Rhenium and technetium tricarbonyl complexes of 1,4‐Substituted pyridyl‐1,2,3‐triazole bidentate ‘click’ ligands conjugated to a targeting RGD peptide

Connell, Timothy U.; Hayne, David J.; Ackermann, Uwe; Tochon-Danguy, Henri; White, Jonathan M.; Donnelly, Paul S.

doi:10.1002/jlcr.3169

Cited by 20 publications

(9 citation statements)

References 48 publications

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“…Replacement of the halide ligand by a neutral pyridine donor in 3 results in a blue-shift in emission of 42 nm over that of 2a with a ten-fold increase in quantum yield. [37] Policar et al noted that the replacement of the pyridyl moiety in the pytz framework with quinolinyl (4, Figure 3 & Table 1) leads to a red-shift in the emission maximum through stabilisation of the ligand-centred LUMO. [38] Furthermore, the use of inverted 1-(pyrid-2-yl)and 1-(quinolin-2-yl)-1,2,3-triazole ligands, in which coordination to rhenium occurs through the less basic N(2) atom (5a & 6), results in a further red-shift in the phosphorescence maxima.…”

Section: Rhenium(i) Complexesmentioning

confidence: 99%

Photophysics and photochemistry of 1,2,3-triazole-based complexes

Scattergood

Sinopoli

Elliott

2017

Coordination Chemistry Reviews

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The copper-catalysed cycloaddition of alkynes and azides to form 1,2,3-triazoles has emerged as a powerful tool in ligand design and the synthesis of novel transition metal complexes. In this review we focus on the photophysical properties of metal complexes bearing 1,2,3-triazole-based ligands with a particular emphasis on those of d 6 metals including rhenium(I), iron(II), ruthenium(II), osmium(II) and iridium(III). We also highlight key examples of triazole complexes of platinum(II) and palladium(II) as well as the lanthanides and coinage metals. 1. Introduction 2. Photophysical properties of d 6 metal triazole-based complexes 2.1 Rhenium(I) complexes 2.2 Iridium(III) complexes 2.3 Ruthenium(II) complexes 2.4 Iron(II) complexes 2.5 Osmium(II) complexes 2.6 Photochemistry of 1,2,3-triazole-based d 6 metal complexes 3. Platinum(II) and palladium(II) complexes 4. Coinage metal complexes 5. Lanthanide complexes 6. Triazole-based sensors for metal ions 7. Conclusions & outlook.

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Section: Rhenium(i) Complexesmentioning

confidence: 99%

Photophysics and photochemistry of 1,2,3-triazole-based complexes

Scattergood

Sinopoli

Elliott

2017

Coordination Chemistry Reviews

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“…21 Recent years have seen a large number of reports concerning luminescent complexes of rhenium(I) and iridium(III) bearing 1,2,3-triazole-derived ligands 22,23 with applications in light-emitting electrochemical cells and light-emitting diodes 24,25 and biological imaging. [26][27][28][29][30] Osmium(II) complexes incorporating 1,2,3-triazolebased ligands are, on the other hand, rather rare. 31 There are only a few reported examples of luminescent dicationic osmium(II) complexes bearing neutral ligands incorporating a 5-membered heterocycle such as 1,2,4triazoles.…”

Section: Introductionmentioning

confidence: 99%

Photophysical and Cellular Imaging Studies of Brightly Luminescent Osmium(II) Pyridyltriazole Complexes

Omar¹,

Scattergood²,

McKenzie

et al. 2018

Inorg. Chem.

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The series of complexes [Os(bpy) 3-n (pytz) n ][PF 6 ] 2 (bpy = 2,2'-bipyridyl, pytz = 1-benzyl-4-(pyrid-2yl)-1,2,3-triazole, 1 n = 0, 2 n = 1, 3 n = 2, 4 n = 3) have been prepared and characterised and are rare examples of luminescent 1,2,3-triazole-based osmium(II) complexes. For 3 we present an attractive and particularly mild preparative route via an osmium(II)  6-arene precursor circumventing the harsh conditions that are usually required. Due to the high spin-orbit coupling constant associated with the Os(II) centre the absorption spectra of the complexes all display absorption bands of appreciable intensity in the range 500-700 nm corresponding to spin-forbidden ground-state-to-3 MLCT transitions, which occur at significantly lower energies than the corresponding spin-allowed 1 MLCT transitions. The homoleptic complex 4 is a bright emitter ( max em = 614 nm) with a relatively high quantum yield of emission of ~ 40 % in deoxygenated acetonitrile solutions at RT. Water soluble chloride salts of 1-4 were also prepared, all of which remain emissive in aerated aqueous solutions at room temperature. The complexes were investigated for their potential as phosphorescent cellular imaging agents whereby efficient excitation into the 3 MLCT absorption bands at the red side of the visible range circumvents 2 autofluorescence from biological specimens which do not absorb in this region of the spectrum. Confocal microscopy reveals 4 to be readily taken up by cancer cell lines (HeLa and EJ) with apparent lysosomal and endosomal localisation, whilst toxicity assays reveal that the compounds have low dark and light toxicity. These complexes therefore provide an excellent platform for the development of efficient luminescent cellular imaging agents with advantageous photophysical properties which enable excitation and emission in the biologically transparent region of the optical spectrum. Optimised ground state geometry atomic coordinates and TDDFT data for complexes 1-4. X-ray crystallographic data for 2 and mer-4. Confocal microscopy images and cellular viability data for cells incubated with 1-4. Crystallographic Data Crystallographic information files are available for complexes 2 (CCDC 1826209) and mer-4 (CCDC 1850035).

