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A synthetic oligonucleotide model for evaluating the oxidation and crosslinking propensities of natural furan-modified DNA

Lieselot Carrette (UGent) and Annemieke Madder (UGent)
(2014) CHEMBIOCHEM. 15(1). p.103-107
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Abstract
We have previously developed a crosslinking methodology for oligonucleotides based on the incorporation of furan moieties, which can be selectively oxidised to reactive intermediates that will quickly react with the opposite bases in DNA, forming toxic interstrand crosslinks (ICLs). Furan moieties also occur in natural DNA, as a result of oxidative stress. Moreover, the furan-containing degradation product of this modified DNA—kinetin—has been found to display beneficial anti-ageing effects. To investigate the apparent discrepancy between the effects of the synthetic and the natural furan modifications in DNA, a quick and easy postsynthetic method providing access to the natural modification in short synthetic oligonucleotides was developed. On checking for potential crosslinking propensity, we found that the furan moiety does indeed undergo oxidation, in this way functioning as an important scavenger for oxidative stress. The reactive intermediate, however, was shown to degrade without producing toxic crosslinked products.
Keywords
kinetin, oligonucleotides, DNA damage, antioxidants, biomimetic synthesis, DAMAGE PRODUCT, KINETIN, CYTOKININ, N-6-FURFURYLADENINE, PROTECTS

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Citation

Please use this url to cite or link to this publication:

Chicago
Carrette, Lieselot, and Annemieke Madder. 2014. “A Synthetic Oligonucleotide Model for Evaluating the Oxidation and Crosslinking Propensities of Natural Furan-modified DNA.” Chembiochem 15 (1): 103–107.
APA
Carrette, L., & Madder, A. (2014). A synthetic oligonucleotide model for evaluating the oxidation and crosslinking propensities of natural furan-modified DNA. CHEMBIOCHEM, 15(1), 103–107.
Vancouver
1.
Carrette L, Madder A. A synthetic oligonucleotide model for evaluating the oxidation and crosslinking propensities of natural furan-modified DNA. CHEMBIOCHEM. 2014;15(1):103–7.
MLA
Carrette, Lieselot, and Annemieke Madder. “A Synthetic Oligonucleotide Model for Evaluating the Oxidation and Crosslinking Propensities of Natural Furan-modified DNA.” CHEMBIOCHEM 15.1 (2014): 103–107. Print.
@article{4293585,
  abstract     = {We have previously developed a crosslinking methodology for oligonucleotides based on the incorporation of furan moieties, which can be selectively oxidised to reactive intermediates that will quickly react with the opposite bases in DNA, forming toxic interstrand crosslinks (ICLs). Furan moieties also occur in natural DNA, as a result of oxidative stress. Moreover, the furan-containing degradation product of this modified DNA---kinetin---has been found to display beneficial anti-ageing effects. To investigate the apparent discrepancy between the effects of the synthetic and the natural furan modifications in DNA, a quick and easy postsynthetic method providing access to the natural modification in short synthetic oligonucleotides was developed. On checking for potential crosslinking propensity, we found that the furan moiety does indeed undergo oxidation, in this way functioning as an important scavenger for oxidative stress. The reactive intermediate, however, was shown to degrade without producing toxic crosslinked products.},
  author       = {Carrette, Lieselot and Madder, Annemieke},
  issn         = {1439-4227},
  journal      = {CHEMBIOCHEM},
  language     = {eng},
  number       = {1},
  pages        = {103--107},
  title        = {A synthetic oligonucleotide model for evaluating the oxidation and crosslinking propensities of natural furan-modified DNA},
  url          = {http://dx.doi.org/10.1002/cbic.201300612},
  volume       = {15},
  year         = {2014},
}

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