Synthesis and biological evaluation of a new triazole–oxotechnetium complex

Martinage, Olivier; Clainche, Loïc Le; Czarny, Bertrand; Dugave, Christophe

doi:10.1039/c2ob25774b

Cited by 7 publications

(7 citation statements)

References 29 publications

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“…S-triphenylmethyl-thioglycolic acid (T A -trityl) was prepared by a modification of the procedure on Martinage et al [36]. Briefly, 1.5 g (5.77 mmol) of triphenylmethanol was added to a 25 mL TFA solution of thioglycolic acid (400 µL, 5.77 mmol) and stirred for 5 h under argon at room temperature.…”

Section: Preparation Of S-triphenylmethyl-thioglycolic Acidmentioning

confidence: 99%

pH Dependent Reversible Formation of a Binuclear Ni2 Metal-Center within a Peptide Scaffold

2019

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A disulfide-bridged peptide containing two Ni2+ binding sites based on the nickel superoxide dismutase protein, {Ni2(SODmds)} has been prepared. At physiological pH (7.4), it was found that the metal sites are mononuclear with a square planar NOS2 coordination environment with the two sulfur-based ligands derived from cysteinate residues, the nitrogen ligand derived from the amide backbone, and a water ligand. Furthermore, S K-edge X-ray absorption spectroscopy indicated that the two cysteinate sulfur atoms ligated to nickel are each protonated. Elevation of the pH to 9.6 results in the deprotonation of the cysteinate sulfur atoms, and yields a binuclear, cysteinate bridged Ni22+ center with each nickel contained in a distorted square planar geometry. At both pH = 7.4 and 9.6, the nickel sites are moderately air sensitive, yielding intractable oxidation products. However, at pH = 9.6, {Ni2(SODmds)} reacts with O2 at an ~3.5-fold faster rate than at pH = 7.4. Electronic structure calculations indicate that the reduced reactivity at pH = 7.4 is a result of a reduction in S(3p) character and deactivation of the nucleophilic frontier molecular orbitals upon cysteinate sulfur protonation.

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Section: Preparation Of S-triphenylmethyl-thioglycolic Acidmentioning

confidence: 99%

pH Dependent Reversible Formation of a Binuclear Ni2 Metal-Center within a Peptide Scaffold

2019

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“…Thus, we anticipated that neutral technetium or rhenium complexes based on triazole chelating systems could exhibit in vivo stabilities similar to those obtained with pyridine chelating analogues. Martinage et al ([TcO] 3+ core) and our preliminary study ([Tc(CO) 3 ] + core) demonstrated the feasibility of developing in vivo stable technetium‐99m complexes , . We then decided to continue our investigations with rhenium(I) with a view to developing new therapeutic tools based on rhenium‐188 (half‐life of 16.9 h, β‐emitter, E = 2.12 MeV).…”

Section: Introductionmentioning

confidence: 97%

“…Martinage et al ([TcO] 3+ core) and our preliminary study ([Tc(CO) 3 ] + core) demonstrated the feasibility of developing in vivo stable technetium-99m complexes. [10,13] We then decided to continue our investigations with rhenium(I) with a view to developing new therapeutic tools based on rhenium-188 (half-life of 16.9 h,emitter, E = 2.12 MeV). To the best of our knowledge, only one example of the rhenium-188 radiolabelling of a chelator containing a triazolyl ring has been reported to date.…”

Section: Introductionmentioning

confidence: 99%

Rhenium Complexes Based on an N₂O Tridentate Click Scaffold: From Synthesis, Structural and Theoretical Characterization to a Radiolabelling Study

et al. 2016

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International audienceA general synthetic approach to a novel range of semirigid bifunctional chelating agents (BCAs) that include an aromatic ring and a triazolyl moiety in the chelating unit has been investigated for the fac-[M(CO)3]+ core (M = 185/187Re or 188Re). The strategy includes the facile preparation of these N2O ligands bearing various functionalized arms (carboxylate, terminal alkyne, aromatic amine). The reaction of commercial [Re(CO)5Cl] ₒr a freshly prepared [Re(OH2)3(CO)3]+ precursor_ with our BCAs in methanol led to the formation of stable neutral tricarbonylrhenium complexes of general formula [Re(CO)3(L)] (LH = 5, 10, 11) in high yields. These compounds were characterized by IR and NMR spectroscopy, mass spectrometry, electrochemistry, and X-ray crystallography for [Re(CO)3(5–H)] and [Re(CO)3(11–H)] as well as by DFT calculations. The analogous rhenium-188 complexes [188Re(CO)3(5)] and [188Re(CO)3(11–H)] were also prepared, in acceptable to excellent yields, by the reaction of 5 or 11 with the fac-[188Re(OH2)3(CO)3]+ precursor in methanol at 80 °C. The structural identities of the radioactive complexes were assessed by HPLC studies. The good affinity of these click ligands for the ReI core combined with the ease of their derivatization make this chelating system promising for the conception of target-specific radiopharmaceuticals for therapeutic purposes. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinhei

