Varacin and Three New Marine Antimicrobial Polysulfides from the Far-Eastern Ascidian Polycitorsp.

Makarieva, Tatyana N.; Stonik, Valentin A.; Dmitrenok, A. S.; Grebnev, Boris B.; Исаков, В. В.; Rebachyk, Nikolai M.; Rashkes, Yakov W.

doi:10.1021/np50116a015

Cited by 78 publications

(81 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This result derives support from the previous finding that benzopentathiepins could decompose into corresponding benzotrithiole and sulfur (Chenard et al, 1985). Nevertheless, it was speculated that varacin A is a natural product based on the finding that the crude varacin obtained on board in the research vessel by rapid chromatographic separation of extract, still contained varacin A (Makarieva et al, 1995).…”

Section: Multisulfide Antitumor Agents Varacinsupporting

confidence: 81%

See 1 more Smart Citation

Disulfide and multisulfide antitumor agents and their modes of action

Lee

2009

Arch. Pharm. Res.

View full text Add to dashboard Cite

A variety of natural products that contain disulfide or multisulfide bonds were found to display potent biological activities, including antitumor activities. At the center of these biological activities are disulfide or multisulfide moieties. The importance of disulfide or multisulfide groups in the areas of chemistry, biology, and pharmacology has been well recognized. Among these agents, especially noteworthy are mitomycin disulfides, leinamycin, thiarubrines, varacins, calicheamicins, and esperamicins. Their general features, including their biological profiles, peculiar structures, and related chemistries, were summarized and more importantly, their working mechanisms were elucidated in detail in this review. Mechanistic studies of these compounds have provided evidence of the key role of disulfide or multisulfide groups. In general, the cleavage of disulfide or multisulfide bonds produces thiol (or thiolate), which triggers an activation cascade leading to the generation of highly reactive electrophile(s) or cytotoxic species that may cause DNA strand scission. The main concerns with the mode of action are the reactivity and stability of disulfide and multisulfide bonds, their cleavage conditions, and the generation of toxic species. A range of studies for each agent was executed to gather important information on their activation, and the obtained information was gradually integrated to give some clues to the agents' working mechanisms. Such information may be further used to generate biomechanistically designed and more potent derivatives.

show abstract

Section: Multisulfide Antitumor Agents Varacinsupporting

confidence: 81%

“…10 ( Makarieva et al, 1995). These compounds contain a trithiole ring instead of the pentathiepin ring found in varacin, and the acyl derivatives of varacin A, B, and C displayed potent in vitro antifungal and antimicrobial activities against Candida albicans.…”

Section: Multisulfide Antitumor Agents Varacinmentioning

confidence: 99%

Disulfide and multisulfide antitumor agents and their modes of action

Lee

2009

Arch. Pharm. Res.

View full text Add to dashboard Cite

show abstract

“…(299). The sulfur-containing antimicrobial metabolites agelasidine A (304), C, and D (305) have been isolated from the sponge Agelas sp.…”

mentioning

confidence: 99%

Mass spectrometry of sulfur‐containing compounds in organic and bioorganic fields

Bortolini¹,

Fogagnolo²

1995

Mass Spectrometry Reviews

View full text Add to dashboard Cite

This survey covers the mass spectrometic properties of organosulfur compounds containing the sulfide, disulfide, and sulfone functional groups. Attention is paid to the uni‐ and biomolecular chemistry of both positive and negative ions, as well as to the reactions of ions, with sulfur containing species, in the gas phase. The role of other functional groups on the decomposition of organic S, SO, SO2 containing gaseous ions is also discussed. The selection of sulfur containing compounds includes many naturally occurring and pharmaceutically significant products, that will be presented in the following order: alkaloids, amino acids, peptides, proteins, carbohydrates, steroids, and metabolites. © 1996 John Wiley & Sons, Inc.

show abstract

“…10) There is only one example of a trimer, lissoclibadin 1 (1), 1,2) and six dimeric polisulfides 2,5,8,11) and more than 10 monomeric cyclic polysulfides [4][5][6][7]9,10) have been isolated from the above ascidians. Various biological activities, such as antifungal activity, 2,[4][5][6]10) antibacterial activity, 2,7,10) cytotoxicity, 2,4,6,11) antimalarial (Plasmodium falciparum) activity, 6) inhibition of protein kinase C, 7,8) and inhibition of IL-8 Ra and Rb receptors 9) have been reported.…”

Section: )mentioning

confidence: 99%

Cytotoxicity of Lissoclibadins and Lissoclinotoxins, Isolated from a Tropical Ascidian Lissoclinum cf. badium, against Human Solid-Tumor-Derived Cell Lines

Oda

Kamoshita

Maruyama

et al. 2007

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

Varacin and Three New Marine Antimicrobial Polysulfides from the Far-Eastern Ascidian Polycitorsp.

Abstract: Varacin [1] and three new antimicrobial marine polysulfides, varacins A-C [3-5], have been isolated from the Far Eastern ascidian Polycitor sp. Their structures have been elucidated by spectroscopic methods and by chemical transformations.

Cited by 78 publications

References 5 publications

Disulfide and multisulfide antitumor agents and their modes of action

Disulfide and multisulfide antitumor agents and their modes of action

Mass spectrometry of sulfur‐containing compounds in organic and bioorganic fields

Cytotoxicity of Lissoclibadins and Lissoclinotoxins, Isolated from a Tropical Ascidian Lissoclinum cf. badium, against Human Solid-Tumor-Derived Cell Lines

Contact Info

Product

Resources

About