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  2. A synthetic trivalent hapten that aggregates anti-2,4-DNP IgG into bicyclic trimers

A synthetic trivalent hapten that aggregates anti-2,4-DNP IgG into bicyclic trimers

  • J Am Chem Soc. 2007 Mar 28;129(12):3722-8. doi: 10.1021/ja067159h.
Basar Bilgiçer 1 Demetri T Moustakas George M Whitesides
Affiliations

Affiliation

  • 1 Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Abstract

This paper describes the synthesis of the trivalent Hapten molecule 1, containing three 2,4-dinitrophenyl (2,4-DNP) groups, and the use of this molecule to aggregate three molecules of anti-2,4-DNP IgG into a complex with 3:2 stoichiometry (IgG312). The equilibrium product IgG312 was generated in approximately 90% yield upon mixing IgG and 1; during incubation, thermodynamically unstable, high-molecular-weight aggregates (>104 nm in diameter) form first and convert subsequently to IgG312. The thermodynamics and the kinetics of the formation of aggregates were studied using size-exclusion high-performance liquid chromatography (SE-HPLC), dynamic LIGHT scattering (DLS), and analytical ultracentrifugation (AUC). An analytical model based on multiple species in equilibrium was developed and used to interpret the SE-HPLC data. The aggregate IgG312 was more stable thermodynamically and kinetically than monomeric aggregates of this IgG with monomeric derivatives of 2,4-DNP; this stability suggests potential applications of these aggregates in biotechnology.

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