Design and synthesis of ferrocene probe molecules for detection by electrochemical methods

Tranchant, Isabelle, Herve, Anne-Cecile, Carlisle, Stephen, Lowe, Phillip, Slevin, Christopher J., Forssten, Camilla, Dilleen, John, Williams, David E., Tabor, Alethea B. and Hailes, Helen C. (2006) Design and synthesis of ferrocene probe molecules for detection by electrochemical methods. Bioconjugate Chemistry, 17 5: 1256-1264. doi:10.1021/bc060038m

Author Tranchant, Isabelle
Herve, Anne-Cecile
Carlisle, Stephen
Lowe, Phillip
Slevin, Christopher J.
Forssten, Camilla
Dilleen, John
Williams, David E.
Tabor, Alethea B.
Hailes, Helen C.
Title Design and synthesis of ferrocene probe molecules for detection by electrochemical methods
Journal name Bioconjugate Chemistry   Check publisher's open access policy
ISSN 1043-1802
Publication date 2006-01-01
Year available 2006
Sub-type Article (original research)
DOI 10.1021/bc060038m
Open Access Status Not yet assessed
Volume 17
Issue 5
Start page 1256
End page 1264
Total pages 9
Language eng
Subject 1600 Chemistry
1605 Policy and Administration
1308 Clinical Biochemistry
1300 Biochemistry, Genetics and Molecular Biology
1303 Specialist Studies in Education
Abstract 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.
Keyword Biochemical Research Methods
Biochemistry & Molecular Biology
Chemistry, Multidisciplinary
Chemistry, Organic
Biochemistry & Molecular Biology
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
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