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 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.
Zheng
Qingdong
Q
Department of Chemistry, Institute for Lasers, Photonics, and Biophotonics, State University of New York at Buffalo, Buffalo, NY 14260 USA. qzheng7@jhu.edu
Xu
Gaixia
G
Prasad
Paras N
PN
D001896:Boron Compounds / Q000737:chemistry*; D002477:Cells / Q000166:cytology*; D018360:Crystallography, X-Ray / Q000379:methods; D005456:Fluorescent Dyes / Q000737:chemistry*; D007090:Image Interpretation, Computer-Assisted / Q000379:methods*; D008968:Molecular Conformation; D011162:Porphobilinogen / Q000031:analogs & derivatives* / Q000737:chemistry; D013050:Spectrometry, Fluorescence / Q000379:methods*
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; C507544:dipyrromethene; D011162:Porphobilinogen