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

Volumn 8, Issue 3, 1997, Pages 391-399

  Yasuzawa, Tohru ^a   Tomer, Kenneth B ^a  

^a NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BODY FLUIDS; COVALENT BONDS; DESORPTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; SULFUR COMPOUNDS;

DISULPHIDE BONDS; ENZYMATIC DIGESTIONS; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN SERUM ALBUMINS; LIQUID MATRIX; MATRIX-ASSISTED LASER DESORPTION IONIZATION MASS SPECTROMETRY; MITOMYCIN C; STRUCTURAL DETERMINATION; STRUCTURAL STUDIES; TRYPTIC PEPTIDES;

PEPTIDES;

EID: 0031148757     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc970038+     Document Type: Article

References (35)

1. Bjornsson, T. D., Meffin, P. J., Swezey, S., and Blaschke, T. F. (1979) Clofibrate Displaces Warfarin from Plasma Protein in Man: An Example of a Pure Displacement Interaction. J. Pharmacol. Exp. Ther. 20, 316-321
2. Carter, D. C., and Ho, J. X. (1994) Structure of Serum Albumin. Adv. Protein Chem. 45, 153-203.
3. Takahashi, N., Takahashi, Y., Blumberg, B. S., and Putnam, F. W. (1987) Amino Acid Substitutions in Genetic Variants of Human Serum Albumin and in Sequences Inferred from Molecular Cloning. Proc. Natl. Acad. Sci. U.S.A. 84, 4413-4417.
4. He, X. M., and Carter, D. C. (1992) Atomic Structure and Chemistry of Human Serum Albumin. Nature 358, 209-215.
5. Sudlow, G., Birkett, D. J., and Wade, D. N. (1975) The Characterization of Two Specific Drug Binding Sites on Human Serum Albumin. Mol. Pharmacol. 11, 824-832.
6. Sudlow, G., Birkett, D. J., and Wade, D. N. (1976) Further Characterization of Specific Drug Binding Sites on Human Serum Albumin. Mol. Pharmacol. 12, 1052-1061.
7. Sjoholm, I., Ekman, B., Kober, A., Ljungstedt-Pahlman, I., Seiving, B., and Sjodin, T. (1979) Binding of Drugs to Human Serum Albumin: XI. The Specificity of Three Binding Sites as Studied with Albumin Immobilized in Microparticles. Mol. Pharmacol. 16, 767-777.
8. Fehske, K. J., Schlafer, U., Wollert, U., and Muller, W. E. (1982) Characterization of an Important Drug Binding Area on Human Serum Albumin Including the High-Affinity Binding Sites of Warfarin and Azapropazone. Mol. Pharmacol. 21, 387-393.
9. Yamasaki, K., Miyoshi, T., Maruyama, T., Takadate, A., and Otagiri, M. (1994) Characterization of Region Ic in Site I on Human Serum Albumin. Microenvironmental Analysis Using Fluorescence Spectroscopy. Biol. Pharm. Bull. 17, 1656-1622.
10. Rocha, J., Bohner, J., and Kompf, J. (1995) Transient Bisalbuminemia: Separation by Isoelectric Focusing of Human Albumin Fractions Linked to Different Numbers of Benzylpenicilloyl Groups. Electrophoresis 16, 1031-1033.
11. Dickinson, R. G., Baker, P. V., and King, A. R. (1994) Studies on The Reactivity of Acyl Glucuronides VII. Salicyl Acyl Glucuronide Reactivity In Vitro and Covalent Binding of Salicylic Acid to Plasma Protein of Humans Taking Aspirin. Biochem. Pharmacol. 47, 469-476.
12. Grubb, N., Weil, A., and Caldwell, J. (1993) Studies on the In Vitro Reactivity of Clofibryl and Fenofibryl Glucuronides. Evidence for Protein Binding via a Schiff's Base Mechanism. Biochem. Pharmacol. 46, 357-364.
13. Bohney, J. P., Fonda, M. L., and Feldhoff, R. C. (1992) Identification of Lys190 as the Primary Binding Site for Pyridoxal 5′-Phosphate in Human Serum Albumin. FEBS Lett. 298, 266-268.
14. Wells, D. S., Janssen, F. W., and Ruelius, H. W. (1987) Interactions Between Oxaprozin Glucronide and Human Serum Albumin. Xenobiotica 17, 1437-1449.
15. Tsuchiya, S., Sakurai, T., and Sekiguchi, S. (1984) Nonenzymatic Glucosylation of Human Serum Albumin and Its Influence on Binding Capacity of Sulfonylureas. Biochem. Pharmacol. 33, 2967-2971.
16. Kono, M., Saitoh, Y., Kasai, M., Sato, A., Shirahata, K., Morimoto, M., and Ashizawa, T. (1989) Synthesis and Antitumor Activity of a Novel Water Soluble Mitomycin Analog; 7-N-[2-[[2-(γ-L-glutamylamino)ethyl]dithio]ethyl]mitomycin C. Chem. Pharm. Bull. 37, 1128-1130.
17. Morimoto, M., Ashizawa, T., Ohno, H., Azuma, M., Kobayashi, E., Okabe, M., Gomi, K., Kono, M., Saito, Y., Kanda, Y., Arai, H., Sato, A., Kasai, M., and Tsuruo, T. (1991) Antitumor Activity of 7-N-[2-[[2-(γ-L-glutamylamino)ethyl]dithio]ethyl]mitomycin C (KW-2149), Against Murine and Human Tumors and a Mitomycin C-resistant Tumor in Vitro and In Vivo. Cancer Res. 51, 110-115.
