Derivate von [<sup>103</sup>Ru]‐methyl‐ruthenocen Konstitution und Organ‐verteilung von Potentiellen Radiopharmaka

Schneider, Michael; Wenzel, Martin

doi:10.1002/jlcr.2580170102

Cited by 9 publications

(2 citation statements)

References 14 publications

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“…Synthesis. RcCH 2 OH (Rc = ruthenocenyl) has previously been synthesized from [RcCH 2 NMe 3 ] + [I] - and by NaBH 4 reduction of RcCHO . We obtained the alcohol from RcCHO using LiAl(O t Bu) 3 H, by analogy with the method described for RuCp*( η 5 -C 5 Me 4 CH 2 OH) 10 (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

The Ruthenocenylmethylium Cation: Isolation and Structures of η⁵-Cyclopentadienyl-η⁶-fulvene-ruthenium(II) Salts

et al. 2001

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Salts of the ruthenocenylmethylium cation, 1 +, can be synthesized from the reaction of ruthenocenylmethanol with either Brønsted or Lewis acids. The X-ray crystal structures of the tetrakis{3,5-bis(trifluoromethyl)phenyl}borate and trifluoromethanesulfonate salts of 1 + reveal that the methylium carbon is bound to the ruthenium with Ru−C bond lengths in the range 2.251(9)−2.40(1) Å and confirm the description of the cation structure as η 5-cyclopentadienyl-η 6-fulvene-ruthenium(II). The UV−vis spectrum of 1 + shows a d−d transition at an energy similar to those of ruthenocene and the η 5-cyclopentadienyl-η 6-benzeneruthenium(II) cation, but with increased absorptivity. Cyclic voltammetry indicates that 1 + is reduced at considerably less negative potential than its isomer, the η 5-cyclopentadienyl-η 6-benzene-ruthenium(II) cation. Chemical reduction with sodium amalgam in tetrahydrofuran leads to the formation of methylruthenocene, 1,2-bis(ruthenocenyl)ethane, and bis(ruthenocenylmethyl)ether. Reaction of 1 + with triphenylphosphine affords the (ruthenocenylmethyl)triphenylphosphonium cation; the crystal structure of the dichloromethane solvate of its tetrafluoroborate salt has been determined. Density functional calculations closely reproduce the crystallographically determined geometry of 1 + and allow rationalization of some characteristics of its structure, spectroscopy, and reactivity. The calculations suggest that the ferrocenylmethylium cation, 3 +, has a geometry similar to 1 + with similar orbital structure, albeit with considerably more d-character to the occupied frontier orbitals.

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Section: Resultsmentioning

confidence: 99%

The Ruthenocenylmethylium Cation: Isolation and Structures of η⁵-Cyclopentadienyl-η⁶-fulvene-ruthenium(II) Salts

et al. 2001

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“…Further characterization of these complexes will be necessary before mechanistic conclusions can be drawn. Ruthenium red has shown some tendency to localize in tumors, with the likely receptor sites being mucopolysaccharides on cell surfaces Ruthenocenes have provided a versatile ogranometallic approach to the synthesis of radioruthenium agents, however, no high specificity has been shown for organs which are not already well-imaged by existing agents [32][33][34][35][36][37][38][39] . A number of ruthenium complexes with chelating ligands either similar or identical to the those employed with clinically used 99m Tc radiopharmaceuticals have been tested with similar results.…”

