Structure-dependent lipid peroxidation by photoirradiation of pyrene and its mono-substituted derivatives

Fullove, Tracie Perkins; Johnson, Britney; Yu, Hongtao

doi:10.1080/10934529.2013.729998

Cited by 6 publications

(7 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Our results further confirm the ability of 1-NP to induce ROS generation because the compound induced protein oxidation and, to a lesser extent, lipid peroxidation. There have been reports on the induction of lipid peroxidation by 1-NP in various experimental systems, including rat hepatocytes, mouse hepatoma cells and methyl linoleate [ 33 , 34 , 35 ]. However, our study is the first demonstrating the ability of 1-NP to induce oxidative damage to macromolecules other than DNA in A549 cells.…”

Section: Discussionmentioning

confidence: 99%

Toxic Effects of the Major Components of Diesel Exhaust in Human Alveolar Basal Epithelial Cells (A549)

Rössner

Strapáčová

Stolcpartova

et al. 2016

IJMS

View full text Add to dashboard Cite

We investigated the toxicity of benzo[a]pyrene (B[a]P), 1-nitropyrene (1-NP) and 3-nitrobenzanthrone (3-NBA) in A549 cells. Cells were treated for 4 h and 24 h with: B[a]P (0.1 and 1 μM), 1-NP (1 and 10 μM) and 3-NBA (0.5 and 5 μM). Bulky DNA adducts, lipid peroxidation, DNA and protein oxidation and mRNA expression of CYP1A1, CYP1B1, NQO1, POR, AKR1C2 and COX2 were analyzed. Bulky DNA adducts were induced after both treatment periods; the effect of 1-NP was weak. 3-NBA induced high levels of bulky DNA adducts even after 4-h treatment, suggesting rapid metabolic activation. Oxidative DNA damage was not affected. 1-NP caused protein oxidation and weak induction of lipid peroxidation after 4-h incubation. 3-NBA induced lipid peroxidation after 24-h treatment. Unlike B[a]P, induction of the aryl hydrocarbon receptor, measured as mRNA expression levels of CYP1A1 and CYP1B1, was low after treatment with polycyclic aromatic hydrocarbon (PAH) nitro-derivatives. All test compounds induced mRNA expression of NQO1, POR, and AKR1C2 after 24-h treatment. AKR1C2 expression indicates involvement of processes associated with reactive oxygen species generation. This was supported further by COX2 expression induced by 24-h treatment with 1-NP. In summary, 3-NBA was the most potent genotoxicant, whereas 1-NP exhibited the strongest oxidative properties.

show abstract

Section: Discussionmentioning

confidence: 99%

Toxic Effects of the Major Components of Diesel Exhaust in Human Alveolar Basal Epithelial Cells (A549)

Rössner

Strapáčová

Stolcpartova

et al. 2016

IJMS

View full text Add to dashboard Cite

show abstract

“…As pyrene exhibits characteristic absorption spectra in the UV-region, pyrene UV absorption spectra was used to determine the critical micellar concentration in different surfactant solutions 38 . Because of its highly conjugated nature as an aromatic molecule, pyrene has several absorption bands extending from 200 to 360 nm 39 . The equilibrium water content of the hydrogels was measured to ensure uniformity 15 .…”

Section: Discussionmentioning

confidence: 99%

Crosslinker-free collagen gelation for corneal regeneration

Islam

Chivu

AbuSamra

et al. 2022

Sci Rep

View full text Add to dashboard Cite

Development of an artificial cornea can potentially fulfil the demand of donor corneas for transplantation as the number of donors is far less than needed to treat corneal blindness. Collagen-based artificial corneas stand out as a regenerative option, having promising clinical outcomes. Collagen crosslinked with chemical crosslinkers which modify the parent functional groups of collagen. However, crosslinkers are usually cytotoxic, so crosslinkers need to be removed from implants completely before application in humans. In addition, crosslinked products are mechanically weak and susceptible to enzymatic degradation. We developed a crosslinker free supramolecular gelation strategy using pyrene conjugated dipeptide amphiphile (PyKC) consisting of lysine and cysteine; in which collagen molecules are intertwined inside the PyKC network without any functional group modification of the collagen. The newly developed collagen implants (Coll-PyKC) are optically transparent and can effectively block UV light, are mechanically and enzymatically stable, and can be sutured. The Coll-PyKC implants support the growth and function of all corneal cells, trigger anti-inflammatory differentiation while suppressing the pro-inflammatory differentiation of human monocytes. Coll-PyKC implants can restrict human adenovirus propagation. Therefore, this crosslinker-free strategy can be used for the repair, healing, and regeneration of the cornea, and potentially other damaged organs of the body.