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“…Bearing that in mind, we anticipated that the formation, using a two‐steps click‐to‐chelate strategy, of a semi‐rigid chelating system containing an aromatic backbone and the triazole unit, should lead in a few steps and with high yield to the corresponding very stable Tc(CO) 3 ‐complex. Even though any semi‐rigid ligand has yet been synthesized, the conception of pre‐organized chelating systems using a click‐to‐chelate approach have been recently highlighted for the preparation of new triazole‐oxotechnetium complexes . So in this paper, we described a simple, rapid, and convenient synthetic route for the first 99m Tc(I)‐specific semi‐rigid tridentate click ligand, which incorporates the design features illustrated in Scheme ; these include the following: (i) a methyl carboxylate arm directly connected at the N1 position of the five‐membered triazole ring as potential bioconjugation site and (ii) a N 2 O tridentate chelating system combining the 1,2,3‐triazole moiety with 2‐aminophenol derivative.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and preliminary biological evaluation of the first^99mTc(I)-specific semi-rigid tridentate ligand based on a click chemistry strategy

Guizani

Saied

Picard

et al. 2014

J. Label Compd. Radiopharm

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A novel bifunctional chelating agent based on a click chemistry strategy has been synthesized and characterized on the basis of spectroscopic techniques. The metal chelating part of this new class of tridentate N2O ligand combined a triazole unit and an aromatic ring. This latter semi-rigid framework induced a pre-organization of the chelating cavity, improving the stability of the corresponding metallic complexes (M = (99m) Tc, Re). Thus, the (99m) Tc(CO)3 complex, obtained with good yield and excellent radiochemical purity (>90%), exhibited a high in vitro serum stability. Tissue biodistribution in normal mice showed a rapid clearance, no long-term retention in organs and no in vivo reoxidation of technetium-99m, making this compound a promising (99m)Tc-chelating system.

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Synthesis and biological evaluation of a new triazole–oxotechnetium complex

Abstract: A new triazole oxotechnetium chelating agent was synthesized via a 'Click-to-Chelate' strategy. In vivo evaluation of the corresponding (99m)Tc complex shows that the tracer exhibits very interesting properties for molecular imaging.

Cited by 7 publications

References 29 publications

pH Dependent Reversible Formation of a Binuclear Ni2 Metal-Center within a Peptide Scaffold

pH Dependent Reversible Formation of a Binuclear Ni2 Metal-Center within a Peptide Scaffold

Rhenium Complexes Based on an N₂O Tridentate Click Scaffold: From Synthesis, Structural and Theoretical Characterization to a Radiolabelling Study

Synthesis and preliminary biological evaluation of the first^99mTc(I)-specific semi-rigid tridentate ligand based on a click chemistry strategy

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Synthesis and biological evaluation of a new triazole–oxotechnetium complex

Abstract: A new triazole oxotechnetium chelating agent was synthesized via a 'Click-to-Chelate' strategy. In vivo evaluation of the corresponding (99m)Tc complex shows that the tracer exhibits very interesting properties for molecular imaging.

Cited by 7 publications

References 29 publications

pH Dependent Reversible Formation of a Binuclear Ni2 Metal-Center within a Peptide Scaffold

pH Dependent Reversible Formation of a Binuclear Ni2 Metal-Center within a Peptide Scaffold

Rhenium Complexes Based on an N2O Tridentate Click Scaffold: From Synthesis, Structural and Theoretical Characterization to a Radiolabelling Study

Synthesis and preliminary biological evaluation of the first99mTc(I)-specific semi-rigid tridentate ligand based on a click chemistry strategy

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Rhenium Complexes Based on an N₂O Tridentate Click Scaffold: From Synthesis, Structural and Theoretical Characterization to a Radiolabelling Study

Synthesis and preliminary biological evaluation of the first^99mTc(I)-specific semi-rigid tridentate ligand based on a click chemistry strategy