble fullerene (C3)   6.30       8
Miscellaneous
Mn2+ +850f 6.11 (cyt c)6.28 (p.r.)6.95 (p.r.)   0   299, 255, 302, 25
Mn-EDTA   inactive (cyt c)       302, 14, 40
[MnBV2–]2 −300 (+460g) 7.40 (cyt c)6.95 (p.r.)       302
[MnBVDME]2 −230 (+450g) 7.70 (cyt c)6.95 (p.r.)       302
[MnMBVDME]2 −260 (+440g) 7.36       299
[MnBVDT2−]2 −260 (+470g) 7.40       299
4-carboxy-Tempo   7.54 (pH 5.4)       140
MnTrM-2-Corrole3+ +910g 5.94       99
OsO4   9.14h       135
CeO2 (3-5 nm particles)   9.55       177
Honokiol   5.50       92
Mn texaphyrin   ∼4.48       289

Mn(III)/Mn(II) reduction potential (E½); SOD activity (O2·– dismuting catalytic rate constant, log kcat); peroxynitrite (PN) reducing activity (ONOO– reduction rate constant, log kred); lipophilicity of MnIIIP (chromatographic retention time, Rf; octanol-water partition coefficient, log Pow).

a

E½ data measured either directly in 0.05 M phosphate buffer, pH 7.8, 0.1 M NaCl, or converted accordingly to this medium, unless noted otherwise.

b

SOD activity measured by the cyt c assay in 0.05 M phosphate buffer, pH 7.8, 25 ± 1°C, unless noted otherwise.

c

Measurements in 0.05 M phosphate buffer, pH 7.4, 37 ± 0.1°C.

d

Data relative to the Rf value of MnTE-2-PyP5+ in plastic-backed silica-gel thin-layer chromatography plates eluted with 1:1:8 KNO3(sat):H2O:MeCN.

e

No SOD-like activity was observed in the presence of EDTA (283).

f

Oxidation potential only, MnIII/MnII redox couple is irreversible.

g

E½ data associated with the MnIV/III reduction potential.

h

pH 5.1–8.7.

p.r., pulse radiolysis.