New potential bimodal imaging contrast agents based on DOTA-like and porphyrin macrocycles

Gros, Claude P.; Eggenspiller, Antoine; Nonat, Aline; Barbe, Jean‐Michel; Denat, Franck

doi:10.1039/c0md00205d

Cited by 51 publications

(37 citation statements)

References 36 publications

(45 reference statements)

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“…Fibrosarcoma tumour accumulation in Swiss mice was found to be 1.59 ± 0.52% ID/g with a T/B ratio of 8.56 ± 0.50 and T/M ratio of 26.5 ± 4.36 at 48 h. Tumour growth was retarded in treated animals, leading to a 68% decrease in tumour size after 8 days, following an initial dose of 92.5 MBq . A structurally similar agent has been prepared with a Gd‐labelled DOTA unit coupled to a porphyrin for potential multi‐functional magnetic resonance imaging/positron emission tomography (PET) imaging, and deuteroporphyrin, was previously functionalized to accommodate 111 In labelling using conventional chelating groups …”

Section: Bifunctional Chelatorsmentioning

confidence: 99%

Radiolabelled porphyrins in nuclear medicine

Waghorn

2013

Labelled Comp Radiopharmac

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Amongst tumour-specific substances, hematoporphyrin and synthetic porphyrin derivatives have been widely investigated to identify and delineate neoplastic and malignant tissue. Whilst the tumour localization exhibited by selected porphyrin species has been exploited through photodynamic therapy, several examples of porphyrin derivatives with varied peripheral functionality have been radiolabelled with the aim of developing porphyrin-based nuclear imaging and therapeutic agents. In this review, we look at the approaches and advances in the preparation and uses of such radiolabelled agents for imaging and therapy.

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Section: Bifunctional Chelatorsmentioning

confidence: 99%

Radiolabelled porphyrins in nuclear medicine

Waghorn

2013

Labelled Comp Radiopharmac

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“…The measurements at high field (recorded at 300 MHz) give relaxivity values from 2.8 to 6.1 m M –1 s –1 , which are typical values for gadolinium complexes with one key water molecule in the first coordination sphere. For example, the relaxivity value for [Gd(dota)(H 2 O)] – measured under the same conditions is in the same order of magnitude (3.6 m M –1 s –1 ) 7…”

Section: Resultsmentioning

confidence: 76%

“…A porphyrin derivative was chosen on the one hand (porphyrins display interesting properties in terms of fluorescence and metal‐center complexation) and, on the other hand, dota‐like (dota = 1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid) derivatives based on the cyclen macrocycle and widely used as CAs especially in magnetic resonance imaging (MRI) 6. Our group previously reported the synthesis of a heterobimetallic complex built upon a porphyrin scaffold 7. Up to now, only a few examples of molecular structures incorporating both porphyrins and tetraazacycloalkanes have been described in the literature, mainly for biomimetic studies and use as CAs 8…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2013

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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 medical‐imaging agents for the enhancement of contrast in bimodal MRI techniques.

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“…99m Tc porphyrin, cyanine dye conjugated porphyrin, and Gd(III)ADTPA conjugated porphyrin derivatives [30][31][32][33][34]. For the same purpose, we aimed here at an indium porphyrin.…”

Section: Introductionmentioning

confidence: 98%

Syntheses and photodynamic properties of glucopyranoside-conjugated indium(III) porphyrins as a bifunctional agent

Nakai

Maeda

Mashima

et al. 2013

J. Porphyrins Phthalocyanines

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Malignant tumor is the most common cause of death, and great efforts have been made to develop new ways for the cancer treatments and the rapid diagnoses. The cancer treatments including surgery, chemotherapy, radiotherapy, immunotherapy, photodynamic therapy (PDT), etc., are in widespread clinical use. Since these treatments are often accompanied with serious side effects, improvements are important to diminish the undesirable side effects. We have focused on the improvement of photodynamic therapy (PDT). In the PDT procedure, the photosensitizer is administrated to patients by intravenous injection, tumor is irradiated with light at the highest uptake of the photosensitizer by tumor, and singlet oxygen produced by the excited photosensitizer results in tumor apoptosis [1][2][3][4]. Therefore, PDT is promising as the less toxic cancer treatment than chemotherapy if the selective uptake of the photosensitizer by tumor is achieved. ABSTRACT: The glucopyranoside-conjugated porphyrins, H 2 TPP{p-O-(CH 2 ) 2 -O-OAcGlc} (1), [InTPP{p-O-(CH 2 ) 2 -O-OAcGlc}]NO 3 (2), H 2 TPP{p-O-(CH 2 ) 2 -O-Glc} (3), [InTPP{p-O-(CH 2 ) 2 -O-Glc}]-NO 3 (4) and ZnTPP{p-O-(CH 2 ) 2 -O-OAcGlc} (5) were synthesized, and characterized by 1 H NMR, 13 C NMR, ESI-MS, UV-vis spectroscopies and elemental analyses. In the 1 H NMR spectrum of 2, two sets of signals were observed for H-atoms of the phenyl group of porphyrin, indicating that 2 has the axial chirality due to a NO 3 ion coordinating to the indium atom. Abilities of the singlet oxygen production of these porphyrins, investigated by using 1,3-diphenylisobenzofuran (DPBF) as a quencher, were higher than those of the free-based and zinc porphyrins, reflecting the heavy atom effect. The photodynamic properties of these porphyrin derivatives were investigated against COLO 679. All of the glucopyranosideconjugated porphyrins exhibited the high photocytotoxicity compared with Laserphyrin ® . Above all, 4 exhibited the highest photocytotoxicity, coinciding with the high abilities of this complex for the singlet oxygen production and the cell permeability.

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New potential bimodal imaging contrast agents based on DOTA-like and porphyrin macrocycles

Cited by 51 publications

References 36 publications

Radiolabelled porphyrins in nuclear medicine

Radiolabelled porphyrins in nuclear medicine

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

Syntheses and photodynamic properties of glucopyranoside-conjugated indium(III) porphyrins as a bifunctional agent

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