Interactions of polysulfanes with components of red blood cells

Schneider, Thomas; Ba, Lalla A.; Khairan, Khairan; Zwergel, Clemens; Bach, Nguyen Duc; Bernhardt, Ingolf; Brandt, Wolfgang; Wessjohann, Ludger A.; Diederich, Marc; Jacob, Claus

doi:10.1039/c0md00203h

Cited by 24 publications

(16 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Remarkably, Xu et al (280) found that DBTS-which they used as a reference standard in their anticancer assaysconsistently displayed the highest anticancer activity. As already mentioned, toxicity against normal cells may increase on increasing the number of tethering sulfur atoms, as shown by Pluth et al (35) for DBTS and DBTTS, and by Schneider et al (213) for DAS, DADS, and DATTS.…”

Section: As Lead Moleculesmentioning

confidence: 78%

SG1002 and Catenated Divalent Organic Sulfur Compounds as Promising Hydrogen Sulfide Prodrugs

Gojon¹,

Morales²

2020

Antioxidants & Redox Signaling

View full text Add to dashboard Cite

Significance: Sulfur has a critical role in protein structure/function and redox status/signaling in all living organisms. Although hydrogen sulfide (H 2 S) and sulfane sulfur (SS) are now recognized as central players in physiology and pathophysiology, the full scope and depth of sulfur metabolome's impact on human health and healthy longevity has been vastly underestimated and is only starting to be grasped. Since many pathological conditions have been related to abnormally low levels of H 2 S/SS in blood and/or tissues, and are amenable to treatment by H 2 S supplementation, development of safe and efficacious H 2 S donors deserves to be undertaken with a sense of urgency; these prodrugs also hold the promise of becoming widely used for disease prevention and as antiaging agents. Recent Advances: Supramolecular tuning of the properties of well-known molecules comprising chains of sulfur atoms (diallyl trisulfide [DATS], S 8) was shown to lead to improved donors such as DATS-loaded polymeric nanoparticles and SG1002. Encouraging results in animal models have been obtained with SG1002 in heart failure, atherosclerosis, ischemic damage, and Duchenne muscular dystrophy; with TC-2153 in Alzheimer's disease, schizophrenia, age-related memory decline, fragile X syndrome, and cocaine addiction; and with DATS in brain, colon, gastric, and breast cancer. Critical Issues: Mode-of-action studies on allyl polysulfides, benzyl polysulfides, ajoene, and 12 ringsubstituted organic disulfides and thiosulfonates led several groups of researchers to conclude that the anticancer effect of these compounds is not mediated by H 2 S and is only modulated by reactive oxygen species, and that their central model of action is selective protein S-thiolation. Future Directions: SG1002 is likely to emerge as the H 2 S donor of choice for acquiring knowledge on this gasotransmitter's effects in animal models, on account of its unique ability to efficiently generate H 2 S without byproducts and in a slow and sustained mode that is dose independent and enzyme independent. Efficient tuning of H 2 S donation characteristics of DATS, dibenzyl trisulfide, and other hydrophobic H 2 S prodrugs for both oral and parenteral administration will be achieved not only by conventional structural modification of a lead molecule but also through the new ''supramolecular tuning'' paradigm. Antioxid. Redox Signal. 33, 1010-1045.

show abstract

Section: As Lead Moleculesmentioning

confidence: 78%

SG1002 and Catenated Divalent Organic Sulfur Compounds as Promising Hydrogen Sulfide Prodrugs

Gojon¹,

Morales²

2020

Antioxidants & Redox Signaling

View full text Add to dashboard Cite

show abstract

“…Such cysteinyl- S -allylations processes can result in altered/impaired protein function [ 57 ]. In addition to the redox activity of these molecules, their lipophilicity may contribute to their biological activity (e.g., by interrupting membrane integrity, binding to hydrophobic sites on proteins) [ 18 , 58 ]. These different modes of action are summarized in Fig.…”

