Preparation and characterization of albumin conjugates of a truncated peptide YY analogue for half-life extension

Bioconjugate Chemistry

Volumn 24, Issue 12, 2013, Pages 2015-2024

  Ehrlich, George K ^a   Michel, Hanspeter ^a   Truitt, Theresa ^a   Riboulet, William ^a   Pop Damkov, Petar ^a   Goelzer, Petra ^a   Hainzl, Dominik ^a   Qureshi, Farooq ^a   Lueckel, Barbara ^b   Danho, Waleed ^c   Conde Knape, Karin ^a   Konkar, Anish ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b Pharma Partnering   (Switzerland)

^c Metabolism and Pharmacokinetics   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ASSAYS; CARBOXYLATION; ESTERS;

% REDUCTIONS; AMINO-ACIDS; FOOD INTAKE; HALF LIVES; HETEROBIFUNCTIONAL LINKER; HUMAN SERUM ALBUMINS; LIFE EXTENSIONS; N-HYDROXYSUCCINIMIDE; PEGYLATED; SUCCINIMIDYL ESTER;

PEPTIDES;

ALBUMIN CONJUGATE; MALEIMIDE; NEUROPEPTIDE Y2 RECEPTOR; PEPTIDE YY; RECOMBINANT HUMAN SERUM ALBUMIN;

ALLOMETRY; ARTICLE; CIRCULATION; CONJUGATION; CONTROLLED STUDY; DRUG HALF LIFE; FOOD INTAKE; GEL PERMEATION CHROMATOGRAPHY; IN VITRO STUDY; IN VIVO STUDY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR WEIGHT; MOUSE; NONHUMAN; PROTEIN ANALYSIS; QUALITY CONTROL;

MUS;

AMINO ACID SEQUENCE; ANIMALS; BINDING SITES; EATING; HALF-LIFE; HUMANS; MALE; MICE; MICE, INBRED C57BL; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MOLECULAR WEIGHT; PEPTIDE YY; PROTEIN BINDING; PROTEIN CONFORMATION; SERUM ALBUMIN; SUBSTRATE SPECIFICITY;

EID: 84890847055     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc400340z     Document Type: Article

References (27)

