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. 2012 Jul 4;134(26):10791-4.
doi: 10.1021/ja304205m. Epub 2012 Jun 25.

Photocontrolled binding and binding-controlled photochromism within anthracene-modified DNA

Jack Manchester  1 , Dario M Bassani, Jean-Louis H A Duprey, Luciana Giordano, Joseph S Vyle, Zheng-yun Zhao, James H R Tucker
Affiliations
Free PMC article

Photocontrolled binding and binding-controlled photochromism within anthracene-modified DNA

Jack Manchester et al. J Am Chem Soc. .
Free PMC article

Abstract

Modified DNA strands undergo a reversible light-induced reaction involving the intramolecular photodimerization of two appended anthracene tags. The photodimers exhibit markedly different binding behavior toward a complementary strand that depends on the number of bases between the modified positions. By preforming the duplex, photochromism can be suppressed, illustrating dual-mode gated behavior.

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Figures

Scheme 1
Scheme 1. The S3-A↔S3-AP Photochromic System, in Which the Anthracene Photodimer Consists of the Head-to-Tail Isomer
Figure 1
Figure 1
Structures of the anucleosidic groups X and Y when incorporated into DNA (phosphodiester groups toward 3′ end).
Figure 2
Figure 2
Normalized graphs showing the change in absorbance as a function of temperature for T0 in the presence of S3-A (red) and S3-AP (dashed blue).
Figure 3
Figure 3
CD spectra of T0 with 1 molar equivalent of S3-A (red), with 1 molar equivalent of S3-AP (dashed blue), and measured alone and then mathematically added to an independent spectrum of S3-AP (black). Conditions: 5 μM, pH 7.0, 10 mM sodium phosphate buffer, 250 mM NaCl, 293 K.
Figure 4
Figure 4
20% Native-PAGE experiment illustrating differing duplex-forming abilities with T0 between strands S0, S2-A, and S2-AP: lane 1, S0; lane 2, T0; lane 3, S0 + T0; lane 4, S2-AP; lane 5, S2-AP + T0; lane 6, S2-A; lane 7, S2-A + T0. Conditions: 25 mM NaCl, 1× TB, 24 h at 100 V, 293 K.
Scheme 2
Scheme 2. Representation of Photocontrolled Binding of T0 and Binding-Controlled Photoreactivity within the S3-A↔S3-AP Photochromic System
See this image and copyright information in PMC

References

    1. For some recent reviews and examples, see:

    2. Sortino S. J. Mater. Chem. 2012, 22, 301.
    3. Mok A. K.; Kedzierski N. A.; Chung P. N.; Lukeman P. S. Chem. Commun. 2011, 47, 4905.and references therein. - PubMed
    4. Lee H.-M.; Larson D. R.; Lawrence D. S. ACS Chem. Biol. 2009, 4, 409. - PMC - PubMed
    5. Mayer G.; Heckel A. Angew. Chem., Int. Ed. 2006, 45, 4900. - PubMed
    6. For a recent special issue on DNA nanotechnology, see:Stulz E.; Clever G.; Shionoya M.; Mao C. Chem. Soc. Rev. 2011, 40, 5633. - PubMed

    1. For examples of azobenzene systems, see:

    2. Nishioka H.; Liang X.; Kato T.; Asanuma H. Angew. Chem., Int. Ed. 2012, 51, 1165.and references therein. - PubMed
    3. Kashida H.; Liang X.; Asanuma H. Curr. Org. Chem. 2009, 13, 1065.
    4. Liu M. Z.; Asanuma H.; Komiyama M. J. Am. Chem. Soc. 2006, 128, 1009. - PubMed
    5. Stafforst T.; Hilvert D. Angew. Chem., Int. Ed. 2010, 49, 9998. - PubMed
    6. Keiper S.; Vyle J. S. Angew. Chem., Int. Ed. 2006, 45, 3306. - PubMed
    7. For a recent review of azobenzene photoswitching within biomolecules, see:Beharry A. A.; Woolley G. A. Chem. Soc. Rev. 2011, 40, 4422. - PubMed

    1. For example of non-azobenzene trans–cis systems, see:

    2. Ogasawara S.; Maeda M. Angew. Chem., Int. Ed. 2009, 48, 6671. - PubMed
    3. Ogasawara S.; Maeda M. Angew. Chem., Int. Ed. 2008, 47, 8839. - PubMed
    4. Lewis F. D.; Liu X. J. Am. Chem. Soc. 1999, 121, 11928.
    5. Herrlein M. K.; Letsinger R. L. Angew. Chem., Int. Ed. Engl. 1997, 36, 599.

    1. For other examples of anthracene photodimerisation in DNA, see:

    2. Pasternak K.; Pasternak A.; Gupta P.; Veedu R. N.; Wengel J. Biorg. Med. Chem. 2011, 19, 7407. - PubMed
    3. Arslan P.; Jyo A.; Ihara T. Org. Biomol. Chem. 2010, 8, 4843. - PubMed
    4. Mukae M.; Ihara T.; Tabara M.; Jyo A. Org. Biomol. Chem. 2009, 7, 1349. - PubMed
    5. Ihara T.; Fujii T.; Mukae M.; Kitamura Y.; Jyo A. J. Am. Chem. Soc. 2004, 126, 8880. - PubMed
    1. McSkimming G.; Tucker J. H. R.; Bouas-Laurent H.; Desvergne J.-P.; Coles S. J.; Hursthouse M. B.; Light M. E. Chem.—Eur. J. 2002, 8, 3331. - PubMed
    2. Molard Y.; Bassani D. M.; Desvergne J.-P.; Moran N.; Tucker J. H. R. J. Org. Chem. 2006, 71, 8523. - PubMed
    3. Molard Y.; Bassani D. M.; Desvergne J.-P.; Horton P. N.; Hursthouse M. B.; Tucker J. H. R. Angew. Chem., Int. Ed. 2005, 44, 1072. - PubMed

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