Modulation of antibody pharmacokinetics by chemical polysialylation

Bioconjugate Chemistry

Volumn 19, Issue 3, 2008, Pages 643-650

  Constantinou, Antony ^a,c   Epenetos, Agamemnon A ^a   Hreczuk Hirst, Dale ^b,d   Jain, Sanjay ^b   Deonarain, Mahendra P ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b Lipoxen Plc   (United Kingdom)

^c JOHN WAYNE CANCER INSTITUTE   (United States)

^d Glycoform Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; BIOCHEMISTRY; BLOOD; CHAINS; MOLECULES; MONOCLONAL ANTIBODIES; PHARMACOKINETICS; PHOSPHATASES; TUMORS;

BLOOD CIRCULATION; CHEMICAL COUPLING; FAB' FRAGMENT; IMMUNOGENICITY; IN-VIVO; PHARMACOKINETICS AND PHARMACODYNAMICS; POLYSIALIC ACID; POLYSIALYLATION; THERAPEUTIC PROTEIN; TUMOR UPTAKE;

POLYETHYLENE GLYCOLS;

ALKALINE PHOSPHATASE PLACENTA ISOENZYME; ANTIBODY CONJUGATE; IMMUNOGLOBULIN F(AB) FRAGMENT; MACROGOL; MONOCLONAL ANTIBODY; MONOCLONAL ANTIBODY H17E2; POLYMER; POLYSIALIC ACID; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIGEN BINDING; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG CONJUGATION; ELECTROPHORETIC MOBILITY; FEMALE; GERM CELL TUMOR; IMMUNOREACTIVITY; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; SIALYLATION; TUMOR XENOGRAFT;

EID: 41149176451     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc700319r     Document Type: Article

References (36)