1. Addison, M. L., Minnion, J. S., Shillito, J. C., Suzuki, K., Tan, T. M., Field, B. C., Germain-Zito, N., Becker-Pauly, C., Ghatei, M. A., Bloom, S. R., and Murphy, K. G. (2011) A role for metallopeptidases in the breakdown of the gut hormone, PYY3-36 Endocrinology 152, 4630-40
2. Nonaka, N., Shioda, S., Niehoff, M. L., and Banks, W. A. (2003) Characterization of blood-brain barrier permeability to PYY3-36 in the mouse J Pharmacol. Exp. Ther. 306, 948-53
3. 3-36) in rabbits Int. J. Obesity 30, 68-72
4. Cabrele, C. and Beck-Sickinger, A. G. (2000) Molecular characterization of the ligand-receptor interaction of the neuropeptide Y family J. Pept. Sci. 6, 97-122
5. 3-36 has beneficial effects on glucose handling and exhibits islet sparing effects in db/db Mice EASD Abstracts 572
6. Conde-Knape, K., Danho, W., Ehrlich, G. K., Fotouhi, N., Fry, D. C., Khan, W., Konkar, A., Rondinone, C. M., Swistok, J., Taub, R. A., and Tilley, J. W. (2008) Neuropeptide-2 Receptor (Y-2R) Agonists and Uses Thereof. U.S. Patent 7,642,244.
7. Danho, W., Ehrlich, G. K., Fry, D., Khan, W., and Swistok, J. (2008) Neuropeptide-2 Receptor (Y-2R) Agonists and Uses Thereof. U.S. Patent 7,410,949 B2.
8. DeCarr, L. B., Buckholz, T. M., Milardo, L. C., Mays, M. R., Ortiz, A., and Lumb, K. J. (2007) A long-acting selective neuropeptide Y2 receptor peptide agonist reduces food intake in mice Bioorg. Med. Chem. Lett. 17, 1916-1919
9. Bendele, A., Seely, J., Richey, C., Sennello, G., and Shopp, G. (1998) Short communication: renal tubular vacuolation in animals treated with polyethylene-glycol-conjugated proteins Toxicol. Sci. 42, 152-7
10. Antonelli, M. and Sandroni, C. (2013) Hydroxyethyl starch for intravenous volume replacement: more harm than benefit J. Am. Med. Assoc. 309, 723-4
11. Andersen, J. T., Cameron, J., Plumridge, A., Evans, L., Sleep, D., and Sandlie, I. (2013) Single-chain variable fragment albumin fusions bind the neonatal Fc receptor (FcRn) in a species dependent manner: implications for in vivo half-life evaluation of albumin-fusion therapeutics. J. Biol. Chem. 288, 24277-85.
12. Chaudhury, C., Brooks, C. L., Carter, D. C., Robinson, J. M., and Anderson, C. L. (2006) Albumin binding to FcRn: distinct from the FcRn-IgG interaction Biochemistry 45, 4983-4990
13. Andersen, J. T., Dee Qian, J., and Sandlie, I. (2006) The conserved histidine 166 residue of the human neonatal Fc receptor heavy chain is critical for the pH-dependent binding to albumin Eur. J. Immunol. 36, 3044-3051
14. Nguyen, A., Reyes, A. E., 2nd, Zhang, M., McDonald, P., Wong, W. L., Damico, L. A., and Dennis, M. S. (2006) The pharmacokinetics of an albumin-binding Fab (AB.Fab) can be modulated as a function of affinity for albumin Protein Eng. Des. Sel. 19, 291-7
15. rAlbumin Human, NF 31, Official Monographs, United States Pharmacopeial Convention, 2013.
16. Alvarez, B., Carballal, S., Turell, L., and Radi, R. (2010) Formation and reactions of sulfenic acid in human serum albumin Meth. Enzymol. 473, 117-136
17. Baraboi, E. -D., Michel, C., Smith, P., Thibaudeau, K., Ferguson, A. V., and Richard, D. (2010) Effects of albumin-conjugated PYY on food intake: the respective roles of the circumventricular organs and vagus nerve Eur. J. Neurosci. 32, 826-839
18. Fry, D. C., Swistok, J., Khan, W., and Danho, W. (2013) Design of a Potent Peptidomimetic of PYY with Twenty Residues Replaced by a Rigid Organic Spacer, In preparation.
19. Gerald, C., Walker, M. W., Criscione, L., Gustafson, E. L., Batzl-Hartmann, C., Smith, K. E., Vaysse, P., Durkin, M. M., Laz, T. M., Linemeyer, D. L., Schaffhauser, A. O., Whitebread, S., Hofbauer, K. G., Taber, R. I., Branchek, T. A., and Weinshank, R. L. (1996) A receptor subtype involved in neuropeptide-Y-induced food intake Nature 382, 168-71
20. Mullins, D., Kirby, D., Hwa, J., Guzzi, M., Rivier, J., and Parker, E. (2001) Identification of potent and selective neuropeptide YY(1) receptor agonists with orexigenic activity in vivo Mol. Pharmacol. 60, 534-40
21. Ehrlich, G. K. (2013) Preparation and characterization of albumin conjugates for half-life extension, Boulder Peptide Symposium, Boulder, CO.
22. Duttaroy, A., Kanakaraj, P., Osborn, B. L., Schneider, H., Pickeral, O. K., Chen, C., Zhang, G., Kaithamana, S., Singh, M., Schulingkamp, R., Crossan, D., Bock, J., Kaufman, T. E., Reavey, P., Carey-Barber, M., Krishnan, S. R., Garcia, A., Murphy, K., Siskind, J. K., McLean, M. A., Cheng, S., Ruben, S., Birse, C. E., and Blondel, O. (2005) Development of a long-acting insulin analog using albumin fusion technology Diabetes 54, 251-258
23. Kim, I., Kim, T. H., Ma, K., Lee, E. S., Kim, D., Oh, K. T., Lee, D. H., Lee, K. C., and Youn, Y. S. (2010) Synthesis and evaluation of human serum albumin-modified exendin-4 conjugate via heterobifunctional polyethylene glycol linkage with protracted hypoglycemic efficacy Bioconjugate Chem. 21, 1513-9
24. Dennis, M. S., Zhang, M., Meng, Y. G., Kadkhodayan, M., Kirchhofer, D., Combs, D., and Damico, L. A. (2002) Albumin binding as a general strategy for improving the pharmacokinetics of proteins J. Biol. Chem. 277, 35035-43
25. Nilvebrant, J., Alm, T., Hober, S., and Löfblom, J. (2011) Engineering bispecificity into a single albumin-binding domain PLoS One 6, e25791
26. Nilvebrant, J., Astrand, M., Löfblom, J., and Hober, S. (2013) Development and characterization of small bispecific albumin-binding domains with high affinity for ErbB3 Cell. Mol. Life Sci. 70, 3873-85
27. Kratz, F. (2008) Albumin as a drug carrier: Design of prodrugs, drug conjugates and nanoparticles J. Controlled Release 132, 171-183