18. Kobayashi, S., Ushiki, J., Takai, K., Okumura, S., Kono, M., Kasai, M., Gomi, K., Morimoto, M., Ueno, H., and Hirata, H. (1993) Disposition and Metabolism of KW-2149, a Novel Anticancer Agent. Cancer Chemother. Pharmacol. 32, 143-150.
19. Ashizawa, T., Okabe, M., Gomi, K., and Hirata, T. (1993) Reduced Bone Marrow Toxicity of KW-2149, a Mitomycin C Derivative, in Mice. Anticancer Drugs 4, 181-188.
20. Fujii, N., Arai, H., Saito, H., Kasai, M., and Nakano, H. (1993) Induction of Protein-DNA Complexes in HeLa S3 Cells by KW-2149, a New Derivative of Mitomycin C. Cancer Res. 53, 4466-4468.
21. Lee, J. H., Naito, M., and Tsuruo, T. (1994) Nonenzymatic Reductive Activation of 7-N-[2-[[2-(γ-L-glutamylamino)ethyl]dithio]ethyl]mitomycin C by Thiol Molecules: a Novel Mitomycin C Derivative Effective on Mitomycin C-Resistant Tumor Cells. Cancer Res. 54, 2398-2403.
22. Bligh, H. F., Bartozek, A., Robson, C. N., Hickson, I. D., Kasper, C. B., Beggs, J. D., and Wolf, C. R. (1990) Activation of Mitomycin C by NADPH: Cytochrome P-450 Reductase. Cancer Res. 50, 7789-7792.
23. Siegel, D., Beall, H., Senekowitsch, C., Kasai, M., Arai, H., Gibson, N. W., and Ross, D. (1992) Bioreductive Activation of Mitomycin C by DT-Diaphorase. Biochemistry 31, 7879-7885.
24. Kaufmann, R., Spengler, B., and Lutzenkirchen, F. (1993) Mass Spectrometric Sequencing of Linear Peptides by Production Analysis in a Reflectron Time-of-flight Mass Spectrometer Using Matrix-assisted Laser Desorption Ionization. Rapid Commun. Mass Spectrom. 7, 902-910.
25. Cohen, S. L., and Chait, B. T. (1996) Influence of Matrix Solution Conditions on the MALDI-MS Analysis of Peptides and Proteins. Anal. Chem. 68, 31-37.
26. Ding, A., Ojingwa, J. C., McDonagh, A. F., Burlingame, A. L., and Benet, L. Z. (1993) Evidence for Covalent Binding of Acyl Glucuronides to Serum Albumin via an Imine Mechanism as Revealed by Tandem Mass Spectrometry. Proc. Natl. Acad. Sci. U.S.A. 90, 3797-3801.
27. Finch, J. W., Crouch, R. K., Knapp, D. R., and Schey, K. L. (1993) Mass Spectrometric Identification of Modifications to Human Serum Albumin Treated with Hydrogen Peroxide. Arch. Biochem. Biophys. 305, 595-599.
28. Campagnini, A., Fisichella, S., Foti, S., Saletti, R., and Sardo, L. (1994) Tryptic Peptide Mapping of Sequence 1-298 of Human Serum Albumin by High-Performance Liquid Chromatography and Fast-Atom Bombardment Mass Spectrometry. Rapid Commun. Mass Spectrom. 8, 459-464.
29. Fisichella, S., Foti, S., Maccarrone, G., and Saletti, R. (1995) Tryptic Peptide Mapping of Sequence 299-585 of Human Serum Albumin by High-Performance Liquid Chromatography and Fast Atom Bombardment Mass Spectrometry. J. Chromatogr. A 693, 33-44.
30. Ding, A., Zia-Amirhosseini, P., McDonagh, A. F., Burlingame, A. L., and Benet, L. Z. (1995) Reactivity of Tolmetin Glucuronide with Human Serum Albumin. Identification of Binding Sites and Mechanisms of Reaction by Tandem Mass Spectrometry. Drug Metab. Dispos. 23, 369-376.
31. Zia-Amirhosseini, P., Ding, A., Burlingame, A. L., McDonagh, A. G., and Benet, L. Z. (1995) Synthesis and Mass-Spectrometric Characterization of Human Serum Albumins Modified by Covalent Binding of Two Non-steroidal Anti-inflammatory Drugs: Tometin and Zomepirac. Biochem. J. 311, 431-435.
32. Day, B. W., Skipper, P. L., Zaia, J., Singh, K., and Tannenbaum, S. R. (1994) Enantiospecificity of Covalent Adduct Formation by Benzo[a]pyrene anti-Diol Epoxide with Human Serum Albumin. Chem. Res. Toxicol. 7, 829-835.
33. Clerc, F. F., Monegier, B., Faucher, D., Pourcet, C., Holt, J. C., Tang, S. Y., Van Dorsselaer, A., Becquart, J., and Vuilhorgne, M. (1994) Primary Structure Control of Recombinant Proteins Using High-Performance Liquid Chromatography, Mass Spectrometry and Microsequencing. J. Chromatogr., B: Biomed. Appl. 662, 245-259.
34. Patterson, S. D., and Katta, V. (1994) Prompt Fragmentation of Bisulfide-Linked Peptides during Matrix-Assisted Laser Desorption Ionization Mass Spectrometry. Anal. Chem. 66, 3727-3732.
35. Pedersen, A. O., and Jacobsen, J. (1980) Reactivity of The Thiol Group in Human and Bovine Albumin at pH 3-9, As Measured by Exchange with 2,2′-dithiodipyridine. Eur. J. Biochem. 106, 291-295.