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“…Therefore, the third H 2 O could be substituted by Cl − or Br − (as co‐ligand) for electrostatic reasons, which generates eventually neutral complex that is more desirable to pass blood brain barrier. Three dentate complexes are supposed to be more stable than bi‐dentate complexes, but according to our experiment, the radiolabeled complex showed the efficient (more than 24 h) in vitro stability.…”

Section: Resultsmentioning

confidence: 71%

New ^99mTc(CO)₃‐radiolabeled arylpiperazine pharmacophore as potent 5HT_1A serotonin receptor radiotracer: Docking studies, chemical synthesis, radiolabeling, and biological evaluation

Erfani

Malek

Ebrahimi

et al. 2019

Labelled Comp Radiopharmac

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In spite of previous efforts, there is lack of a radiotracer for imaging the 5HT 1A receptor density in human brain, which is involved in several neurological brain disorders. The aim of this study was to prepare a new derivative of 1-(2-methoxyphenyl)piperazine (MPP) as a main chemical structure of 5HT 1A receptor antagonist with 3-carbon linker and radiolabeled by [ 99m Tc][Tc(CO) 3 (H 2 O) 3 ] + precursor. Docking studies before chemical synthesis showed similar fashion of interaction for both WAY100635 (potent 5HT 1A receptor antagonist) and new designed ligand, despite of addition of 99m Tc(CO) 3 group in the structure of new ligand. MPP-(CH 2 ) 3 -N 3 was synthesized via three efficient and reliable chemical synthesis steps (more than 80% yield) then radiolabeled by addition of 2-ethynylpyridine and [ 99m Tc] [Tc(CO) 3 (H 2 O) 3 ] + precursor in one pot procedure (more than 95% radiochemical efficiency) through click chemistry method. After incubation, radiotracer was found stable in vitro up to 2 hours. Binding assays showed about 33% specific binding of radiotracer to the 5HT 1A receptors. Brain biodistribution studies indicated (0.26 ± 0.05)% ID/g hippocampus uptake at 30 minutes post injection, which its specificity was verified through blocking studies. These results suggested that new designed radioligand might serve as a potent SPECT imaging agent to estimate status of 5HT 1A receptors. KEYWORDS 1-(2-methoxyphenyl)piperazine (MPP), 2-ethynylpyridine, 5HT 1A homology model, click chemistry, docking, WAY100635

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Rhenium and technetium tricarbonyl complexes of 1,4‐Substituted pyridyl‐1,2,3‐triazole bidentate ‘click’ ligands conjugated to a targeting RGD peptide

Cited by 20 publications

References 48 publications

Photophysics and photochemistry of 1,2,3-triazole-based complexes

Photophysics and photochemistry of 1,2,3-triazole-based complexes

Photophysical and Cellular Imaging Studies of Brightly Luminescent Osmium(II) Pyridyltriazole Complexes

New ^99mTc(CO)₃‐radiolabeled arylpiperazine pharmacophore as potent 5HT_1A serotonin receptor radiotracer: Docking studies, chemical synthesis, radiolabeling, and biological evaluation

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Rhenium and technetium tricarbonyl complexes of 1,4‐Substituted pyridyl‐1,2,3‐triazole bidentate ‘click’ ligands conjugated to a targeting RGD peptide

Cited by 20 publications

References 48 publications

Photophysics and photochemistry of 1,2,3-triazole-based complexes

Photophysics and photochemistry of 1,2,3-triazole-based complexes

Photophysical and Cellular Imaging Studies of Brightly Luminescent Osmium(II) Pyridyltriazole Complexes

New 99mTc(CO)3‐radiolabeled arylpiperazine pharmacophore as potent 5HT1A serotonin receptor radiotracer: Docking studies, chemical synthesis, radiolabeling, and biological evaluation

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New ^99mTc(CO)₃‐radiolabeled arylpiperazine pharmacophore as potent 5HT_1A serotonin receptor radiotracer: Docking studies, chemical synthesis, radiolabeling, and biological evaluation