Applications of Tailored Ferrocenyl Molecules as Electrochemical Probes of Biochemical Interactions

Tranchant, Isabelle; Hervé, Anne-Cécile; Carlisle, Stephen; Lowe, Phillip T.; Slevin, Christopher J.; Forssten, Camilla; Dilleen, John W.; Tabor, Alethea B.; Williams, David E.; Hailes, Helen C.

doi:10.1021/bc060039e

Cited by 6 publications

(2 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, we have identified that, to enable electrochemical measurements to be made in protein solutions, plasma, and blood, an amide at linker A, carbamate at linker B, short PEG unit, and fatty acid moiety are required for use in biomolecular binding studies, to mimic fatty acid binding. Applications of the model compound 17 and analogues as an electrochemical probe of biochemical interaction will be described in a future paper (30).…”

Section: Discussionmentioning

confidence: 99%

Design and Synthesis Of Ferrocene Probe Molecules for Detection by Electrochemical Methods

et al. 2006

Self Cite

View full text Add to dashboard Cite

A series of ferrocenyl conjugates to fatty acids have been designed and synthesized to establish the key properties required for use in biomolecular binding studies. Amperometric detection of the ferrocene conjugates was sought in the region of 0.3 V (vs Ag/AgCl) for use in protein/blood solutions. Different linkers and solubilizing moieties were incorporated to produce a conjugate with optimal electrochemical properties. In electrochemical studies, the linker directly attached to the ferrocene was found to affect significantly the E(1/2) value and the stability of the ferrocenium cation. Ester-linked ferrocene conjugates had E(1/2) ranging from +400 to +410 mV, while amide-linked compounds ranged from +350 to +370 mV and the amines +260 to +270 mV. Folding of long-chain substituents around the ferrocene, also significantly affected by the choice of linker, was inferred as a secondary effect that increased E(1/2). The stability of the ferrocenium cation decreased systematically as E(1/2) increased. Disubstituted ferrocene ester and amide conjugates, with oxidation potentials of +640 and +570 mV, respectively, showed only a barely discernible reduction wave in cyclic voltammetry at 50 mV/s. Electrochemical measurements identified two lead compounds with the common structural characteristics of an amide and carbamate linker (compounds 17 and 21) with a C(11) fatty acid chain attached. It is envisaged that such molecules can be used to mimic and study the biomolecular binding interaction between fatty acids and molecules such as human serum albumin.

show abstract

Section: Discussionmentioning

confidence: 99%

Design and Synthesis Of Ferrocene Probe Molecules for Detection by Electrochemical Methods

et al. 2006

Self Cite

View full text Add to dashboard Cite

show abstract

“…Research on improving the electron transfer has been focused on the mediators and conductive polymers, where Ferrocene derivatives and Prussian blue have been used as mediators [1][2][3][4][5][6]. Similar conducting polymers such as polypyrrole, polyoxane, poly(ethylene oxide), and poly(toluidine blue O) are also used as mediating conductive polymers [3,[7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Development of glucose sensor using two-photon adsorbed photopolymerization

Kim

Park

Lee

et al. 2009

Bioprocess Biosyst Eng

View full text Add to dashboard Cite

A novel glucose sensor was constructed, and its analytical potential examined. A chip-type three-electrode system for use in a flow-type electrochemical glucose sensor was fabricated using a UV lithography technique on a glass slide. An Ag/AgCl reference electrode was made by electroplating silver onto a Pt electrode and dipping in a saturated KCl solution for 30 min. In addition, a glucose-sensing electrode was fabricated using a two-photon adsorbed photopolymerization technique with a photo-reactive resin containing a glucose oxidase enzyme, ferrocene mediator, non-ionic surfactant, and carbon nanotubes. The cyclic voltammetry of the potassium ferrocyanide in the Pt sensor system showed a stable electrode condition. The response of the modified Pt sensor confirms the feasibility of using a two-photon adsorbed photopolymerization technique for the easy fabrication of functional biosensors.

show abstract

Stereoselective Synthesis and Biological Evaluation of Ferrocene‐Containing 5‐Hydroxyeicosatetraenoic Acid Analogues

et al. 2011

View full text Add to dashboard Cite

The stereoselective synthesis of a set of four stable 5-hydroxyeicosatetraenoic acid (HETE) analogues with a ferrocene backbone is described. The common substructure of all HETEs, the (2E,4Z)-1-hydroxyhexadiene moiety, was formally replaced by a ferrocenylmethanol fragment. Whereas the hydrophilic side chain remained the same as that of 5-HETE (butyrate), the lipophilic side chain was simplified by replacing the "natural" (Z,Z)-1,4-decadiene side chain with (Z)-1-heptene, 1-heptyne, 1-octyne, or phenylacetylene. As a key building block, Kagan's chiral acetal (derived from ferrocenecarbaldehyde) was used for the stereoselective generation of the planar-chiral substructure through diastereoselective ortho-lithiation and subsequent formylation, methoxycarbonylation or iodination, respectively. The lipophilic side chain was installed either by a "salt-free" Wittig reaction or (better) by Pd-catalyzed Sonogashira coupling. The

show abstract

Applications of Tailored Ferrocenyl Molecules as Electrochemical Probes of Biochemical Interactions

Cited by 6 publications

References 25 publications

Design and Synthesis Of Ferrocene Probe Molecules for Detection by Electrochemical Methods

Design and Synthesis Of Ferrocene Probe Molecules for Detection by Electrochemical Methods

Development of glucose sensor using two-photon adsorbed photopolymerization

Stereoselective Synthesis and Biological Evaluation of Ferrocene‐Containing 5‐Hydroxyeicosatetraenoic Acid Analogues

Contact Info

Product

Resources

About