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Article ; Online: Vitamin E/Coenzyme Q-Dependent "Free Radical Reductases": Redox Regulators in Ferroptosis.

Kagan, Valerian E / Straub, Adam C / Tyurina, Yulia Y / Kapralov, Alexandr A / Hall, Robert / Wenzel, Sally E / Mallampalli, Rama K / Bayir, Hülya

Antioxidants & redox signaling

2023 Volume 40, Issue 4-6, Page(s) 317–328

Abstract: Significance: ...

Abstract	Significance:
MeSH term(s)	Ubiquinone ; Vitamin E ; Ferroptosis ; Oxidation-Reduction ; Oxidoreductases/metabolism ; Lipid Peroxidation ; Free Radicals/metabolism ; Electron Transport Complex I/metabolism
Chemical Substances	free radical reductase (EC 1.8.4.-) ; Ubiquinone (1339-63-5) ; Vitamin E (1406-18-4) ; Oxidoreductases (EC 1.-) ; Free Radicals ; Electron Transport Complex I (EC 7.1.1.2)
Language	English
Publishing date	2023-10-16
Publishing country	United States
Document type	Journal Article ; Review ; Research Support, N.I.H., Extramural
ZDB-ID	1483836-9
ISSN	1557-7716 ; 1523-0864
ISSN (online)	1557-7716
ISSN	1523-0864
DOI	10.1089/ars.2022.0154
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Article: Photoluminescence Response in Carbon Nanomaterials to Enzymatic Degradation

He, Xiaoyun / White, David L / Kapralov, Alexandr A / Kagan, Valerian E / Star, Alexander

Analytical chemistry. 2020 Aug. 17, v. 92, no. 19

2020

Abstract: Myeloperoxidase (MPO), a key enzyme released by neutrophils during inflammation, has been shown to catalyze the biodegradation of carbon nanomaterials. In this work, we perform photoluminescence studies on the MPO-catalyzed oxidation of graphene oxide ( ... ...

Abstract	Myeloperoxidase (MPO), a key enzyme released by neutrophils during inflammation, has been shown to catalyze the biodegradation of carbon nanomaterials. In this work, we perform photoluminescence studies on the MPO-catalyzed oxidation of graphene oxide (GO) and surfactant-coated pristine (6,5) single-walled carbon nanotubes (SWCNTs). The enzymatic degradation mechanism involves the introduction of defects, which promotes further degradation. Interestingly, the photoluminescence responses of GO and SWCNTs to enzymatic degradation are counterposed. Although the near-infrared (NIR) fluorescence intensity of SWCNTs at 998 nm is either unchanged or decreases depending on the surfactant identity, the blue fluorescence intensity of GO at 440 nm increases with the progression of oxidation by MPO/H₂O₂/Cl– due to the formation of graphene quantum dots (GQDs). Turn-on GO fluorescence is also observed with neutrophil-like HL-60 cells, indicative of potential applications of GO for imaging MPO activity in live cells. Based on these results, we further construct two ratiometric sensors using SWCNT/GO nanoscrolls by incorporating surfactant-wrapped pristine SWCNTs as the internal either turn-off (with sodium cholate (SC)) or reference (with carboxymethylcellulose (CMC)) sensor. The ratiometric approach enables the sensors to be more stable to external noise by providing response invariant to the absolute intensity emitted from the sensors. Our sensors show linear response to MPO oxidative machinery and hold the promise to be used as self-calibrating carbon nanomaterial-based MPO activity indicators.
Keywords	analytical chemistry ; biodegradation ; carbon nanotubes ; carboxymethylcellulose ; fluorescence ; graphene ; graphene oxide ; inflammation ; myeloperoxidase ; neutrophils ; oxidation ; photoluminescence ; sodium cholate ; surfactants
Language	English
Dates of publication	2020-0817
Size	p. 12880-12890.
Publishing place	American Chemical Society
Document type	Article
Note	NAL-AP-2-clean
ZDB-ID	1508-8
ISSN	1520-6882 ; 0003-2700
ISSN (online)	1520-6882
ISSN	0003-2700
DOI	10.1021/acs.analchem.0c01380
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Article ; Online: Photoluminescence Response in Carbon Nanomaterials to Enzymatic Degradation.

