Tuning the Properties of Rigidified Acyclic DEDPA2– Derivatives for Application in PET Using Copper-64 DOI Creative Commons

Daniel Torralba-Maldonado,

Axia Marlin,

Fátima Lucio‐Martínez

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 63(46), P. 22297 - 22307

Published: Nov. 7, 2024

We present a detailed investigation of the coordination chemistry toward [natCu/64Cu]copper series H2DEDPA derivatives (H2DEDPA = 6,6′-((ethane-1,2-diylbis(azanediyl))bis(methylene))dipicolinic acid) containing cyclohexyl (H2CHXDEDPA), cyclopentyl (H2CpDEDPA) or cyclobutyl (H2CBuDEDPA) spacers. Furthermore, we also developed strategy that allowed synthesis H2CBuDEDPA analogue an additional NHBoc group at ring, which can be used for conjugation to targeting units. The X-ray structures Cu(II) complexes evidence distorted octahedral around metal ion in all cases. Cyclic voltammetry experiments (0.15 M NaCl) quasi-reversible reduction waves associated with Cu(I). show high thermodynamic stability, log KCuL values 25.11(1), 22.18(1) and 20.19(1) CHXDEDPA2–, CpDEDPA2– CBuDEDPA2–, respectively (25 °C, 1 NaCl). Dissociation kinetics reveal both spontaneous- proton-assisted pathways operate physiological pH. Quantitative labeling 64CuCl2 was observed 0.1 nmol CHXDEDPA2– CpDEDPA2–, 0.025 CBuDEDPA2– CBuDEDPA-NHBoc2–, no significant differences 15, 30, 60 min. radio-complexes are stable PBS over period 24 h.

Language: Английский

Bispidine Coordination Chemistry DOI Creative Commons
Katharina Bleher, Patrick Cieslik, Peter Comba

et al.

Dalton Transactions, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Bispidines are extremely rigid ligands, easy to prepare in a large variety, with denticities of four ten, various donor sets and charges, for mono- oligonuclear transition metal, main group rare earth complexes. In the last approx. 20 years significantly more than 50 new bispidine based ligands were prepared their coordination chemistry studied. Biological probes medicinal applications is one area chemistry, where fast complex formation, high stability, metal ion selectivity inertness utmost importance. Oxygen activation oxidation catalysis another focus catalyst efficiency stability as well product important requirements. Particularly successful these areas presented discussed detail, addition fundamental principles that show importance ligand rigidity, cavity size shape overarching properties.

Language: Английский

Citations

0
Synthesis of Bispidine-Based Prostate-Specific Membrane Antigen-Targeted Conjugate and Initial Investigations DOI Creative Commons
Aleksei E. Machulkin, Stanislav A. Petrov,

Maria D. Kraynova

et al.

Organics, Journal Year: 2025, Volume and Issue: 6(1), P. 7 - 7

Published: Feb. 10, 2025

Nowadays, PSMA ligands are widely used for radiotheragnostic purposes in prostate cancer. The synthesis of a PSMA-Bisp conjugate was developed and realized with good yield (overall ~58% the last two steps). All newly synthesized compounds were characterized by physicochemical methods: 1H 13C NMR, HRMS, LCMS (for biologically tested samples). Subsequently, Bisp1 (diacetate bispidine ligand), Bisp-alkyne (bifunctional derivative Bisp1), its labeled 64Cu mild conditions. In vitro studies [64Cu]Cu-PSMA-Bisp have shown great stability model solutions. Finally, compared to well-known PSMA-617 they showed similar excess bovine serum (BVS), at same time, labeling is extremely high kinetics conditions, while requires heating (90 °C). Thus, this can be incredibly promising nuclear medicine.

Language: Английский

Citations

0
Metal Complexes of Bispidine Derivatives: Achievements and Prospects for the Future DOI Creative Commons
Altynay B. Kaldybayeva, V. К. Yu, Feyyaz Durap

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(5), P. 1138 - 1138

Published: March 3, 2025

Multidentate bispidine ligands, including tetra-, penta-, hexa-, hepta-, and octadentate variants, exhibit strong coordination tendencies due to their intrinsic rigidity, significant reorganization potential, ability efficiently encapsulate metal ions. These structural attributes profoundly influence the thermodynamic stability, ion selectivity, redox behavior, spin-state configuration of resulting complexes. Metal ions, in turn, serve as highly suitable candidates for remarkable kinetic inertness, rapid complex formation kinetics, low potential. This review focuses on ligands incorporating core (3,7-diazabicyclo[3.3.1]nonane) provides an overview advancements synthesis complexes involving p-, d-, f-block elements. Furthermore, rationale behind growing interest bispidine-based applications radiopharmaceuticals, medicinal chemistry, organic is explored, particularly context potential diagnostic catalytic drug development.

Language: Английский

Citations

0
Tuning the Properties of Rigidified Acyclic DEDPA2– Derivatives for Application in PET Using Copper-64 DOI Creative Commons

Daniel Torralba-Maldonado,

Axia Marlin,

Fátima Lucio‐Martínez

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 63(46), P. 22297 - 22307

Published: Nov. 7, 2024

We present a detailed investigation of the coordination chemistry toward [natCu/64Cu]copper series H2DEDPA derivatives (H2DEDPA = 6,6′-((ethane-1,2-diylbis(azanediyl))bis(methylene))dipicolinic acid) containing cyclohexyl (H2CHXDEDPA), cyclopentyl (H2CpDEDPA) or cyclobutyl (H2CBuDEDPA) spacers. Furthermore, we also developed strategy that allowed synthesis H2CBuDEDPA analogue an additional NHBoc group at ring, which can be used for conjugation to targeting units. The X-ray structures Cu(II) complexes evidence distorted octahedral around metal ion in all cases. Cyclic voltammetry experiments (0.15 M NaCl) quasi-reversible reduction waves associated with Cu(I). show high thermodynamic stability, log KCuL values 25.11(1), 22.18(1) and 20.19(1) CHXDEDPA2–, CpDEDPA2– CBuDEDPA2–, respectively (25 °C, 1 NaCl). Dissociation kinetics reveal both spontaneous- proton-assisted pathways operate physiological pH. Quantitative labeling 64CuCl2 was observed 0.1 nmol CHXDEDPA2– CpDEDPA2–, 0.025 CBuDEDPA2– CBuDEDPA-NHBoc2–, no significant differences 15, 30, 60 min. radio-complexes are stable PBS over period 24 h.

Language: Английский

Citations

0