Derivatization of chlorin e6 with maleimide enhances its photodynamic efficacy in HepG2 cells

2020 ◽  
Vol 24 (09) ◽  
pp. 1093-1098
Author(s):  
Xiuhan Guo ◽  
Shisheng Wang ◽  
Fan Zhang ◽  
Guangzhe Li ◽  
Yueqing Li ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Hepg2 Cells ◽  
Redox System ◽  
Chlorin E6 ◽  
Ros Scavenging ◽  
Cellular Redox ◽  
New Strategy ◽  
Maleimide Group ◽  
High Level ◽  
Derivatives Of

Three derivatives of chlorin e6 (1–3) were synthesized by introduction of maleimide, cysteine and glutathione at C-13 carboxyl of the chlorin scaffold. The evaluation of their PDT effects showed that compound 1, the derivative with a maleimide group, exhibited more potent photocytotoxicity against HepG2 cells (IC[Formula: see text] 3.2 [Formula: see text]M) than 2 (IC[Formula: see text] 6.7 [Formula: see text]M) and 3 (IC[Formula: see text] 10.2 [Formula: see text]M), although the cellular uptake of 1 was slightly lower than that of 2 and 3. The high PDT effect of 1 was found to be in agreement with the high level of intracellular singlet oxygen. Further investigation of the mechanism revealed that 1 can significantly lower the GSH level in HepG2 cells due to the addiction reaction of maleimide and GSH, thus resulting in the reduction of ROS scavenging and the enhancement of cellular oxidative stress. This approach to improve PDT effects of photosensitizers by means of interfering with the cellular redox system and enhancing cellular oxidative stress offers a new strategy for development of photosensitizers in cancer therapy.

scholarly journals Characterization of Purified Red Cabbage Anthocyanins: Improvement in HPLC Separation and Protective Effect against H2O2-Induced Oxidative Stress in HepG2 Cells

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 124 ◽  
Author(s):  
Sheng Fang ◽  
Fubin Lin ◽  
Daofeng Qu ◽  
Xianrui Liang ◽  
Liping Wang
Keyword(s):  
Oxidative Stress ◽  
Hepg2 Cells ◽  
Antioxidant Activities ◽  
Hplc Separation ◽  
Column Temperature ◽  
Red Cabbage ◽  
Chemical Profiles ◽  
Derivatives Of ◽  
Intracellular Oxidative Stress

In this study, the chemical profiles and antioxidant activities of red cabbage anthocyanin (RCA)-enriched extract are evaluated. The effects of column temperature on the HPLC resolution of the RCAs are studied. The HPLC resolutions became better as the column temperature increased from 20 °C–45 °C. An optimized HPLC condition was achieved at 45 °C and used for the quantification and qualification of the RCAs. The anthocyanins in the enriched powder are all derivatives of cyanidin (268 ± 2 μg/mg), mainly with 19% nonacylated, 51% monoacylated, and 31% diacylated structures with ferulic, sinapic, p-coumaric, and caffeic acids characterized by HPLC-MS. The RCA extracts markedly reduced intracellular oxidative stress production by H2O2 on HepG2 cells and consequently ameliorated cell apoptosis and improved viability. The analytical method and cellular antioxidant activity demonstration of the RCAs will greatly facilitate their functional applications.

scholarly journals Melatonin maintains the function of the blood redox system at combined ethanol-induced toxicity and subclinical inflammation in mice

2020 ◽  
Author(s):  
Natalia Kurhaluk ◽  
Halyna Tkachenko ◽  
Oleksandr Lukash ◽  
Pawel J. Winklewski ◽  
Magdalena Wszedybyl-Winklewska
Keyword(s):  
Oxidative Stress ◽  
Free Radical Oxidation ◽  
Redox System ◽  
Erythrocyte Membranes ◽  
Redox Systems ◽  
Negative Effects ◽  
Melatonin Treatment ◽  
Radical Oxidation ◽  
Acute Ethanol ◽  
High Level