He, Xiaoyun / White, David L / Kapralov, Alexandr A / Kagan, Valerian E / Star, Alexander

Analytical chemistry

2020 Volume 92, Issue 19, Page(s) 12880–12890

Abstract	Myeloperoxidase (MPO), a key enzyme released by neutrophils during inflammation, has been shown to catalyze the biodegradation of carbon nanomaterials. In this work, we perform photoluminescence studies on the MPO-catalyzed oxidation of graphene oxide (GO) and surfactant-coated pristine (6,5) single-walled carbon nanotubes (SWCNTs). The enzymatic degradation mechanism involves the introduction of defects, which promotes further degradation. Interestingly, the photoluminescence responses of GO and SWCNTs to enzymatic degradation are counterposed. Although the near-infrared (NIR) fluorescence intensity of SWCNTs at 998 nm is either unchanged or decreases depending on the surfactant identity, the blue fluorescence intensity of GO at 440 nm increases with the progression of oxidation by MPO/H
MeSH term(s)	Biocatalysis ; Graphite/chemistry ; Graphite/metabolism ; HL-60 Cells ; Humans ; Luminescence ; Nanotubes, Carbon/chemistry ; Peroxidase/chemistry ; Peroxidase/metabolism ; Photochemical Processes
Chemical Substances	Nanotubes, Carbon ; graphene oxide ; Graphite (7782-42-5) ; MPO protein, human (EC 1.11.1.7) ; Peroxidase (EC 1.11.1.7)
Language	English
Publishing date	2020-09-04
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	1508-8
ISSN	1520-6882 ; 0003-2700
ISSN (online)	1520-6882
ISSN	0003-2700
DOI	10.1021/acs.analchem.0c01380
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Article ; Online: NO

Mikulska-Ruminska, Karolina / Anthonymuthu, Tamil S / Levkina, Anastasia / Shrivastava, Indira H / Kapralov, Alexandr A / Bayır, Hülya / Kagan, Valerian E / Bahar, Ivet

International journal of molecular sciences

2021 Volume 22, Issue 10

Abstract: We recently discovered an anti-ferroptotic mechanism inherent to M1 macrophages whereby high levels of ... ...

Abstract	We recently discovered an anti-ferroptotic mechanism inherent to M1 macrophages whereby high levels of NO
MeSH term(s)	Arachidonate 15-Lipoxygenase/metabolism ; Cell Death/physiology ; Ferroptosis/physiology ; Humans ; Lipidomics ; Macrophages/metabolism ; Molecular Dynamics Simulation ; Nitric Oxide/metabolism ; Oxidation-Reduction ; Phosphatidylethanolamine Binding Protein/metabolism ; Phosphatidylethanolamines ; Phospholipids/metabolism
Chemical Substances	Phosphatidylethanolamine Binding Protein ; Phosphatidylethanolamines ; Phospholipids ; Nitric Oxide (31C4KY9ESH) ; phosphatidylethanolamine (39382-08-6) ; Arachidonate 15-Lipoxygenase (EC 1.13.11.33)
Language	English
Publishing date	2021-05-17
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2019364-6
ISSN	1422-0067 ; 1422-0067 ; 1661-6596
ISSN (online)	1422-0067
ISSN	1422-0067 ; 1661-6596
DOI	10.3390/ijms22105253
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Article ; Online: Redox phospholipidomics discovers pro-ferroptotic death signals in A375 melanoma cells in vitro and in vivo.

