N6-Furfuryladenine, Kinetin, Protects against Fenton Reaction-Mediated Oxidative Damage to DNA

doi:10.1006/bbrc.1999.1669

Biochemical and Biophysical Research Communications

Volume 265, Issue 2, 19 November 1999, Pages 499-502

https://doi.org/10.1006/bbrc.1999.1669 Get rights and content

Abstract

N⁶-Furfuryladenine (kinetin) has been shown to have anti-ageing effects on several different systems including plants, human cells in culture, and fruitflies. Since most of the experimental data point toward kinetin acting as an antioxidant both in vitro and in vivo, and since much evidence supporting a causal role of oxidative damage in ageing is accumulating, we tested the antioxidant properties of kinetin directly. Using 8-oxo-2′deoxyguanosine (8-oxo-dG) in calf thymus DNA as a marker for oxidative damage, we demonstrate that kinetin significantly (P < 0.005) protects the DNA against oxidative damage mediated by the Fenton reaction. Kinetin inhibited 8-oxo-dG formation in a dose-dependent manner with a maximum of 50% protection observed at 100 μM kinetin.

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Cited by (94)

Effects of kinetin supplementation on the post-thaw motility, viability, and structural integrity of dog sperm
2020, Cryobiology
Citation Excerpt :
Results were confirmed by the enhanced expression levels of protamine-related genes (PRM2 and PRM3) in kinetin-supplemented sperm samples. Kinetin significantly protected the thymus DNA from oxidative damage [51]. This is the first attempt to evaluate the effects of kinetin supplementation on post-thaw quality of dog sperm.
Oxidative stress is one of the major issues associated with cryopreservation because it causes a marked reduction in the post-thaw quality of semen. This study investigated the ability of kinetin to preserve the structural and functional integrity of dog sperm during cryopreservation. Pooled ejaculates were divided into 5 equal aliquots, diluted with buffer 2 supplemented with different concentrations of kinetin (0, 25, 50, 100, and 200 μM), and finally cryopreserved. The optimal concentration of kinetin was 50 μM based on the significantly improved (P < 0.05) motion characteristics and viability of post-thaw sperm samples. Moreover, kinetin-supplemented samples exhibited significantly higher (P < 0.05) sperm counts with the intact plasma membrane, normal acrosomes, mitochondria, and chromatin than control. The beneficial effects of kinetin were also reflected by the significant increase in the expression levels of anti-apoptotic (B-cell lymphoma, BCL2) and protamine-related genes (protamine 2, PRM2; protamine 3, PRM3), and decrease in the expression of pro-apoptotic (BCL2-associated X, BAX) and mitochondrial reactive oxygen species-modulating genes (ROS modulator 1, ROMO1) in kinetin-supplemented sperm samples than in control. The results demonstrated that supplementation of buffer 2 with 50 μM kinetin is ideal for reducing the magnitude of oxidative damage during semen cryoprocessing and improving the post-thaw quality of dog semen.
Resonant electron capture by kinetin and 6-benzylaminopurine molecules
2020, Chemical Physics Letters
Electron-induced reactions with adenine-type cytokinin molecules, i.e., kinetin and 6-benzylaminopurine, which differ in lateral substituents, were studied. The main fragmentation channels of the molecular negative ions formed by electron capture in the energy range 0–12 eV were revealed. The observed effective dissociative processes were demonstrated to be mostly similar. The quantum chemical calculations of neutral and charged species were performed in order to interpret the experimental data. We established that the effective processes of the formation of individual fragment ions in the energy range of 0–3 eV could be associated with the antioxidant properties of the studied cytokinins.
The plant hormone kinetin in disease therapy and healthy aging
2019, Ageing Research Reviews
It has been more than 60 years since the discovery of kinetin, the first known member of a group of plant hormones called cytokinins. In this review we summarize the health-promoting activity of kinetin in animal systems, ranging from cells cultured in vitro through invertebrates to mammals. Kinetin has been shown to modulate aging, to delay age-related physiological decline and to protect against some neurodegenerative diseases. We also review studies on its mechanism of action, as well as point out gaps in our current knowledge.
New cytokinin derivatives possess UVA and UVB photoprotective effect on human skin cells and prevent oxidative stress
2018, European Journal of Medicinal Chemistry
Citation Excerpt :
Although ArCK N9-ribosides are cytotoxic, THP, THF and N9-chloroalkyl derivatives showed none or only marginal cytotoxicity [21]. The antioxidant properties of Kin have been reported in both in vitro and in vivo experiments [14–19] and the ability of Kin to stimulate antioxidant enzymes catalase (CAT), glutathione peroxidase (GPX) and glutathione reductase (GSR) has been published [18]. Both Kin and BAP positively influenced glutathione (GSH) content and decreased the level of lipid membrane peroxidation in human skin fibroblasts [18].
