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Manganese Porphyrin-Based SOD Mimetics Produce Polysulfides from Hydrogen Sulfide

Indiana University School of Medicine—South Bend, South Bend, IN 46617, USA
Department of Biological Sciences, University of Notre Dame, Notre Dame, IN 46556, USA
Department of Electrical Engineering, University of Notre Dame, Notre Dame, IN 46556, USA
Department of Radiation Oncology, School of Medicine, Duke University, Durham, NC 27710, USA
Department of Chemistry, Sonoma State University, Rohnert Park, CA 94928, USA
NIHR Southampton Biomedical Research Center, University of Southampton, Southampton, General Hospital, Southampton SO16 6YD, UK
Clinical & Experimental Sciences, Faculty of Medicine, Southampton General Hospital and Institute for Life Sciences, University of Southampton, Southampton SO16 6YD, UK
Central Arkansas Veteran’s Healthcare System, Little Rock, AR 72205, USA
Departments of Medicine and Biochemistry, University of Arkansas for Medical Sciences, Little Rock, AR 72202, USA
Author to whom correspondence should be addressed.
Antioxidants 2019, 8(12), 639;
Received: 22 November 2019 / Revised: 4 December 2019 / Accepted: 6 December 2019 / Published: 12 December 2019
(This article belongs to the Special Issue Redox Regulation of Cell Signalling)
Manganese-centered porphyrins (MnPs), MnTE-2-PyP5+ (MnTE), MnTnHex-2-PyP5+ (MnTnHex), and MnTnBuOE-2-PyP5+ (MnTnBuOE) have received considerable attention because of their ability to serve as superoxide dismutase (SOD) mimetics thereby producing hydrogen peroxide (H2O2), and oxidants of ascorbate and simple aminothiols or protein thiols. MnTE-2-PyP5+ and MnTnBuOE-2-PyP5+ are now in five Phase II clinical trials warranting further exploration of their rich redox-based biology. Previously, we reported that SOD is also a sulfide oxidase catalyzing the oxidation of hydrogen sulfide (H2S) to hydrogen persulfide (H2S2) and longer-chain polysulfides (H2Sn, n = 3–7). We hypothesized that MnPs may have similar actions on sulfide metabolism. H2S and polysulfides were monitored in fluorimetric assays with 7-azido-4-methylcoumarin (AzMC) and 3′,6′-di(O-thiosalicyl)fluorescein (SSP4), respectively, and specific polysulfides were further identified by mass spectrometry. MnPs concentration-dependently consumed H2S and produced H2S2 and subsequently longer-chain polysulfides. This reaction appeared to be O2-dependent. MnP absorbance spectra exhibited wavelength shifts in the Soret and Q bands characteristic of sulfide-mediated reduction of Mn. Taken together, our results suggest that MnPs can become efficacious activators of a variety of cytoprotective processes by acting as sulfide oxidation catalysts generating per/polysulfides. View Full-Text
Keywords: H2S; reactive sulfur species; reactive oxygen species; Mn porphyrins; BMX-001; antioxidants H2S; reactive sulfur species; reactive oxygen species; Mn porphyrins; BMX-001; antioxidants
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Olson, K.R.; Gao, Y.; Arif, F.; Patel, S.; Yuan, X.; Mannam, V.; Howard, S.; Batinic-Haberle, I.; Fukuto, J.; Minnion, M.; Feelisch, M.; Straub, K.D. Manganese Porphyrin-Based SOD Mimetics Produce Polysulfides from Hydrogen Sulfide. Antioxidants 2019, 8, 639.

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