Tyurina, Yulia Y / Kapralov, Alexandr A / Tyurin, Vladimir A / Shurin, Galina / Amoscato, Andrew A / Rajasundaram, Dhivyaa / Tian, Hua / Bunimovich, Yuri L / Nefedova, Yulia / Herrick, William G / Parchment, Ralph E / Doroshow, James H / Bayir, Hulya / Srivastava, Apurva K / Kagan, Valerian E

Redox biology

2023 Volume 61, Page(s) 102650

Abstract: Growing cancer cells effectively evade most programs of regulated cell death, particularly apoptosis. This necessitates a search for alternative therapeutic modalities to cause cancer cell's demise, among them - ferroptosis. One of the obstacles to using ...

Abstract	Growing cancer cells effectively evade most programs of regulated cell death, particularly apoptosis. This necessitates a search for alternative therapeutic modalities to cause cancer cell's demise, among them - ferroptosis. One of the obstacles to using pro-ferroptotic agents to treat cancer is the lack of adequate biomarkers of ferroptosis. Ferroptosis is accompanied by peroxidation of polyunsaturated species of phosphatidylethanolamine (PE) to hydroperoxy- (-OOH) derivatives, which act as death signals. We demonstrate that RSL3-induced death of A375 melanoma cells in vitro was fully preventable by ferrostatin-1, suggesting their high susceptibility to ferroptosis. Treatment of A375 cells with RSL3 caused a significant accumulation of PE-(18:0/20:4-OOH) and PE-(18:0/22:4-OOH), the biomarkers of ferroptosis, as well as oxidatively truncated products - PE-(18:0/hydroxy-8-oxo-oct-6-enoic acid (HOOA) and PC-(18:0/HOOA). A significant suppressive effect of RSL3 on melanoma growth was observed in vivo (utilizing a xenograft model of inoculation of GFP-labeled A375 cells into immune-deficient athymic nude mice). Redox phospholipidomics revealed elevated levels of 18:0/20:4-OOH in RSL3-treated group vs controls. In addition, PE-(18:0/20:4-OOH) species were identified as major contributors to the separation of control and RSL3-treated groups, with the highest variable importance in projection predictive score. Pearson correlation analysis revealed an association between tumor weight and contents of PE-(18:0/20:4-OOH) (r = -0.505), PE-18:0/HOOA (r = -0.547) and PE 16:0-HOOA (r = -0.503). Thus, LC-MS/MS based redox lipidomics is a sensitive and precise approach for the detection and characterization of phospholipid biomarkers of ferroptosis induced in cancer cells by radio- and chemotherapy.
MeSH term(s)	Animals ; Mice ; Humans ; Lipid Peroxidation ; Cell Death ; Mice, Nude ; Chromatography, Liquid ; Tandem Mass Spectrometry ; Oxidation-Reduction ; Melanoma
Language	English
Publishing date	2023-02-28
Publishing country	Netherlands
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	2701011-9
ISSN	2213-2317 ; 2213-2317
ISSN (online)	2213-2317
ISSN	2213-2317
DOI	10.1016/j.redox.2023.102650
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Article ; Online: Elucidating the contribution of mitochondrial glutathione to ferroptosis in cardiomyocytes.

Jang, Sehwan / Chapa-Dubocq, Xavier R / Tyurina, Yulia Y / St Croix, Claudette M / Kapralov, Alexandr A / Tyurin, Vladimir A / Bayır, Hülya / Kagan, Valerian E / Javadov, Sabzali

Redox biology

2021 Volume 45, Page(s) 102021

Abstract: Ferroptosis is a programmed iron-dependent cell death associated with peroxidation of lipids particularly, phospholipids. Several studies suggested a possible contribution of mitochondria to ferroptosis although the mechanisms underlying mitochondria- ... ...

