Preparation, 99mTc-labeling and biodistribution studies of a PNA oligomer containing a new ligand derivative of 2,2′-dipicolylamine

Gasser, Gilles; Jäger, K; Zenker, Martin; Bergmann, Ralf; Steinbach, Jörg; Stephan, Holger; Metzler‐Nolte, Nils

doi:10.1016/j.jinorgbio.2010.06.011

Cited by 42 publications

(41 citation statements)

References 75 publications

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“…137 Similar results were found when a mouse model (NMRI nu/nu) was used. 137 An interesting alternative approach for the use of radioactive PNA probes for therapeutic purposes deserves to be mentioned in this perspective. In the so-called "pretargeting using PNA" developed by Hnatowich et al, 120,127,128 a single-stranded PNA bound to a protein/antibody -which binds, for example, specifically to receptors over-expressed in cancer cells -is administered first into an animal or human, followed by admission of the complementary single-stranded radiolabeled PNA.…”

Section: Metal-containing Pnas As Radioactive Probessupporting

confidence: 71%

“…Of interest for in vivo pharmacokinetics, our groups recently reported the biodistribution studies of a 12-mer PNA bioconjugate labeled with a tricarbonyl 99m Tc complex in Wistar rats. 137 These investigations showed a fast blood clearance and only a modest accumulation in the kidneys. 137 Similar results were found when a mouse model (NMRI nu/nu) was used.…”

Section: Metal-containing Pnas As Radioactive Probesmentioning

confidence: 94%

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Metal-containing peptide nucleic acid conjugates

2011

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Peptide Nucleic Acids (PNAs) are non-natural DNA/RNA analogues with favourable physicochemical properties and promising applications. Discovered nearly 20 years ago, PNAs have recently re-gained quite a lot of attention. In this Perspective article, we discuss the latest advances on the preparation and utilisation of PNA monomers and oligomers containing metal complexes. These metalconjugates have found applications in various research fields such as in the sequence-specific detection of nucleic acids, in the hydrolysis of nucleic acids and peptides, as radioactive probes or as modulators of PNA˙DNA hybrid stability, and last but not least as probes for molecular and cell biology.

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Section: Metal-containing Pnas As Radioactive Probessupporting

confidence: 71%

Section: Metal-containing Pnas As Radioactive Probesmentioning

confidence: 94%

Metal-containing peptide nucleic acid conjugates

2011

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“…[18][19][20][21][22][23][24][25][26][27][28][29][30] We then report on 31 with triphenyl phosphine, diisopropyl azodicarboxylate and diphenylphosphoryl azide in THF following a similar procedure described by our groups (Scheme 1). 32 The presence of L-N 3 Figure S2 in the SI). 19 In comparison, for L-N 3, only a singlet is observed for these four protons ( Figure S1 in the SI).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterisation and bioimaging of a fluorescent rhenium-containing PNA bioconjugate

et al. 2012

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A new rhenium tricarbonyl complex of a bis(quinoline)-derived ligand (2-azido-N,N-bis((quinolin-2-yl)methyl)ethanamine, L-N(3)), namely [Re(CO)(3)(L-N(3))]Br was synthesized and characterized indepth, including by X-ray crystallography. [Re(CO)(3)(L-N(3))]Br exhibits a strong UV absorbance in the range 300-400 nm with a maximum at 322 nm, and upon photoexcitation, shows two distinct emission bands at about 430 and 560 nm in various solvents (water, ethylene glycol). [Re(CO)(3)(L-N(3))]Br could be conjugated, on a solid phase, to a peptide nucleic acid (PNA) oligomer using the copper(I)-catalyzed azide-alkyne cycloaddition reaction (Cu-AAC, "click" chemistry) and an alkyne-containing PNA building block to give Re-PNA. It was demonstrated that upon hybridisation with a complementary DNA strand (DNA), the position of the maxima and emission intensity for the hybrid Re-PNA·DNA remained mainly unchanged compared to those of the single strand Re-PNA. The rhenium-containing PNA oligomer Re-PNA could be then mediated in living cells where they have been shown to be non-toxic contrary to the general notion that organometallic compounds are usually unstable under physiological conditions and/or cytotoxic. Furthermore, Re-PNA could be detected in living cells using fluorescent microscopy.

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“…The position of the stretching vibration modes of the CO ligands and the lifetimes were then used to probe protein solvation and electrostatics . Alkyne‐containing peptide nucleic acids were labelled with azido‐modified dipicolylamine/amide rhenium tricarbonyl or 99 m‐technetium tricarbonyl moieties for radiotherapeutic purposes . Other representative examples dealt with the labelling of peptides/proteins with bipyridyl rhenium tricarbonyl luminescent labels, and cymantrene entity as IR probe …”

Section: Introductionmentioning

confidence: 99%

‘Clickable’ cyclopentadienyl iron carbonyl complexes for bioorthogonal conjugation of mid‐infrared labels to a model protein and PAMAM dendrimer

Fischer‐Durand

Lizińska

Guérineau

et al. 2019

Applied Organom Chemis

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Owing to the intrinsic limitations of the conventional bioconjugation methods involving native nucleophilic functions of proteins, we sought to develop alternative approaches to introduce metallocarbonyl infrared labels onto proteins on the basis of the [3 + 2] dipolar azide‐alkyne cycloaddition (AAC). To this end, two cyclopentadienyl iron dicarbonyl (Fp) complexes carrying a terminal or a strained alkyne handle were synthesized. Their reactivity was examined towards a model protein and poly (amidoamine) (PAMAM) dendrimer, both carrying azido groups. While the copper (I)‐catalysed azide‐alkyne cycloaddition (CuAAC) proceeded smoothly with the terminal alkyne metallocarbonyl derivative, labelling by strain‐promoted azide‐alkyne cycloaddition (SPAAC) was less successful in terms of final coupling ratios. Infrared spectral characterization of the bioconjugates showed the presence of two bands in the 2000 cm−1 region, owing to the stretching vibration modes of the carbonyl ligands of the Fp entities.

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Preparation, 99mTc-labeling and biodistribution studies of a PNA oligomer containing a new ligand derivative of 2,2′-dipicolylamine

Cited by 42 publications

References 75 publications

Metal-containing peptide nucleic acid conjugates

Metal-containing peptide nucleic acid conjugates

Synthesis, characterisation and bioimaging of a fluorescent rhenium-containing PNA bioconjugate

‘Clickable’ cyclopentadienyl iron carbonyl complexes for bioorthogonal conjugation of mid‐infrared labels to a model protein and PAMAM dendrimer

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