Near infrared dipyrrin-based fluorogenic chelators for metal ions

Sujatha Thyagarajan, Brahma Ghosh, Mikhail A. Filatov, Anna V. Moore, Andrei V. Cheprakov, Sergei A. Vinogradov

Research output: Chapter in Book/Report/Conference proceedingConference contributionpeer-review

Abstract

We present a new family of dipyrrins, whose spectral properties are tunable over the visible/near infrared range by way of annealing the pyrrolic residues with external aromatic fragments. Complexes of the π-extended with many metal ions were found to be highly fluorescent, and their fluorescence is modulated depending on the mode of the metal coordination. Structural and spectroscopic data were consolidated on the basis of the Kasha's exciton coupling theory, suggesting rational pathways to practically useful fluorogenic dipyrrin-based ligands. Water-soluble dendritic π-extended dipyrrin BDP-1 was prepared and evaluated as a fluorescent sensor for Zn2+. BDP-1 shows micromolar binding affinity for Zn2+ and high selectivity compared to Ca 2+, Mg2+ and many other metal ions.

Original languageEnglish
Title of host publicationReporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications III
DOIs
Publication statusPublished - 2011
Externally publishedYes
EventReporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications III - San Francisco, CA, United States
Duration: 24 Jan 201126 Jan 2011

Publication series

NameProgress in Biomedical Optics and Imaging - Proceedings of SPIE
Volume7910
ISSN (Print)1605-7422

Conference

ConferenceReporters, Markers, Dyes, Nanoparticles, and Molecular Probes for Biomedical Applications III
Country/TerritoryUnited States
CitySan Francisco, CA
Period24/01/1126/01/11

Keywords

  • BODIPY
  • Dendrimer
  • Dipyrrin
  • Dipyrromethenes
  • Fluorescence
  • Near infrared
  • Zinc

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