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Hydrogen Sulfide (H2S)-Donor Molecules: Chemical, Biological, and Therapeutical Tools
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Hydrogen Sulfide (H2S)-Donor Molecules: Chemical, Biological, and Therapeutical Tools

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Molecular Pharmacology".

Deadline for manuscript submissions: closed (30 May 2023) | Viewed by 11715

Special Issue Editors

Prof. Dr. Giuseppe Caliendo

E-Mail Website
Guest Editor
Department of Pharmacy, School of Medicine, University of Naples Federico II, Via D. Montesano 49, 80131 Napoli, Italy
Interests: drug discovery; medicinal chemistry; green chemistry; small molecules; peptides; peptidomimetics; heterocyclic compounds
Dr. Angela Corvino

E-Mail Website
Guest Editor
Department of Pharmacy, School of Medicine, University of Naples Federico II, Via D. Montesano 49, 80131 Napoli, Italy
Interests: medicinal chemistry; drug design; synthesis; small-molecules; peptides; peptido-mimetics

Special Issue Information

Dear Colleagues,

Hydrogen sulfide (H2S) has been recognized as the third endogenous pleiotropic gasotransmitter, along with nitric oxide and carbon monoxide, playing a significant role in many biological processes. Since endogenous concentrations of this gaseous signaling molecule are generally low, to better define its physio–pathological functions, exogenous sources of H2S are needed. On this basis, the challenge for many research groups is the development of H2S-donor molecules that are able to release H2S in a tightly controlled way, mimicking the physiological production of this gas. Thus, the identification of novel chemical tools could be useful to further investigate the involvement of H2S both in health and disease states.

The aim of this Special Issue is to collect novel research regarding H2S-releasing compounds as innovative pharmacological tools and to provide further evidence of the crucial role of H2S in physiological and pathological processes.

Prof. Dr. Giuseppe Caliendo
Dr. Angela Corvino
Guest Editors

Manuscript Submission Information

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Keywords

  • hydrogen sulfide (H2S)
  • H2S-donors
  • hybrids
  • pharmacological tools
  • cell signaling

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Published Papers (6 papers)

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Editorial

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3 pages, 508 KiB  
Editorial
Hydrogen Sulfide (H2S)-Donor Molecules: Chemical, Biological, and Therapeutical Tools
by Angela Corvino and Giuseppe Caliendo
Int. J. Mol. Sci. 2024, 25(14), 7932; https://doi.org/10.3390/ijms25147932 - 20 Jul 2024
Viewed by 899
Abstract
This Special Issue aims to gather new research on hydrogen sulfide (H2S)-releasing compounds (Figure 1) as cutting-edge pharmacological tools and to advance the understanding of the critical role that H2S plays in physiological and pathological processes [...] Full article
(This article belongs to the Special Issue Hydrogen Sulfide (H2S)-Donor Molecules: Chemical, Biological, and Therapeutical Tools)
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Research