Abstract Background The goal of this study was to assess the effect of melatonin on blood redox systems in mice simultaneously exposed to ethanol and low-dose lipopolysaccharide (LPS). Methods Oxidative stress parameters were assessed in eight groups: untreated control, melatonin (10 mg kg−1, 10 days), LPS (injected once intraperitoneally at a dose of 150 μg per mouse), LPS with previous melatonin treatment, acute ethanol-induced stress (AES, 0.75 g kg−1 per day, 10 days), AES with previous melatonin treatment, LPS- and AES-induced toxicity, and melatonin treatment. Results Both ethanol and LPS induced oxidative stress. The combination of these two factors was even more toxic to the organism. Melatonin stabilized erythrocyte membranes and decreased the high level of free radical oxidation at the initial and final stages. Furthermore, melatonin limited protein damage through maintenance in the functional ability of the blood redox system to counteract pathological conditions. Conclusions Melatonin limited the negative effects associated with alcohol consumption and low-intensity inflammation.

scholarly journals Oxidative Stress Modulation by Cameroonian Spice Extracts in HepG2 Cells: Involvement of Nrf2 and Improvement of Glucose Uptake

Metabolites ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 182 ◽  
Author(s):  
Achille Parfait Atchan Nwakiban ◽  
Stefania Cicolari ◽  
Stefano Piazza ◽  
Fabrizio Gelmini ◽  
Enrico Sangiovanni ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Antioxidant Capacity ◽  
Glucose Uptake ◽  
Gallic Acid ◽  
Hepg2 Cells ◽  
Biological Activities ◽  
Array Detector ◽  
Ros Scavenging ◽  
Antioxidant Power ◽  
Tetrapleura Tetraptera

Oxidative stress plays a relevant role in the progression of chronic conditions, including cardiometabolic diseases. Several Cameroonian plants, including spices, are traditionally used as herbal medicines for the treatment of diseases where oxidative stress contributes to insulin resistance, like type 2 diabetes mellitus. This study evaluated the antioxidant capacity and the effects on oxidative-stress-induced impairment of glucose uptake of 11 Cameroonian spice extracts. H2O2-induced reactive oxygen species (ROS) production by human HepG2 cells was significantly reduced by 8/11 extracts. The most effective extracts, Xylopia parviflora, Echinops giganteus, and Dichrostachys glomerata, showed a concentration-dependent ROS-scavenging activity, which involved Nrf2 translocation into the nucleus. Xylopia parviflora, Tetrapleura tetraptera, Dichrostachys glomerata, Aframomum melegueta, and Aframomum citratum extracts showed the highest antioxidant capacity, according to oxygen radical absorbance capacity (ORAC) (2.52–88 μM Trolox Eq/g of extract), ferric-reducing antioxidant power (FRAP) (40.23–233.84 mg gallic acid Eq/g of extract), and total phenol (8.96–32.96% mg gallic acid Eq/g of extract) assays. In HepG2 cells, glucose uptake was stimulated by 4/11 extracts, similarly to insulin and metformin. H2O2-induced oxidative stress reduced glucose uptake, which was rescued by pretreatment with Xylopia aethiopica, Xylopia parviflora, Scorodophloeus zenkeri, Monodora myristica, and Dichrostachys glomerata extracts. The ROS-scavenging ability of the spice extracts may reside in some secondary metabolites observed by phytochemical profiling (reverse-phase high-performance liquid chromatography coupled to a diode array detector (HPLC-UV-DAD)). Further studies are needed to better clarify their biological activities and potential use to control oxidative stress and promote insulin sensitivity.

scholarly journals Gametogenesis-Related Fluctuations in Ovothiol Levels in the Mantle of Mussels from Different Estuaries: Fighting Oxidative Stress for Spawning in Polluted Waters

Biomolecules ◽  
2020 ◽  
Vol 10 (3) ◽  
pp. 373
Author(s):  
Oihane Diaz de Cerio ◽  
Lander Reina ◽  
Valeria Squatrito ◽  
Nestor Etxebarria ◽  
Belen Gonzalez-Gaya ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Marine Invertebrates ◽  
Sampling Site ◽  
Redox System ◽  
Polluted Site ◽  
Strong Increase ◽  
Cellular Redox ◽  
Advanced Stages ◽  
Metabolite Content ◽  
Polluted Waters

