Haobo Ge

University of Bath

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Sofia I. Pascu

University of Bath

Gabriele Kociok‐Köhn

University of Bath

Fernando Cortezon‐Tamarit

University of Bath

Charareh Pourzand

University of Bath

Rory L. Arrowsmith

University of Bath

Jonathan R. Dilworth

University of Oxford

Sara Raquel Mota Merelo de Aguiar

University of Bath

Kexin Song

Jilin University

Navaratnarajah Kuganathan

Imperial College London

Stanley W. Botchway

Science and Technology Facilities Council

Cooperative Institutions

University of Bath

University of Cambridge

University College London

University of Oxford

University of Manchester

University of Surrey

Science Oxford

Cardiff University

Oxford Research Group

Consejo Superior de Investigaciones Científicas

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CCDC 2218619: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Fernando Cortezon‐Tamarit Kexin Song Navaratnarajah Kuganathan Rory L. Arrowsmith Sara Raquel Mota Merelo de Aguiar

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc2dgncx

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CCDC 2218621: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Fernando Cortezon‐Tamarit Kexin Song Navaratnarajah Kuganathan Rory L. Arrowsmith Sara Raquel Mota Merelo de Aguiar

10.5517/ccdc.csd.cc2dgnfz

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CCDC 2218769: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Fernando Cortezon‐Tamarit Kexin Song Navaratnarajah Kuganathan Rory L. Arrowsmith Sara Raquel Mota Merelo de Aguiar

10.5517/ccdc.csd.cc2dgt6x

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Hybrid Hierarchical Heterostructures of Nanoceramic Phosphors as Imaging Agents for Multiplexing and Living Cancer Cells Translocation

ACS Applied Bio Materials (2021)

David G. Calatayud Teresa Jardiel Mara S. Bernardo Vincenzo Mirabello Haobo Ge

Existing fluorescent labels used in life sciences are based on organic compounds with limited lifetime or on quantum dots which are either expensive or toxic and have low kinetic stability in biological environments. To address these challenges, luminescent nanomaterials have been conceived as hierarchical, core–shell structures with spherical morphology and highly controlled dimensions. These tailor-made nanophosphors incorporate Ln:YVO4 nanoparticles (Ln = Eu(III) and Er(III)) as 50 nm cores and display intense and narrow emission maxima centered at ∼565 nm. These cores can be encapsulated in silica shells with highly controlled dimensions as well as functionalized with chitosan or PEG5000 to reduce nonspecific interactions with biomolecules in living cells. Confocal fluorescence microscopy in living prostate cancer cells confirmed the potential of these platforms to overcome the disadvantages of commercial fluorophores and their feasibility as labels for multiplexing, biosensing, and imaging in life science assays.

Nanomaterials

Biomolecule

Fluorescence-lifetime imaging microscopy

Biological Imaging

10.1021/acsabm.0c01417

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Multiphoton fluorescence lifetime imaging microscopy (FLIM) and super-resolution fluorescence imaging with a supramolecular biopolymer for the controlled tagging of polysaccharides

Nanoscale (2019)

Haobo Ge Fernando Cortezon‐Tamarit Hui-Chen Wang Adam C. Sedgwick Rory L. Arrowsmith

A new coumarin-appended boronate ester for fluorogenic imaging which binds polysaccharides in solution and in cells.

Biopolymer

Fluorescence-lifetime imaging microscopy

10.1039/c8nr10344e

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Structural Investigations, Cellular Imaging, and Radiolabeling of Neutral, Polycationic, and Polyanionic Functional Metalloporphyrin Conjugates

Bioconjugate Chemistry (2021)

Valeria Ciaffaglione Philip A. Waghorn Rüdiger M. Exner Fernando Cortezon‐Tamarit Samuel P. Godfrey

