Development of UV-Excitable Red and Near-Infrared Fluorescent Labels and Their Application for Simultaneous Multicolor Bioimaging by Single-Wavelength Excitation
详细信息    查看全文
  • 作者:Tetsuya Mizuno (1)
    Keitaro Umezawa (2)
    Yutaka Shindo (2)
    Daniel Citterio (1)
    Kotaro Oka (2)
    Koji Suzuki (1)
  • 关键词:Bioimaging ; BODIPY ; Fluorescent dyads ; Near ; infrared fluorophore
  • 刊名:Journal of Fluorescence
  • 出版年:2013
  • 出版时间:September 2013
  • 年:2013
  • 卷:23
  • 期:5
  • 页码:1007-1018
  • 全文大小:427KB
  • 参考文献:1. Tomosugi W, Matsuda T, Tani T, Nemoto T, Kotera I, Saito K, Horikawa K, Nagai T (2009) An ultramarine fluorescent protein with increased photostability and pH insensitivity. Nat Methods 6(5):351鈥?53 CrossRef
    2. Niino Y, Hotta K, Oka K (2009) Simultaneous live cell imaging using dual FRET sensors with a single excitation light. PLoS One 4(6):e6036 CrossRef
    3. Weissleder R (2001) A clearer vision for in vivo imaging. Nat Biotechnol 19(4):316鈥?17 CrossRef
    4. Zhao Q, Huang C, Li F (2011) Phosphorescent heavy-metal complexes for bioimaging. Chem Soc Rev 40(5):2508鈥?524 CrossRef
    5. Ziessel R, Harriman A (2011) Artificial light-harvesting antennae: electronic energy transfer by way of molecular funnels. Chem Commun 47(2):611鈥?31 CrossRef
    6. Harriman A, Izzet G, Ziessel R (2006) Rapid energy transfer in cascade-type bodipy dyes. J Am Chem Soc 128(33):10868鈥?0875 CrossRef
    7. Ulrich G, Ziessel R, Harriman A (2008) The chemistry of fluorescent bodipy dyes: versatility unsurpassed. Angew Chem Int Ed 47(7):1184鈥?201 CrossRef
    8. Ulrich G, Goze C, Guardigli M, Roda A, Ziessel R (2005) Pyrromethene dialkynyl borane complexes for cascatelle energy transfer and protein labeling. Angew Chem Int Ed 44(24):3694鈥?698 CrossRef
    9. Goze C, Ulrich G, Ziessel R (2007) Tetrahedral boron chemistry for the preparation of highly efficient 鈥淐ascatelle鈥?devices. J Org Chem 72(2):313鈥?22 CrossRef
    10. Goeb S, Ziessel R (2007) Convenient synthesis of green diisoindolodithienylpyrromethene-dialkynyl borane dyes. Org Lett 9(5):737鈥?40 CrossRef
    11. Harriman A, Mallon LJ, Goeb S, Ulrich G, Ziessel R (2009) Electronic energy transfer to the S2 level of the acceptor in functionalised boron dipyrromethene dyes. Chem Eur J 15(18):4553鈥?564 CrossRef
    12. Ulrich G, Goeb S, De Nicola A, Retailleau P, Ziessel R (2011) Chemistry at boron: synthesis and properties of red to near-IR fluorescent dyes based on boron-substituted diisoindolomethene frameworks. J Org Chem 76(11):4489鈥?505 CrossRef
    13. Coskun A, Akkaya EU (2006) Signal ratio amplification via modulation of resonance energy transfer: proof of principle in an emission ratiometric Hg(II) sensor. J Am Chem Soc 128(45):14474鈥?4475 CrossRef
    14. Wu L, Loudet A, Barhoumi R, Burghardt RC, Burgess K (2009) Fluorescent cassettes for monitoring three-component interactions in vitro and in living cells. J Am Chem Soc 131(26):9156鈥?157 CrossRef
    15. Lin W, Yuan L, Cao Z, Feng Y, Song J (2010) Through-bond energy transfer cassettes with minimal spectral overlap between the donor emission and acceptor absorption: Coumarin鈥搑hodamine dyads with large pseudo-Stokes shifts and emission shifts. Angew Chem Int Ed 49(2):375鈥?79 CrossRef
    16. Jiao GS, Thoresen LH, Burgess K (2003) Fluorescent, through-bond energy transfer cassettes for labeling multiple biological molecules in one experiment. J Am Chem Soc 125(48):14668鈥?4669 CrossRef
    17. Bandichhor R, Petrescu AD, Vespa A, Kier AB, Schroeder F, Burgess K (2006) Water-soluble through-bond energy transfer cassettes for intracellular imaging. J Am Chem Soc 128(33):10688鈥?0689 CrossRef
    18. Thivierge C, Han J, Jenkins RM, Burgess K (2011) Fluorescent proton sensors based on energy transfer. J Org Chem 76(13):5219鈥?228 CrossRef
    19. Loudet A, Bandichhor R, Wu LX, Burgess K (2008) Functionalized BF2 chelated azadipyrromethene dyes. Tetrahedron 64(17):3642鈥?654 CrossRef
    20. Jose J, Ueno Y, Castro JC, Li L, Burgess K (2009) Energy transfer dyads based on Nile Red. Tetrahedron Lett 50(47):6442鈥?445 CrossRef
    21. Ueno Y, Jose J, Loudet A, P茅rez-Bol铆var CS, Anzenbacher P, Burgess K (2010) Encapsulated energy-transfer cassettes with extremely well resolved fluorescent outputs. J Am Chem Soc 133(1):51鈥?5 CrossRef
