Direct ring conjugation of catecholamines and their immunological interactions

John S. Mitchell, Yinqiu Wu, Christian J. Cook, Lyndsay Main

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6 Citations (Scopus)

Abstract

Catecholamine derivatives were synthesized with potential applications as coating antigens in biosensors or in the raising of specific antibodies. Thioether-bridged derivatives of the catecholamines dopamine, norepinephrine, and epinephrine that attach carboxylic acid functionalities directly to the aromatic ring via an easily incremented linker chain were synthesized by an electrochemical method. These derivatives were purified by convenient ion-exchange chromatography, exact positions of conjugation determined by NMR, and a dopamine derivative immobilized in situ in a BIAcore surface plasmon resonance (SPR) biosensor and its antibody binding studied in comparison with immobilization via the catecholamine primary amine. Binding of an antibody raised to an amine-conjugated protein conjugate showed clear distinction between conjugations at different positions on the catecholamine, illustrating the importance of rational conjugate design in immunosensing of the catecholamines.

Original languageEnglish
Pages (from-to)268-274
Number of pages7
JournalBioconjugate Chemistry
Volume18
Issue number1
DOIs
Publication statusPublished - Jan 2007
Externally publishedYes

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