Labelling of peptides with 99mTc complexes through the modified C-terminal group

Koźmiński, Przemysław; Gniazdowska, Ewa; Fuks, L.; Oszczak, A.

doi:10.1007/s10967-011-1384-4

Cited by 7 publications

(6 citation statements)

References 19 publications

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“…For example, the side-chain amino group was converted into an isocyanide by reacting with an isocyanocontaining acid; the resulting moiety was applied in a 4 + 1 labeling reaction with a 99m Tc complex (as described in section 2.3 and Chart 5). 260 Very often, substituted phenylalanine residues are applied; these allow for several types of conjugation strategies that can also be used to attach an OM group. In 1998, Beck and co- Apart from direct metalation of the acetylene moiety, OM reagents with an organic moiety that specifically reacts with the acetylene group can be applied.…”

Section: Indirect Metalation Of Amino Acid Side-chain Functionalitiesmentioning

confidence: 99%

Organometallic–Peptide Bioconjugates: Synthetic Strategies and Medicinal Applications

2016

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Peptides are important biological molecular entities in biomedical research. They can be prepared in a large variety of shapes, with a host of chemical functions, and tailored for specific applications. Organometallic medicinal chemistry is a relatively young field that explores biomedical and bioanalytical applications of organometallic complexes, that is, metal compounds with at least one direct, covalent metal-carbon bond. The conjugation of peptides to such medicinally active organometallic moieties started only about 20 years ago, and it has been very beneficial for the development of bioorganometallic chemistry in general. Similarly, the biomedical properties of peptides have been altered by their conjugation to organometallic (OM) moieties. In this review, synthetic methods by which OM moieties can be conjugated to peptides via a carbon-metal bond are described, and selected medicinal applications of such conjugates are discussed. Inorganic coordination complexes between metal ions and peptides are excluded from this review. Also, the labeling of peptides with radiometals and applications of radiolabeled peptides will not be treated herein. First, modifications of the peptide backbone (either N- or C-terminally, or both) with organometallic moieties will be described, including the insertion of OM moieties as part of the peptide backbone. Then side-chain modifications will be reported, among them the most recent strategies for chemoselective arene metalation on peptides. Finally, approaches by which multiple metalation can be achieved are explored. In each section, selected examples of biological applications are highlighted.

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Section: Indirect Metalation Of Amino Acid Side-chain Functionalitiesmentioning

confidence: 99%

Organometallic–Peptide Bioconjugates: Synthetic Strategies and Medicinal Applications

2016

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“…1 H NMR spectrum (CDCl 3 , δ, ppm; the atom numbering is the same as in Figure ): 8.855 d (2H, H bipy4,13 , 3 J 6.0 Hz), 8.59 d (2H, H bipy7,10 , 3 J 8.0 Hz), 8.34 t (2H, H bipy5,12 , 3 J 6.0 Hz), 7.65 t (2H, H bipy6,11 , 3 J 6.0 Hz), 4.48 s (2H, CN–C H 2 –COO−), 4.20 q (2H, C H 2 –CH 3 , 3 J 8.0 Hz), 1.25 t (3H, –C H 3 , 3 J 8.0 Hz). 13 C{ 1 H} NMR spectrum (CDCl 3 , δ, ppm): 163.2 (1C, –COO−), 155.3 (2C, bipy , ), 153.0 (2C, bipy , ), 140.6 (2C, bipy , ), 127.4 (2C, bipy , ), 125.1 (2C, bipy , ), 63.2 (1C, –O– C H 2 –CH 3 ), 46.2 (1C, CN– C H 2 –COO−), 13.9 (1C, –O–CH 2 – C H 3 ). Calculated for [C 18 H 15 N 3 O 5 Tc](ClO 4 ), %: C 39.25, H 2.75, N 7.63, 99 Tc 17.79.…”

Section: Methodsmentioning

confidence: 99%

“…Among monodentate ligands for implementing the 2 + 1 B approach (tethering of a biomolecule via monodentate ligand), isonitriles seem to be the best choice , owing to the favorable combination of σ-donor and π-acceptor properties (ensuring high stability of the complexes), low steric demand, good complexation kinetics, and versatility in linking to biomolecules. For example, complexes with ω-isonitrile-derivatized higher fatty acids , show promise for myocardial imaging, whereas isonitrile-derivatized lower fatty acids can serve as bifunctional molecules for tethering the 99m Tc(CO) 3 + core to diverse biomolecules. , Isonitriles as ligands for the 99m Tc(CO) 3 + core have been examined in combination with diverse bidentate ligands. ,,− As a rule, anionic bidentate ligands were chosen. It is believed that, with neutral bidentate ligands, the sixth coordination site in the tricarbonyl complexes will be occupied by the chloride ion necessarily present in the reaction medium, and its replacement by a monodentate ligand will be hindered.…”

