Deciphering intracellular targets of organochalcogen based redox catalysts

Schneider, Thomas; Muthukumar, Yazh; Hinkelmann, Bettina; Franke, Raimo; Döring, Mandy; Jacob, Claus; Sasse, Florenz

doi:10.1039/c2md20049j

Cited by 17 publications

(16 citation statements)

References 11 publications

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“…Cell morphology was evaluated using α‐tubulin and DAPI staining, where cells were challenged with 30 µg/mL of the active compound and visualized under a fluorescent microscope, described in detail by Schneider et al . ().…”

Section: Methodsmentioning

confidence: 97%

Coprinuslactone protects the edible mushroom Coprinus comatus against biofilm infections by blocking both quorum‐sensing and MurA

Carvalho

Gulotta

Amaral

et al. 2016

Environmental Microbiology

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Pathogens embedded in biofilms are involved in many infections and are very difficult to treat with antibiotics because of higher resistance compared with planktonic cells. Therefore, new approaches for their control are urgently needed. One way to search for biofilm dispersing compounds is to look at defense strategies of organisms exposed to wet environments, which makes them prone to biofilm infections. It is reasonable to assume that mushrooms have developed mechanisms to control biofilms on their sporocarps (fruiting bodies). A preliminary screening for biofilms on sporocarps revealed several species with few or no bacteria on their sporocarps. From the edible mushroom Coprinus comatus where no bacteria on the sporocarp could be detected (3R,4S)-2-methylene-3,4-dihydroxypentanoic acid 1,4-lactone, named coprinuslactone, was isolated. Coprinuslactone interfered with quorum-sensing and dispersed biofilms of Pseudomonas aeruginosa, where it also reduced the formation of the pathogenicity factors pyocyanin and rhamnolipid B. Coprinuslactone also damaged Staphylococcus aureus cells in biofilms at subtoxic concentrations. Furthermore, it inhibited UDP-N-acetylglucosamine enolpyruvyl transferase (MurA), essential for bacterial cell wall synthesis. These two modes of action ensure the inhibition of a broad spectrum of pathogens on the fruiting body but may also be useful for future clinical applications.

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Section: Methodsmentioning

confidence: 97%

Coprinuslactone protects the edible mushroom Coprinus comatus against biofilm infections by blocking both quorum‐sensing and MurA

Carvalho

Gulotta

Amaral

et al. 2016

Environmental Microbiology

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“…Impedance measurements of the treated and control cells were performed on an RT-CES system (xCELLigence) from Acea Biosciences (Roche) as described previously 104 . In brief, for the time-dependent cell response profiling, 60 μl of Dulbecco’s modified Eagle’s medium (DMEM) was added to 96-well E-Plates to obtain background readings, followed by the addition of 120 μl of L-929 cell suspension.…”

Section: Methodsmentioning

confidence: 99%

Characteristics, chemical compositions and biological activities of propolis from Al-Bahah, Saudi Arabia

Elnakady

Rushdi

Franke

et al. 2017

Sci Rep

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Propolis has been used to treat several diseases since ancient times, and is an important source of bioactive natural compounds and drug derivatives. These properties have kept the interest of investigators around the world, leading to the investigation of the chemical and biological properties and application of propolis. In this report, the chemical constituents that are responsible for the anticancer activities of propolis were analyzed. The propolis was sourced from Al-Baha in the southern part of the Kingdom of Saudi Arabia. Standard protocols for chemical fractionation and bioactivity-guided chemical analysis were used to identify the bio-active ethyl acetate fraction. The extraction was performed in methanol and then analyzed by gas chromatography-mass spectrometry (GC-MS). The major compounds are triterpenoids, with a relative concentration of 74.0%; steroids, with a relative concentration of 9.8%; and diterpenoids, with a relative concentration of 7.9%. The biological activity was characterized using different approaches and cell-based assays. Propolis was found to inhibit the proliferation of cancer cells in a concentration-dependent manner through apoptosis. Immunofluorescence staining with anti-α-tubulin antibodies and cell cycle analysis indicated that tubulin and/or microtubules are the cellular targets of the L-acetate fraction. This study demonstrates the importance of Saudi propolis as anti-cancer drug candidates.

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“…71) A structure-activity relationship study confirmed that cytotoxic activity of 1,4-naphthoquinones is closely associated with their electron accepting capability, which gives rise to reactive oxygen species (ROS) production leading to DNA damage and cell death. [72][73][74] Besides the mechanism of ROS production, a cytotoxic effect of clinically used quinone-based anticancer drugs is closely related to inhibition of DNA topoisomerase II enzyme, which is an essential enzyme required for DNA replication, chromosome condensation and chromosome segregation. 75,76) However, recently along with the study of the effect of these compounds on the viability and proliferation of tumor cells of various natures, there has been a series of investigations regarding the antitumor activity of 1,4-naphthoquinones, which studied their ability to affect key membrane and intracellular molecular targets of tumor cells involved in oncogenesis.…”

Section: Cardioprotective and Anti-ischemic Propertiesmentioning

confidence: 99%

“…90) Recently, 41 novel 1,4-naphthoquinone derivatives were synthesized and 14 antiamyloidogenic compounds were initially discovered using in vitro β-amyloid aggregation assay. Followup docking and biophysical studies revealed that four of them (8-hydroxy-2-((3-methoxybenzyl) amino) naphthalene-1,4-dione (72), 2-(benzylamino)-5-hydroxynaphthalene-1,4-dione (73), 6-chloro-7-((2-iodophenyl) amino) isoquinoline-5,8-dione (74) and 1H-pyrrolo[3,2-g] isoquinoline-4,9-dione (75) (Fig. 19) penetrate the blood-brain barrier, bind directly to β-amyloid aggregates and enhance fluorescence properties upon interaction.…”

Section: Cardioprotective and Anti-ischemic Propertiesmentioning

confidence: 99%

1,4-Naphthoquinones: Some Biological Properties and Application

2020

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Over the past decade, a number of new 1,4-naphthoquinones have been isolated from natural sources and new 1,4-naphthoquinones with diverse structural features have been synthesized. Cardioprotective, antiischemic, hepatoprotective, neuroprotective and some other new properties were found for these compounds; their role in protecting against neurodegenerative diseases has been established. Their anti-inflammatory, antimicrobial and antitumor activities have been studied in more detail; new, previously unknown intracellular molecular targets and mechanisms of action have been discovered. Some compounds of this class are already being used as a medicinal drugs and some substances can be used as biochemical tools and probes for non-invasive detection of pathological areas in cells and tissues in myocardial infarction and neurodegenerative diseases using modern molecular imaging techniques.

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Deciphering intracellular targets of organochalcogen based redox catalysts

Cited by 17 publications

References 11 publications

Coprinuslactone protects the edible mushroom Coprinus comatus against biofilm infections by blocking both quorum‐sensing and MurA

Coprinuslactone protects the edible mushroom Coprinus comatus against biofilm infections by blocking both quorum‐sensing and MurA

Characteristics, chemical compositions and biological activities of propolis from Al-Bahah, Saudi Arabia

1,4-Naphthoquinones: Some Biological Properties and Application

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