Simultaneous nitrosylation and N-nitrosation of a Ni-thiolate model complex of Ni-containing SOD

Truong, Phan T.; Broering, Ellen P.; Dzul, Stephen P.; Chakraborty, Indranil; Stemmler, Timothy L.; Harrop, Todd C.

doi:10.1039/C8SC03321H

Title: Simultaneous nitrosylation and N-nitrosation of a Ni-thiolate model complex of Ni-containing SOD

Journal Article · Wed Nov 21 00:00:00 EST 2018 · Chemical Science

DOI:https://doi.org/10.1039/C8SC03321H· OSTI ID:1471780

^[1];

^[1]; Dzul, Stephen P. ^[2]; Chakraborty, Indranil ^[3]; Stemmler, Timothy L. ^[2];

^[1]

Department of Chemistry, Center for Metalloenzyme Studies, The University of Georgia, Athens, USA
Departments of Pharmaceutical Sciences, Biochemistry, and Molecular Biology, Wayne State University, Detroit, USA
Department of Chemistry and Biochemistry, Florida International University, Miami, USA

Nitric oxide (NO) is used as a substrate analogue/spectroscopic probe of metal sites that bind and activate oxygen and its derivatives. To assess the interaction of superoxide with the Ni center in Ni-containing superoxide dismutase (NiSOD), we studied the reaction of NO⁺ and NO with the model complex, Et₄N[Ni(nmp)(SPh-o-NH₂-p-CF₃)] (1; nmp^2– = dianion of N-(2-mercaptoethyl)picolinamide; ^–SPh-o-NH₂-p-CF₃ = 2-amino-4-(trifluoromethyl)benzenethiolate) and its oxidized analogue 1ox, respectively. The ultimate products of these reactions are the disulfide of ^–SPh-o-NH₂-p-CF₃ and the S,S-bridged tetrameric complex [Ni₄(nmp)₄], a result of S-based redox activity. However, introduction of NO to 1 affords the green dimeric {NiNO}¹⁰ complex (Et₄N)₂[{Ni(κ²-SPh-o-NNO-p-CF₃)(NO)}₂] (2) via NO-induced loss of nmp^2– as the disulfide and N-nitrosation of the aromatic thiolate. Complex 2 was characterized by X-ray crystallography and several spectroscopies. These measurements are in-line with other tetrahedral complexes in the {NiNO}¹⁰ classification. In contrast to the established stability of this metal-nitrosyl class, the Ni–NO bond of 2 is labile and release of NO from this unit was quantified by trapping the NO with a Co^II–porphyrin (70–80% yield). In the process, the Ni ends up coordinated by two o-nitrosaminobenzenethiolato ligands to result in the structurally characterized trans-(Et₄N)₂[Ni(SPh-o-NNO-p-CF₃)₂] (3), likely by a disproportionation mechanism. The isolation and characterization of 2 and 3 suggest that: (i) the strongly donating thiolates dominate the electronic structure of Ni-nitrosyls that result in less covalent Ni–NO bonds, and (ii) superoxide undergoes disproportionation via an outer-sphere mechanism in NiSOD as complexes in the {NiNO}^9/8 state have yet to be isolated.

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Research Organization:: SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Biological and Environmental Research (BER); National Science Foundation (NSF); National Institutes of Health (NIH)

Grant/Contract Number:: AC02-76SF00515; CHE-1506375; DK068139; DK101230; 1S10RR028859-01

OSTI ID:: 1471780

Alternate ID(s):: OSTI ID: 1624965

Journal Information:: Chemical Science, Journal Name: Chemical Science Vol. 9 Journal Issue: 45; ISSN 2041-6520

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

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Cited by: 2 works

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