Inorganic sulfur–nitrogen compounds: from gunpowder chemistry to the forefront of biological signaling

Cortese‐Krott, Miriam M.; Butler, Anthony R.; Woollins, J. Derek; Feelisch, Martin

doi:10.1039/c5dt05034k

Cited by 64 publications

(61 citation statements)

References 114 publications

(201 reference statements)

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“…The thiol in l ‐cysteine acts as a strong electron donor that facilitates the formation of high‐valent metal intermediates . Similarly, hydrogen sulfide plays a role in biological signaling . Therefore, an understanding of metal‐sulfur coordination chemistry is important to both the problems of biology and chemical industry …”

Section: Introductionsupporting

confidence: 51%

Coordination Chemistry of Organoruthenium Compounds with Benzoylthiourea Ligands and their Biological Properties

Parveen

Tong

Rauf

et al. 2019

Chemistry An Asian Journal

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Benzoylthiourea derivatives feature several donor atoms capable of coordinating to metal centers. We report here a series of Ru(η6‐p‐cymene) complexes employing benzoylthiourea derivatives as ligands. Such ligands often coordinate to metal centers through their S and O donor atoms. We isolated complexes where the ligands were mono‐ or bidentately coordinated to Ru involving the S donor atom and surprisingly in bidentate coordination mode a deprotonated thiourea nitrogen resulting in a 4‐membered ring structure around the metal center. DFT calculations were used to explain the differences in coordination behavior. These were complemented by stability studies and biological investigations of the compounds as anticancer agents. Several of the synthesized derivatives exhibited significant cell growth inhibitory activity, with the complexes featuring bidentate ligands being more potent than their monodentate counterparts. This can be explained by the higher stability of the former under the conditions employed in cell culture assays.

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Section: Introductionsupporting

confidence: 51%

Coordination Chemistry of Organoruthenium Compounds with Benzoylthiourea Ligands and their Biological Properties

Parveen

Tong

Rauf

et al. 2019

Chemistry An Asian Journal

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“…Intriguingly, and within the same context, a similar “reactive sulfur nitrogen species” was postulated in 2014 by an international group led by Martin Feelisch [86]. This nitrosopersulfide anion (SSNO − ) seemed to be a more stable intermediate following the thionitrite anion (SNO − ) in a cascade of unusual RS(N)S explaining eventually the sustained bioactivity of • NO.…”

Section: What Are Rss?mentioning

confidence: 79%

The Reactive Sulfur Species Concept: 15 Years On

et al. 2017

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Fifteen years ago, in 2001, the concept of “Reactive Sulfur Species” or RSS was advocated as a working hypothesis. Since then various organic as well as inorganic RSS have attracted considerable interest and stimulated many new and often unexpected avenues in research and product development. During this time, it has become apparent that molecules with sulfur-containing functional groups are not just the passive “victims” of oxidative stress or simple conveyors of signals in cells, but can also be stressors in their own right, with pivotal roles in cellular function and homeostasis. Many “exotic” sulfur-based compounds, often of natural origin, have entered the fray in the context of nutrition, ageing, chemoprevention and therapy. In parallel, the field of inorganic RSS has come to the forefront of research, with short-lived yet metabolically important intermediates, such as various sulfur-nitrogen species and polysulfides (Sx2−), playing important roles. Between 2003 and 2005 several breath-taking discoveries emerged characterising unusual sulfur redox states in biology, and since then the truly unique role of sulfur-dependent redox systems has become apparent. Following these discoveries, over the last decade a “hunt” and, more recently, mining for such modifications has begun—and still continues—often in conjunction with new, innovative and complex labelling and analytical methods to capture the (entire) sulfur “redoxome”. A key distinction for RSS is that, unlike oxygen or nitrogen, sulfur not only forms a plethora of specific reactive species, but sulfur also targets itself, as sulfur containing molecules, i.e., peptides, proteins and enzymes, preferentially react with RSS. Not surprisingly, today this sulfur-centred redox signalling and control inside the living cell is a burning issue, which has moved on from the predominantly thiol/disulfide biochemistry of the past to a complex labyrinth of interacting signalling and control pathways which involve various sulfur oxidation states, sulfur species and reactions. RSS are omnipresent and, in some instances, are even considered as the true bearers of redox control, perhaps being more important than the Reactive Oxygen Species (ROS) or Reactive Nitrogen Species (RNS) which for decades have dominated the redox field. In other(s) words, in 2017, sulfur redox is “on the rise”, and the idea of RSS resonates throughout the Life Sciences. Still, the RSS story isn’t over yet. Many RSS are at the heart of “mistaken identities” which urgently require clarification and may even provide the foundations for further scientific revolutions in the years to come. In light of these developments, it is therefore the perfect time to revisit the original hypotheses, to select highlights in the field and to question and eventually update our concept of “Reactive Sulfur Species”.

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“…This observation is significant because it further confirms that metal sulfides can play a regulatory role in vivo with respect to NO availability (e.g., so-called NO/H 2 S "cross talk"). 4,36,37 We have also discovered that oxidation of [SNO] -with NO results in formation of [SSNO] -. This represents a new route to [SSNO] -, and provides us with a better understanding of the fundamental chemistry of this important, but poorly understood, ion.…”

mentioning

confidence: 99%