Abstract	Ferroptosis is a programmed iron-dependent cell death associated with peroxidation of lipids particularly, phospholipids. Several studies suggested a possible contribution of mitochondria to ferroptosis although the mechanisms underlying mitochondria-mediated ferroptotic pathways remain elusive. Reduced glutathione (GSH) is a central player in ferroptosis that is required for glutathione peroxidase 4 to eliminate oxidized phospholipids. Mitochondria do not produce GSH, and although the transport of GSH to mitochondria is not fully understood, two carrier proteins, the dicarboxylate carrier (DIC, SLC25A10) and the oxoglutarate carrier (OGC, SLC25A11) have been suggested to participate in GSH transport. Here, we elucidated the role of DIC and OGC as well as mitochondrial bioenergetics in ferroptosis in H9c2 cardioblasts. Results showed that mitochondria are highly sensitive to ferroptotic stimuli displaying fragmentation, and lipid peroxidation shortly after the onset of ferroptotic stimulus. Inhibition of electron transport chain complexes and oxidative phosphorylation worsened RSL3-induced ferroptosis. LC-MS/MS analysis revealed a dramatic increase in the levels of pro-ferroptotic oxygenated phosphatidylethanolamine species in mitochondria in response to RSL3 (ferroptosis inducer) and cardiac ischemia-reperfusion. Inhibition of DIC and OGC aggravated ferroptosis and increased mitochondrial ROS, membrane depolarization, and GSH depletion. Dihydrolipoic acid, an essential cofactor for several mitochondrial multienzyme complexes, attenuated ferroptosis and induced direct reduction of pro-ferroptotic peroxidized phospholipids to hydroxy-phospholipids in vitro. In conclusion, we suggest that ferroptotic stimuli diminishes mitochondrial bioenergetics and stimulates GSH depletion and glutathione peroxidase 4 inactivation leading to ferroptosis.
Language	English
Publishing date	2021-06-01
Publishing country	Netherlands
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	2701011-9
ISSN	2213-2317 ; 2213-2317
ISSN (online)	2213-2317
ISSN	2213-2317
DOI	10.1016/j.redox.2021.102021
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Article ; Online: Targeting myeloid regulators by paclitaxel-loaded enzymatically degradable nanocups.

Burkert, Seth C / Shurin, Galina V / White, David L / He, Xiaoyun / Kapralov, Alexandr A / Kagan, Valerian E / Shurin, Michael R / Star, Alexander

Nanoscale

2018 Volume 10, Issue 37, Page(s) 17990–18000

Abstract: Tumor microenvironment is characterized by immunosuppressive mechanisms associated with the accumulation of immune regulatory cells - myeloid-derived suppressor cells (MDSC). Therapeutic depletion of MDSC has been associated with inhibition of tumor ... ...

Abstract	Tumor microenvironment is characterized by immunosuppressive mechanisms associated with the accumulation of immune regulatory cells - myeloid-derived suppressor cells (MDSC). Therapeutic depletion of MDSC has been associated with inhibition of tumor growth and therefore represents an attractive approach to cancer immunotherapy. MDSC in cancer are characterized by enhanced enzymatic capacity to generate reactive oxygen and nitrogen species (RONS) which have been shown to effectively degrade carbonaceous materials. We prepared enzymatically openable nitrogen-doped carbon nanotube cups (NCNC) corked with gold nanoparticles and loaded with paclitaxel as a therapeutic cargo. Loading and release of paclitaxel was confirmed through electron microscopy, Raman spectroscopy and LC-MS analysis. Under the assumption that RONS generated by MDSCs can be utilized as a dual targeting and oxidative degradation mechanism for NCNC, here we report that systemic administration of paclitaxel loaded NCNC delivers paclitaxel to circulating and lymphoid tissue MDSC resulting in the inhibition of growth of tumors (B16 melanoma cells inoculated into C57BL/6 mice) in vivo. Tumor growth inhibition was associated with decreased MDSC accumulation quantified by flow cytometry that correlated with bio-distribution of gold-corked NCNC resolved by ICP-MS detection of residual gold in mouse tissue. Thus, we developed a novel immunotherapeutic approach based on unique nanodelivery vehicles, which can be loaded with therapeutic agents that are released specifically in MDSC via NCNC selective enzymatic "opening" affecting change in the tumor microenvironment.
MeSH term(s)	Animals ; Drug Carriers ; Gold ; Melanoma, Experimental/drug therapy ; Metal Nanoparticles ; Mice ; Mice, Inbred C57BL ; Myeloid-Derived Suppressor Cells/drug effects ; Myeloid-Derived Suppressor Cells/metabolism ; Nanotubes, Carbon ; Paclitaxel/administration & dosage ; Reactive Nitrogen Species/metabolism ; Reactive Oxygen Species/metabolism ; Tumor Microenvironment
Chemical Substances	Drug Carriers ; Nanotubes, Carbon ; Reactive Nitrogen Species ; Reactive Oxygen Species ; Gold (7440-57-5) ; Paclitaxel (P88XT4IS4D)
Language	English
Publishing date	2018-10-08
Publishing country	England
Document type	Journal Article
ZDB-ID	2515664-0
ISSN	2040-3372 ; 2040-3364
ISSN (online)	2040-3372
ISSN	2040-3364
DOI	10.1039/c8nr04437f
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Article ; Online: Payload drug vs. nanocarrier biodegradation by myeloperoxidase- and peroxynitrite-mediated oxidations: pharmacokinetic implications.

