Synthesis of a psilocin hapten and a protein-hapten conjugate
Christian Albers, Matthias Lehr, Justus Beike, Helga Köhler, Bernd Brinkmann
Journal of Pharmacy and Pharmacology September 1, 2002 DOI: 10.1211/002235702320402116 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Synthesis and characterization study Peer reviewed |
|---|---|
| Topics | Psilocybin |
| Keywords | Hapten Conjugate Indole test Moiety Mass spectrometry Bovine serum albumin Alkyl Stereochemistry Chromatography Derivative finance |
| Citations | 7 |
| Key points | The 3-carboxypropyl psilocin derivative was stable and could be conjugated to BSA with an average incorporation ratio of 4–5 hapten molecules per protein molecule. |
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.