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Synthesis 2008(22): 3657-3662  
DOI: 10.1055/s-0028-1083206
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Spectroscopic Characterization of BODIPY-Modified Uridines as Potential Fluorescent Probes for Nucleic Acids

Thomas Ehrenschwender, Hans-Achim Wagenknecht*
Institute for Organic Chemistry, University of Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany
Fax: +49(941)9434617; e-Mail: achim.wagenknecht@chemie.uni-regensburg.de;
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Publikationsverlauf

Received 9 June 2008
Publikationsdatum:
23. Oktober 2008 (online)

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Abstract

BODIPY-modified nucleosides that contain the fluorophore attached to the 5-position of uridine via a short phenylene bridge have been prepared and characterized by optical spectroscopy and by electrochemistry. The target compounds were synthesized using a Pd-catalyzed cross-coupling of 4-formyl­-phenylboronic acid to 5-iodo-2′-desoxyuridine, followed by acid-catalyzed formation of the BODIPY chromophore. The weakly electron-donating ethyl substituents in positions 2 and 6 of the BODIPY­ dye, shift both the absorption and emission properties of the corresponding modified uridines bathochromically and alter their redox properties. In contrast, exchange of the fluoro ligands at the boron center of the chromophores by methoxy groups does not change the optical properties but increases the electron-rich character of the BODIPY-modified uridines significantly.

