Unsymmetrical pincer CNN palladium complex of 7-ferrocenylmethyl-3-methyl-3,7-diazabicyclo[3.3.1]nonane

Bulygina, L. A.; Kagramanov, Nikolay D.; Khrushcheva, N. S.; Перегудов, А. С.; Sokolov, V. I.

doi:10.1016/j.jorganchem.2017.06.009

Cited by 12 publications

(6 citation statements)

References 40 publications

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“…Protonation of the tertiary amine moieties under physiological conditions would also improve the compound's water solubility due to the known bispidine ‘proton sponge’ effect [33] . In order to form the desired highly stable bispidine carbon‐metal bond, a different route from previous studies, which focussed on catalysis chemistry, was necessary [34–39] . Trimethylstannyl was chosen as a viable leaving group for the transmetallation with mercury due to its tolerance for the unavoidable aqueous conditions used for the radiometal's production and handling [40]…”

Section: Methodsmentioning

confidence: 99%

“… [33] In order to form the desired highly stable bispidine carbon‐metal bond, a different route from previous studies, which focussed on catalysis chemistry, was necessary. [ 34 , 35 , 36 , 37 , 38 , 39 ] Trimethylstannyl was chosen as a viable leaving group for the transmetallation with mercury due to its tolerance for the unavoidable aqueous conditions used for the radiometal's production and handling. [40] …”

mentioning

confidence: 99%

“…[33] In order to form the desired highly stable bispidine carbon-metal bond, a different route from previous studies, which focussed on catalysis chemistry, was necessary. [34][35][36][37][38][39] Trimethylstannyl was chosen as a viable leaving group for the transmetallation with mercury due to its tolerance for the unavoidable aqueous conditions used for the radiometal's production and handling. [40] The objective of this work was the synthesis of a mercury compound, stable in vivo, which has solubility and functionality such that it could be attached to a cancer-targeting carrier for drug development in radiopharmacy.…”

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confidence: 99%

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Radiolabelled Cyclic Bisarylmercury: High Chemical and in vivo Stability for Theranostics

et al. 2021

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We show the synthesis of an in vivo stable mercury compound with functionality suitable for radiopharmaceuticals. The designed cyclic bisarylmercury was based on the water tolerance of organomercurials, higher bond dissociation energy of HgÀ Ph to HgÀ S, and the experimental evidence that acyclic structures suffer significant cleavage of one of the HgÀ R bonds. The bispidine motif was chosen for its in vivo stability, chemical accessibility, and functionalization properties. Radionuclide production results in 197(m) HgCl 2 (aq), so the desired mercury compound was formed via a water-tolerant organotin transmetallation. The Hg-bispidine compound showed high chemical stability in tests with an excess of sulfur-containing competitors and high in vivo stability, without any observable protein interaction by human serum assay, and good organ clearance demonstrated by biodistribution and SPECT studies in rats. In particular, no retention in the kidneys was observed, typical of unstable mercury compounds. The nat Hg analogue allowed full characterization by NMR and HRMS.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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Radiolabelled Cyclic Bisarylmercury: High Chemical and in vivo Stability for Theranostics

et al. 2021

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“…19,20 This was addressed by the development of a large variety of picolinic acid and hydroxyquinoline-based ligands such as octapa, py4pa, octox, macropa, and py-macrodipa (Scheme 1), and some of the radiochemical results are promising. 21−27 Bispidine (3,7-diazabicyclo[3.3.1]nonane)-based ligands are adamantane derived with very rigid structures, ideal for the complexation of large metal ions such as Mn II , 28,29 Bi III , 30 Pd II , 31 and Ln III . 32 These ligands, first described by Mannich and Mohs, 33 are highly modular and allow for a large variety of denticities and donor group combinations.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Bispidine (3,7-diazabicyclo[3.3.1]nonane)-based ligands are adamantane derived with very rigid structures, ideal for the complexation of large metal ions such as Mn II , , Bi III , Pd II , and Ln III . These ligands, first described by Mannich and Mohs, are highly modular and allow for a large variety of denticities and donor group combinations .…”

Section: Introductionmentioning

confidence: 99%

Toward Personalized Medicine: One Chelator for Imaging and Therapy with Lutetium-177 and Actinium-225

et al. 2022

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We report a nonadentate bispidine (3,7-diazabicyclo[3.3.1]nonane) that unveils the potential to bind theranostically relevant radionuclides, including indium-111, lutetium-177, and actinium-225 under mild labeling conditions. This radiopharmaceutical candidate allows the simultaneous application of imaging and treatment (radionuclide theranostics) without changing the type of the bioconjugate; that is, it allows the strong binding to an imaging and a therapeutic radionuclide by the same chelator. Since sophisticated coordination chemistry is required to achieve high thermodynamic and kinetic stability (inertness), it is not surprising that only a few chelators have been reported that are able to strongly bind several radionuclides to a satisfactory extent. Bispidine-derived ligands have proven to be ideal for di- and trivalent metal ions with generally fast complexation kinetics and high in vitro and in vivo stabilities. The presented (radio)complexes are formed under mild conditions (pH 6, <40 °C) and exhibit thermodynamic stability and inertness in human serum comparable to the corresponding DOTA complexes. The bispidine-based complexing agent was conjugated to a peptide, targeting somatostatin type 2 receptors (SSTR2), overexpressed on neuroendocrine tumors. The 177Lu- and 225Ac-labeled conjugates were investigated, considering their binding to two different SSTR2-positive cell lines, including the human pancreatic carcinoid tumor (BON-SSTR2+) and the murine pheochromocytoma cell line (MPC). The biodistribution and accumulation pattern in MPC tumor-bearing mice was also evaluated. The LuIII and AcIII complexes studied show how ligand structures can be optimized in general by extending the denticity and varying the donor set in order to allow for fast complex formation and medically relevant inertness.

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The first non-symmetrically substituted conjugates of bispidine with monoterpenoids and amino acids. Synthesis and application for catalysis of addition of diethylzinc to aldehydes

Ponomarev,

Mozhaitsev,

Li-Zhulanov

et al. 2024

Russ Chem Bull

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Unsymmetrical pincer CNN palladium complex of 7-ferrocenylmethyl-3-methyl-3,7-diazabicyclo[3.3.1]nonane

Cited by 12 publications

References 40 publications

Radiolabelled Cyclic Bisarylmercury: High Chemical and in vivo Stability for Theranostics

Radiolabelled Cyclic Bisarylmercury: High Chemical and in vivo Stability for Theranostics

Toward Personalized Medicine: One Chelator for Imaging and Therapy with Lutetium-177 and Actinium-225

The first non-symmetrically substituted conjugates of bispidine with monoterpenoids and amino acids. Synthesis and application for catalysis of addition of diethylzinc to aldehydes

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