Seo, Wanji / Kapralov, Alexandr A / Shurin, Galina V / Shurin, Michael R / Kagan, Valerian E / Star, Alexander

Nanoscale

2015 Volume 7, Issue 19, Page(s) 8689–8694

Abstract: With the advancement of nanocarriers for drug delivery into biomedical practice, assessments of drug susceptibility to oxidative degradation by enzymatic mechanisms of inflammatory cells become important. Here, we investigate oxidative degradation of a ... ...

Abstract	With the advancement of nanocarriers for drug delivery into biomedical practice, assessments of drug susceptibility to oxidative degradation by enzymatic mechanisms of inflammatory cells become important. Here, we investigate oxidative degradation of a carbon nanotube-based drug carrier loaded with Doxorubicin. We employed myeloperoxidase-catalysed and peroxynitrite-mediated oxidative conditions to mimic the respiratory burst of neutrophils and macrophages, respectively. In addition, we revealed that the cytostatic and cytotoxic effects of free Doxorubicin, but not nanotube-carried drug, on melanoma and lung carcinoma cell lines were abolished in the presence of tumor-activated myeloid regulatory cells that create unique myeloperoxidase- and peroxynitrite-induced oxidative conditions. Both ex vivo and in vitro studies demonstrate that the nanocarrier protects the drug against oxidative biodegradation.
MeSH term(s)	Animals ; Antibiotics, Antineoplastic/chemistry ; Antibiotics, Antineoplastic/pharmacology ; Biocatalysis ; Cell Line, Tumor ; Cell Survival/drug effects ; Doxorubicin/chemistry ; Doxorubicin/pharmacology ; Drug Carriers/chemistry ; Humans ; Hydrogen-Ion Concentration ; Mice ; Nanotubes, Carbon/chemistry ; Oxidation-Reduction ; Peroxidase/metabolism ; Peroxynitrous Acid/chemistry
Chemical Substances	Antibiotics, Antineoplastic ; Drug Carriers ; Nanotubes, Carbon ; Peroxynitrous Acid (14691-52-2) ; Doxorubicin (80168379AG) ; Peroxidase (EC 1.11.1.7)
Language	English
Publishing date	2015-05-21
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, U.S. Gov't, P.H.S.
ZDB-ID	2515664-0
ISSN	2040-3372 ; 2040-3364
ISSN (online)	2040-3372
ISSN	2040-3364
DOI	10.1039/c5nr00251f
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Article ; Online: Inhibition of Peroxidase Activity of Cytochrome c: De Novo Compound Discovery and Validation.

Bakan, Ahmet / Kapralov, Alexandr A / Bayir, Hulya / Hu, Feizhou / Kagan, Valerian E / Bahar, Ivet

Molecular pharmacology

2015 Volume 88, Issue 3, Page(s) 421–427

Abstract: Cytochrome c (cyt c) release from mitochondria is accepted to be the point of no return for eliciting a cascade of interactions that lead to apoptosis. A strategy for containing sustained apoptosis is to reduce the mitochondrial permeability pore opening. ...

