New Biologically Active Hydrogen Sulfide Donors

Roger, Thomas; Raynaud, Françoise; Bouillaud, Frédéric; Ransy, Céline; Simonet, Serge; Crespo, Christine; Bourguignon, Marie-Pierre; Villeneuve, Nicole; Vilaine, Jean‐Paul; Artaud, Isabelle; Galardon, Erwan

doi:10.1002/cbic.201300552

Cited by 63 publications

(49 citation statements)

References 38 publications

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“…Dithioperoxyanhydrides have been reported as another type of thiol-activated H 2 S donors (Roger et al 2013). These compounds have some similarity with the perthiol-based donors, owing to the disulfide linkage in their structures.…”

Section: Dithioperoxyanhydridesmentioning

confidence: 99%

Medicinal Chemistry: Insights into the Development of Novel H2S Donors

Zhao

Pacheco

Xian

2015

Handbook of Experimental Pharmacology

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Hydrogen sulfide (H2S) was traditionally considered as a toxic gas. However, recent studies have demonstrated H2S is an endogenously generated gaseous signaling molecule (gasotransmitter) with importance on par with that of two other well-known endogenous gasotransmitters, nitric oxide (NO) and carbon monoxide (CO). Although H2S's exact mechanisms of action are still under investigation, the production of endogenous H2S and the exogenous administration of H2S have been demonstrated to elicit a wide range of physiological responses including modulation of blood pressure and protection of ischemia reperfusion injury, exertion of anti-inflammatory effects, and reduction of metabolic rate. These results strongly suggest that modulation of H2S levels could have potential therapeutic values. In this regard, synthetic H2S-releasing agents (i.e., H2S donors) are not only important research tools, but also potential therapeutic agents. This chapter summarizes the knowledge of currently available H2S donors. Their preparation, H2S releasing mechanisms, and biological applications are discussed.

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Section: Dithioperoxyanhydridesmentioning

confidence: 99%

Medicinal Chemistry: Insights into the Development of Novel H2S Donors

Zhao

Pacheco

Xian

2015

Handbook of Experimental Pharmacology

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“…137 These donors were synthesized by either iodine oxidation of the thiocarboxylates 138 or reactions between thiocarboxylic acids and methoxycarbonylsulfenyl chloride 139 (Scheme 17). H 2 S release was confirmed in both buffers and cellular lysates.…”

Section: H2s Donorsmentioning

confidence: 99%

Hydrogen sulfide (H₂S) releasing agents: chemistry and biological applications

2014

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Hydrogen sulfide (H2S) is a newly recognized signaling molecule with very potent cytoprotective actions. The fields of H2S physiology and pharmacology have been rapidly growing in recent years, but a number of fundamental issues must be addressed to advance our understanding of the biology and clinical potential of H2S in the future. Hydrogen sulfide releasing agents (also known as H2S donors) have been widely used in the field. These compounds are not only useful research tools, but also potential therapeutic agents. It is therefore important to study the chemistry and pharmacology of exogenous H2S and to be aware of the limitations associated with the choice of donors used to generate H2S in vitro and in vivo. In this review we summarized the developments and limitations of current available donors including H2S gas, sulfide salts, garlic-derived sulfur compounds, Lawesson’s reagent/analogs, 1,2-dithiole-3-thiones, thiol-activated donors, photo-caged donors, and thioamino acids. Some biological applications of these donors were also discussed.

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“…The need to develop donors with improved properties for use as research tools and potential therapeutic agents, led to the synthesis of thioaminoacids , arylthioamides (Martelli et al, 2013), N-mercapto (N-SH)-based derivatives (Zhao et al, 2011(Zhao et al, , 2015, 1,2-dithiole-3-thiones (Caliendo et al, 2010), dithioperoxyanhydrides (Roger et al, 2013), and photoinduced (Zheng et al, 2015) and esterasesensitive prodrugs (Zheng et al, 2016) as H 2 S donors. Water solubility, oral bioavailability, an intermediate H 2 S release rate, and generation of H 2 S in a controlled fashion (as, for example, after enzymatic activation), are among the desirable properties of an "ideal" donor.…”

Section: Introductionmentioning

confidence: 99%

Cardioprotection by H2S Donors: Nitric Oxide-Dependent and -Independent Mechanisms

Chatzianastasiou

Bibli²,

Andreadou³

et al. 2016

Journal of Pharmacology and Experimental Therapeutics

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Hydrogen sulfide (H 2 S) is a signaling molecule with protective effects in the cardiovascular system. To harness the therapeutic potential of H 2 S, a number of donors have been developed. The present study compares the cardioprotective actions of representative H 2 S donors from different classes and studies their mechanisms of action in myocardial injury in vitro and in vivo. Exposure of cardiomyocytes to H 2 O 2 led to significant cytotoxicity, which was inhibited by sodium sulfide (Na 2 S), thiovaline (TV), GYY4137[morpholin-4-ium 4 methoxyphenyl(morpholino) phosphinodithioate], and AP39 [(10-oxo-10-(4-(3-thioxo-3H-1,2-dithiol5yl)-phenoxy)decyl) triphenylphospho-nium bromide]. Inhibition of nitric oxide (NO) synthesis prevented the cytoprotective effects of Na 2 S and TV, but not GYY4137 and AP39, against H 2 O 2 -induced cardiomyocyte injury. Mice subjected to left anterior descending coronary ligation were protected from ischemia-reperfusion injury by the H 2 S donors tested. Inhibition of nitric oxide synthase (NOS) in vivo blocked only the beneficial effect of Na 2 S. Moreover, Na 2 S, but not AP39, administration enhanced the phosphorylation of endothelial NOS and vasodilator-associated phosphoprotein. Both Na 2 S and AP39 reduced infarct size in mice lacking cyclophilin-D (CypD), a modulator of the mitochondrial permeability transition pore (PTP). Nevertheless, only AP39 displayed a direct effect on mitochondria by increasing the mitochondrial Ca 21 retention capacity, which is evidence of decreased propensity to undergo permeability transition. We conclude that although all the H 2 S donors we tested limited infarct size, the pathways involved were not conserved. Na 2 S had no direct effects on PTP opening, and its action was nitric oxide dependent. In contrast, the cardioprotection exhibited by AP39 could result from a direct inhibitory effect on PTP acting at a site different than CypD.

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New Biologically Active Hydrogen Sulfide Donors

Cited by 63 publications

References 38 publications

Medicinal Chemistry: Insights into the Development of Novel H2S Donors

Medicinal Chemistry: Insights into the Development of Novel H2S Donors

Hydrogen sulfide (H₂S) releasing agents: chemistry and biological applications

Cardioprotection by H2S Donors: Nitric Oxide-Dependent and -Independent Mechanisms

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New Biologically Active Hydrogen Sulfide Donors

Cited by 63 publications

References 38 publications

Medicinal Chemistry: Insights into the Development of Novel H2S Donors

Medicinal Chemistry: Insights into the Development of Novel H2S Donors

Hydrogen sulfide (H2S) releasing agents: chemistry and biological applications

Cardioprotection by H2S Donors: Nitric Oxide-Dependent and -Independent Mechanisms

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Product

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Hydrogen sulfide (H₂S) releasing agents: chemistry and biological applications