5
views
0
recommends
+1 Recommend
0 collections
    0
    shares
      • Record: found
      • Abstract: found
      • Article: not found

      NBu4SH provides a convenient source of HS− soluble in organic solution for H2S and anion-binding research

      Read this article at

      ScienceOpenPublisher
      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          We report here a simple method to prepare and characterize analytically-pure NBu 4SH, which provides access to an organic-soluble source of HS .

          Abstract

          Hydrogen sulfide (H 2S) has gained significant interest within the scientific community due to its expanding roles in different (patho)physiological processes. Despite this importance, the chemical mechanisms by which H 2S exerts its action remain under-scrutinized. Biomimetic investigations in organic solution offer the potential to clarify these mechanisms and to delineate the differential reactivity between H 2S and HS . However, such studies are hampered by the lack of readily-available sources of HS that are soluble in organic solution. Here we present a simple method for preparing analytically pure tetrabutylammonium hydrosulfide (NBu 4SH), which we anticipate will be of significant utility to researchers in the H 2S and anion-binding communities.

          Related collections

          Most cited references27

          • Record: found
          • Abstract: found
          • Article: not found

          A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds anions and forms dialkylphosphate [3]rotaxanes.

          Since the discovery of crown ethers, macrocycles have been recognized as powerful platforms for supramolecular chemistry. Although their numbers and variations are now legion, macrocycles that are simple to make using high-yielding reactions in one pot and on the multigram scale are rare. Here we present such a discovery obtained during the creation of a C5-symmetric cyanostilbene 'campestarene' macrocycle, cyanostar, that employs Knoevenagel condensations in the preparation of its cyanostilbene repeat unit. In the solid state, cyanostars form π-stacked dimers constituted of chiral P and M enantiomers. The electropositive central cavity stabilizes anions with CH hydrogen-bonding units that are activated by electron-withdrawing cyano groups. In solution, the cyanostar shows high-affinity binding as 2:1 sandwich complexes, log β2 ≈ 12 and ΔG ≈ -70 kJ mol(-1), of large anions (BF4(-), ClO4(-) and PF6(-)) usually considered weakly coordinating. The cyanostar's size preference allowed formation of an unprecedented [3]rotaxane templated around a dialkylphosphate.
            Bookmark
            • Record: found
            • Abstract: found
            • Article: not found

            Biology and therapeutic potential of hydrogen sulfide and hydrogen sulfide-releasing chimeras.

            Hydrogen sulfide, H2S, is a colorless gas with a strong odor that until recently was only considered to be a toxic environmental pollutant with little or no physiological significance. However, the past few years have demonstrated its role in many biological systems and it is becoming increasingly clear that H2S is likely to join nitric oxide (NO) and carbon monoxide (CO) as a major player in mammalian biology. In this review, we have provided an overview of the chemistry and biology of H2S and have summarized the chemistry and biological activity of some natural and synthetic H2S-donating compounds. The naturally occurring compounds discussed include, garlic, sulforaphane, erucin, and iberin. The synthetic H2S donors reviewed include, GYY4137; cysteine analogs; S-propyl cysteine, S-allyl cysteine, S-propargyl cysteine, and N-acetyl cysteine. Dithiolethione and its NSAID and other chimeras such as, L-DOPA, sildenafil, aspirin, diclofenac, naproxen, ibuprofen, indomethacin, and mesalamine have also been reviewed in detail. The newly reported NOSH-aspirin that releases both NO and H2S has also been discussed. Copyright © 2012 Elsevier Inc. All rights reserved.
              Bookmark
              • Record: found
              • Abstract: found
              • Article: not found

              Chemical Characterization of the Smallest S-Nitrosothiol, HSNO; Cellular Cross-talk of H2S and S-Nitrosothiols

              Dihydrogen sulfide recently emerged as a biological signaling molecule with important physiological roles and significant pharmacological potential. Chemically plausible explanations for its mechanisms of action have remained elusive, however. Here, we report that H2S reacts with S-nitrosothiols to form thionitrous acid (HSNO), the smallest S-nitrosothiol. These results demonstrate that, at the cellular level, HSNO can be metabolized to afford NO+, NO, and NO– species, all of which have distinct physiological consequences of their own. We further show that HSNO can freely diffuse through membranes, facilitating transnitrosation of proteins such as hemoglobin. The data presented in this study explain some of the physiological effects ascribed to H2S, but, more broadly, introduce a new signaling molecule, HSNO, and suggest that it may play a key role in cellular redox regulation.
                Bookmark

                Author and article information

                Journal
                ICHBD9
                Dalton Transactions
                Dalton Trans.
                Royal Society of Chemistry (RSC)
                1477-9226
                1477-9234
                2015
                2015
                : 44
                : 46
                : 19782-19785
                Article
                10.1039/C5DT03355A
                5c6f3254-bf8a-4544-9a72-7fcd1da6ed7c
                © 2015
                History

                Comments

                Comment on this article