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

Marina Lledos; David Gonzalez Calatayud; Fernando Cortezon-Tamarit; Haobo Ge; Charareh Pourzand; Stanley W. Botchway; Mariona Sodupe; Agusti Lledos; Ian Eggleston; Sofia I. Pascu

doi:10.1002/chem.202400858

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

Marina Lledos
, David Gonzalez Calatayud
, Fernando Cortezon-Tamarit
, Haobo Ge
, Charareh Pourzand
, Stanley W. Botchway
, Mariona Sodupe
, Agusti Lledos
, Ian Eggleston
, Sofia I. Pascu

Rutherford Appleton Laboratory
Universitat Autònoma de Barcelona
Universidad Autónoma de Madrid

Research output: Contribution to journal › Article › peer-review

4 Citations (SciVal)

Abstract

A 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).

Original language	English
Article number	e202400858
Journal	Chemistry - A European Journal
Volume	30
Issue number	49
Early online date	18 Jun 2024
DOIs	https://doi.org/10.1002/chem.202400858
Publication status	Published - 2 Sept 2024

Data Availability Statement

Supplementary Information available in ESI include: Syntheticprotocols with full characterization details, spectroscopic andanalysis data, nanoparticle characterization, cellular imaging andMTT assays. TD DTF data including cartesian coordinates formodel compounds are also given in ESI. Data for this researchare given in the Electronic supplementary (ESI) and availablefrom the authors upon request

Acknowledgements

The authors gratefully acknowledge the collaborative support from Megan Green and the Material and Chemical Characterisation Facility (MC2) at the University of Bath for technical support and assistance in this work.

Funding

The authors thank the ERC for funding through the Consolidator Grant O2Sense (617107), ERC PoC Tools\u2010To\u2010Sense (963937), and the University of Bath for the URSA\u2010Science Strategic PhD studentship to ML. SIP also thanks the following grants for funding: STFC CDN+ Biosensing and NIR Imaging of New Biomarkers for Prostate Cancer, BBSRC (BB/W019655/1: Multi User High\u2010 Content Confocal Fluorescence Microscope); EP/K0171 60/1: \u2018New manufacturable approaches to the deposition and patterning of graphene materials\u2019; EP/L016354/1: EPSRC Centre for Doctoral Training in Sustainable Chemical Technologies EP/ G03768X/1: Doctoral Training Centre in Sustainable Chemical Technologies. DGC thanks to the Ministerio de Ciencia, Innovaci' on y Universidades (Spain) for funding (TED2021132779B\u2010100 and TED2021\u2010129876B\u2212I00). The authors gratefully acknowledge the collaborative support from Megan Green and the Material and Chemical Characterisation Facility (MC2) at the University of Bath for technical support and assistance in this work.

Funders	Funder number
University of Bath
STFC Batteries Network
Erciyes Üniversitesi	617107
Erciyes Üniversitesi
Biotechnology and Biological Sciences Research Council	BB/W019655/1, EP/L016354/1, EP/K0171 60/1
Thomas Pocklington Trust	963937
Thomas Pocklington Trust
Ministerio de Universidades	TED2021‐129876B−I00, TED2021132779B‐100
Ministerio de Universidades
Wellcome EPSRC Centre for Medical Engineering	EP/ G03768X/1
Wellcome EPSRC Centre for Medical Engineering

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Confocal microscopy and Airyscan super resolution
Multiphoton FLIM
TD-DFT calculations
conjugatable tripodal D-biotin conjugates
multiplexing with BODIPY tags

ASJC Scopus subject areas

General Chemistry
Catalysis
Organic Chemistry

Access to Document

10.1002/chem.202400858Licence: CC BY

Cite this

Lledos, M., Gonzalez Calatayud, D., Cortezon-Tamarit, F., Ge, H., Pourzand, C., Botchway, S. W., Sodupe, M., Lledos, A., Eggleston, I., & Pascu, S. I. (2024). Tripodal BODIPY-Tagged and Functional Molecular Probes: Synthesis, Computational Investigations and Explorations by Multiphoton Fluorescence Lifetime Imaging Microscopy. Chemistry - A European Journal, 30(49), Article e202400858. https://doi.org/10.1002/chem.202400858

Tripodal BODIPY-Tagged and Functional Molecular Probes: Synthesis, Computational Investigations and Explorations by Multiphoton Fluorescence Lifetime Imaging Microscopy. / Lledos, Marina; Gonzalez Calatayud, David; Cortezon-Tamarit, Fernando et al.
In: Chemistry - A European Journal, Vol. 30, No. 49, e202400858, 02.09.2024.

Research output: Contribution to journal › Article › peer-review

Lledos, M, Gonzalez Calatayud, D, Cortezon-Tamarit, F, Ge, H , Pourzand, C, Botchway, SW, Sodupe, M, Lledos, A, Eggleston, I & Pascu, SI 2024, 'Tripodal BODIPY-Tagged and Functional Molecular Probes: Synthesis, Computational Investigations and Explorations by Multiphoton Fluorescence Lifetime Imaging Microscopy', Chemistry - A European Journal, vol. 30, no. 49, e202400858. https://doi.org/10.1002/chem.202400858

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abstract = "A 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).",

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

Abstract

Data Availability Statement

Acknowledgements

Funding

UN SDGs

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Multi User High-Content Confocal Microscope

Cite this

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

Abstract

Data Availability Statement

Acknowledgements

Funding

UN SDGs

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Projects

Multi User High-Content Confocal Microscope

Cite this