Identification of the sites of deoxyhaemoglobin PEGylation

Biochemical Journal

Volumn 403, Issue 1, 2007, Pages 189-196

  Iafelice, Roberto ^a   Cristoni, Simone ^b   Caccia, Dario ^a   Russo, Rosaria ^a   Rossi Bernardi, Luigi ^a   Lowe, Kenneth C ^c   Perrella, Michele ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b Ion Source and Biotechnologies   (Italy)

^c UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Blood substitute; Haemoglobin (Hb) based oxygen carrier; N ethylmaleimide (NEM); Protein mass spectroscopy (protein MS); Protein poly(ethylene glycol)ation (protein PEGylation); Protein thiolation

Indexed keywords

BLOOD SUBSTITUTES; MASS SPECTROMETERS; NITROGEN COMPOUNDS; POLYETHYLENE GLYCOLS; REACTION KINETICS;

ENZYMATIC DIGESTION; HAEMOGLOBIN (HB)-BASED OXYGEN CARRIERS; N-ETHYLMALEIMIDE (NEM); PROTEIN MASS SPECTROSCOPY (PROTEIN MS); PROTEIN POLY(ETHYLENE GLYCOL)ATION (PROTEIN PEGYLATION); PROTEIN THIOLATION;

HEMOGLOBIN;

CYSTEINE; DEOXYHEMOGLOBIN; LYSINE; MACROGOL; N ETHYLMALEIMIDE; PEPSIN A; PHYTIC ACID; TRYPSIN;

ALPHA CHAIN; ARTICLE; AUTOOXIDATION; BETA CHAIN; CHEMICAL REACTION; COMPLEX FORMATION; CONJUGATION; MASS SPECTROMETRY; OXYGEN AFFINITY; PRIORITY JOURNAL;

AMINO ACID SEQUENCE; BINDING SITES; HEMOGLOBIN A; HEMOGLOBINS; HUMANS; KINETICS; LYSINE; OXYGEN; POLYETHYLENE GLYCOLS; SPECTROPHOTOMETRY; SULFHYDRYL COMPOUNDS;

EID: 34147137846     PISSN: 02646021     EISSN: None     Source Type: Journal    
DOI: 10.1042/BJ20061556     Document Type: Article

References (24)

1. Working, P. K., Newman, M. S., Johnson, J. and Cornacoff, J. B. (1997) Safety of polyethylene glycol) and polyethylene glycol) derivatives. In Poly(ethylene glycol) Chemistry and Biological Applications (Harris, J. M. and Zalipsky, S., eds.), pp. 45-57, ACS Books, Washington, DC
2. Veronese, F. M. (2001) Peptide and protein PEGylation: a review of problems and solutions. Biomaterials 22, 405-417
3. Roberts, M. J., Bentley, M. D. and Harris, J. M. (2002) Chemistry for peptide and protein PEGylation. Adv. Drug Deliv. Rev. 54, 459-476
4. Jue, R., Lambert, J. M., Pierce, L. R. and Traut, R. R. (1978) Addition of sulfhydryl groups to Escherichia coli ribosomes by protein modification with 2-iminothiolane. Biochemistry 17, 5399-5406
5. Duncan, R. (2003) The dawning era of polymer therapeutics. Nat. Rev. Drug Discov. 2, 347-360
6. Acharia, A. S, Manjula, B. N. and Smith, P. K. (1996) Haemoglobin crosslinkers, U.S. Pat. 5,585,484
7. Vandegriff, K. D., Malavalli, A., Wooldrige, J., Lohman, J. and Winslow, R. M. (2003) MP4, a new nonvasoactive PEG-Hb conjugate. Transfusion 43, 509-516
8. 2 and 2,3-diphosphoglycerate. Br. Med. Bull. 32, 209-212
9. Walder, J. A., Zaugg, R. H., Walder, R. Y., Steele, J. M. and Klotz, I. M. (1979) Diaspirins that cross-link beta chains of haemoglobin: bis(3,5-dibromosalicyl) succinate and bis(3,5-dibromosalicyl) fumarate. Biochemistry 18, 4265-4270
10. Bonaventura, J., Bonaventura, C., Sullivan, B., Ferruzzi, G., McCurdy, P. R., Fox, J. and Moo-Penn, W. F. (1976) Haemoglobin providence. J. Biol. Chem. 251, 7563-7571
11. Dickerson, R. E. and Geis, I. (1983) Haemoglobin: Structure, Function, Evolution and Pathology, The Benjamin/Cummings Publishing Company, Manlo Park, CA
12. Baldwin, J. M. (1975) Structure and function of haemoglobin. Prog. Biophys. Mol. Biol. 29, 225-320
13. Tsai, A. G., Cebrales, P., Winslow, R. M. and Intaglietta, M. (2003) Microvascular oxygen distribution in awake hamster window chamber model during hyperoxia. Am. J. Physiol. Heart Circ. Physiol. 285, H1537-H1545
14. Winslow, R. M. (2004) Oxygen transport agents: a new approach to red blood cell alternatives. Altern. Transfus. Med. 5, 498-506
15. Buehler, P. W., Boykins, R. A., Jia, Y., Norris, S., Freedberg, D. E. and Alayash, A. I. (2005) Structural and functional characterization of glutaraldehyde-polymerized bovine haemoglobin and its isolated fractions. Anal. Chem. 77, 3466-3478
16. Arnone, A. (1972) X-ray diffraction study of binding of 2,3-diphosphoglycerate to human deoxyhaemoglobin. Nature 237, 146-149
17. 2 binding to human haemoglobin. FEBS Lett. 78, 287-290
18. Russo, R., Benazzi, L. and Perrella, M. (2001) The Bohr effect of haemoglobin intermediates and the role of salt bridges in the tertiary/quaternary transitions. J. Biol. Chem. 276, 13628-13634
19. Singh, R., Kats, L., Blattler, W. A. and Lambert, J. M. (1996) Formation of N-substituted 2-iminothiolanes when amino groups in proteins and peptides are modified by 2-iminothiolane. Anal. Biochem. 236, 114-125
20. Ampulsky, R. S., Ayers, V. E. and Morell, S. A. (1969) Determination of the reactive sulfhydryl groups in heme proteins with 4,4′- dipyridinedisulfide. Anal. Biochem. 32, 163-169
21. Porollo, A., Adamczak, R. and Meller, J. (2004) POLYVIEW: a flexible visualization tool for structural and functional annotations of proteins. Bioinformatics 20, 2460-2462
22. Waller, D. A. and Liddington, R. C. (1990) Refinement of a partially oxygenated T state human haemoglobin at 1.5 A resolution. Acta Crystallogr. Sect. B Struct. Sci. 46, 409-418
23. Richard, V., Dodson, G. G. and Mauguen, Y. (1993) Human deoxyhaemoglobin-2,3-diphosphoglycerate complex low-salt structure at 2.5 Å resolution. J. Mol. Biol. 233, 270-274
24. Perutz, M. F. (1970) Stereochemistry of cooperative effects in haemoglobin. Nature 228, 726-739