Hypoxia‐Selective DNA Interstrand Cross‐Link Formation by Two Modified Nucleosides

Kuang, Yunyan; Sun, Huabing; Blain, J. Craig; Peng, Xiaohua

doi:10.1002/chem.201201960

Cited by 20 publications

(35 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…13–15 Greenberg and co‐workers17–21 described several modified nucleosides that efficiently induced the interstrand cross‐linking of DNA upon photoirradiation. Recently, we reported hypoxia‐selective ICL formation from nitroimidazole‐modified thymidine upon UV irradiation 22…”

Section: Methodsmentioning

confidence: 99%

Chemical and Toxicological Investigations of a Previously Unknown Poisonous European Mushroom Tricholoma terreum

Yin

Feng

Shang

et al. 2014

Chemistry A European J

View full text Add to dashboard Cite

The established tradition of consuming and marketing wild mushrooms has focused attention on mycotoxicity, which has become a global issue. In the present study, we describe the toxins found in a previously unknown poisonous European mushroom Tricholoma terreum. Fifteen new triterpenoids terreolides A-F (1-6) and saponaceolides H-P (8-16) were isolated from the fruiting bodies of the toxic mushroom T. terreum. Terreolides A-C (1-3) possessed a unique 5/6/7 trioxaspiroketal system, whereas terreolides D-F (4-6) possessed an unprecedented carbon skeleton. Two abundant compounds in the mushroom, saponaceolide B (7) and saponaceolide M (13), displayed acute toxicity, with LD50 values of 88.3 and 63.7 mg kg(-1) when administered orally in mice. Both compounds were found to increase serum creatine kinase levels in mice, indicating that T. terreum may be the cause of mushroom poisoning ultimately leading to rhabdomyolysis.

show abstract

Section: Methodsmentioning

confidence: 99%

Chemical and Toxicological Investigations of a Previously Unknown Poisonous European Mushroom Tricholoma terreum

Yin

Feng

Shang

et al. 2014

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…17,18 These experiments also suggest that other purported precursors to the 5-(2'-deoxyuridinyl)methyl radical ( 6 ) and related molecules that produce ICLs may also generate 10 , and that other phenyl selenides used to generate radicals in DNA produce the corresponding carbocations. 3,4,6,19 Finally, the recent report by Li showing that 6 can be oxidized leaves open the possibility that the radical may indirectly lead to interstrand cross-links. 20 …”

mentioning

confidence: 99%

Deconvoluting the Reactivity of Two Intermediates Formed from Modified Pyrimidines

et al. 2013

View full text Add to dashboard Cite

Generation of the 5-(2'-deoxyuridinyl)methyl radical (6) was reexamined. Trapping by 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl confirms that 6 is generated. However, trapping by methoxyamine reveals that the respective carbocation (10) is also produced. Examining the effects of these traps on products in DNA reveals that the carbocation and not 6 yields interstrand cross-links. Cross-link formation from the carbocation is consistent with DFT calculations that predict that addition of the former at the N1 position of dA is essentially barrierless.

show abstract

“…Recently, we reported hypoxia-selective ICL formation from nitroimidazole-modified thymidine upon UV-irradiation. [22] …”

mentioning

confidence: 99%

Photoswitchable Formation of a DNA Interstrand Cross‐Link by a Coumarin‐Modified Nucleotide

et al. 2014

Self Cite

View full text Add to dashboard Cite

A coumarin-modified pyrimidine nucleoside (1) has been synthesized using Cu(I)-catalyzed click reaction and incorporated into oligodeoxynucleotides (ODNs). Interstrand cross-links are produced upon irradiation of ODN containing 1 at 350 nm. Cross-linking occurs via [2+2] cycloaddition reaction with the opposing thymidine, 2′-deoxycytidine, or 2′-deoxyadenosine. A much higher reactivity was observed with dT than dC or dA. Irradiation of the dT-1 and dC-1 cross-linked products at 254 nm leads to a reversible ring-opening reaction, while such phenomenon was not observed with dA-1 adducts. The reversible reaction is ultrafast and complete within 50 s – 90 s. Consistent photoswitching behavior was observed over 6 cycles of irradiation at 350 nm and 254 nm. To the best of our knowledge, this is the first example of photoswitchable interstrand cross-linking formation induced by a modified pyrimidine nucleoside. Compound 1 is a novel tool for developing reversible DNA photoswitches which will lead to new applications in chemistry, biology, and nanotechnology.

show abstract

Hypoxia‐Selective DNA Interstrand Cross‐Link Formation by Two Modified Nucleosides

Cited by 20 publications

References 30 publications

Chemical and Toxicological Investigations of a Previously Unknown Poisonous European Mushroom Tricholoma terreum

Chemical and Toxicological Investigations of a Previously Unknown Poisonous European Mushroom Tricholoma terreum

Deconvoluting the Reactivity of Two Intermediates Formed from Modified Pyrimidines

Photoswitchable Formation of a DNA Interstrand Cross‐Link by a Coumarin‐Modified Nucleotide

Contact Info

Product

Resources

About