Conformationally Restricted Dipyrromethene Boron Difluoride (BODIPY) Dyes: Highly Fluorescent, Multicolored Probes for Cellular Imaging

Novel fluorescent, conformationally restricted dipyrromethene boron difluoride (BODIPY) dyes have been prepared by introducing a naphthalenyl group at the meso position of the BODIPY core. These BODIPY dyes exhibit increased fluorescence quantum yields compared with dyes that have a meso‐position ph...

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Published inChemistry : a European journal Vol. 14; no. 19; pp. 5812 - 5819
Main Authors Zheng, Qingdong, Xu, Gaixia, Prasad, Paras N.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 27.06.2008
WILEY‐VCH Verlag
Wiley
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Abstract Novel fluorescent, conformationally restricted dipyrromethene boron difluoride (BODIPY) dyes have been prepared by introducing a naphthalenyl group at the meso position of the BODIPY core. These BODIPY dyes exhibit increased fluorescence quantum yields compared with dyes that have a meso‐position phenyl group with internal rotation. The absorption and emission wavelengths of such conformationally restricted BODIPY dyes can be easily tuned to the near‐IR range by derivatization through a condensation reaction with benzaldehyde derivatives. The two‐photon absorption properties of these BODIPY dyes were also investigated and the results show that they exhibit increased two‐photon excited fluorescence compared to analogue dyes that contain a phenyl group. The one‐ and two‐photon fluorescence imaging of living cells by using selected BODIPY dyes has been successfully demonstrated. Green for go! Highly fluorescent BODIPY dyes that emit light ranging from the green to near‐IR region have been synthesized by introducing a bulky naphthalenyl group at the meso position. The one‐ and two‐photon fluorescence imaging of living cells with these dyes has been successfully demonstrated (see graphic).
AbstractList Novel fluorescent, conformationally restricted dipyrromethene boron difluoride (BODIPY) dyes have been prepared by introducing a naphthalenyl group at the meso position of the BODIPY core. These BODIPY dyes exhibit increased fluorescence quantum yields compared with dyes that have a meso-position phenyl group with internal rotation. The absorption and emission wavelengths of such conformationally restricted BODIPY dyes can be easily tuned to the near-IR range by derivatization through a condensation reaction with benzaldehyde derivatives. The two-photon absorption properties of these BODIPY dyes were also investigated and the results show that they exhibit increased two-photon excited fluorescence compared to analogue dyes that contain a phenyl group. The one- and two-photon fluorescence imaging of living cells by using selected BODIPY dyes has been successfully demonstrated.Novel fluorescent, conformationally restricted dipyrromethene boron difluoride (BODIPY) dyes have been prepared by introducing a naphthalenyl group at the meso position of the BODIPY core. These BODIPY dyes exhibit increased fluorescence quantum yields compared with dyes that have a meso-position phenyl group with internal rotation. The absorption and emission wavelengths of such conformationally restricted BODIPY dyes can be easily tuned to the near-IR range by derivatization through a condensation reaction with benzaldehyde derivatives. The two-photon absorption properties of these BODIPY dyes were also investigated and the results show that they exhibit increased two-photon excited fluorescence compared to analogue dyes that contain a phenyl group. The one- and two-photon fluorescence imaging of living cells by using selected BODIPY dyes has been successfully demonstrated.
Novel fluorescent, conformationally restricted dipyrromethene boron difluoride (BODIPY) dyes have been prepared by introducing a naphthalenyl group at the meso position of the BODIPY core. These BODIPY dyes exhibit increased fluorescence quantum yields compared with dyes that have a meso-position phenyl group with internal rotation. The absorption and emission wavelengths of such conformationally restricted BODIPY dyes can be easily tuned to the near-IR range by derivatization through a condensation reaction with benzaldehyde derivatives. The two-photon absorption properties of these BODIPY dyes were also investigated and the results show that they exhibit increased two-photon excited fluorescence compared to analogue dyes that contain a phenyl group. The one- and two-photon fluorescence imaging of living cells by using selected BODIPY dyes has been successfully demonstrated.