Over the past decade, porphyrin derivatives have emerged as invaluable synthetic building blocks and theranostic kits for the delivery of cellular fluorescence imaging and photodynamic therapy. Tetraphenylporphyrin (TPP), its metal complexes, and related derivatives have been investigated for their use as dyes in histology and as components of multimodal imaging probes. The photophysical properties of porphyrin-metal complexes featuring radiometals have been a focus of our attention for the realization of fluorescence imaging probes coupled with radioimaging capabilities and therapeutic potential having "true" theranostic promise. We report hereby on the synthesis, radiochemistry, structural investigations, and preliminary in vitro and in vivo uptake studies on a range of functionalized porphyrin-based derivatives. In pursuit of developing new porphyrin-based probes for multimodality imaging applications, we report new functionalized neutral, polycationic, and polyanionic porphyrins incorporating nitroimidazole and sulfonamide moieties, which were used as targeting groups to improve the notoriously poor pharmacokinetics of porphyrin tags. The resulting functional metalloporphyrin species were stable under serum challenges and the nitroimidazole and sulfonamide derivatives remained fluorescent, allowing in vitro confocal studies and visualization of the lysosomal uptake in a gallium(III) sulfonamide derivative. The molecular structures of selected porphyrin derivatives were determined by single crystal X-ray diffraction using synchrotron radiation. We also investigated the nature of the emission/excitation behavior of model functional porphyrins using in silico approaches such as TD DFT in simple solvation models. The conjugation of porphyrins with the [7-13] and [7-14] fragments of bombesin was also achieved, to provide targeting of the gastrin releasing peptide receptor (GRPR). Depending on the metal, probe conjugates of relevance for single photon emission computed tomography (SPECT) or positron emission tomography (PET) probes have been designed and tested hereby, using TPP and related functional free base porphyrins as the bifunctional chelator synthetic scaffold and 111In[In] or 68Ga[Ga], respectively, as the central metal ions. Interestingly, for simple porphyrin conjugates good radiochemical incorporation was obtained for both radiometals, but the presence of peptides significantly diminished the radio-incorporation yields. Although the gallium-68 radiochemistry of the bombesin conjugates did not show radiochemical incorporation suitable for in vivo studies, likely because the presence of the peptide changed the behavior of the TPP-NH2 synthon taken alone, the optical imaging assays indicated that the conjugated peptide tags do mediate uptake of the porphyrin units into cells.

Fluorescence-lifetime imaging microscopy

10.1021/acs.bioconjchem.0c00691

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Functional, Aromatic, and Fluorinated Monothiosemicarbazones: Investigations into Their Structures and Activity toward the Gallium-68 Incorporation by Microwave Irradiation

ACS Omega (2022)

Sophia Sarpaki Fernando Cortezon‐Tamarit Rüdiger M. Exner Kexin Song Sara Raquel Mota Merelo de Aguiar

We report on the synthesis and spectroscopic characterization of a new series of coordinating monothiosemicarbazones incorporating aromatic backbones, featuring O/N/S donor centers monosubstituted with different aliphatic, aromatic, fluorinated, and amine-functionalized groups at their N centers. Their ability to bind metal ions such as Zn(II) and Ga(III) was explored, and the formation of two different coordination isomers of the Zn(II) complex was demonstrated by X-ray diffraction studies using synchrotron radiation. These studies showed the planar geometry for the coordinated mono(thiosemicarbazone) ligand and that the metal center can adopt either a heavily distorted tetrahedral Zn center (placed in an N/S/S/N environment, with CN = 4) or a pseudo-octahedral geometry, where the Zn(II) center is in the O/N/S/S/N/O environment, and CN = 6. Furthermore, 2-(4,5-dimethyl-2-thiazolyl)-3,5-diphenyl-2H-tetrazolium bromide (MTT) assays and cellular imaging in living cells were subsequently performed in two different cancer cell lines: PC-3 (a standard cell line derived from a bone metastasis of a stage IV prostate cancer) and EMT6 (a commercial murine mammary carcinoma cell line). The radiolabeling of new functional and aromatic monothiosemicarbazones with either gallium-68 (under pH control) or fluorine-18 is discussed. The potential of this class of compounds to act as synthetic scaffolds for molecular imaging agents of relevance to positron emission tomography was evaluated in vitro, and the cellular uptake of a simultaneously fluorinated and [68Ga]-labeled mono(thiosemicarbazone) was investigated and is reported here.

10.1021/acsomega.1c07396

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

Chemistry - A European Journal (2024)

Marina Lledos David G. Calatayud Fernando Cortezon‐Tamarit Haobo Ge Charareh Pourzand

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).

BODIPY

Fluorescence-lifetime imaging microscopy

10.1002/chem.202400858

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CCDC 2218622: Experimental Crystal Structure Determination

The Cambridge Structural Database (2023)

Fernando Cortezon‐Tamarit Kexin Song Navaratnarajah Kuganathan Rory L. Arrowsmith Sara Raquel Mota Merelo de Aguiar

10.5517/ccdc.csd.cc2dgng0

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CCDC 1001452: Experimental Crystal Structure Determination

The Cambridge Structural Database (2014)

Laura H. Davies Benjamin B. Kasten Paul D. Benny Rory L. Arrowsmith Haobo Ge

10.5517/cc12m2xp

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