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15 pages, 3415 KiB  
Article
Characterization of Glutathione Dithiophosphates as Long-Acting H2S Donors
by Rezeda A. Ishkaeva, Nail N. Khaertdinov, Aleksey V. Yakovlev, Marina V. Esmeteva, Diana V. Salakhieva, Ilyas S. Nizamov, Guzel F. Sitdikova and Timur I. Abdullin
Int. J. Mol. Sci. 2023, 24(13), 11063; https://doi.org/10.3390/ijms241311063 - 4 Jul 2023
Viewed by 1691
Abstract
Considering the important cytoprotective and signaling roles but relatively narrow therapeutic index of hydrogen sulfide (H2S), advanced H2S donors are required to achieve a therapeutic effect. In this study, we proposed glutathione dithiophosphates as new combination donors of H [...] Read more.
Considering the important cytoprotective and signaling roles but relatively narrow therapeutic index of hydrogen sulfide (H2S), advanced H2S donors are required to achieve a therapeutic effect. In this study, we proposed glutathione dithiophosphates as new combination donors of H2S and glutathione. The kinetics of H2S formation in dithiophosphate solutions suggested a continuous H2S release by the donors, which was higher for the dithiophosphate of reduced glutathione than oxidized glutathione. The compounds, unlike NaHS, inhibited the proliferation of C2C12 myoblasts at submillimolar concentrations due to an efficient increase in intracellular H2S. The H2S donors more profoundly affected reactive oxygen species and reduced glutathione levels in C2C12 myocytes, in which these parameters were elevated compared to myoblasts. Oxidized glutathione dithiophosphate as well as control donors exerted antioxidant action toward myocytes, whereas the effect of reduced glutathione dithiophosphate at (sub-)micromolar concentrations was rather modulating. This dithiophosphate showed an enhanced negative inotropic effect mediated by H2S upon contraction of the atrial myocardium, furthermore, its activity was prolonged and reluctant for washing. These findings identify glutathione dithiophosphates as redox-modulating H2S donors with long-acting profile, which are of interest for further pharmacological investigation. Full article
(This article belongs to the Special Issue Hydrogen Sulfide (H2S)-Donor Molecules: Chemical, Biological, and Therapeutical Tools)
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11 pages, 2479 KiB  
Article
Erucin, an H2S-Releasing Isothiocyanate, Exerts Anticancer Effects in Human Triple-Negative Breast Cancer Cells Triggering Autophagy-Dependent Apoptotic Cell Death
by Ivana Bello, Martina Smimmo, Roberta d’Emmanuele di Villa Bianca, Mariarosaria Bucci, Giuseppe Cirino, Elisabetta Panza and Vincenzo Brancaleone
Int. J. Mol. Sci. 2023, 24(7), 6764; https://doi.org/10.3390/ijms24076764 - 5 Apr 2023
Cited by 8 | Viewed by 2694
Abstract
Breast cancer is the most frequent form of cancer occurring in women of any age. Among the different types, the triple-negative breast cancer (TNBC) subtype is recognized as the most severe form, being associated with the highest mortality rate. Currently, there are no [...] Read more.
Breast cancer is the most frequent form of cancer occurring in women of any age. Among the different types, the triple-negative breast cancer (TNBC) subtype is recognized as the most severe form, being associated with the highest mortality rate. Currently, there are no effective treatments for TNBC. For this reason, the research of novel therapeutics is urgently needed. Natural products and their analogs have historically made a major contribution to pharmacotherapy and the treatment of various human diseases, including cancer. In this study, we explored the potential anti-cancer effects of erucin, the most abundant H2S-releasing isothiocyanate present in arugula (Eruca sativa) in MDA-MB-231 cells, a validated in vitro model of TNBC. We found that erucin, in a concentration-dependent manner, significantly inhibited MDA-MB-231 cell proliferation by inducing apoptosis and autophagy. Additionally, erucin prevented intracellular ROS generation promoting the expression of key antioxidant genes and halted MDA-MB-231 cell migration, invasion, and colony formation. In conclusion, using a cellular and molecular biology approach, we show that the consumption of erucin could represent a novel and promising strategy for intervention against TNBC. Full article
(This article belongs to the Special Issue Hydrogen Sulfide (H2S)-Donor Molecules: Chemical, Biological, and Therapeutical Tools)
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22 pages, 6260 KiB  
Article
Design, Synthesis and Evaluation of Novel Molecular Hybrids between Antiglaucoma Drugs and H2S Donors
by Rosa Sparaco, Valentina Citi, Elisa Magli, Alma Martelli, Eugenia Piragine, Vincenzo Calderone, Giorgia Andreozzi, Elisa Perissutti, Francesco Frecentese, Vincenzo Santagada, Giuseppe Caliendo, Beatrice Severino, Angela Corvino and Ferdinando Fiorino
Int. J. Mol. Sci. 2022, 23(22), 13804; https://doi.org/10.3390/ijms232213804 - 9 Nov 2022
Cited by 4 | Viewed by 1900
Abstract
Glaucoma is a group of eye diseases consisting of optic nerve damage with corresponding loss of field vision and blindness. Hydrogen sulfide (H2S) is a gaseous neurotransmitter implicated in various pathophysiological processes. It is involved in the pathological mechanism of glaucomatous [...] Read more.
Glaucoma is a group of eye diseases consisting of optic nerve damage with corresponding loss of field vision and blindness. Hydrogen sulfide (H2S) is a gaseous neurotransmitter implicated in various pathophysiological processes. It is involved in the pathological mechanism of glaucomatous neuropathy and exerts promising effects in the treatment of this disease. In this work, we designed and synthetized new molecular hybrids between antiglaucoma drugs and H2S donors to combine the pharmacological effect of both moieties, providing a heightened therapy. Brinzolamide, betaxolol and brimonidine were linked to different H2S donors. The H2S-releasing properties of the new compounds were evaluated in a phosphate buffer solution by the amperometric approach, and evaluated in human primary corneal epithelial cells (HCEs) by spectrofluorometric measurements. Experimental data showed that compounds 1c, 1d and 3d were the hybrids with the best properties, characterized by a significant and long-lasting production of the gasotransmitter both in the aqueous solution (in the presence of L-cysteine) and in the intracellular environment. Because, to date, the donation of H2S by antiglaucoma H2S donor hybrids using non-immortalized corneal cells has never been reported, these results pave the way to further investigation of the potential efficacy of the newly synthesized compounds. Full article
(This article belongs to the Special Issue Hydrogen Sulfide (H2S)-Donor Molecules: Chemical, Biological, and Therapeutical Tools)
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23 pages, 4542 KiB  
Article
Vasoactive Effects of Chronic Treatment with Fructose and Slow-Releasing H2S Donor GYY-4137 in Spontaneously Hypertensive Rats: The Role of Nitroso and Sulfide Signalization
by Andrea Berenyiova, Martina Cebova, Basak Gunes Aydemir, Samuel Golas, Miroslava Majzunova and Sona Cacanyiova
Int. J. Mol. Sci. 2022, 23(16), 9215; https://doi.org/10.3390/ijms23169215 - 16 Aug 2022
Cited by 3 | Viewed by 1633
Abstract
Increased fructose consumption induces metabolic-syndrome-like pathologies and modulates vasoactivity and the participation of nitric oxide (NO) and hydrogen sulfide (H2S). We investigated whether a slow-releasing H2S donor, GYY-4137, could exert beneficial activity in these conditions. We examined the effect [...] Read more.
Increased fructose consumption induces metabolic-syndrome-like pathologies and modulates vasoactivity and the participation of nitric oxide (NO) and hydrogen sulfide (H2S). We investigated whether a slow-releasing H2S donor, GYY-4137, could exert beneficial activity in these conditions. We examined the effect of eight weeks of fructose intake on the blood pressure, biometric parameters, vasoactive responses, and NO and H2S pathways in fructose-fed spontaneously hypertensive rats with or without three weeks of GYY-4137 i.p. application. GYY-4137 reduced triacylglycerol levels and blood pressure, but not adiposity, and all were increased by fructose intake. Fructose intake generally enhanced endothelium-dependent vasorelaxation, decreased adrenergic contraction, and increased protein expression of interleukin-6 (IL-6), tumor necrosis factor alpha (TNFα), and concentration of conjugated dienes in the left ventricle (LV). Although GYY-4137 administration did not affect vasorelaxant responses, it restored disturbed contractility, LV oxidative damage and decreased protein expression of TNFα in fructose-fed rats. While the participation of endogenous H2S in vasoactive responses was not affected by fructose treatment, the expression of H2S-producing enzyme cystathionine β-synthase in the LV was increased, and the stimulation of the NO signaling pathway improved endothelial function in the mesenteric artery. On the other hand, chronic treatment with GYY-4137 increased the expression of H2S-producing enzyme cystathionine γ-lyase in the LV and stimulated the beneficial pro-relaxant and anti-contractile activity of endogenous H2S in thoracic aorta. Our results suggest that sulfide and nitroso signaling pathways could trigger compensatory vasoactive responses in hypertensive rats with metabolic disorder. A slow H2S-releasing donor could partially amend metabolic-related changes and trigger beneficial activity of endogenous H2S. Full article
(This article belongs to the Special Issue Hydrogen Sulfide (H2S)-Donor Molecules: Chemical, Biological, and Therapeutical Tools)
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Review