1. Hamidi, M., Azadi, A., and Rafiei, P. (2006) Pharmacokinetic consequences of pegylation. Drug Delivery 13, 399-409.
2. Mehvar, R. (2000) Dextrans for targeted and sustained delivery of therapeutic and imaging agents. J. Controlled Release 69, 1-25.
3. Cantin, A. M., Woods, D. E., Cloutier, D., Dufour, D. E., and Leduc, R. (2002) Polyethylene glycol conjugation at Cys232 prolongs the half-life of alphal proteinase inhibitor. Am. J. Respir. Cell Mol. Biol. 27, 659-65.
4. Conover, C. D., Gilbert, C. W., Shum, K. L., and Shorr, R. G. (1997) The impact of polyethylene glycol conjugation on bovine hemoglobin's circulatory half-life and renal effects in a rabbit toploaded transfusion model. Artif. Organs 21, 907-15.
5. Hawkins, D. S., Park, J. R., Thomson, B. G., Felgenhauer, J. L., Holcenberg, J. S., Panosyan, E. H., and Avramis, V. I. (2004) Asparaginase pharmacokinetics after intensive polyethylene glycolconjugated L-asparaginase therapy for children with relapsed acute lymphoblastic leukemia. Clin. Cancer Res. 10, 5335-41.
6. Grace, M. J., Cutler, D. L., and Bordens, R. W. (2006) Pegylated IFNs for chronic hepatitis C: an update. Exp. Opin. Drug Delivery 2, 219-26.
7. Ng, E. W., Shima, D. T., Calias, P., Cunningham, E. T., Jr., Guyer, D. R., and Adamis, A. P. (2006) Pegaptanib, a targeted anti-VEGF aptamer for ocular vascular disease. Nat. Rev. Drug Discovery 5, 123-32.
8. Beranova, M., Wasserbauer, R., Vancurova, D., Stifter, M., Ocenaskova, J., and Mara, M. (1990) Effect of cytochrome P-450 inhibition and stimulation on intensity of polyethylene degradation in microsomal fraction of mouse and rat livers. Biomaterials 11, 521-4.
9. Caliceti, P., Schiavon, O., and Veronese, F. M. (1999) Biopharmaceutical properties of uricase conjugated to neutral and amphiphilic polymers. Bioconjugate Chem. 10, 638-46.
10. Cheng, T. L., Wu, P. Y., Wu, M. F., Chern, J. W., and Roffler, S. R. (1999) Accelerated clearance of polyethylene glycol-modified proteins by anti-polyethylene glycol IgM. Bioconjugate Chem. 10, 520-8.
11. Sroda, K., Rydlewski, J., Langner, M., Kozubek, A., Grzybek, M., and Sikorski, A. F. (2005) Repeated injections of PEG-PE liposomes generate anti-PEG antibodies. Cell Mol. Biol. Lett. 10, 37-47.
12. Gregoriadis, G., Jain, S., Papaioannou, I., and Laing, P. (2005) Improving the therapeutic efficacy of peptides and proteins; a role for polysialic acids. Int. J. Pharm. 300, 125-30.
13. Muhlenhoff, M., Eckhardt, M., and Gerardy-Schahn, R. (1998) Polysialic acid: three-dimensional structure, biosynthesis and function. Curr. Opin. Struct. Biol. 8, 558-64.
14. Gregoriadis, G., McCormack, B., Wang, Z., and Lifely, R. (1993) Polysialic acids: potential in drug delivery. FEBS Lett. 315, 271-6.
15. Gregoriadis, G., Fernandes, A., Mital, M., and McCormack, B. (2000) Polysialic acids: potential in improving the stability and pharmacokinetics of proteins and other therapeutics. Cell. Mol. Life Sci. 57, 1964-9.
16. Fernandes, A., and Gregoriadis, G. (1997) Polysialylated asparaginase: preparation, activity and pharmacokinetics. Biochem. Biophys. Acta 1341, 26-34.
17. Jain, S., Hreczuk-Hirst, D. H., McCormack, B., Mital, M., Epenetos, A. E., Laing, P., and Gregoriadis, G. (2003) Polysialylated insulin: synthesis, characterization and biological activity in vivo. Biochem. Biophys. Acta 1622, 42-9.
18. Fernandes, A. I., and Gregoriadis, G. (2001) The effect of polysialylation on the immunogenicity and antigenicity of asparaginase: implication in its pharmacokinetics. Int. J. Pharm. 217, 215-24.
19. Crocker, P. R., and Varki, A. (2001) Siglecs, sialic acids and innate immunity. Trends Immunol. 22, 337-42.
20. Stockert, R. J. (1995) The asialoglycoprotein receptor: relationships between structure, function, and expression. Physiol. Rev. 75, 591-609.
21. Siddiqui, M. A., and Scott, L. J. (2005) Infliximab: a review of its use in Crohn's disease and rheumatoid arthritis. Drugs 65, 2179-208.
22. Kramer, I., and Lipp, H. P. (2007) Bevacizumab a humanized anti-angiogenic monoclonal antibody for the treatment of colorectal cancer. J. Clin. Pharm. Ther. 32, 1-14.
23. Cefalu, W. T. (2004) Evolving strategies for insulin delivery and therapy. Drugs 64, 1149-61.
24. Sharples, E. J., Thiemermann, C., and Yaqoob, M. M. (2006) Novel applications of recombinant erythropoietin. Curr. Opin. Pharmacol. 6, 184-9.
25. Travers, P., and Bodmer, W. F. (1984) Preparation and characterization of monoclonal antibodies against placental alkaline phosphatase and other human trophoblast-associated determinants. Int. J. Cancer 33, 633-41.
26. Epenetos, A. A., Travers, P., Gatter, K. C., Oliver, R. D., Mason, D. Y., and Bodmer, W. F. (1984) An immunohistological study of testicular germ cell tumours using two different monoclonal antibodies against placental alkaline phosphatase. Br. J. Cancer 49, 11-5.
27. Svennerholm, L. (1957) Quantitative estimation of sialic acids. II. A colorimetric resorcinol hydrochloric acid method. Biochem. Biophys. Acta 24, 604-11.
28. Deonarain, M. P., Rowlinson-Busza, G., George, A. J., and Epenetos, A. A. (1997) Redesigned anti-human placental alkaline phosphatase single-chain Fv: soluble expression, characterization and in vivo tumour targeting. Protein Eng. 10, 89-98.
29. Yang, K., Basu, A., Wang, M., Chintala, R., Hsieh, M. C., Liu, S., Hua, J., Zhang, Z., Zhou, J., Li, M., Phyu, H., Petti, G., Mendez, M., Janjua, H., Peng, P., Longley, C., Borowski, V., Mehlig, M., and Filpula, D. (2003) Tailoring structure-function and pharmacokinetic properties of single-chain Fv proteins by site-specific PEGylation. Protein Eng. 16, 761-70.
30. Natarajan, A., Xiong, C. Y., Albrecht, H., DeNardo, G. L., and DeNardo, S. J. (2005) Characterization of sitespecific ScFv PEGylation for tumor-targeting pharmaceuticals. Bioconjugate Chem. 16, 113-21.
31. Knauf, M. J., Bell, D. P., Hirtzer, P., Luo, Z. P., Young, J. D., and Katre, N. V. (1988) Relationship of effective molecular size to systemic clearance in rats of recombinant interleukin-2 chemically modified with water-soluble polymers. J. Biol. Chem. 263, 15064-70.
32. Adams, G. P., Schier, R., McCall, A. M., Simmons, H. H., Horak, E. M., Alpaugh, R. K., Marks, J. D., and Weiner, L. M. (2001) High affinity restricts the localization and tumor penetration of single-chain Fv antibody molecules. Cancer Res. 61, 4750-5.
33. Adams, G. P., Shaller, C. C., Chappell, L. L., Wu, C., Horak, E. M., Simmons, H. H., Litwin, S., Marks, J. D., Weiner, L. M., and Brechbiel, M. W. (2000) Delivery of the alpha-emitting radioisotope bismuth-213 to solid tumors via single-chain Fv and diabody molecules. Nucl. Med. Biol. 27, 339-46.
34. Kaushik, V. V., and Moots, R. J. (2005) CDP-870 (certolizumab) in rheumatoid arthritis. Exp. Opin. Biol. Ther. 5, 601-6.
35. Nakaoka, R., Tabata, Y., Yamaoka, T., and Ikada, Y. (1997) Prolongation of the serum half-life of superoxide dismutase by poly, (ethylene) glycol) modification. J. Controlled Release 46, 253-261.
36. Dhalluin, C., Ross, A., Leuthold, L. A., Foser, S., Gsell, B., Muller, F., and Senn, H. (2005) Structural and biophysical characterization of the 40 kDa PEG-interferon-alpha 2a and its individual positional isomers. Bioconjugate Chem. 16, 504-17.