Abstract	Cytochrome c (cyt c) release from mitochondria is accepted to be the point of no return for eliciting a cascade of interactions that lead to apoptosis. A strategy for containing sustained apoptosis is to reduce the mitochondrial permeability pore opening. Pore opening is enhanced by peroxidase activity of cyt c gained upon its complexation with cardiolipin in the presence of reactive oxygen species. Blocking access to the heme group has been proposed as an effective intervention method for reducing, if not eliminating, the peroxidase activity of cyt c. In the present study, using a combination of druggability simulations, pharmacophore modeling, virtual screening, and in vitro fluorescence measurements to probe peroxidase activity, we identified three repurposable drugs and seven compounds that are validated to effectively inhibit the peroxidase activity of cyt c.
MeSH term(s)	Amino Acid Sequence ; Catalytic Domain ; Electron Transport Complex IV/antagonists & inhibitors ; Electron Transport Complex IV/chemistry ; Enzyme Inhibitors/chemistry ; Enzyme Inhibitors/pharmacology ; Humans ; Molecular Docking Simulation ; Molecular Sequence Data ; Peroxidases/antagonists & inhibitors ; Peroxidases/chemistry ; Small Molecule Libraries/chemistry ; Small Molecule Libraries/pharmacology
Chemical Substances	Enzyme Inhibitors ; Small Molecule Libraries ; Peroxidases (EC 1.11.1.-) ; Electron Transport Complex IV (EC 1.9.3.1)
Language	English
Publishing date	2015-09
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	124034-1
ISSN	1521-0111 ; 0026-895X
ISSN (online)	1521-0111
ISSN	0026-895X
DOI	10.1124/mol.115.097816
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Article ; Online: Nanoemitters and innate immunity: the role of surfactants and bio-coronas in myeloperoxidase-catalyzed oxidation of pristine single-walled carbon nanotubes.

Chiu, Cheuk Fai / Dar, Haider H / Kapralov, Alexandr A / Robinson, Renã A S / Kagan, Valerian E / Star, Alexander

Nanoscale

2017 Volume 9, Issue 18, Page(s) 5948–5956

Abstract: Single-walled carbon nanotubes (SWCNTs) are experimentally utilized in in vivo imaging and photothermal cancer therapy owing to their unique physicochemical and electronic properties. For these applications, pristine carbon nanotubes are often modified ... ...

Abstract	Single-walled carbon nanotubes (SWCNTs) are experimentally utilized in in vivo imaging and photothermal cancer therapy owing to their unique physicochemical and electronic properties. For these applications, pristine carbon nanotubes are often modified by polymer surfactant coatings to improve their biocompatibility, adding more complexity to their recognition and biodegradation by immuno-competent cells. Here, we investigate the oxidative degradation of SWCNTs catalyzed by neutrophil myeloperoxidase (MPO) using bandgap near-infrared (NIR) photoluminescence and Raman spectroscopy. Our results show diameter-dependence at the initial stages of the oxidative degradation of sodium cholate-, DNA-, and albumin-coated SWCNTs, but not phosphatidylserine-coated SWCNTs. Moreover, sodium deoxycholate- and phospholipid-polyethylene glycol coated SWCNTs were not oxidized under the same reaction conditions, indicating that a surfactant can greatly impact the biodegradability of a nanomaterial. Our data also revealed that possible binding between MPO and surfactant coated-SWCNTs was unfavorable, suggesting that oxidation is likely caused by a hypochlorite generated through halogenation cycles of free MPO, and not MPO bound to the surface of SWCNTs. The identification of SWCNT diameters and coatings that retain NIR fluorescence during the interactions with the components of an innate immune system is important for their applications in in vivo imaging.
Language	English
Publishing date	2017-04-24
Publishing country	England
Document type	Journal Article
ZDB-ID	2515664-0
ISSN	2040-3372 ; 2040-3364
ISSN (online)	2040-3372
ISSN	2040-3364
DOI	10.1039/c6nr07706d
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