Synthesis of a psilocin hapten and a protein-hapten conjugate

Derivatives of psilocin with functionalized alkyl spacers at the indole nitrogen were synthesized as haptens for a radioimmunoassay. The 3-aminopropyl and 4-aminobutyl analogues decomposed during synthesis, but the 3-carboxypropyl derivative was stable. This compound was coupled to bovine serum albumin (BSA) via N-hydroxysuccinimide ester-mediated conjugation. Mass spectrometry showed an average incorporation of 4–5 psilocin hapten molecules per BSA molecule, characterizing the protein–hapten conjugate.

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Abstract

Abstract Derivatives of psilocin with ω-functionalized alkyl spacers in position 1 of the indole ring were synthesized as haptens for use in a radioimmunoassay. Whereas the psilocin analogues with a 3-aminopropyl and a 4-aminobutyl moiety at the indole nitrogen decomposed during synthesis, the analogous 3-carboxypropyl psilocin derivative proved to be stable. This compound was coupled to bovine serum albumin (BSA) using the N-hydroxysuccinimide ester-mediated conjugation. The protein–hapten conjugate was characterized by matrix-assisted laser desorption ionization mass spectrometry. The mass spectrometry data indicated an average incorporation ratio of 4–5 molecules of psilocin hapten per molecule of BSA.