    22. Loudet A, Ueno Y, Wu L, Jose J, Barhoumi R, Burghardt R, Burgess K (2011) Organelle-selective energy transfer: a fluorescent indicator of intracellular environment. Bioorg Med Chem Lett 21(6):1849鈥?851 CrossRef
    23. Umezawa K, Matsui A, Nakamura Y, Citterio D, Suzuki K (2009) Bright, color-tunable fluorescent dyes in the vis/NIR Region: establishment of new 鈥渢ailor-made鈥?multicolor fluorophores based on borondipyrromethene. Chem Eur J 15(5):1096鈥?106 CrossRef
    24. Eaton DF (1988) Reference materials for fluorescence measurement. Pure Appl Chem 60(7):1107鈥?114 CrossRef
    25. Magde D, Brannon JH, Cremers TL, Olmsted J (1979) Absolute luminescence yield of cresyl violet. A standard for the red. J Phys Chem 83(6):696鈥?99 CrossRef
    26. Dempster DN, Morro T, Rankin R, Thompson GF (1972) Photochemical characteristics of cyanine dyes. 1. 3,3鈥?Diethyloxadicarbocyanine iodide and 3,3鈥?diethylthiadicarbocyanine iodide. J Chem Soc, Faraday Trans 2 68(9):1479鈥?496 CrossRef
    27. Umezawa K, Nakamura Y, Makino H, Citterio D, Suzuki K (2008) Bright, color-tunable fluorescent dyes in the visible-near-infrared region. J Am Chem Soc 130(5):1550鈥?551 CrossRef
    28. Matsui A, Umezawa K, Shindo Y, Fujii T, Citterio D, Oka K, Suzuki K (2011) A near-infrared fluorescent calcium probe: a new tool for intracellular multicolour Ca2+ imaging. Chem Commun 47(37):10407鈥?0409 CrossRef
    29. Thivierge C, Loudet A, Burgess K (2011) Brilliant BODIPY鈭抐luorene copolymers with dispersed absorption and emission maxima. Macromolecules 44(10):4012鈥?015 CrossRef
    30. Haugland RP (2005) The Handbook: a guide to fluorescent probes and labeling technologies. Invitrogen Corp, Eugene
    31. GE Healthcare Bioscience catalogue (2006) GE Healthcare UK Ltd., Amersham
    32. Clapham DE (2007) Calcium signaling. Cell 131(6):1047鈥?058 CrossRef
    33. Carter DC, Ho JX (1994) Structure of serum albumin. Adv Protein Chem 45:153鈥?03 CrossRef
    34. Fuentes E, Nadal A, Jacob R, McNaughton P (1997) Actions of serum and plasma albumin on intracellular Ca2+ in human endothelial cells. J Physiol 504(Pt 2):315鈥?26 CrossRef
    35. Grynkiewicz G, Poenie M, Tsien RY (1985) A new generation of Ca2+ indicators with greatly improved fluorescence properties. J Biol Chem 260(6):3440鈥?450
    36. Carlson HJ, Campbell RE (2009) Genetically encoded FRET-based biosensors for multiparameter fluorescence imaging. Curr Opin Biotechnol 20(1):19鈥?7 CrossRef
    37. Keppler A, Gendreizig S, Gronemeyer T, Pick H, Vogel H, Johnsson K (2003) A general method for the covalent labeling of fusion proteins with small molecules in vivo. Nat Biotechnol 21(1):86鈥?9 CrossRef
    38. Gautier A, Juillerat A, Heinis C, Correa IR, Kindermann M, Beaufils F, Johnsson K (2008) An engineered protein tag for multiprotein labeling in living cells. Chem Biol 15(2):128鈥?36 CrossRef
    39. Los GV, Encell LP, McDougall MG, Hartzell DD, Karassina N, Zimprich C, Wood MG, Learish R, Ohana RF, Urh M, Simpson D, Mendez J, Zimmerman K, Otto P, Vidugiris G, Zhu J, Darzins A, Klaubert DH, Bulleit RF, Wood KV (2008) HaloTag: a novel protein labeling technology for cell imaging and protein analysis. ACS Chem Biol 3(6):373鈥?82 CrossRef
    40. Ojida A, Honda K, Shinmi D, Kiyonaka S, Mori Y, Hamachi I (2006) Oligo-Asp Tag/Zn(II) complex probe as a new pair for labeling and fluorescence imaging of proteins. J Am Chem Soc 128(32):10452鈥?0459 CrossRef
  • 作者单位:Tetsuya Mizuno (1)
    Keitaro Umezawa (2)
    Yutaka Shindo (2)
    Daniel Citterio (1)
    Kotaro Oka (2)
    Koji Suzuki (1)

    1. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan
    2. Department of Bioinformatics, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan
文摘
We report a new type of UV-excitable red/NIR-emissive fluorescent dyads (PKF series). Conjugation of a pyrene and a novel bright red/near-infrared (NIR) fluorophore resulted in large quasi-Stokes shift while retaining intense fluorescence emission and sharp spectral bands. Labeling of PKF dyads to biomolecules was performed by means of introduction of a succinimidyl ester. Simultaneous Ca2+/albumin dual-color intracellular imaging by PKF in combination with fura-2 (UV-excitable/VIS-emissive Ca2+ indicator) reveals its usefulness as a new bioimaging tool.

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700