A Convenient Three-Component Synthesis of Substituted Cyclopentadienyl Tricarbonyl Rhenium Complexes

Minutolo, Filippo; Katzenellenbogen, John A.

doi:10.1021/ja980433q

Cited by 40 publications

(37 citation statements)

References 15 publications

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“…The use of other metals in place of the initial ferrocenyl to give complexes of CpTc(CO) 3 and CpRe(CO) 3 have already been reported. [19,33,34] These metallic elements give access to interesting radionuclides both for imaging ( 99m Tc), and for radiotherapy ( 188 Re). [35] In terms of synthesis however there is still work to be done, and this will be the focus of future studies.…”

Section: Discussionmentioning

confidence: 99%

The Presence of a Ferrocenyl Unit on an Estrogenic Molecule is Not Always Sufficient to Generate in vitro Cytotoxicity

et al. 2006

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We recently reported the dual (antihormonal and cytotoxic) functionality of ferrocifens, which are organometallic complexes derived from hydroxytamoxifen, the standard molecule in the treatment of hormone-dependent breast cancers. To test the hypothesis that the presence of a ferrocenyl substituent on molecules with an affinity for the estrogen receptor is sufficient to give them cytotoxic properties in vitro, we prepared complexes derived from estradiol with a ferrocenyl substituent at positions 7alpha and 17alpha. The complexes thus obtained retain a satisfactory level of affinity for the estrogen receptor (RBA values higher than 12 %). At low concentrations (0.1-1 microM) the complexes show an estrogenic effect in vitro equivalent to that of estradiol on hormone-dependent (MCF-7) breast cancer cells, and no cytotoxic effect on hormone-independent (MDA-MB-231) breast cancer cells. At high concentrations (up to 50 microM) the 17alpha-ethynylferrocenyl estradiol and 7alpha-ferrocenylmethylthio estradiol become cytotoxic (IC(50)=13.2 microM and 18.8 microM, respectively) while the 17alpha-ferrocenylestradiol remains non toxic. The low toxicity of these compounds support our hypothesis that electronic communication between the ferrocenyl and phenol moieties in the hydroxyferrocifens series is a key parameter in the generation of cytotoxic effects at submicromolar concentrations.

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Section: Discussionmentioning

confidence: 99%

The Presence of a Ferrocenyl Unit on an Estrogenic Molecule is Not Always Sufficient to Generate in vitro Cytotoxicity

et al. 2006

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“…Still, these applied high temperatures and organic solvents are hardly applicable on a routine level. [104][105][106] Complexes of the type [(Cp-R) 99m Tc(CO) 3 ] would be particularly interesting since it has been shown many times in bioorganometallic chemistry that pianostool-structured compounds can topologically mimic phenyl rings in pharmaceuticals. [107][108][109] Whereas cyclopentadiene is insoluble and unstable in water, we found acetylcyclopentadiene (AHCp) to have a pK a in water of about 8 and to decompose only very slowly.…”

Section: Basic Chemistry Of [M(oh 2 ) 3 (Co) 3 ] + In Watermentioning

confidence: 99%

The Chemistry of Technetium–Water Complexes within the Manganese Triad: Challenges and Perspectives

Alberto

2008

Eur J Inorg Chem

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The chemistry of technetium is essentially driven by radiopharmaceutical applications. These comprise the syntheses of novel complexes but, moreover, the combination of targeting biomolecules with metal complexes. Aqua ions are especially convenient for facilitatating the introduction of metal cations into biomolecules, but are nonexistent for Tc and Re in the Mn triad. This microreview will discuss the chemistry of those Tc complexes that contain H2O as ligands. Special attention will be payed to organometallic aqua ions, i.e. complexes that are typically organometallic with water as ligand. Of particular interest is the coordination chemistry of [M(OH2)3(CO)3]+ (M = Mn, Tc, Re) complexes in water since it is the origin of the widely applied radiopharmaceutical research with 99mTc and 188Re. The chemistry of organometallic aqua ions is not confined to Werner‐type ligands, hence, a further emphasis will be placed on pure organometallic chemistry in water.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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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%

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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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A Convenient Three-Component Synthesis of Substituted Cyclopentadienyl Tricarbonyl Rhenium Complexes

Cited by 40 publications

References 15 publications

The Presence of a Ferrocenyl Unit on an Estrogenic Molecule is Not Always Sufficient to Generate in vitro Cytotoxicity

The Presence of a Ferrocenyl Unit on an Estrogenic Molecule is Not Always Sufficient to Generate in vitro Cytotoxicity

The Chemistry of Technetium–Water Complexes within the Manganese Triad: Challenges and Perspectives

Current use and future potential of organometallic radiopharmaceuticals

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