Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition

2015

The Cu(I)-catalysed Huisgen cycloaddition, known as “click” reaction, has been applied to the synthesis of a range of triazole-linked porphyrin/corrole to DOTA/NOTA derivatives. Microwave irradiation significantly accelerates the reaction. The synthesis of heterobimetallic complexes was easily achieved in up to 60% isolated yield. Heterobimetallic complexes were easily prepared as potential MRI/PET (SPECT) bimodal contrast agents incorporating one metal (Mn, Gd) for the enhancement of contrast for MRI applications and one “cold” metal (Cu, Ga, In) for future radionuclear imaging applications. Preliminary relaxivity measurements showed that the reported complexes are promising contrast agent…

Non-linear optical, electrochemical and spectroelectrochemical properties of amphiphilic inner salt porphyrinic systems

2016

Three zwitterionic meso-substituted A3B- and AB2C-porphyrins containing one sulfonato alkylpyridinium substituent and three or two alkoxy-substituted phenyl groups were synthesized in good yield and fully characterized as to their physicochemical properties by a variety of techniques. This new series of inner salt donor-acceptor meso-substituted porphyrin derivatives were prepared for possible application as amphiphilic probes for membrane insertion in the area of combined second-harmonic and two-photon fluorescence cellular microscopy. To this end, the linear and nonlinear optical properties of the compounds were characterized, together with their electrochemical and spectroelectrochemica…

Design of Porphyrin-dota-Like Scaffolds as All-in-One Multimodal Heterometallic Complexes for Medical Imaging

2013

A series of four multimodal ligands incorporating one porphyrin moiety and one or more dota-like macrocycles all-in-one in the same molecular architecture have been synthesized and full characterized. The corresponding gadolinium(III) complexes were also synthesized and heterometallic complexes incorporating both gadolinium(III) and copper(II) ions were prepared as potential MRI/PET multimodal contrast agents. One ligand (L4) includes an amine moiety that can be activated for easy conversion into an isothiocyanate group for further anchoring to a biological vector. Preliminary relaxivity, cytotoxicity, and MRI studies showed that the complexes developed in this work are very promising medic…

Inside Cover: Synthesis and Characterization of Carbazole-Linked Porphyrin Tweezers (Chem. Eur. J. 34/2015)

2015

Synthesis and Antiviral Activity Evaluation of Nitroporphyrins and Nitrocorroles as Potential Agents against Human Cytomegalovirus Infection.

2015

Different nitroporphyrinoid derivatives were synthesized and studied as potential agents against human Cytomegalovirus. Interestingly, two nitrocorroles display strong activity against human Cytomegalovirus with IC 50 < 0.5 μM. These compounds also possess antiproliferative activities without detected in vivo toxicity. Therefore, nitrocorroles appear for the first time as potential active compounds that can be applied in human health.

Synthetic strategy for preparation of a folate corrole DOTA heterobimetallic Cu–Gd complex as a potential bimodal contrast agent in medical imaging

2015

Abstract An efficient sequential route to synthesize heterobimetallic complexes is reported herein. A folate, Cu corrole, Gd DOTA complex that addresses the requirements of a potential contrast agent (CA) for bimodal imaging (e.g., MRI/PET) is reported. The over-expression of the folate receptor in a variety of malignant tumors, along with its limited expression in healthy tissues, makes this an attractive tumor-specific molecular target. Synthesis of a bimetallic ligand potentially targeting the folate receptor, was easily achieved in only a few steps. Interestingly, preliminary studies showed that the relaxivity of the folic heterobimetallic derivative was higher in comparison to a clinic…

Synthesis and characterization of zinc carboxy–porphyrin complexes for dye sensitized solar cells

2018

Two zinc porphyrins, 2 and 8, have been synthesized. Porphyrin 8 displays better electronic communication between the dye and the TiO2 electrode. Photophysical measurements and electrochemistry experiments suggest that both porphyrins are very promising sensitizers for dye-sensitized solar cells (DSSCs). It was found that their molecular orbital energy levels favor electron injection and dye regeneration in DSSCs. Solar cells sensitized by 2 and 8 were fabricated, and it was found that they show power conversion efficiencies (PCEs) of 5.27% and 7.13%, respectively. Photovoltaic measurements (J–V curves) together with the incident photon-to-electron conversion efficiency spectra of the two c…

Synthesis and Characterization of Carbazole-Linked Porphyrin Tweezers

2015

Herein the synthesis, spectroscopic characterization, two-photon absorption and electrochemical properties of 3,6-disubstituted carbazole tweezers is reported. A dimer resulting from a Glaser homocoupling was isolated during a Sonogashira coupling reaction between a diethynyl-carbazole spacer and a 5-bromo-triarylporphyrin and the properties of this original compound were compared with the 3,6-disubstituted carbazole bisporphyrin tweezers. The dyads reported herein present a two-photon absorption maximum at 920 nm with two-photon absorption cross-section in the 1200 GM range. Despite a strong linear absorption in the Soret region and moderate fluorescence quantum yield, they both lead to a …

Redox properties of nitrophenylporphyrins and electrosynthesis of nitrophenyl-linked Zn porphyrin dimers or arrays

2014

Five nitrophenylporphyrins were investigated as to their electrochemical properties in CH 2 Cl 2 containing 0.1 M TBAP. The investigated compounds are represented as ( NO 2 Ph )x Ph 4-x PorM , where Por represents the dianion of the porphyrin macrocycle, Ph is a phenyl group on meso-position of the macrocycle, NO 2 Ph is a meso-substituted nitrophenyl group, M = 2 H , Pd II or Zn II and x = 1 or 2. Each porphyrin undergoes an initial one electron reduction at E1/2 = -1.07 to -1.12 V where the added negative charge is almost totally localized on the meso-nitrophenyl group of the compound. This reversible reduction is then followed by one or more irreversible reductions of the nitrophenyl an…

CCDC 882546: Experimental Crystal Structure Determination

2013

Related Article: Antoine Eggenspiller, Clément Michelin, Nicolas Desbois, Philippe Richard, Jean-Michel Barbe, Franck Denat, Cynthia Licona, Christian Gaiddon, Amira Sayeh, Philippe Choquet, Claude P. Gros|2013|Eur.J.Org.Chem.|2013|6629|doi:10.1002/ejoc.201300678