Section: Introductionmentioning

confidence: 99%

“…8.855 d (2H, H bipy4,13 , 3 J 6.0 Hz), 8.59 d (2H, H bipy7,10 , 3 J 8.0 Hz), 8.34 t (2H, H bipy5,12 , 3 J 6.0 Hz), 7.65 t (2H, H bipy6,11 , 3 J 6.0 Hz), 4.48 s (2H, CN− CH 2 −COO−), 4.20 q (2H, CH 2 −CH 3 , 3 J 8.0 Hz), 1.25 t (3H, −CH 3 , 3 J 8.0 Hz) 13. C{ 1 H} NMR spectrum (CDCl 3 , δ, ppm): 163.2 (1C, −COO−), 155.3 (2C, bipy8,9 ), 153.0 (2C, bipy4,13 ), 140.6 (2C, bipy6,11 ), 127.4 (2C, bipy5,12 ), 125.1 https://doi.org/10.1021/acs.inorgchem.3c02204 Inorg. Chem.…”

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confidence: 99%

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2 + 1 Tricarbonyl Complexes of Technetium(I) with a Combination of N,N-Bidentate Ligands and Ethyl Isocyanoacetate: How Strong Is the Interfering Effect of Chloride Ions on Their Formation?

Sidorenko,

Miroslavov,

Tyupina

et al. 2023

Inorg. Chem.

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Technetium(I) 2 + 1 tricarbonyl complexes with a combination of N,N-bidentate ligands (2,2′-bipyridine, bipy; 1,10phenanthroline, phen) and ethyl isocyanoacetate were prepared and characterized by NMR, IR, UV/visible, and luminescence spectroscopies and by high-performance liquid chromatography (HPLC). The crystal structures of [ 99 Tc(CO) 3 (bipy)(CNCH 2 COOEt)](ClO 4 ) (in the form of a solvate with 0.5CH 2 Cl 2 ) and [ 99 Tc(CO) 3 (phen)-(CNCH 2 COOEt)](ClO 4 ) (in the form of an adduct with an outersphere phen molecule) were determined by single-crystal X-ray diffraction. To evaluate the interfering effect of chloride ions on the formation of the 2 + 1 complexes, the kinetics of the replacement of labile monodentate ligand X in the complexes [MX(CO) 3 (N ∧ N)] (M = Re, 99 Tc; N ∧ N = bipy, phen; X = Cl − , ClO 4 − ) by CNCH 2 COOEt in ethanol were compared. The 99 Tc bipy complexes with X = ClO 4 − (according to the IR data, perchlorate anion in ethanol is displaced from the coordination sphere by the solvent molecule) and X = Cl − are characterized by close ligand replacement rates. In the case of the 99 Tc complexes with phen and Re complexes with both phen and bipy, the chloride complexes are appreciably less reactive than the chloride-free complexes. The technetium complexes are considerably more reactive in ligand replacement than their rhenium analogues. In the chloride-containing medium (saline), the complex [ 99m Tc(CO) 3 (bipy)(CNCH 2 COOEt)] + can be prepared under the conditions acceptable for nuclear medical applications, although higher isonitrile concentrations are required as compared to the chloride-free system.

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“…Different radiometals require BFCs with different donor atoms and chelator frameworks. Therefore, it is important to understand the coordination chemistry of BFCs with any given radiometal to be labeled [9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

The foundations of the development of technologies of the synthesis of radiopharmaceuticals

Larkina

Podrezova

Bragina

et al. 2017

AIP Conference Proceedings

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The selection of precursors (for example chelating agents) and development of a technique of chemical modification of the target molecules retaining its ability to bind to specific receptors are very important in the synthesis of radiopharmaceuticals. As some important precursors for target radiopharmaceuticals omega-iodo-aliphatic carboxylic acids and their esters can be used. We have developed an environmentally safe process for producing omega-iodoaliphatic carboxylic acids and their esters of the available, inexpensive and low toxic aliphatic cyclic ketones. We proposed a new method for the synthesis of the chelating agents omega-thia-or (bis(2-hydroxyethyl)amino)-aliphatic carboxylic acids (chelate 1 and chelate 2), which was caused by the existing disadvantages in the existing methods. Thus, based on our method the precursors (chelates) with yield of over 70-90% on the final stage were synthesized, and then the high effectiveness in producing target radiopharmaceuticals using different biomolecules was showed. 99m Tc-chelates complexes were prepared with radiochemical purity >91% and found to be stable at room temperature for six hours.

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Labelling of peptides with 99mTc complexes through the modified C-terminal group

Cited by 7 publications

References 19 publications

Organometallic–Peptide Bioconjugates: Synthetic Strategies and Medicinal Applications

Organometallic–Peptide Bioconjugates: Synthetic Strategies and Medicinal Applications

2 + 1 Tricarbonyl Complexes of Technetium(I) with a Combination of N,N-Bidentate Ligands and Ethyl Isocyanoacetate: How Strong Is the Interfering Effect of Chloride Ions on Their Formation?

The foundations of the development of technologies of the synthesis of radiopharmaceuticals

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