The anomalous electrochemistry of the ferrocenylamines

Britton, Wayne E.; Kashyap, R. P.; El‐Hashash, M. A.; El-Kady, Mohammed.; Herberhold, Max

doi:10.1021/om00136a033

Cited by 69 publications

(37 citation statements)

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“…For example, we have recently developed prodrugs (e.g., 1 , Figure ), which were activated by ROS within cancer cells with the release of N ‐alkylaminoferrocenes (AmFc, for example, 2 ) . The latter products are strong one‐electron‐reducing agents, as was evidenced by their low oxidation potential (−0.37 V vs. ferrocene). In the preliminary experiment, we observed that 2 was oxidized by Pt IV prodrug 5 with formation of ion 2 + , was as indicated by the appearance of the characteristic broad absorbance band at approximately 900 nm in the UV/Vis spectrum of a mixture of 5 and 2 (2 equiv; see the Supporting Information, Figure S11).…”

Section: Figurementioning

confidence: 99%

Cancer‐Specific, Intracellular, Reductive Activation of Anticancer Pt^IV Prodrugs

Reshetnikov

Daum

Mokhir

2017

Chemistry A European J

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Because cellular uptake of anticancer Pt and Pt drugs occurs by different mechanisms, the latter ones can exhibit substantial activity towards cells, which have either intrinsic or acquired resistance towards Pt drugs. However, this positive effect is diminished due to reductive activation of Pt drugs in extracellular space that can be one of the reasons why they have not yet been approved for clinical use despite over 60 clinical trials conducted worldwide. Herein, we suggest a solution to this problem by achieving highly specific intracellular versus extracellular prodrug reduction. In particular, we prepared a hybrid Pt prodrug containing two pro-reductants. This hybrid was uptaken by cells, the pro-reductants were activated in the cancer-specific microenvironment (high H O ), and reduced Pt by two one-electron transfers. The drug formed in this way induced cell death both in cisplatin-sensitive and resistant cell lines, but remained nontoxic to normal cells.

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Section: Figurementioning

confidence: 99%

Cancer‐Specific, Intracellular, Reductive Activation of Anticancer Pt^IV Prodrugs

Reshetnikov

Daum

Mokhir

2017

Chemistry A European J

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“…Analysis of the redox equilibrium under n.c.a. conditions and the effect of reference compound 3 as a carrierThe hypothesis that [ 18 F]4 underlies a redox equilibrium is based on the fact that ferrocene-derived compounds have a very low oxidation potential 23. 24 Although the oxidised species 4 + is usually not observed during nonradioactive synthesis of 4, [ 18 F]4 + appeared frequently under no-carrier-added (n.c.a.)…”

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Radiosynthesis of an ¹⁸F‐fluoroglycosylated aminoferrocene for in‐vivo imaging of reactive oxygen species activity by PET

Toms

Reshetnikov

Maschauer

et al. 2018

Labelled Comp Radiopharmac

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The imaging of reactive oxygen species (ROS) at the molecular level with high sensitivity and specificity by positron emission tomography (PET) could be of enormous interest to increase our knowledge about ROS activity and signalling, especially in tumours. The aim of this research was to optimise the click chemistry‐based radiosynthesis of an 18F‐labelled aminoferrocene glycoconjugate that was derived from an N‐alkylaminoferrocene lead structure known to have anticancer activity in vitro. Applying the solvent system phosphate buffer/THF (12/5), Cu(OAc)2 and sodium ascorbate as reducing agent at 60°C, the alkyne 1 reacted with the 18F‐labelled glycosyl azide [18F]2 in the presence of carrier 3 (47μM) to obtain carrier‐added [18F]4 in a radiochemical yield of 85%. Interestingly, the addition of carrier was essential for sufficient radiochemical yield, because it suppressed the oxidation of no‐carrier‐added (n.c.a.) [18F]4. Future work will include the formulation of c.a. [18F]4 for studying its biodistribution in tumour‐bearing mice.

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“…[41] The strong resemblance of the spectral features in the low-energy region independently reported for the cation…”

Section: +mentioning

confidence: 73%

[Fp*Fc][PF6]: A remarkable non-symmetric dinuclear cation in a very stable mixed-valent state

Argouarch

Grelaud

Roisnel

et al. 2017

Journal of Organometallic Chemistry

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Abstract.We report herein dicarbonyl(pentamethylcyclopentadienyl)(ferroceniumyl)iron hexafluorophosphate, which contains a dimetallic cation with a remarkably stable mixed-valent (MV) structure and unexpected redox features. The electronic structure of this compound is discussed in the light of the existing Hush model, which suggests an unusually strong electronic coupling between the two iron centers, despite the non-symmetric environment of the metallic centers. End-to-end charge delocalization is not the main contributor to the extra-large stability of this MV complex, which originates from electronic effects other than the energetic difference between the two MV redox isomers (G 0 ). This open-shell derivative has also been briefly tested as a catalyst in the reductive etherification of aldehydes by hydrosilanes.

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The anomalous electrochemistry of the ferrocenylamines

Cited by 69 publications

References 0 publications

Cancer‐Specific, Intracellular, Reductive Activation of Anticancer Pt^IV Prodrugs

Cancer‐Specific, Intracellular, Reductive Activation of Anticancer Pt^IV Prodrugs

Radiosynthesis of an ¹⁸F‐fluoroglycosylated aminoferrocene for in‐vivo imaging of reactive oxygen species activity by PET

[Fp*Fc][PF6]: A remarkable non-symmetric dinuclear cation in a very stable mixed-valent state

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The anomalous electrochemistry of the ferrocenylamines

Cited by 69 publications

References 0 publications

Cancer‐Specific, Intracellular, Reductive Activation of Anticancer PtIV Prodrugs

Cancer‐Specific, Intracellular, Reductive Activation of Anticancer PtIV Prodrugs

Radiosynthesis of an 18F‐fluoroglycosylated aminoferrocene for in‐vivo imaging of reactive oxygen species activity by PET

[Fp*Fc][PF6]: A remarkable non-symmetric dinuclear cation in a very stable mixed-valent state

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Product

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Cancer‐Specific, Intracellular, Reductive Activation of Anticancer Pt^IV Prodrugs

Cancer‐Specific, Intracellular, Reductive Activation of Anticancer Pt^IV Prodrugs

Radiosynthesis of an ¹⁸F‐fluoroglycosylated aminoferrocene for in‐vivo imaging of reactive oxygen species activity by PET