The remarkable stability of chimeric, sialic acid-derived α/δ-peptides in human blood plasma

Chemical Biology and Drug Design

Volumn 75, Issue 5, 2010, Pages 455-460

  Saludes, Jonel P ^a   Natarajan, Arutselvan ^b   Denardo, Sally J ^b   Gervay Hague, Jacquelyn ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cellulose acetate electrophoresis; Chimeric peptides; DOTA; Glutamic acid; Neu2en; Plasma stability; Radiochelate; Sialic acid

Indexed keywords

ALPHA PEPTIDE; BETA PEPTIDE; CHIMERIC PROTEIN; GLUTAMIC ACID NEU2EN 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID CONJUGATE; INDIUM 111; NEU2EN DEXTRO GLUTAMIC ACID 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID CONJUGATE; PEPTIDE; SIALIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ARTICLE; BLOOD ANALYSIS; CHEMICAL STRUCTURE; CONJUGATION; ELECTROPHORESIS; HUMAN; ISOTOPE LABELING; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN METABOLISM; PROTEIN MODIFICATION; PROTEIN PROTEIN INTERACTION; PROTEIN STABILITY; RADIOACTIVITY; SOLID PHASE SYNTHESIS;

CATALYTIC DOMAIN; COMPUTER SIMULATION; HALF-LIFE; HETEROCYCLIC COMPOUNDS, 1-RING; HUMANS; N-ACETYLNEURAMINIC ACID; PEPTIDES; PROTEIN STABILITY; PROTEIN STRUCTURE, SECONDARY; SIALIC ACIDS;

EID: 77949949429     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2010.00954.x     Document Type: Article

References (30)