show abstract

“…Due to its greater photo-stability 8 and higher intersystem crossing yield, 1-BP produces more triplet excited state species 38 . These longer-lived triplet state species of 1-BP can generate more singlet oxygen than any of the other four compounds.…”

Section: Discussionmentioning

confidence: 99%

“…It is suggested that damages to cellular constituents DNA, protein and lipids are the main reasons leading to phototoxicity 6,7 . In a recent study, we reported that light-induced lipid peroxidation by 1-substituted pyrenes are strongly structure dependent 8 . Although any form of damage to the cell can lead to cellular death, DNA damages may be repaired and the cellular function may be partially or even fully restored.…”

Section: Introductionmentioning

confidence: 98%

“…6,7 In a recent study, we reported that light-induced lipid peroxidation by 1-substituted pyrenes is strongly structure dependent. 8 Although any form of damage to the cell can lead to cellular death, DNA damage may be repaired and the cellular function may be partially or even fully restored. The goal of this article is to study DNA damage and repair in human skin keratinocyte cells caused by co-exposure to pyrene, 1-amino (1-AP), 1-bromo (1-BP), 1-hydroxy (1-HP), and 1-nitropyrenes (NP) and UVA light.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

DNA damage and repair of human skin keratinocytes concurrently exposed to pyrene derivatives and UVA light

Fullove

2013

Toxicol. Res.

Self Cite

View full text Add to dashboard Cite

Polycyclic aromatic hydrocarbons (PAHs), a class of mutagenic environmental contaminants, insert toxicity through both metabolic activation and light irradiation. Pyrene, one of the most widely studied PAHs, along with its mono-substituted derivatives, 1-amino, 1-bromo, 1-hydroxy, and 1-nitropyrene, were chosen to study the effect of substituents on their phototoxicity, DNA damage and repair. Both alkaline Comet assay, which detects direct DNA damages, and Fpg endonuclease Comet assay, which detects oxidative DNA damages, were conducted at 0, 2, 4, 8, and 24 h of incubation of the cells in minimal growth medium after concomitant exposure to pyrene derivatives and UVA light. All these compounds are photocytotoxic and the phototoxicity is both incubation time and PAH dose dependent; whereas, those without light are not toxic. The LC50 obtained are in the range of 3.5 – 9.3 µM. Cellular DNA damages, both direct and oxidative, are observed immediately after the cells are treated with UVA light and the pyrene derivatives at a concentration of 1.0 µM. The amount of DNA damages (both direct and oxidative) increase from 0 to 4 h of incubation. After 4 hours, subsequent damage induction declines, and this is perceived to be mainly through DNA repair. After longer incubation of 8 h, the damaged cellular DNA start to be repaired, resulting in greatly reduced amount of DNA damages, and the DNA damage reaches the minimum at 24 h of incubation. 1-Amopyrene and 1-hydroxypyrene cause more DNA oxidative damages immediately after the exposure (0 h of incubation), and these damages are repaired within the same timeframe as the other tested compounds. The oxidative DNA damages caused by 1-bromopyrene are repaired starting at 2 h of incubation, earlier than the damages caused by all the other compounds.

show abstract

Structure-dependent lipid peroxidation by photoirradiation of pyrene and its mono-substituted derivatives

Cited by 6 publications

References 54 publications

Toxic Effects of the Major Components of Diesel Exhaust in Human Alveolar Basal Epithelial Cells (A549)

Toxic Effects of the Major Components of Diesel Exhaust in Human Alveolar Basal Epithelial Cells (A549)

Crosslinker-free collagen gelation for corneal regeneration

DNA damage and repair of human skin keratinocytes concurrently exposed to pyrene derivatives and UVA light

Contact Info

Product

Resources

About