Section: Specifically Binds To Glycoproteins On the Surface Of Rat Acmentioning

confidence: 99%

Ruthenium Anticancer Agents and Relevant Reactions of Ruthenium—Purine Complexes

Clarke¹

1983

ACS Symposium Series

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Attempts to incorporate ruthenium into pharmaceutical agents have typically followed two avenues of approach. Early studies were directed toward ruthenium-containing chemotherapeutic agents 1 and more recently workers have begun to explore the possibility of using 97 Ru for diagnostic organ imaging. 2,3While ruthenium complexes have shown promise along both directions, there has been only one clinical trial of a ruthenium compound, which involved 103 RuCl 3 for radio-imaging tumors. 4 At present, the only commonly used ruthenium compound for biomedical purposes is the cytological stain, ruthenium red. 5 The interactions of ruthenium complexes with biologically important molecules have recently been reviewed and the early literature dealing with the metabolic fate of different types of ruthenium compounds has been summarized elsewhere. 1,3,6Antitumor A^aatt With few exceptions, 7 approaches to ruthenium antineoplastic agents have related to the putative mechanism of action of the clinically employed cis-C^N^KPt. 1 ' 8 The binding of ammi ne complexes of both Ru(II) and Ru(III) to nucleotides and nucleic acids is, in many ways, analogous to that of cisplatin. ' 9 On the other hand, ruthenium(II) complexes usually undergo ligand substitution somewhat more rapidly and the tripositive oxidation state is much more accessible under mild conditions. Advantage can be taken from the ready availability of both the Ru(II) and Ru(III) oxidation states under physiological conditions and the general inertness of these ions toward substitution, when coordinated to nitrogen ligands.Studies reported in an earlier symposium revealed the general anticancer activity of compounds containing the 0097-6156/83/0209-0335$06.00/0

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Synthesen von [¹⁹¹Os]‐Osmocen‐Derivaten und Vergleich ihrer Organ‐Verteilung mit Ruthenocen‐Derivaten bei Mäusen

Schachschneider

Wenzel

1982

Labelled Comp Radiopharmac

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Derivate von [¹⁰³Ru]‐methyl‐ruthenocen Konstitution und Organ‐verteilung von Potentiellen Radiopharmaka

Abstract: Tumor affinity of all compountls tested was low.

Cited by 9 publications

References 14 publications

The Ruthenocenylmethylium Cation: Isolation and Structures of η⁵-Cyclopentadienyl-η⁶-fulvene-ruthenium(II) Salts

The Ruthenocenylmethylium Cation: Isolation and Structures of η⁵-Cyclopentadienyl-η⁶-fulvene-ruthenium(II) Salts

Ruthenium Anticancer Agents and Relevant Reactions of Ruthenium—Purine Complexes

Synthesen von [¹⁹¹Os]‐Osmocen‐Derivaten und Vergleich ihrer Organ‐Verteilung mit Ruthenocen‐Derivaten bei Mäusen

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Derivate von [103Ru]‐methyl‐ruthenocen Konstitution und Organ‐verteilung von Potentiellen Radiopharmaka

Abstract: Tumor affinity of all compountls tested was low.

Cited by 9 publications

References 14 publications

The Ruthenocenylmethylium Cation: Isolation and Structures of η5-Cyclopentadienyl-η6-fulvene-ruthenium(II) Salts

The Ruthenocenylmethylium Cation: Isolation and Structures of η5-Cyclopentadienyl-η6-fulvene-ruthenium(II) Salts

Ruthenium Anticancer Agents and Relevant Reactions of Ruthenium—Purine Complexes

Synthesen von [191Os]‐Osmocen‐Derivaten und Vergleich ihrer Organ‐Verteilung mit Ruthenocen‐Derivaten bei Mäusen

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Derivate von [¹⁰³Ru]‐methyl‐ruthenocen Konstitution und Organ‐verteilung von Potentiellen Radiopharmaka

The Ruthenocenylmethylium Cation: Isolation and Structures of η⁵-Cyclopentadienyl-η⁶-fulvene-ruthenium(II) Salts

The Ruthenocenylmethylium Cation: Isolation and Structures of η⁵-Cyclopentadienyl-η⁶-fulvene-ruthenium(II) Salts

Synthesen von [¹⁹¹Os]‐Osmocen‐Derivaten und Vergleich ihrer Organ‐Verteilung mit Ruthenocen‐Derivaten bei Mäusen