Science China Chemistry

, Volume 55, Issue 1, pp 125–130 | Cite as

Tuning the optical properties of BODIPY dye through Cu(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction

Articles Special Topic The Frontiers of Chemical Biology and Synthesis
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Abstract

Borondipyrromethenes (BODIPY) are a class of fluorescent dyes whose fluorescence quantum yields are generally high and independent of the solvent. In this paper, we report the synthesis of a new type of BODIPY compound that carries an azido group on the 3-position of the pyrrole core. The azido group quenches the fluorescence of the dye due to its weak electron-donating effect. The fluorescence of the BODIPY dye can be switched on after reacting with alkynes via a Cu(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction. We further demonstrate that this azido-BODIPY compound can be used in the cell imaging applications.

Keywords

CuAAC reaction fluorogenic BODIPY dye cell imaging fluorescent probe 
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References

  1. 1.
    Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew Chem Int Ed, 2002, 41: 2596–2599CrossRefGoogle Scholar
  2. 2.
    Tornoe CW, Christensen C, Meldal M. Peptidotriazoles on solid phase: [1xxx2xxx3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem, 2002, 67: 3057–3064CrossRefGoogle Scholar
  3. 3.
    Sivakumar K, Xie F, Cash BM, Long S, Barnhill HN, Wang Q. A fluorogenic 1,3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes. Org Lett, 2004, 6: 4603–4606CrossRefGoogle Scholar
  4. 4.
    Zhou Z, Fahrni CJ. A fluorogenic probe for the copper(I)-catalyzed azide-alkyne ligation reaction: Modulation of the fluorescence emission via (3)(n,pi*)-(1)(pi,pi*) inversion. J Am Chem Soc, 2004, 126: 8862–8863CrossRefGoogle Scholar
  5. 5.
    Sawa M, Hsu TL, Itoh T, Sugiyama M, Hanson SR, Vogt PK, Wong CH. Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo. Proc Nat Acad Sci USA, 2006, 103: 12371–12376CrossRefGoogle Scholar
  6. 6.
    Xie F, Sivakumar K, Zeng QB, Bruckman MA, Hodges B, Wang Q. A fluorogenic “click” reaction of azidoanthracene derivatives. Tetrahedron, 2008, 64: 2906–2914CrossRefGoogle Scholar
  7. 7.
    Beatty KE, Liu JC, Xie F, Dieterich DC, Schuman EM, Wang Q, Tirrell DA. Fluorescence visualization of newly synthesized proteins in mammalian cells. Angew Chem Int Ed, 2006, 45: 7364–7367CrossRefGoogle Scholar
  8. 8.
    Le Droumaguet C, Wang C, Wang Q. Fluorogenic click reaction. Chem Soc Rev, 2010, 39: 1233–1239CrossRefGoogle Scholar
  9. 9.
    Bergstrom F, Mikhalyov I, Hagglof P, Wortmann R, Ny T, Johansson LBA. Dimers of dipyrrometheneboron difluoride (BODIPY) with light spectroscopic applications in chemistry and biology. J Am Chem Soc, 2002, 124: 196–204CrossRefGoogle Scholar
  10. 10.
    Trieflinger C, Rurack K, Daub M. “Turn ON/OFF your LOV light”: Boron-dipyrromethene-flavin dyads as biomimetic switches derived from the LOV domain. Angew Chem Int Ed, 2005, 44: 2288–2291CrossRefGoogle Scholar
  11. 11.
    Zhao WL, Carreira EM. Conformationally restricted aza-bodipy: A highly fluorescent, stable, near-infrared-absorbing dye. Angew Chem Int Ed, 2005, 44: 1677–1679CrossRefGoogle Scholar
  12. 12.
    Harriman A, Izzet G, Ziessel R. Rapid energy transfer in cascade-type bodipy dyes. J Am Chem Soc, 2006, 128: 10868–10875CrossRefGoogle Scholar
  13. 13.
    Sapsford KE, Berti L, Medintz IL. Materials for fluorescence resonance energy transfer analysis: Beyond traditional donor-acceptor combinations. Angew Chem Int Ed, 2006, 45: 4562–4588CrossRefGoogle Scholar
  14. 14.
    Liras M, Prieto JB, Pintado-Sierra M, Arbeloa FL, Garcia-Moreno I, Costela A, Infantes L, Sastre R, Amat-Guerri F. Synthesis, photophysical properties, and laser behavior of 3-amino and 3-acetamido BODIPY dyes. Org Lett, 2007, 9: 4183–4186CrossRefGoogle Scholar
  15. 15.
