Table 1.
Selected Physicochemical Properties of Some SOD Mimics
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Lipophilicity |
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|---|---|---|---|---|---|---|
| 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).
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.
SOD activity measured by the cyt c assay in 0.05 M phosphate buffer, pH 7.8, 25 ± 1°C, unless noted otherwise.
Measurements in 0.05 M phosphate buffer, pH 7.4, 37 ± 0.1°C.
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.
No SOD-like activity was observed in the presence of EDTA (283).
Oxidation potential only, MnIII/MnII redox couple is irreversible.
E½ data associated with the MnIV/III reduction potential.
pH 5.1–8.7.
p.r., pulse radiolysis.