Tripodal BODIPY‐Tagged and Functional Molecular Probes: Synthesis, Computational Investigations and Explorations by Multiphoton Fluorescence Lifetime Imaging Microscopy

Author:

Lledos Marina1,Calatayud David G.2,Cortezon‐Tamarit Fernando1,Ge Haobo13,Pourzand Charareh34,Botchway Stanley W.5,Sodupe Mariona6,Lledós Agustí6,Eggleston Ian M.34,Pascu Sofia I.14ORCID

Affiliation:

1. Department of Chemistry University of Bath Bath BA2 7AY U.K.

2. Department of Inorganic Chemistry Universidad Autonoma de Madrid Francisco Tomas y Valiente 7 28049 Madrid Spain

3. Department of Life Sciences University of Bath BA2 7AY Bath UK

4. Centre for Therapeutic Innovation University of Bath BA2 7AY Bath UK

5. STFC Research Complex at Harwell Rutherford Appleton Laboratory, Harwell, Science and Innovation Campus Harwell Oxfordshire OX11 0QX UK

6. Departament de Química Universitat Autònoma de Barcelona Cerdanyola del Vallès 08193 Barcelona Spain

Abstract

AbstractA range of novel BODIPY derivatives with a tripodal aromatic core was synthesized and characterized spectroscopically. These new fluorophores showed promising features as probes for in vitro assays in live cells and offer strategic routes for further functionalization towards hybrid nanomaterials. Incorporation of biotin tags facilitated proof‐of‐concept access to targeted bioconjugates as molecular probes. Computational explorations using DFT and TD‐DFT calculations identified the most stable tripodal linker conformations and predicted their absorption and emission behavior. The uptake and speciation of these molecules in living prostate cancer cells was imaged by single‐ and two‐photon excitation techniques coupled with two‐photon fluorescence lifetime imaging (2P FLIM).

Funder

Engineering and Physical Sciences Research Council

Biotechnology and Biological Sciences Research Council

Publisher

Wiley

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