Synthesis and characterization of 2-mercaptoethanesulfonic acid albumin.
Autoimmune patients treated with ifosfamide (CAS 3778-73-2) and mesna (2-mercaptoethanesulfonic acid, CAS 3375-50-6) in some cases suffered from severe allergic reactions that were proposed to be due to mesna linked to serum albumin by a disulfide bond. To prove the existence of the hypothetic mesna albumin adduct in vivo it was synthesized: The free thiol group of albumin (molecular mass determined by MALDI spectroscopy: 67009 Da) was converted to S-phenylsulfonyl albumin and reacted with mesna to albumin mesna (molecular mass: 67159 Da). In an alternative synthesis albumin was incubated with mesna at pH 8, 40 degrees C (molecular mass of the adduct: 67166 Da).
Universitätsklinikum, Zentrum der Biologischen Chemie, Institut für Biochemie II, Johann Wolfgang Goethe-Universität, Frankfurt/Main, Germany.
H H
HH
Bauer
S
S
Ehmig
J W
JW
Engels
G
G
Voelcker
D000418:Albumins / Q000737:chemistry*; D002846:Chromatography, Affinity; D006801:Humans; D006863:Hydrogen-Ion Concentration; D015080:Mesna / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D008970:Molecular Weight; D012709:Serum Albumin / Q000138:chemical synthesis / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
C114241:2-mercaptoethanesulfonic acid albumin; D000418:Albumins; D012709:Serum Albumin; D015080:Mesna