    Riddle JA, Jiang X, Huffman J, Lee D. Signal-amplifying resonance energy transfer: A dynamic multichromophore array for allosteric switching. Angew Chem Int Ed, 2007, 46: 7019–7022CrossRefGoogle Scholar
  16. 16.
    Nagai A, Miyake J, Kokado K, Nagata Y, Chujo Y. Highly luminescent BODIPY-based organoboron polymer exhibiting supramolecular self-assemble structure. J Am Chem Soc, 2008, 130: 15276–15278CrossRefGoogle Scholar
  17. 17.
    Kaloudi-Chantzea A, Karakostas N, Raptopoulou CP, Psycharis V, Saridakis E, Griebel J, Hermann R, Pistolis G. Coordination-driven self assembly of a brilliantly fluorescent rhomboid cavitand composed of bodipy-dye subunits. J Am Chem Soc, 2010, 132: 16327–16329CrossRefGoogle Scholar
  18. 18.
    Nepomnyashchii AB, Cho S, Rossky PJ, Bard AJ. Dependence of electrochemical and electrogenerated chemiluminescence properties on the structure of bodipy dyes unusually large separation between sequential electron transfers. J Am Chem Soc, 2010, 132: 17550–17559CrossRefGoogle Scholar
  19. 19.
    Nepomnyashchii AB, Broring M, Ahrens J, Bard AJ. Synthesis, photophysical, electrochemical, and electrogenerated chemiluminescence studiesMultiple sequential electron transfers in BODIPY monomers, dimers, trimers, and polymer. J Am Chem Soc, 2011, 133: 8633–45CrossRefGoogle Scholar
  20. 20.
    Whited MT, Djurovich PI, Roberts ST, Durrell AC, Schlenker CW, Bradforth SE, Thompson ME. Singlet and triplet excitation management in a bichromophoric near-infrared-phosphorescent BODIPY-benzoporphyrin platinum complex. J Am Chem Soc, 2011, 133: 88–96CrossRefGoogle Scholar
  21. 21.
    Yogo T, Urano Y, Ishitsuka Y, Maniwa F, Nagano T. Highly efficient and photostable photosensitizer based on BODIPY chromophore. J Am Chem Soc, 2005, 127: 12162–12163CrossRefGoogle Scholar
  22. 22.
    Hagihara S, Miyazaki A, Matsuo I, Tatami A, Suzuki T, Ito Y. Fluorescently labeled inhibitor for profiling cytoplasmic peptide:N-glycanase. Glycobiology, 2007, 17: 1070–1076CrossRefGoogle Scholar
  23. 23.
    Bricks JL, Kovalchuk A, Trieflinger C, Nofz M, Buschel M, Tolmachev AI, Daub J, Rurack K. On the development of sensor molecules that display Fe-III-amplified fluorescence. J Am Chem Soc, 2005, 127: 13522–13529CrossRefGoogle Scholar
  24. 24.
    Qin WW, Baruah M, Stefan A, Van der Ameraer M, Boens N. Photophysical properties of BODIPY-derived hydroxyaryl fluorescent pH probes in solution. Chem Physchem, 2005, 6: 2343–2351CrossRefGoogle Scholar
  25. 25.
    Peng XJ, Du JJ, Fan JL, Wang JY, Wu YK, Zhao JZ, Sun SG, Xu T. A selective fluorescent sensor for imaging Cd2+ in living cells. J Am Chem Soc, 2007, 129: 1500–1501CrossRefGoogle Scholar
  26. 26.
    Lee JS, Kang NY, Kim YK, Samanta A, Feng SH, Kim HK, Vendrell M, Park JH, Chang YT. Synthesis of a BODIPY library and its application to the development of live cell glucagon imaging probe. J Am Chem Soc, 2009, 131: 10077–10082CrossRefGoogle Scholar
  27. 27.
    Devaraj NK, Hilderbrand S, Upadhyay R, Mazitschek R, Weissleder R. Bioorthogonal turn-on probes for imaging small molecules inside living cells. Angew Chem Int Ed, 2010, 49: 2869–2872Google Scholar
  28. 28.
    Nierth A, Kobitski AY, Nienhaus GU, Jaschke A. Anthracene-BODIPY dyads as fluorescent sensors for biocatalytic diels-alder reactions. J Am Chem Soc, 2010, 132: 2646–2654CrossRefGoogle Scholar
  29. 29.
    Ulrich G, Ziessel R, Harriman A. The chemistry of fluorescent bodipy dyes: Versatility unsurpassed. Angew Chem Int Ed, 2008, 47: 1184–1201CrossRefGoogle Scholar
  30. 30.
    Goze C, Ulrich G, Charbonnière L, Cesario M, Prangé T, Ziessel R. Cation sensors based on terpyridine-functionalized boradiazaindacene. Chem Eur J, 2003, 9: 3748–3755CrossRefGoogle Scholar
  31. 31.
    Qin WW, Rohand T, Baruah M, Stefan A, Van der Auweraer M, Dehaen W, Boens N. Solvent-dependent photophysical properties of borondipyrromethene dyes in solution. Chem Phys Lett, 2006, 420: 562–568CrossRefGoogle Scholar
