Structural determination of the conjugate of human serum albumin with a mitomycin C derivative, KW-2149, by matrix-assisted laser desorption/ionization mass spectrometry

Bioconjugate Chemistry
T Yasuzawa, K B Tomer

Abstract

A new mitomycin C derivative, KW-2149, is known to form a covalent conjugate with human serum albumin (HSA). This conjugate exhibits 1/20 of the anticellular activity of unconjugated KW-2149. Structural studies of this conjugate were carried out using a combination of enzymatic digestion, high-performance liquid chromatography (HPLC), and matrix-assisted laser desorption/ionization (MALDI) mass spectrometry. The tryptic peptide T5 (residues 21-41) was the only peptide found to be modified by KW-2149 moieties, the [(gamma-L-glutamylamino)ethyl]thio group or the (2-aminoethyl)thio group, through a disulfide bond. Although the latter peptide lost its mitomycin C moiety in the course of tryptic digestion, these data strongly suggest that KW-2149 was bound to Cys-34, the only free cysteine on HSA.

Citations

Feb 3, 2009·Chemical & Pharmaceutical Bulletin·Sang Hyup Lee, Harold Kohn
Feb 24, 2007·Toxicology in Vitro : an International Journal Published in Association with BIBRA·Maja AleksicAnne Dell
Jul 17, 2007·Chemical Research in Toxicology·Itai ChipindaPaul D Siegel
Apr 24, 2009·Archives of Pharmacal Research·Sang Hyup Lee
Apr 25, 2002·Journal of the American Chemical Society·Younghwa NaHarold Kohn
Apr 1, 2004·Journal of the American Chemical Society·Sang Hyup Lee, Harold Kohn

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