68Ga-5, 10, 15, 20-Tetrakis (2, 4, 6-trimethoxy phenyl) porphyrin: a novel radio-labeled porphyrin complex for positron emission tomography

Fazaeli, Yousef; Hosseini, Mohammad Amin; Shahabinia, Fatemeh; Feizi, Shahzad

doi:10.1007/s10967-019-06465-1

Cited by 6 publications

(3 citation statements)

References 21 publications

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“…For the synthesis of PPCl 2 ·Cl and PP(OMe) 2 + , we utilized modified reported methods. ,,, The crystal structure of the PP(OMe) 2 + compound is also reported earlier with perchlorate as the counterion . The free-base porphyrin (H 2 246TMP) and all of the studied phosphorus(V) porphyrins were prepared as described below or in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Hypervalent Phosphorus(V) Porphyrins with meso-Methoxyphenyl Substituents: Significance of the Number and Position of Methoxy Groups in Promoting Intramolecular Charge Transfer

et al. 2022

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To study the photophysical and redox properties as a function of meso-aryl units, a series of hypervalent phosphorus(V) porphyrins, PP(OMe)2·PF6, PMP(OMe)2·PF6, PDMP(OMe)2·PF6, P345TMP(OMe)2·PF6, and P246TMP(OMe)2·PF6, with phenyl (P), 4-methoxyphenyl (MP), 3,5-dimethoxyphenyl (DMP), 3,4,5-trimethoxyphenyl (345TMP), and 2,4,6-trimethoxyphenyl (246TMP) units, respectively, have been synthesized. The P(+5) in the cavity makes the porphyrin ring electron-poor, whereas the methoxy groups make the meso-phenyl rings electron-rich. The presence of electron-rich and electron-poor portions within the porphyrin molecule promoted an intramolecular charge transfer (ICT). Also, the study suggests that the ICT depends on the number and position of the methoxy groups. The ICT is more prominent in m-methoxy-substituted phosphorus(V) porphyrins (PDMP(OMe)2.PF6, P345TMP(OMe)2·PF6) and almost no ICT was found in no-methoxy, o-methoxy, and/or p-methoxy phosphorus(V) porphyrins (PP(OMe)2·PF6, PMP(OMe)2·PF6, P246TMP(OMe)2·PF6). Transient absorption studies indicate that the ICT takes place on the picosecond time scale. The most striking results come from P246TMP(OMe)2·PF6, where each phenyl ring carries three methoxy units, like the P345TMP(OMe)2·PF6, but it failed to induce the ICT process. Electrochemical studies and time-dependent density functional theory (TD-DFT) calculations were used to support the experimental results. This study extensively explores why and how slight variations in meso-aryl substitutions lead to intricate changes in the photophysical and redox properties of phosphorus(V) porphyrins.

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Section: Methodsmentioning

confidence: 99%

Hypervalent Phosphorus(V) Porphyrins with meso-Methoxyphenyl Substituents: Significance of the Number and Position of Methoxy Groups in Promoting Intramolecular Charge Transfer

et al. 2022

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“…As was mentioned above, the introduction of substitutes on the peripheral positions of the porphyrin core increases the hydrophilicity of porphyrin derivatives to promote renal clearance over hepatobiliary clearance [ 78 ]. Some hydrophilic porphyrin derivatives have been proposed for complexation with 68 Ga, such as 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (log P o/w = 0.62) [ 79 ], 5,10,15,20-tetrakis(2,4,6-tri methoxyphenyl)porphyrin (log P o/w = −1.14) [ 80 ], 5,10,15,20-tetrakis( p -carboxy- methyleneoxyphenyl)porphyrin (log P o/w = −0.25) [ 75 ], and 5,10,15,20-tetrakis(4-methyl-pyridyl)porphyrin (log P o/w = −4.3) [ 81 ]. Complexation reactions with Ga(III) were conducted in the presence of acetate buffer in a boiling water bath for a period in the range of 15 [ 74 ] to 60 min [ 79 ].…”

Section: Porphyrins As Ligands For Radiometalsmentioning

confidence: 99%

Porphyrins as Chelating Agents for Molecular Imaging in Nuclear Medicine

2022

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Porphyrin ligands, showing a significant affinity for cancer cells, also have the ability to chelate metallic radioisotopes to form potential diagnostic radiopharmaceuticals. They can be applied in single-photon emission computed tomography (SPECT) and positron emission tomography (PET) to evaluate metabolic changes in the human body for tumor diagnostics. The aim of this paper is to present a short overview of the main metallic radionuclides complexed by porphyrin ligands and used in these techniques. These chelation reactions are discussed in terms of the complexation conditions and kinetics and the complex stability.

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“…[34,[36][37][38][39][40] In view of the multimodalb iomedical applicationso fm etalloporphyrin, and in particularf or PET/PDT purposes, 68 Ga has also been used previously with porphyrins. [41][42][43][44][45][46][47] Work in this area started with the incorporation of 68 Ga into the porphyrin core directly;h owever this involved vigorous heatingu sing a microwavef or efficient radiolabeling. [41][42][43][44] Furthermore, this prevents the incorporation of other metals into the porphyrin cavity,r educing the options available for optimizing the system.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of a Bispidine‐Based Chelator for Gallium‐68 and of the Porphyrin Conjugate as PET/PDT Theranostic Agent

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Gillet

et al. 2020

Chemistry A European J

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In this study a bispidine ligand has been applied to the complexation of gallium(III) and radiolabelled with gallium‐68 for the first time. Despite its 5‐coordinate nature, the resulting complex is stable in serum for over two hours, demonstrating a ligand system well matched to the imaging window of gallium‐68 positron emission tomography (PET). To show the versatility of the bispidine ligand and its potential use in PET, the bifunctional chelator was conjugated to a porphyrin, producing a PET/PDT‐theranostic, which showed the same level of stability to serum as the non‐conjugated gallium‐68 complex. The PET/PDT complex killed >90 % of HT‐29 cells upon light irradiation at 50 μm. This study shows bispidines have the versatility to be used as a ligand system for gallium‐68 in PET.

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68Ga-5, 10, 15, 20-Tetrakis (2, 4, 6-trimethoxy phenyl) porphyrin: a novel radio-labeled porphyrin complex for positron emission tomography

Cited by 6 publications

References 21 publications

Hypervalent Phosphorus(V) Porphyrins with meso-Methoxyphenyl Substituents: Significance of the Number and Position of Methoxy Groups in Promoting Intramolecular Charge Transfer

Hypervalent Phosphorus(V) Porphyrins with meso-Methoxyphenyl Substituents: Significance of the Number and Position of Methoxy Groups in Promoting Intramolecular Charge Transfer

Porphyrins as Chelating Agents for Molecular Imaging in Nuclear Medicine

Evaluation of a Bispidine‐Based Chelator for Gallium‐68 and of the Porphyrin Conjugate as PET/PDT Theranostic Agent

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