Transition metal complexes as electrochemical markers for steroids

Osella, Domenico; Stein, Edison; Jaouen, Gérard; Zanello, Piero

doi:10.1016/0022-328x(91)86193-t

Cited by 11 publications

(5 citation statements)

References 21 publications

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“…The reaction with L-cysteine resulted in formation of S 8 and GSH was oxidized (GSSG). These results can be explained by the ability of cobalt-alkyne complexes to be reduced under complex decomposition (Osella et al 1991;Osella & Fiedler 1992). The reductive decomposition of Co-ASS was confirmed by monitoring the decrease of the Co-ASS concentration and the formation of the free alkyne ligand by HPLC.…”

Section: Interaction With Thiolsmentioning

confidence: 81%

Stability, protein binding and thiol interaction studies on [2-acetoxy-(2-propynyl)benzoate]hexacarbonyldicobalt

Ott

Gust

2005

Biometals

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Cobalt-alkyne complexes are a new class of potent cytotoxic drugs. The lead compound [2-acetoxy-(2-propynyl)benzoate]hexacarbonyldicobalt (Co-ASS) showed high effects on several human cancer cell lines. In order to evaluate further the in-vitro properties and reactivity of this substance we performed stability and protein binding studies and investigated the interaction of this complex with 1,2-ethanedithiol, L-cysteine and glutathione. UV-Vis, HPLC and AAS studies showed that the compound was sufficiently stable under in-vitro conditions. Binding to human serum albumin increased from approximately 25% at the beginning to over 50% after 48 h of incubation as determined by ethanol preciptation and size exclusion chromatography. The interaction with thiols resulted in disulfide bond formation of the thiols.

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Section: Interaction With Thiolsmentioning

confidence: 81%

Stability, protein binding and thiol interaction studies on [2-acetoxy-(2-propynyl)benzoate]hexacarbonyldicobalt

Ott

Gust

2005

Biometals

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“…The Co2(CO)6(alkyne) (1)(2)(3)(4) derivatives were synthesized according to the literature14 procedures, by reacting Co2(CO)8 with ethynylestradiol, 1-ethynyl-1-cyclohexanol, but-2-yne, and ethyne, respectively. Their purity was checked by IR and *H NMR spectroscopy on Perkin-Elmer 580 B and JEOL EX-400 instruments, respectively.…”

Section: Methodsmentioning

confidence: 99%

“…The addition of the bimetallic fragment (having an accessible LUMO) to the steroid makes the resulting bioorganometallic molecule cathodically detectable. Since the spectroelectrochemical results on 1 reported here indicate an unexpected reversibility of the overall electrochemical reduction/ reoxidation cycle, we reinvestigate the electrochemical behavior of Co2(CO)6(HC2E) (1) (Figure 1) and those of some homologues, namely Co2(CO)6(lethynyl-l-cyclohexanol), hereafter Co2(CO)6(HC2C6H10OH) (2), Co2(CO)6(MeC2Me) (3), and Co2(CO)6(HC2H) (4) by means of dc and ac polarography and cyclic voltammetry (CV) in order to better understand the fragment generation/recombination mechanism.…”

Section: Introductionmentioning

confidence: 99%

Reinvestigation of the electrochemical behavior of the Co2(CO)6(ethynylestradiol) complex. Evidence of efficient recombination of the electrogenerated fragments

Osella¹,

Fiedler²

1992

Organometallics

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The electrochemical behavior of Co^COlgtethynylestradiol) complexes has been reinvestigated by means of electrochemical and spectroscopic techniques. The electrogenerated [Co2(CO)e(ethynylestradiol)]m onoanion is very unstable and undergoes fast cleavage of the Co-Co bond, producing Co(CO)4". An efficient recombination Co(CO)4* radical (produced from reoxidation of Co(CO)4") with the [Co(CO)2(ethynylestradiol)]• radical, adsorbed on the electrode, regenerates almost qualitatively the parent complex, in the chemical time scale.

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“…Thus, estradiol, mestranol 451 , and the steroid 452 , readily accessible via reaction of the appropriate Grignard reagent with estrone (80% yield), were transformed into the corresponding organometallic species 453 – 455 with average to good yields (40–86%) (Scheme ). − The RBA found for compounds 453 and 455 were, respectively, 5% and 12% (relative to estradiol, 100%), consistent with the receptor being recognized despite significant steric hindrance at the 17α position. Compound 453 was also the subject of an electrochemical study by Osella and co-workers. , …”

Section: Other Biological Developmentsmentioning

confidence: 99%