DNA Damage by Fasicularin

Dutta, Sanjay; Abe, Hideki; Aoyagi, Sakae; Kibayashi, Chihiro; Gates, Kent S.

doi:10.1021/ja053735i

Cited by 162 publications

(62 citation statements)

References 23 publications

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“…21–23 AP sites are prevalent lesions in genomic DNA that are generated by a wide variety of endogenous cellular processes, 24–28 drugs, 25 bioactive natural products, 29–34 and environmental carcinogens. 25,26 AP sites exist as an equilibrium mixture of the ring-closed hemiacetal 5 and the ring-opened aldehyde 6 (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Chemical Structure and Properties of Interstrand Cross-Links Formed by Reaction of Guanine Residues with Abasic Sites in Duplex DNA

Catalano¹,

Liu

Andersen

et al. 2015

J. Am. Chem. Soc.

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A new type of interstrand cross-link resulting from the reaction of a DNA abasic site with a guanine residue on the opposing strand of the double helix was recently identified, but the chemical connectivity of the cross-link was not rigorously established. The work described here was designed to characterize the chemical structure and properties of dG–AP cross-links generated in duplex DNA. The approach involved characterization of the nucleoside cross-link “remnant” released by enzymatic digestion of DNA duplexes containing the dG–AP cross-link. We first carried out a chemical synthesis and complete spectroscopic structure determination of the putative cross-link remnant 9b composed of a 2-deoxyribose adduct attached to the exocyclic N2-amino group of dG. A reduced analogue of the cross-link remnant was also prepared (11b). Liquid chromatography–tandem mass spectrometric (LC-MS/MS) analysis revealed that the retention times and mass spectral properties of synthetic standards 9b and 11b matched those of the authentic cross-link remnants released by enzymatic digestion of duplexes containing the native and reduced dG–AP cross-link, respectively. These results establish the chemical connectivity of the dG–AP cross-link released from duplex DNA and provide a foundation for detection of this lesion in biological samples. The dG–AP cross-link in duplex DNA was remarkably stable, decomposing with a half-life of 22 days at pH 7 and 23 °C. The intrinsic chemical stability of the dG–AP cross-link suggests that this lesion in duplex DNA may have the power to block DNA-processing enzymes involved in transcription and replication.

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Section: Introductionmentioning

confidence: 99%

Chemical Structure and Properties of Interstrand Cross-Links Formed by Reaction of Guanine Residues with Abasic Sites in Duplex DNA

Catalano¹,

Liu

Andersen

et al. 2015

J. Am. Chem. Soc.

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“…DNA replication, in tumor cells, can be blocked by the intercalations between the small molecule and the base pairs of DNA. 32) Thus, the characterization of the interaction between metal complex and DNA in vitro is of great importance due to the contribution for insights into its binding mechanism and the toxicological effect of metal based chemotherapeutic drug. 33) To better understand the antitumor activity of complex 1, the DNA binding property of 1 was studied by UV-Vis absorption, fluorescence spectrum and agarose gel electrophoresis.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structure Characterization and Antitumor Activity Study of a New Iron(III) Complex of 5-Nitro-8-hydroxylquinoline (HNOQ)

Zhang

Meng

Liu

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Similarly, the interactions between small molecules and DNA are believed to be one of the primary action mechanisms of the antitumor activity. The DNA replication in tumor cells can be blocked via the intercalations of the small molecule between the base pairs of DNA [47,48]. Generally, the active compounds show an approximately planar structure and some hydrophobic characteristics to maximize the intercalations.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Cytotoxicity, DNA Binding and Apoptosis of Rhein-Phosphonate Derivatives as Antitumor Agents

Yao

Wei

et al. 2013

IJMS

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Several rhein-phosphonate derivatives (5a–c) were synthesized and evaluated for in vitro cytotoxicity against HepG-2, CNE, Spca-2, Hela and Hct-116 cell lines. Some compounds showed relatively high cytotoxicity. Especially compounds 5b exhibited the strongest cytotoxicity against HepG-2 and Spca-2 cells (IC50 was 8.82 and 9.01 μM), respectively. All the synthesized compounds exhibited low cytotoxicity against HUVEC cells. Further experiments proved that 5b could disturb the cell cycle in HepG-2 cells and induce apoptosis. In addition, the binding properties of a model conjugate 5b to DNA were investigated by methods (UV-Vis, fluorescence, CD spectroscopy). Results indicated that 5b showed moderate ability to interact ct-DNA.

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DNA Damage by Fasicularin

Cited by 162 publications

References 23 publications

Chemical Structure and Properties of Interstrand Cross-Links Formed by Reaction of Guanine Residues with Abasic Sites in Duplex DNA

Chemical Structure and Properties of Interstrand Cross-Links Formed by Reaction of Guanine Residues with Abasic Sites in Duplex DNA

Synthesis, Structure Characterization and Antitumor Activity Study of a New Iron(III) Complex of 5-Nitro-8-hydroxylquinoline (HNOQ)

Synthesis, Cytotoxicity, DNA Binding and Apoptosis of Rhein-Phosphonate Derivatives as Antitumor Agents

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