Novel fluorescent, conformationally restricted dipyrromethene boron difluoride (BODIPY) dyes have been prepared by introducing a naphthalenyl group at the meso position of the BODIPY core. These BODIPY dyes exhibit increased fluorescence quantum yields compared with dyes that have a meso‐position phenyl group with internal rotation. The absorption and emission wavelengths of such conformationally restricted BODIPY dyes can be easily tuned to the near‐IR range by derivatization through a condensation reaction with benzaldehyde derivatives. The two‐photon absorption properties of these BODIPY dyes were also investigated and the results show that they exhibit increased two‐photon excited fluorescence compared to analogue dyes that contain a phenyl group. The one‐ and two‐photon fluorescence imaging of living cells by using selected BODIPY dyes has been successfully demonstrated. Green for go! Highly fluorescent BODIPY dyes that emit light ranging from the green to near‐IR region have been synthesized by introducing a bulky naphthalenyl group at the meso position. The one‐ and two‐photon fluorescence imaging of living cells with these dyes has been successfully demonstrated (see graphic).
Novel fluorescent, conformationally restricted dipyrromethene boron difluoride (BODIPY) dyes have been prepared by introducing a naphthalenyl group at the meso position of the BODIPY core. These BODIPY dyes exhibit increased fluorescence quantum yields compared with dyes that have a meso ‐position phenyl group with internal rotation. The absorption and emission wavelengths of such conformationally restricted BODIPY dyes can be easily tuned to the near‐IR range by derivatization through a condensation reaction with benzaldehyde derivatives. The two‐photon absorption properties of these BODIPY dyes were also investigated and the results show that they exhibit increased two‐photon excited fluorescence compared to analogue dyes that contain a phenyl group. The one‐ and two‐photon fluorescence imaging of living cells by using selected BODIPY dyes has been successfully demonstrated.
Author Prasad, Paras N.
Xu, Gaixia
Zheng, Qingdong
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  email: qzheng7@jhu.edu
  organization: Department of Chemistry, Institute for Lasers, Photonics, and Biophotonics, State University of New York at Buffalo, Buffalo, NY 14260 USA, Fax: (+1) 716-645-6945
– sequence: 2
  givenname: Gaixia
  surname: Xu
  fullname: Xu, Gaixia
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  organization: Department of Chemistry, Institute for Lasers, Photonics, and Biophotonics, State University of New York at Buffalo, Buffalo, NY 14260 USA, Fax: (+1) 716-645-6945
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Issue 19
Keywords dyes/pigments
2-PHOTON EXCITATION
luminescence
FLUOROPHORES
two-photon absorption
imaging agents
fluorescent probes
Language English
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Snippet Novel fluorescent, conformationally restricted dipyrromethene boron difluoride (BODIPY) dyes have been prepared by introducing a naphthalenyl group at the meso...
Novel fluorescent, conformationally restricted dipyrromethene boron difluoride (BODIPY) dyes have been prepared by introducing a naphthalenyl group at the meso...
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SubjectTerms Boron Compounds - chemistry
Cells - cytology
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray - methods
dyes/pigments
Fluorescent Dyes - chemistry
fluorescent probes
Image Interpretation, Computer-Assisted - methods
imaging agents
luminescence
Molecular Conformation
Physical Sciences
Porphobilinogen - analogs & derivatives
Porphobilinogen - chemistry
Science & Technology
Spectrometry, Fluorescence - methods
two-photon absorption
Title Conformationally Restricted Dipyrromethene Boron Difluoride (BODIPY) Dyes: Highly Fluorescent, Multicolored Probes for Cellular Imaging
URI https://api.istex.fr/ark:/67375/WNG-D8ZM650G-F/fulltext.pdf
https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.200800309
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https://www.ncbi.nlm.nih.gov/pubmed/18494008
https://www.proquest.com/docview/69257448
Volume 14
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