Boronic Acids in the Three-Component Synthesis of Carbon-Substituted Cyclopentadienyl Tricarbonyl Rhenium Complexes

Minutolo, Filippo; Katzenellenbogen, John A.

doi:10.1021/ja982146s

Cited by 26 publications

(22 citation statements)

References 16 publications

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“…99m TcO 4 -was reduced in presence of ferrocene derivatives and Mn(CO) 5 Br. Katzenellenbogen and co-workers have recently presented a modification of this "double ligand transfer" (DLT) reaction [10,11]. However, the harsh reaction conditions in organic media and the often poor yields preclude practical application.…”

Section: The Technetium-and Rhenium-tricarbonyl Corementioning

confidence: 99%

“…Neurotensin analogues [NT (8)(9)(10)(11)(12)(13)] targeting receptors expressed on a variety of carcinomas [63] have been labelled with 99m TcCO. Eleven NT (8)(9)(10)(11)(12)(13) analogues were functionalised at the N-terminus with an N α -Ac histidine or a histidine similar to 0 Tyr 3 octreotate [13,64].…”

Section: Examples Of Peptides Labelled With Tc/re-tricarbonylmentioning

confidence: 99%

“…Eleven NT (8)(9)(10)(11)(12)(13) analogues were functionalised at the N-terminus with an N α -Ac histidine or a histidine similar to 0 Tyr 3 octreotate [13,64]. The almost quantitative formation of uniform and stable products was observed at ligand concentrations of 10 -5 to 5×10 -5 M at 75°C.…”

Section: Examples Of Peptides Labelled With Tc/re-tricarbonylmentioning

confidence: 99%

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Current use and future potential of organometallic radiopharmaceuticals

Schibli

Schubiger

2002

European Journal of Nuclear Medicine and Molecular Imaging

299

256

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Contrary to common belief, organometallic compounds exhibit remarkable stability in aerobic and even diluted aqueous solutions. Technetium-sestamibi (Cardiolite) is one of the most prominent examples of this class of compounds routinely used in nuclear medicine. This review summarises the recent progress in labelling of biomolecules with organometallic complexes for diagnostic and therapeutic application in radiopharmacy and exemplifies in detail developments focussing on organometallic technetium- and rhenium-tricarbonyl technologies. The value of such technologies has been recognised and they have become a valuable alternative to common labelling methodologies. An increasing number of groups have started to employ an organometallic precursor for the purpose of radioactive labelling of various classes of biomolecules, and the advantages and limitations of this new technique are compared with those of other labelling methods. The synthetic access to appropriate precursors via double-ligand exchange or aqueous carbonyl kit preparation for routine application is described. Strategies and examples for the design of appropriate bifunctional chelating agents for the Tc/Re-tricarbonyl core are given. The functionalization of biomolecules such as tracers for the central nervous system (dopaminergic and serotonergic), tumour affine peptides (somatostatin receptors, neuroreceptors) and tumour binding single-chain antibody fragments is summarised. Where possible and appropriate, the in vitro and in vivo results in respect of these examples are compared with those obtained with classical (99m)Tc/(188)Re(V)- and (111)In-labelled analogues. The preclinical results show the in many ways superior characteristics of organometallic labelling techniques.

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Section: The Technetium-and Rhenium-tricarbonyl Corementioning

confidence: 99%

Section: Examples Of Peptides Labelled With Tc/re-tricarbonylmentioning

confidence: 99%

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Current use and future potential of organometallic radiopharmaceuticals

Schibli

Schubiger

2002

European Journal of Nuclear Medicine and Molecular Imaging

299

256

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“…However, the major drawback in the initial uses of the DLT reaction for labeling biomolecules is in the additional steps needed to conjugate the substituted CpMet(CO) 3 to the biological molecule of interest (24). Recent developments in our laboratory, which provide alternative routes to CpRe(CO) 3 complexes without a requirement for substitution with an electronwithdrawing group, include the "three-component condensation" reaction (25)(26)(27) and the stannane approach (28).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Cyclopentadienyltricarbonyl Rhenium Phenyltropanes by Double Ligand Transfer: Organometallic Ligands for the Dopamine Transporter

et al. 2001

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Cyclopentadienyltricarbonyl rhenium (CpRe(CO)(3)) systems can be prepared from ferrocenes and perrhenate by a double ligand transfer (DLT) reaction that gives reasonable yields and shows excellent functional group tolerance. We used this reaction for the direct preparation of CpRe(CO)(3)-phenyltropane conjugates. Such agents, when labeled with technetium-99m, might function as imaging agents for the dopamine transporter (DAT) system that would be useful for assessing the onset and severity of Parkinson's disease. Of the CpRe(CO)(3)-tropane conjugates prepared by the DLT reaction (as well as other analogues prepared by related methods), those substituted at the N-8 position seem most promising; their affinity for the DAT in all cases was high, and their ferrocene precursors for the DLT reaction can be prepared in a convenient manner. By contrast, the 3 beta-conjugates were poor DAT binders. The modular nature of these systems offers considerable flexibility that could be used to improve the binding characteristics of these compounds further.

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“…We reasoned that if we removed this halogen from the metal precursor, then we might be able to introduce a variety of exogenous nucleophiles and have them become incorporated in the Cp ring. Indeed, we found that by replacing BrTc(CO) 5 with the Re(CO) 3 + or Tc(CO) 3 + , cations in which the halogen had been removed using silver triflate, we could introduce other nucleophiles (Scheme 12). The nucleophiles that worked best were carboxylates, which gave as products acyloxyCpMet(CO) 3 (Scheme 3, left), and boronic acids, which gave aryl and vinyl CpMet (CO) 3 systems (Scheme 3, right).…”

Section: B Three-componentmentioning

confidence: 99%

Novel Chemical Strategies for Labeling Small Molecule Ligands for Androgen, Progestin, and Peroxisome Proliferator-Activated Receptors for Imaging Prostate and Breast Cancer and the Heart

Katzenellenbogen¹

2007

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Boronic Acids in the Three-Component Synthesis of Carbon-Substituted Cyclopentadienyl Tricarbonyl Rhenium Complexes

Cited by 26 publications

References 16 publications

Current use and future potential of organometallic radiopharmaceuticals

Current use and future potential of organometallic radiopharmaceuticals

Synthesis of Cyclopentadienyltricarbonyl Rhenium Phenyltropanes by Double Ligand Transfer: Organometallic Ligands for the Dopamine Transporter

Novel Chemical Strategies for Labeling Small Molecule Ligands for Androgen, Progestin, and Peroxisome Proliferator-Activated Receptors for Imaging Prostate and Breast Cancer and the Heart

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