Reactive oxygen species present a challenge for marine organisms releasing gametes into the water. Thiol-containing molecules protect cells against oxidative stress, and ovothiol (OSH), an antioxidant-reducing mercaptohistidine, has been described as especially relevant in the oocytes of marine invertebrates. Ovothiol synthase (ovoA), in charge of the first step in OSH synthesis, was sequenced in mussels, Mytilus galloprovincialis. Transcription levels of ovoA in mantle did not significantly change along the reproductive cycle. No alterations of ovoA transcription were observed after a laboratory copper (10 µg/L) exposure or in mussels captured in a highly polluted site. Conversely, the metabolomic analysis of the hydrophilic metabolite content in mantle clearly classified mussels according to their site of origin, especially at the most advanced stages of oogenesis. Quantification of OSH-A and -B and glutathione (GSH), revealed stable levels in mantle at early gametogenesis in the unpolluted sampling site, but a strong increase in female mantle previous to spawning in the polluted site. These increased concentrations under pollution suggest that OSH-A accumulates along oogenesis, independent of gene transcription regulation. The concerted accumulation of OSH-A and GSH suggests the building of a balanced cellular redox-system to scavenge ROS produced in the oocyte before and during fertilization.

Synthesis and in vitro phototoxicity of novel π-extension derivatives of chlorin e6

2017 ◽  
Vol 41 (23) ◽  
pp. 14279-14287 ◽  
Author(s):  
Lei Cao ◽  
Xiuhan Guo ◽  
Liu Wang ◽  
Shisheng Wang ◽  
Yueqing Li ◽  
...  
Keyword(s):  
Hepg2 Cells ◽  
Chlorin E6 ◽  
Derivatives Of

32-Aryl substitution generated the maximum wavelength redshift and increased the in vitro phototoxicity against HepG2 cells simultaneously.

Hsp104 as a key modulator of prion-mediated oxidative stress in Saccharomyces cerevisiae

2013 ◽  
Vol 454 (2) ◽  
pp. 217-225 ◽  
Author(s):  
Kuljit Singh ◽  
Aliabbas A. Saleh ◽  
Ankan K. Bhadra ◽  
Ipsita Roy
Keyword(s):  
Oxidative Stress ◽  
Saccharomyces Cerevisiae ◽  
Cell Viability ◽  
Protein Translation ◽  
Analysis Data ◽  
Cellular Redox ◽  
High Level ◽  
Almost All ◽  
Cellular Defence

Maintenance of cellular redox homoeostasis forms an important part of the cellular defence mechanism and continued cell viability. Despite extensive studies, the role of the chaperone Hsp104 (heat-shock protein of 102 kDa) in propagation of misfolded protein aggregates in the cell and generation of oxidative stress remains poorly understood. Expression of RNQ1-RFP in Saccharomyces cerevisiae cells led to the generation of the prion form of the protein and increased oxidative stress. In the present study, we show that disruption of Hsp104 in an isogenic yeast strain led to solubilization of RNQ1-RFP. This reduced the oxidative stress generated in the cell. The higher level of oxidative stress in the Hsp104-containing (parental) strain correlated with lower activity of almost all of the intracellular antioxidant enzymes assayed. Surprisingly, this did not correspond with the gene expression analysis data. To compensate for the decrease in protein translation induced by a high level of reactive oxygen species, transcriptional up-regulation takes place. This explains the discrepancy observed between the transcription level and functional enzymatic product. Our results show that in a ΔHsp104 strain, due to lower oxidative stress, no such mismatch is observed, corresponding with higher cell viability. Thus Hsp104 is indirectly responsible for enhancing the oxidative stress in a prion-rich environment.

Serum of 8-OHdG as a potential biomarker of oxidative DNA damage in workers exposed to harmful working environments

2020 ◽  
pp. 783-783
Author(s):  
I. A. Umnyagina ◽  
L. A. Strakhova ◽  
T. V. Blinova
Keyword(s):  
Oxidative Stress ◽  
Dna Damage ◽  
Blood Serum ◽  
Oxidative Dna Damage ◽  
Working Environment ◽  
Working Environments ◽  
Potential Biomarker ◽  
High Level ◽  
Damage Marker

In the blood serum of 70% individuals exposed to harmful factors of the working environment, a high level of oxidative stress and the DNA damage marker 8-Hydroxy-2’-Deoxyguanosine (8-OHdG) were detected.