  32. 32.
    Rohand T, Baruah M, Qin WW, Boens N, Dehaen W. Functionalisation of fluorescent BODIPY dyes by nucleophilic substitution. Chem Commun, 2006, 266–268Google Scholar
  33. 33.
    Rohand T, Qin WW, Boens N, Dehaen W. Palladium-catalyzed coupling reactions for the functionalization of BODIPY dyes with fluorescence spanning the visible spectrum. Eur J Org Chem, 2006, 4658–4663Google Scholar
  34. 34.
    Rurack K, Kollmannsberger M, Daub J. Molecular switching in the near infrared (NIR) with a functionalized boron-Dipyrromethene dye. Angew Chem Int Ed, 2001, 40: 385–387CrossRefGoogle Scholar
  35. 35.
    Basaric N, Baruah M, Qin WW, Metten B, Smet M, Dehaen W, Boens N. Synthesis and spectroscopic characterisation of BODIPY (R) based fluorescent off-on indicators with low affinity for calcium. Org Biomol Chem, 2005, 3: 2755–2761CrossRefGoogle Scholar
  36. 36.
    Qi X, Jun EJ, Xu L, Kim SJ, Hong JSJ, Yoon YJ, Yoon JY. New BODIPY derivatives as OFF-ON fluorescent chemosensor and fluorescent chemodosimeter for Cu2+: Cooperative selectivity enhancement toward Cu2+. J Org Chem, 2006, 71: 2881–2884CrossRefGoogle Scholar
  37. 37.
    Zeng L, Miller EW, Pralle A, Isacoff EY, Chang CJ. A selective turn-on fluorescent sensor for imaging copper in living cells. J Am Chem Soc, 2006, 128: 10–11CrossRefGoogle Scholar
  38. 38.
    Miller EW, Albers AE, Pralle A, Isacoff EY, Chang CJ. Boronate-based fluorescent probes for imaging cellular hydrogen peroxide. J Am Chem Soc, 2005, 127: 16652–16659CrossRefGoogle Scholar
  39. 39.
    Yuan MJ, Li YL, Li JB, Li CH, Liu XF, Lv J, Xu JL, Liu HB, Wang S, Zhu D. A colorimetric and fluorometric dual-modal assay for mercury ion by a molecule. Org Lett, 2007, 9: 2313–2316CrossRefGoogle Scholar
  40. 40.
    Bozdemir OA, Guliyev R, Buyukcakir O, Selcuk S, Kolemen S, Gulseren G, Nalbantoglu T, Boyaci H, Akkaya EU. Selective manipulation of ict and pet processes in styryl-bodipy derivatives: applications in molecular logic and fluorescence sensing of metal ions. J Am Chem Soc, 2010, 132: 8029–8036CrossRefGoogle Scholar
  41. 41.
    Littler BJ, Miller MA, Hung CH, Wagner RW, O'shea DF, Boyle PD, Lindsey JS. Refined synthesis of 5-substituted dipyrromethanes. J Org Chem, 1999, 64: 1391–1396CrossRefGoogle Scholar
  42. 42.
    Cornforth JW, Firth ME. Identification of two chromogens in the Elson-Morgan determination of hexosamines. A new synthesis of 3-methylpyrrole. Structure of the “pyrrolene-phthalides”. J Chem Soc, 1958, 1091–1099Google Scholar
  43. 43.
    Baruah M, Qin WW, Basaric N, De Borggraeve WM, Boens N. BODIPY-based hydroxyaryl derivatives as fluorescent pH probes. J Org Chem, 2005, 70: 4152–4157CrossRefGoogle Scholar
  44. 44.
    De P, Gondi SR, Sumerlin BS. Folate-conjugated thermoresponsive block copolymers: Highly efficient conjugation and solution self-assembly. Biomacromolecules, 2008, 9: 1064–1070CrossRefGoogle Scholar
  45. 45.
    Saeed AO, Magnusson JP, Moradi E, Soliman M, Wang W, Stolnik S, Thurecht KJ, Howdle SM, Alexander C. Modular construction of multifunctional bioresponsive cell-targeted nanoparticles for gene delivery. Bioconjugate Chem, 2011, 22: 156–168CrossRefGoogle Scholar
  46. 46.
    Leamon CP, Reddy JA. Folate-targeted chemotherapy. Adv Drug Delivery Rev, 2004, 56: 1127–1141CrossRefGoogle Scholar
  47. 47.
    Suthiwangcharoen N, Li T, Li K, Thompson P, You S, Wang Q. M13 bacteriophage-polymer nanoassemblies as drug delivery vehicles. Nano Res, 2011, 1–11Google Scholar

Copyright information

© Science China Press and Springer-Verlag Berlin Heidelberg 2011

Authors and Affiliations

  1. 1.Natural Products Center, Chengdu Institute of BiologyChinese Academy of SciencesChengduChina
  2. 2.Department of Chemistry and BiochemistryUniversity of South CarolinaColumbiaUSA

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