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16 pages, 1502 KiB  
Review
Plants and Mushrooms as Possible New Sources of H2S Releasing Sulfur Compounds
by Valentina Citi, Marco Passerini, Vincenzo Calderone and Lara Testai
Int. J. Mol. Sci. 2023, 24(15), 11886; https://doi.org/10.3390/ijms241511886 - 25 Jul 2023
Cited by 3 | Viewed by 1994
Abstract
Hydrogen sulfide (H2S), known for many decades exclusively for its toxicity and the smell of rotten eggs, has been re-discovered for its pleiotropic effects at the cardiovascular and non-cardiovascular level. Therefore, great attention is being paid to the discovery of molecules [...] Read more.
Hydrogen sulfide (H2S), known for many decades exclusively for its toxicity and the smell of rotten eggs, has been re-discovered for its pleiotropic effects at the cardiovascular and non-cardiovascular level. Therefore, great attention is being paid to the discovery of molecules able to release H2S in a smart manner, i.e., slowly and for a long time, thus ensuring the maintenance of its physiological levels and preventing “H2S-poor” diseases. Despite the development of numerous synthetically derived molecules, the observation that plants containing sulfur compounds share the same pharmacological properties as H2S led to the characterization of naturally derived compounds as H2S donors. In this regard, polysulfuric compounds occurring in plants belonging to the Alliaceae family were the first characterized as H2S donors, followed by isothiocyanates derived from vegetables belonging to the Brassicaceae family, and this led us to consider these plants as nutraceutical tools and their daily consumption has been demonstrated to prevent the onset of several diseases. Interestingly, sulfur compounds are also contained in many fungi. In this review, we speculate about the possibility that they may be novel sources of H2S-donors, furnishing new data on the release of H2S from several selected extracts from fungi. Full article
(This article belongs to the Special Issue Hydrogen Sulfide (H2S)-Donor Molecules: Chemical, Biological, and Therapeutical Tools)
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