Direct determination of naturally occurring biologically active compound–serum albumin conjugate by matrix‐assisted laser desorption/ionization mass spectrometry

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<jats:p>Opium alkaloids were conjugated with bovine serum albumin (BSA) to give individual antigen conjugates which were analyzed using BSA as an internal standard by matrix‐assisted laser desorption/ionization (MALDI) mass spectrometry. It became clear that 9 molecules of thebaine were conjugated in a thebaine–BSA conjugate. Codeine and morphine contents in individual conjugates were determined to be 12 and 6 molecules, respectively. Using a relative molecular mass of BSA, 11.5 molecules of forskolin conjugated with BSA. Tetrahydrocannabinolic acid (THCA)–carrier protein conjugates using <jats:italic>β</jats:italic>‐alanine or without <jats:italic>β</jats:italic>‐alanine as a linker were analyzed. From these results it became evident that the hapten molecules of THCA–<jats:italic>β</jats:italic>‐alanine–BSA, THCA–BSA, THCA–<jats:italic>β</jats:italic>‐alanine–human serum albumin (HSA) and THCA–HSA were 17.2, 12.7, 27.8 and 54.4, respectively. Crocin–HSA conjugates were synthesized by two methods using succinate and NaIO<jats:sub>4</jats:sub> cleavage of sugar moiety. A broad molecular peak of crocin–HSA conjugate appeared at around <jats:italic>m/z</jats:italic> 98,342 resulting in 30 molecules of crocin‐hemisuccinate conjugated with HSA. The crocin–HSA synthesized via NaIO<jats:sub>4</jats:sub> oxidation showed a sharp molecular peak around 69,504 compared to that of hemisuccinate preparation. The number of crocin combined with HSA was, however, smaller 3.1 molecules.</jats:p><jats:p>Analysis of monoclonal antibody by MALDI mass spectrometry determined the exact molecular weight and their purities.</jats:p>

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