Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2007 Feb 21;129(7):1852-3.
doi: 10.1021/ja067294u. Epub 2007 Jan 25.

Interstrand cross-links generated by abasic sites in duplex DNA

Sanjay Dutta  1 , Goutam Chowdhury, Kent S Gates
Affiliations

Interstrand cross-links generated by abasic sites in duplex DNA

Sanjay Dutta et al. J Am Chem Soc. .
No abstract available

PubMed Disclaimer

Figures

Figure 1
Figure 1
Figure 2
Figure 2
Interstrand crosslinking of duplexes A, C, and D. In a typical crosslinking reaction, the abasic-site-containing DNA duplex was incubated in MES buffer (50 mM, pH 5.5) for 7 d in the presence of NaCNBH3 (270 mM) at 30 C. The sample was lyophilized, dissolved in formamide loading buffer, the DNA fragments resolved on a 20% denaturing polyacrylamide gel, and visualized by phosphorimaging. Lanes: 1, 6, and 10, uracil-containing precursors to duplexes A, C, and D, respectively (as size markers); lanes 2–5, duplex A; 7–9, duplex C; 11–13, duplex D. Lanes: 2, 7, 11, freshly prepared abasic duplex (without subsequent incubation); 3, 8, 12, standard crosslinking reaction; 4, standard crosslinking reaction+piperidine workup; 5, 9, 13, standard crosslinking reaction+methoxyamine (CH3ONH2). In lane 4, the non-piperidine-labile band co-migrating with 4 likely consists of the NaCNBH3-reduced, alcohol analog of 4.
Figure 3
Figure 3
Evidence for the role of the opposing guanine residue in the crosslinking reaction. Crosslinking reactions were conducted as described in the legend of Figure 2. Lanes 1, 5, 9, uracil-containing precursors to duplexes A, B, and E, respectively (as size markers). Lanes: 2–4, duplex A; 6–8, duplex B; 10–12, duplex E. Lanes: 2, 6, 10 freshly prepared abasic duplex (without subsequent incubation); 3, 7, 11, standard crosslinking conditions; 4, 8, 12, standard crosslinking conditions+CH3ONH2. The bands marked “4” likely consist of a mixture of 4 the NaCNBH3-reduced, alcohol analog of 4.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
See this image and copyright information in PMC

References

    1. Evans AR, Limp-Foster M, Kelley MR. Mutation Res. 2000;461:83–108. - PubMed
    2. Lhomme J, Constant JF, Demeunynck M. Biopolymers. 2000;52:65–83. - PubMed
    3. Loeb LA, Preston BD. Ann Rev Genet. 1986;20:201–230. - PubMed
    4. Boiteux S, Guillet M. DNA Repair. 2004;3:1–12. - PubMed

    1. For examples of abasic sites stemming from DNA alkylation: see: Gates KS, Nooner T, Dutta S. Chem Res Toxicol. 2004;17:839–856.Nooner T, Dutta S, Gates KS. Chem Res Toxicol. 2004;17:942–949.

    1. Freese E, Cashel M. Biochim Biophys Acta. 1964;91:67–77. - PubMed
    1. Burnotte J, Verly WG. Biochim Biophys Acta. 1972;262:449–452. - PubMed
    2. Goffin C, Verly WG. FEBS Lett. 1983;161:140–144. - PubMed
    3. Goffin C, Verly WG. Biochim Biophys Acta. 1984;783:1–5. - PubMed
    4. Mittal A, Musarrat J. Med Sci Res. 1990;18:633–635.
    5. Prakash AS, Gibson NW. Carcinogenesis. 1992;13:425–431. - PubMed
    1. Noll DM, Mason TM, Miller PS. Chem Rev. 2006;106:277–301. - PMC - PubMed
    2. Schärer OD. ChemBioChem. 2005;6:27–32. - PubMed
    3. Rajski SR, Williams RM. Chem Rev. 1998;98:2723–2795. - PubMed

Publication types