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 in | Chemistry : a European journal Vol. 14; no. 19; pp. 5812 - 5819 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
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). |
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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 |
Author_xml | – sequence: 1 givenname: Qingdong surname: Zheng fullname: Zheng, Qingdong 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 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: 3 givenname: Paras N. surname: Prasad fullname: Prasad, Paras N. email: pnprasad@buffalo.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 |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/18494008$$D View this record in MEDLINE/PubMed |
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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 |
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