Hydrogen peroxide and quercetin induced changes on cell viability, apoptosis and oxidative stress in HepG2 cells

2020 ◽  
Vol 01 ◽  
Author(s):  
Ayşe Mine Yılmaz ◽  
Gökhan Biçim ◽  
Kübra Toprak ◽  
Betül Karademir Yılmaz ◽  
Irina Milisav ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Cell Cycle ◽  
Hydrogen Peroxide ◽  
Cell Viability ◽  
Hepg2 Cells ◽  
Proteasome Activity ◽  
Cell Cycle Phases ◽  
Induced Changes ◽  
And Oxidative Stress ◽  
Quercetin Treatment

Background: Different cellular responses influence the progress of cancer. In this study, we have investigated the effect of hydrogen peroxide and quercetin induced changes on cell viability, apoptosis and oxidative stress in human hepatocellular carcinoma (HepG2) cells. Methods: The effects of hydrogen peroxide and quercetin on cell viability, cell cycle phases and oxidative stress related cellular changes were investigated. Cell viability was assessed by WST-1 assay. Apoptosis rate, cell cycle phase changes and oxidative stress were measured by flow cytometry. Protein expressions of p21, p27, p53, NF-Kβ-p50 and proteasome activity were determined by Western blot and fluorometry, respectively. Results: Hydrogen peroxide and quercetin treatment resulted in decreased cell viability and increased apoptosis in HepG2 cells. Proteasome activity was increased by hydrogen peroxide but decreased by quercetin treatment. Conclusion: Both agents resulted in decreased p53 protein expression and increased cell death by different mechanisms regarding proteostasis and cell cycle phases.

Monitoring the encapsulation of chlorin e6 derivatives into polymer carriers by NMR spectroscopy

2019 ◽  
Vol 23 (11n12) ◽  
pp. 1576-1586 ◽  
Author(s):  
Sara Pfister ◽  
Luca Sauser ◽  
Ilche Gjuroski ◽  
Julien Furrer ◽  
Martina Vermathen
Keyword(s):  
Relaxation Time ◽  
Nmr Spectroscopy ◽  
Core Region ◽  
Chlorin E6 ◽  
Polypropylene Glycol ◽  
Polymer Carriers ◽  
H Nmr ◽  
Line Shape Analysis ◽  
Dynamic Methods ◽  
Derivatives Of

The encapsulation of five derivatives of chlorin e6 with different hydrophobicity and aggregation properties into a series of five poloxamer-type triblock copolymer micelles (BCMs) with varying numbers of polyethylene and polypropylene glycol (PEG, PPG) units was monitored using 1H NMR spectroscopy. NMR chemical shift and line shape analysis, as well as dynamic methods including diffusion ordered spectroscopy (DOSY) and T1 and T2 relaxation time measurements of the chlorin and the polymer resonances, proved useful to assess the chlorin–BCM compatibility. The poloxamers had high capability to break up aggregates formed by chlorins up to intermediate hydrophobicity. Physically entrapped chlorins were always localized in the BCM core region. The loading capacity correlated with chlorin polarity for all poloxamers among which those with the lowest number of PPG units were most efficient. DOSY data revealed that relatively weakly aggregating chlorins partition between the aqueous bulk and micellar environment whereas more hydrophobic chlorins are well retained in the BCM core region, rendering these systems more stable. T1 and T2 relaxation time measurements indicated that motional freedom in the BCM core region contributes to encapsulation efficiency. The BCM corona dynamics were rather insensitive towards chlorin entrapment except for the poloxamers with short PEG chains. The presented data demonstrate that 1H NMR spectroscopy is a powerful complementary tool for probing the compatibility of porphyrinic compounds with polymeric carriers such as poloxamer BCMs, which is a prerequisite in the development of stable and highly efficient drug delivery systems suitable for medical applications like photodynamic therapy of tumors.

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