954. New syntheses of trisulphides

Milligan, Brian; Saville, B.; Swan, JM

doi:10.1039/jr9610004850

Cited by 47 publications

(26 citation statements)

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“…DAS and DADS were purchased from Tokyo Kasei Kogyo Co., Ltd. (Tokyo, Japan). DATS was synthesized by using Bunte salt (17). DATS and commercial DADS were purified by high pressure liquid chromatography (Alliance 2695 system; Waters Co., Milford, MA) on an Inertsil ODS-3 column (6 mm ϫ 250 mm; GL Science, Tokyo, Japan).…”

Section: Methodsmentioning

confidence: 99%

Diallyl Trisulfide Suppresses the Proliferation and Induces Apoptosis of Human Colon Cancer Cells through Oxidative Modification of β-Tubulin

Hosono¹,

Fukao²,

Ogihara

et al. 2005

Journal of Biological Chemistry

218

157

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Allyl sulfides are characteristic flavor components obtained from garlic. These sulfides are thought to be responsible for their epidemiologically proven anticancer effect on garlic eaters. This study was aimed at clarifying the molecular basis of this anticancer effect of garlic by using human colon cancer cell lines HCT-15 and DLD-1. The growth of the cells was significantly suppressed by diallyl trisulfide (DATS, HCT-15 IC 50 ‫؍‬ 11.5 M, DLD-1 IC 50 ‫؍‬ 13.3 M); however, neither diallyl monosulfide nor diallyl disulfide showed such an effect. The proportion of HCT-15 and that of DLD-1 cells residing at the G 1 and S phases were decreased by DATS, and their populations at the G 2 /M phase were markedly increased for up to 12 h. The cells with a sub-G 1 DNA content were increased thereafter. Caspase-3 activity was also dramatically increased by DATS. Fluorescence-activated cell sorter analysis performed on the cells arrested at the G 1 /S boundary revealed cell cycle-dependent induction of apoptosis through the transition of the G 2 /M phase to the G 1 phase by DATS. DATS inhibited tubulin polymerization in an in vitro cell-free system. DATS disrupted microtubule network formation of the cells, and microtubule fragments could be seen at the interphase. Peptide mass mapping by liquid chromatography-tandem mass spectrometry analysis for DATS-treated tubulin demonstrated that there was a specific oxidative modification of cysteine residues Cys-12␤ and Cys-354␤ to form S-allylmercaptocysteine with a peptide mass increase of 72.1 Da. The potent antitumor activity of DATS was also demonstrated in nude mice bearing HCT-15 xenografts. This is the first paper describing intracellular target molecules directly modified by garlic components.Allyl sulfides, e.g. diallyl monosulfide (DAS), 4 diallyl disulfide (DADS), and diallyl trisulfide (DATS), are characteristic flavor components of the essential oil prepared from garlic (Allium sativum L.). Garlic is widely served around the world, and it has been reported that allyl sulfides inhibit both the initiation and promotion stages of tumorigenesis in experimental carcinogenesis models for various types of cancer (1-5). Recently, several lines of investigation have shown that allyl sulfides suppress cell growth and induce apoptosis in multiple cancer cell lines (6 -12). We previously reported that the sulfur-containing volatile oils prepared from garlic and onion inhibit proliferation and induce differentiation of the human promyelocytic leukemia cell line HL-60 (13). However, the molecular mechanisms underlying the antitumorigenesis of allyl sulfides are still not fully understood.Microtubules are ubiquitous proteins present in eukaryotes as components of the cytoskeleton and play pivotal roles in a variety of cellular processes involving cell division, motility, and intracellular trafficking (14). The microtubules are dynamic polymers composed of ␣␤-tubulin heterodimers, and they form the mitotic spindles, which are known to introduce the replicated DNA molecules to the res...

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Section: Methodsmentioning

confidence: 99%

Diallyl Trisulfide Suppresses the Proliferation and Induces Apoptosis of Human Colon Cancer Cells through Oxidative Modification of β-Tubulin

Hosono¹,

Fukao²,

Ogihara

et al. 2005

Journal of Biological Chemistry

218

157

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“…Organic polysulfanes were synthesized by Muhammad Jawad Nasim at the Jacob’s laboratory (Division of Bioorganic Chemistry, University of Saarland, Saarbruecken, Germany) according to the literature [3,4]. All other chemicals were purchased from Sigma-Aldrich Chemie GmbH (Steinheim, Germany) and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

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

et al. 2017

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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.

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“…Diallylsulfide and diallyldisulfide were purchased from Sigma (Bornem, Belgium) and distilled before use. Diallyltrisulfide was synthesized according to the method of Milligan et al (12) and purified by vacuum distillation; diallyltetrasulfide was synthesized following the method of Derbesy and Harpp (13) and purified by column chromatography. Identity and purity of the compounds were confirmed by GC-MS, 1 H-NMR, 13 C-NMR or GC-MS and HPLC, respectively.…”

Section: Methodsmentioning

confidence: 99%

Antiproliferative effect of natural tetrasulfides in human breast cancer cells is mediated through the inhibition of the cell division cycle 25 phosphatases

Viry¹,

Ali²,

Kirsch³

et al. 2011

Int J Oncol

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Abstract. For many years, in vitro and in vivo studies have reported that organosulfur compounds (OSCs), naturally found in Allium vegetables, are able to suppress the proliferation of various tumor cells. In spite of recent advances, the specific molecular mechanisms involved in OSC activity are still unclear. Considering the antiproliferative effects observed in cancer cells, we postulated that OSCs might target the cell division cycle (Cdc) 25 phosphatases which are crucial enzymes of the cell cycle. Our findings suggest phosphatases Cdc25 as possible targets of naturally occuring polysulfides contributing to their anticancer properties. We report on the inhibitory activity of tetrasulfides occurring naturally in garlic and onion towards the human Cdc25 phosphatases. Diallyl-and dipropyltetrasulfides have emerged as interesting irreversible inhibitors of the Cdc25 isoforms A and C in vitro. Furthermore, growth of both sensitive (MCF-7) and resistant (Vcr-R) human breast carcinoma cells was significantly decreased by these tetrasulfides. The observed antiproliferative effect appeared to be associated with a G 2 -M cell cycle arrest.

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954. New syntheses of trisulphides

Cited by 47 publications

References 0 publications

Diallyl Trisulfide Suppresses the Proliferation and Induces Apoptosis of Human Colon Cancer Cells through Oxidative Modification of β-Tubulin

Diallyl Trisulfide Suppresses the Proliferation and Induces Apoptosis of Human Colon Cancer Cells through Oxidative Modification of β-Tubulin

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

Antiproliferative effect of natural tetrasulfides in human breast cancer cells is mediated through the inhibition of the cell division cycle 25 phosphatases

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