Eleven 6-furfurylaminopurine (kinetin, Kin) derivatives were synthesized to obtain biologically active compounds. The prepared compounds were characterized using ¹H NMR, mass spectrometry combined with HPLC purity determination and elemental C, H, N analyses. The biological activity of new derivatives was tested on plant cells and tissues in cytokinin bioassays, such as tobacco callus, detached wheat leaf chlorophyll retention bioassay and Amaranthus bioassay. The selected compounds were subsequently tested on normal human dermal fibroblasts (NHDF) and keratinocyte cell lines (HaCaT) to exclude possible phototoxic effects and, on the other hand, to reveal possible UVA and UVB photoprotective activity. The protective antioxidant activity of the prepared cytokinin derivatives was further studied and compared to previously prepared antisenescent compound 6-furfurylamino-9-(tetrahydrofuran-2-yl)purine (Kin-THF) using induced oxidative stress (OS) on nematode Caenorhabditis elegans damaged by 5-hydroxy-1,4-naphthoquinone (juglone), a generator of reactive oxygen species. The observed biological activity was interpreted in relation to the structure of the prepared derivatives. The most potent oxidative stress protection of all the prepared compounds was shown by 6-(thiophen-2-ylmethylamino)-9-(tetrahydrofuran-2-yl)purine (6) and 2-chloro-6-furfurylamino-9-(tetrahydrofuran-2-yl)purine (9) derivatives and the results were comparable to Kin-THF. Compounds 6 and 9 were able to significantly protect human skin cells against UV radiation in vitro. Both the derivatives 6 and 9 showed higher protective activity in comparison to previously known structurally similar compounds Kin and Kin-THF. The obtained results are surprising due to the fact that the prepared compounds showed to be inactive in the ORAC assay which proved that the compounds did not act as direct antioxidants as they were unable to directly scavenge oxygen radicals.
Physiological and biochemical effects of nanoparticulate copper, bulk copper, copper chloride, and kinetin in kidney bean (Phaseolus vulgaris) plants
2017, Science of the Total Environment
Citation Excerpt :
The effects were observed in nCu × KN, bCu × KN, and CuCl2 × KN treatments (Fig. 3). Olsen et al. (1999) observed that KN can bind to metal ions and increase its translocation, which could result in plant biomass increase (Barbafieri et al., 2012). It is also known that Cu forms complexes with KN (Novotná et al., 2012a, b).
It is essential to understand the interactions of engineered nanoparticles (ENPs) with additives used in agriculture and their impacts on crop plants. In this study, kidney bean (Phaseolus vulgaris) plants were grown in potting soil amended with either nano copper (nCu), bulk copper (bCu), or copper chloride (CuCl₂) at 0, 50, and 100 mg/kg, combined with 0, 10, or 100 μM of kinetin (KN). Plant growth, Cu, micro and macroelement concentrations, chlorophyll content, and enzymatic activity were examined in 55-day old plants. Results showed that root Cu content was at least 10-fold higher, compared to other tissues. Accumulation of Cu in roots was decreased by 100 μM KN up to 25%. A concentration-dependent increase of Cu content in leaves by Cu × KN was observed. Chlorophyll production was diminished by CuCl₂ + KN between 22 and 30%, showing a hormetic response. Catalase activity was repressed by 65% to 82% in bCu and CuCl₂ treatments. From all essential elements, Ca, Mn, and P were reduced by 33% to 97% in bCu, CuCl₂, and CuCl₂ + KN treatments. However, this did not impact stem elongation and tissue biomass that increased up to 55% under exposure to bCu and CuCl₂. Our results demonstrate that KN combined with ionic Cu could have negative implications in kidney bean plants, since this combination impacted chlorophyll production and nutrient element accumulation.
Interkingdom Hormonal Regulations between Plants and Animals Provide New Insight into Food Safety
2024, Journal of Agricultural and Food Chemistry

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¹: Present address: School of Biological Sciences, University of Manchester, Oxford Road, Manchester M13 9PT, UK.

²: Corresponding author. Fax: +45 86 12 31 78. E-mail: [email protected].

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Regular ArticleN6-Furfuryladenine, Kinetin, Protects against Fenton Reaction-Mediated Oxidative Damage to DNA

Abstract

J. Biol. Chem.

J. Biol. Chem.

Biochem. Biophys. Res. Commun.

Biochem. Biophys. Res. Commun.

Free Radical Biol. Med.

Mutat. Res.

Mutat. Res.

FEBS Lett.

Planta

Science

Regular Article
N⁶-Furfuryladenine, Kinetin, Protects against Fenton Reaction-Mediated Oxidative Damage to DNA