Key words

absorption - BODIPY - cyclic voltammetry - fluorescence - nucleoside

    References

  • 1a Karolin J. Johansson LB.-A. Strandberg L. Ny T. J. Am. Chem. Soc.  1994,  116:  7801 
    Google Scholar
  • 1b Yee M.-C. Fas SC. Stohlmeyer MM. Wandless TJ. Cimprich KA. J. Biol. Chem.  2005,  280:  29053 
    Google Scholar
  • 1c Johnson ID. Kang HC. Haugland RP. Anal. Biochem.  1991,  198:  228 
    Google Scholar
  • 1d Ferguson CG. Bigman CS. Richardson RD. van Meeteren LA. Moolenaar WH. Prestwich GD. Org. Lett.  2006,  8:  2023 
    Google Scholar
  • 1e Peters C. Billich A. Ghobrial M. Högenauer K. Ullrich T. Nussbaumer P. J. Org. Chem.  2007,  72:  1842 
    Google Scholar
  • 2 For a review, see: Loudet A. Burgess K. Chem. Rev.  2007,  107:  4891 
    CrossrefPubMedGoogle Scholar
  • 3 For a review, see: Ulrich G. Ziessel R. Harriman A. Angew. Chem. Int. Ed.  2008,  47:  1184 
    CrossrefPubMedGoogle Scholar
  • 4a Rohand T. Qin W. Boens N. Dehaen W. Eur. J. Org. Chem.  2006,  4658 
    Google Scholar
  • 4b Bröring M. Krüger R. Link S. Kleeberg C. Köhler S. Xie X. Ventura B. Flamigni L. Chem. Eur. J.  2008,  14:  2976 
    Google Scholar
  • 4c Baruah M. Qin W. Vallee R. Beljonne D. Rohand T. Dehaen W. Boens N. Org. Lett.  2005,  4377 
    Google Scholar
  • 5a Kollmannsberger M. Gareis T. Heinl S. Daub J. Angew. Chem. Int. Ed.  1997,  36:  1333 
    Google Scholar
  • 5b Trieflinger C. Rurack K. Daub J. Angew. Chem. Int. Ed.  2005,  44:  2288 
    Google Scholar
  • 6 Wan C.-W. Burghart A. Chen J. Bergström F. Johansson LB.-Å. Wolford MF. Kim TG. Topp MR. Hochstrasser RM. Burgess K. Chem. Eur. J.  2003,  9:  4430 
    CrossrefGoogle Scholar
  • 7 Gabe Y. Ueno T. Urano Y. Kojima H. Nagano T. Anal. Bioanal. Chem.  2006,  386:  621 
    CrossrefGoogle Scholar
  • 8 Goeb S. Ziessel R. Org. Lett.  2007,  9:  737 
    CrossrefPubMedGoogle Scholar
  • 9 Meng Q. Kim DH. Bai X. Bi L. Turro NJ. Ju J. J. Org. Chem.  2006,  71:  3248 
    Google Scholar
  • 10a Worthington AS. Burkart MD. Org. Biomol. Chem.  2006,  4:  44 
    Google Scholar
  • 10b Sculimbrene BR. Imperiali B. J. Am. Chem. Soc.  2006,  128:  7346 
    Google Scholar
  • 11a Cornelius M. Woerth CGTC. Kliem H.-C. Wiessler M. Schmeiser HH. Electrophoresis  2005,  26:  2591 
    Google Scholar
  • 11b Shinya K. Takahiro K. Kazutaka Y. Masaki T. Toyokazu T. Yoichi K. Ryuichiro K. Nucleic Acids Res.  2001,  29:  e34 
    Google Scholar
  • 11c Bi L. Kim DH. Ju J. J. Am. Chem. Soc.  2006,  128:  2542 
    Google Scholar
  • 12a Skorobogatyi MV. Malakhov AD. Pchelintseva AA. Turban AA. Bondarev SL. Korshun VA. ChemBioChem  2006,  7:  810 
    Google Scholar
  • 12b Skorobogatyi MV. Ustinov AV. Stepanova IA. Pchelintseva AA. Petrunina AL. Andronova GA. Malakhov AD. Korshun VA. Org. Biomol. Chem.  2006,  4:  1091 
    Google Scholar
  • 13a Tor Y. Valle SD. Jaramillo D. Srivatsan SG. Rios A. Weizman H. Tetrahedron  2007,  63:  3608 
    Google Scholar
  • 13b Greco NJ. Tor Y. Tetrahedron  2007,  63:  3515 
    Google Scholar
  • 14 Thoresen LH. Jiao G.-S. Haaland WC. Metzker ML. Burgess K. Chem. Eur. J.  2003,  9:  4603 
    CrossrefGoogle Scholar
  • 15 Ryu JH. Seo YJ. Hwang GT. Lee JY. Kim BH. Tetrahedron  2007,  63:  3538 
    CrossrefGoogle Scholar
  • 16 Fegan A. Shirude PS. Balasubramanian S. Chem. Commun.  2008,  2004 
    CrossrefGoogle Scholar
  • 17 Khan SI. Grinstaff MW. J. Am. Chem. Soc.  1999,  121:  4704 
    CrossrefGoogle Scholar
  • 18 Wagner C. Wagenknecht H.-A. Chem. Eur. J.  2005,  11:  1871 
    CrossrefGoogle Scholar
  • 19a Mayer E. Valis L. Huber R. Amann N. Wagenknecht H.-A. Synthesis  2003,  2335 
    Google Scholar
  • 19b Kaden P. Mayer E. Trifonov A. Fiebig T. Wagenknecht H.-A. Angew. Chem. Int. Ed.  2005,  44:  1636 
    Google Scholar
  • 19c Mayer-Enthart E. Wagenknecht H.-A. Angew. Chem. Int. Ed.  2006,  45:  3372 
    Google Scholar
  • 19d Wanninger-Weiß C. Wagenknecht H.-A. Eur. J. Org. Chem.  2008,  64 
    Google Scholar
  • 20a Rist M. Amann N. Wagenknecht H.-A. Eur. J. Org. Chem.  2003,  2498 
    Google Scholar
  • 20b Mayer E. Valis L. Wagner C. Rist M. Amann N. Wagenknecht H.-A. ChemBioChem  2004,  5:  865 
    Google Scholar
  • 20c Wagner C. Rist M. Mayer-Enthart E. Wagenknecht H.-A. Org. Biomol. Chem.  2005,  3:  2062 
    Google Scholar
  • 20d Trifonov A. Raytchev M. Buchvarov I. Rist M. Barbaric J. Wagenknecht H.-A. Fiebig T. J. Phys. Chem. B  2005,  109:  19490 
    Google Scholar
  • 20e Barbaric J. Wagenknecht H.-A. Org. Biomol. Chem.  2006,  4:  2088 
    Google Scholar
  • For reviews, see:
  • 21a Wojczewski C. Stolze K. Engels JW. Synlett  1999,  1667 
    Google Scholar
  • 21b Ranasinghe RT. Brown T. Chem. Commun.  2005,  5487 
    Google Scholar
  • 21c Waggoner A. Curr. Opin. Chem. Biol.  2006,  10:  62 
    Google Scholar
  • 21d Cobb AJA. Org. Biomol. Chem.  2007,  5:  3260 
    Google Scholar
  • 22 Wanninger-Weiß C. Di Pasquale F. Ehrenschwender T. Marx A. Wagenknecht H.-A. Chem. Commun.  2008,  1443 
    CrossrefGoogle Scholar
  • 23 For a review, see: Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Google Scholar
  • 24 Torimura M. Kurata S. Yamada K. Yokomaku T. Kamagata Y. Kanagawa T. Kurane R. Anal. Sci.  2001,  17:  155 
    CrossrefGoogle Scholar
  • 25 Steenken S. Jovanovic SV. J. Am. Chem. Soc.  1997,  119:  617 
    CrossrefGoogle Scholar
  • 26 Weller A. Z. Phys. Chem. (Leipzig)  1982,  133:  93 
    CrossrefGoogle Scholar