Section: Introductionmentioning

confidence: 99%

Redox Modulation at Work: Natural Phytoprotective Polysulfanes From Alliums Based on Redox-Active Sulfur

Ali¹,

Gould

Tinson

et al. 2018

Curr Pharmacol Rep

View full text Add to dashboard Cite

Purpose of reviewThis article provides a brief overview of natural phytoprotective products of allium with a special focus on the therapeutic potential of diallyl polysulfanes from garlic, their molecular targets and their fate in the living organisms. A comprehensive overview of antimicrobial and anticancer properties of published literature is presented for the reader to understand the effective concentrations of polysulfanes and their sensitivity towards different human pathogenic microbes, fungi, and cancer cell lines.Recent findingsThe article finds polysulfanes potentials as new generation novel antibiotics and chemo preventive agent. The effective dose rates of polysulfanes for antimicrobial properties are in the range of 0.5–40 mg/L and for anticancer 20–100 μM. The molecular targets for these redox modulators are mainly cellular thiols as well as inhibition and/or activation of certain cellular proteins in cancer cell lines.SummaryAntimicrobial and anticancer activities of polysulfanes published in the literature indicate that with further development, they could be promising candidates for cancer prevention due to their selectivity towards abnormal cells.

show abstract

“…Simply looking at the concentration, reactivity and biological impact, direct oxidative modifications of thiol groups in proteins, enzymes or indeed oxidation of GSH are more likely to occur, and therefore cellular redox homeostasis and signalling pathways of the cellular thiolstat become affected [2,50,51]. As above, the interaction of such organic polysulfanes with GSNO via H 2 S may become only relevant under certain, exceptional conditions, for instance during periods of low peptide or protein thiol content.…”

Section: Resultsmentioning

confidence: 99%

Inorganic Reactive Sulfur-Nitrogen Species: Intricate Release Mechanisms or Cacophony in Yellow, Blue and Red?

et al. 2017

Self Cite

View full text Add to dashboard Cite

Since the heydays of Reactive Sulfur Species (RSS) research during the first decade of the Millennium, numerous sulfur species involved in cellular regulation and signalling have been discovered. Yet despite the general predominance of organic species in organisms, recent years have also seen the emergence of inorganic reactive sulfur species, ranging from inorganic polysulfides (HSx−/Sx2−) to thionitrous acid (HSNO) and nitrosopersulfide (SSNO−). These inorganic species engage in a complex interplay of reactions in vitro and possibly also in vivo. Employing a combination of spectrophotometry and sulfide assays, we have investigated the role of polysulfanes from garlic during the release of nitric oxide (•NO) from S-nitrosoglutathione (GSNO) in the absence and presence of thiol reducing agents. Our studies reveal a distinct enhancement of GSNO decomposition by compounds such as diallyltrisulfane, which is most pronounced in the presence of cysteine and glutathione and presumably proceeds via the initial release of an inorganic mono- or polysulfides, i.e., hydrogen sulfide (H2S) or HSx−, from the organic polysulfane. Albeit being of a preliminary nature, our spectrophotometric data also reveals a complicated underlying mechanism which appears to involve transient species such as SSNO−. Eventually, more in depth studies are required to further explore the underlying chemistry and wider biological and nutritional implications of this interplay between edible garlic compounds, reductive activation, inorganic polysulfides and their interplay with •NO storage and release.

show abstract

Interactions of polysulfanes with components of red blood cells

Cited by 24 publications

References 24 publications

SG1002 and Catenated Divalent Organic Sulfur Compounds as Promising Hydrogen Sulfide Prodrugs

SG1002 and Catenated Divalent Organic Sulfur Compounds as Promising Hydrogen Sulfide Prodrugs

Redox Modulation at Work: Natural Phytoprotective Polysulfanes From Alliums Based on Redox-Active Sulfur

Inorganic Reactive Sulfur-Nitrogen Species: Intricate Release Mechanisms or Cacophony in Yellow, Blue and Red?

Contact Info

Product

Resources

About