Hsp70 Induction and Anticancer Activity of U-133, the Acetylated Trisglucosydic Derivative of Echinochrome

Yurchenko, Ekaterina A.

doi:10.4172/2161-0444.1000274

Cited by 11 publications

(3 citation statements)

References 39 publications

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“…The conjugation of naphthoquinones with non-toxic carbohydrates is one of the most successful ways for improving their solubility [ 15 , 16 , 17 , 18 , 19 ]. Moreover, the conjugation of naphthoquinones with carbohydrates led to novel structures with new types of biological activity [ 20 , 21 ]. Such naphthoquinone–carbohydrate conjugates include classical O - and S -glycosides (carbohydrates linked directly to naphthoquinone via glycosidic bond), non-glycosidic conjugates (connection with the carbohydrate component via not glycosidic ether linkage), and N -glycosyl triazoles (a triazolic ring connecting the carbohydrate moiety to naphthoquinone).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones

et al. 2020

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A series of new tetracyclic oxathiine-fused quinone-thioglycoside conjugates based on biologically active 1,4-naphthoquinones and 1-mercapto derivatives of per-O-acetyl d-glucose, d-galactose, d-xylose, and l-arabinose have been synthesized, characterized, and evaluated for their cytotoxic and antimicrobial activities. Six tetracyclic conjugates bearing a hydroxyl group in naphthoquinone core showed high cytotoxic activity with EC50 values in the range of 0.3 to 0.9 μM for various types of cancer and normal cells and no hemolytic activity up to 25 μM. The antimicrobial activity of conjugates was screened against Gram-positive bacteria (Staphylococcus aureus, Bacillus cereus), Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), and fungus Candida albicans by the agar diffusion method. The most effective juglone conjugates with d-xylose or l-arabinose moiety and hydroxyl group at C-7 position of naphthoquinone core at concentration 10 µg/well showed antimicrobial activity comparable with antibiotics vancomicin and gentamicin against Gram-positive bacteria strains. In liquid media, juglone-arabinosidic tetracycles showed highest activity with MIC 6.25 µM. Thus, a positive effect of heterocyclization with mercaptosugars on cytotoxic and antimicrobial activity for group of 1,4-naphthoquinones was shown.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones

et al. 2020

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“…The quinone solubility could be enhanced by the conjugation of naphthoquinones with nontoxic carbohydrates, [17][18][19] providing an access to the novel structures with various types of biological activity. [20][21][22][23][24] The aim of our study was the synthesis of new thioglucoside derivatives of polyhydroxynaphthoquinones structurally similar to echinochrome and evaluation of their antiradical and anti-HSV-1 effects in vitro.…”

mentioning

confidence: 99%

“…The quinone solubility could be enhanced by the conjugation of naphthoquinones with nontoxic carbohydrates, 17 -19 providing an access to the novel structures with various types of biological activity. 20 -24…”

mentioning

confidence: 99%

Synthesis and Screening of Anti-HSV-1 Activity of Thioglucoside Derivatives of Natural Polyhydroxy-1,4-Naphthoquinones

Полоник

Крылова²,

Компанец³

et al. 2019

Natural Product Communications

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Four 1,4-naphthoquinone dithioglucoside derivatives based on natural polyhydroxy-1,4-naphthoquinones were synthesized. These thioglucosides were screened for their antiradical and antiviral activity in vitro. Antiradical activity of tested compounds was determined by the 2,2-diphenyl-1-picrylhydrazyl radical scavenging assay. The anti-herpes simplex virus type 1 (anti-HSV-1) activity of thioglucosides was analyzed by the cytopathic effect inhibition assay and mode of antiviral action was determined by the addition of the tested compounds to uninfected cells, to the virus prior to infection, or to herpes-infected cells. Most effective inhibition of HSV-1 replication was observed at pretreatment of virus by the compounds (direct virucidal effect). The dithioglucoside conjugate with the single β-OH group and lipophilic ethyl substituent in naphthoquinone core showed the greatest antiviral activity.

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New Diorcinol J Produced by Co-Cultivation of Marine Fungi Aspergillus sulphureus and Isaria felina

et al. 2016

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Hsp70 Induction and Anticancer Activity of U-133, the Acetylated Trisglucosydic Derivative of Echinochrome

Cited by 11 publications

References 39 publications

Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones

Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones

Synthesis and Screening of Anti-HSV-1 Activity of Thioglucoside Derivatives of Natural Polyhydroxy-1,4-Naphthoquinones

New Diorcinol J Produced by Co-Cultivation of Marine Fungi Aspergillus sulphureus and Isaria felina

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