1. Manning M.C., Patel K., Borchardt R.T. (1989) Stability of protein pharmacauticals. Pharm Res 6 : 903 918.
2. Werle M., Bernkop-Schnurch A. (2006) Strategies to improve plasma half life time of peptide and protein drugs. Amino Acids 30 : 351 367.
3. Adessi C., Soto C. (2002) Converting a peptide into a drug: strategies to improve stability and bioavailability. Curr Med Chem 9 : 963 978.
4. Saludes J.P., Ames J.B., Gervay-Hague J. (2009) Synthesis and structural characterization of sialic acid-glutamic acid hybrid foldamers as conformational surrogates of alpha-2,8-linked polysialic acid. J Am Chem Soc 131 : 5495 5505.
5. Nakata D., Troy F.A. (2005) Degree of polymerization (DP) of polysialic acid (PolySia) on neural cell adhesion molecules (N-CAMs) - Development and application of a new strategy to accurately determine the DP of polySia chains on N-CAMs. J Biol Chem 280 : 38305 38316.
6. Ledermann J.A., Pasini F., Olabiran Y., Pelosi G. (1994) Detection of the neural cell-adhesion molecule (NCAM) in serum of patients with small-cell lung cancer (SCLC) with limited or extensive disease, and bone marrow infiltration. Int J Cancer Suppl 8 : 49 52.
7. Brisson J.R., Baumann H., Imberty A., Perez S., Jennings H.J. (1992) Helical epitope of the group-B meningococcal alpha(2-8)-linked sialic-acid polysaccharide. Biochemistry 31 : 4996 5004.
8. Gregoriadis G., McCormack B., Wang Z., Lifely R. (1993) Polysialic acids - potential in drug delivery. FEBS Lett 315 : 271 276.
9. Falciani C., Lozzi L., Pini A., Corti F., Fabbrini M., Bernini A., Lelli B., Niccolai N., Bracci L. (2007) Molecular basis of branched peptides resistance to enzyme proteolysis. Chem Biol Drug Des 69 : 216 221.
10. Li M., Meares C.F. (1993) Synthesis, metal chelate stability studies, and enzyme digestion of a peptide-linked DOTA derivative and its corresponding radiolabeled immunoconjugates. Bioconjug Chem 4 : 275 283.
11. Cole W.C., DeNardo S.J., Meares C.F., McCall M.J., DeNardo G.L., Epstein A.L. et al. (1987) Comparative serum stability of radiochelates for antibody radiopharmaceuticals. J Nucl Med 28 : 83 90.
12. Li M., Meares C.F., Zhong G.R., Miers L., Xiong C.Y., DeNardo S.J. (1994) Labeling monoclonal-antibodies with Yttrium-90-DOTA and Indium-111-DOTA chelates - a simple and efficient method. Bioconjug Chem 5 : 101 104.
13. DeNardo S.J., Peng J.S.B., DeNardo G.L., Mills S.L., Epstein A.L. (1986) Immunochemical aspects of monoclonal-antibodies important for radiopharmaceutical development. Nucl Med Biol 13 : 303 310.
14. Gregar T.Q., Gervay-Hague J. (2004) Synthesis of oligomers derived from amide-linked neuraminic acid analogues. J Org Chem 69 : 1001 1009.
15. Natarajan A., Kumaresan P.R., DeNardo S.J., DeNardo G.L., Mirick G., Lam K.S. (2008) Development of TNKase specific cleavable peptide linked radioimmunoconjugates for radioimmunotherapy. Bioorg Med Chem Lett 18 : 4802 4805.
16. De Leon-Rodriguez L.M., Kovacs Z. (2008) The synthesis and chelation chemistry of DOTA-peptide conjugates. Bioconjug Chem 19 : 391 402.
17. Cooper M.S., Sabbah E., Mather S.J. (2006) Conjugation of chelating agents to proteins and radiolabeling with trivalent metallic isotopes. Nat Protoc 1 : 314 317.
18. Wild D., Schmitt J.S., Ginj M., Macke H.R., Bernard B.F., Krenning E. et al. (2003) DOTA-NOC, a high-affinity ligand of somatostatin receptor subtypes 2, 3 and 5 for labelling with various radiometals. Eur J Nucl Med Mol Imaging 30 : 1338 1347.
19. Sosabowski J.K., Mather S.J. (2006) Conjugation of DOTA-like chelating agents to peptides and radiolabeling with trivalent metallic isotopes. Nat Protoc 1 : 972 976.
20. Liu S., He Z.J., Hsieh W.Y., Fanwick P.E. (2003) Synthesis, characterization, and X-ray crystal structure of In(DOTA-AA) (AA = p-aminoanilide): a model for In-111-labeled DOTA-biomolecule conjugates. Inorg Chem 42 : 8831 8837.
21. Schechter I., Berger A. (1967) On size of active site in proteases.I. Papain. Biochem Biophys Res Commun 27 : 157 162.
22. Frackenpohl J., Arvidsson P.I., Schreiber J.V., Seebach D. (2001) The outstanding biological stability of beta- and gamma-peptides toward proteolytic enzymes: an in vitro investigation with fifteen peptidases. Chembiochem 2 : 445 455.
23. Powell M.F., Stewart T., Otvos L., Urge L., Gaeta F.C.A., Sette A. et al. (1993) Peptide stability in drug development.2. Effect of single amino acid substitution and glycosylation on peptide reactivity in human serum. Pharm Res 10 : 1268 1273.
24. Fernandes A.I., Gregoriadis G. (1997) Polysialylated asparaginase: preparation, activity and pharmacokinetics. Biochim Biophys Acta 1341 : 26 34.
25. Sadowsky J.D., Murray J.K., Tomita Y., Gellman S.H. (2007) Exploration of backbone space in foldamers containing alpha- and beta-amino acid residues: developing protease-resistant oligomers that bind tightly to the BH3-recognition cleft of Bcl-x(L). Chembiochem 8 : 903 916.
26. Disney M.D., Hook D.F., Namoto K., Seeberger P.H., Seebach D. (2005) N-linked glycosylated beta-peptides are resistant to degradation by glycoamidase A. Chem Biodivers 2 : 1624 1634.
27. Seebach D., Abele S., Schreiber J.V., Martinoni B., Nussbaum A.K., Schild H. et al. (1998) Biological and pharmacokinetic studies with beta-peptides. Chimia 52 : 734 739.
28. Hook D.F., Bindschadler P., Mahajan Y.R., Sebesta R., Kast P., Seebach D. (2005) The proteolytic stability of 'designed' beta-peptides containing alpha-peptide-bond mimics and of mixed alpha,beta-peptides: application to the construction of MHC-binding peptides. Chem Biodivers 2 : 591 632.
29. Schmitt M.A., Weisblum B., Gellman S.H. (2007) Interplay among folding, sequence, and lipophilicity in the antibacterial and hemolytic activities of alpha/beta-peptides. J Am Chem Soc 129 : 417 428.
30. Ahmed S., Kaur K. (2009) The proteolytic stability and cytotoxicity studies of L-aspartic acid and L-diaminopropionic acid derived beta-peptides and a mixed alpha/beta-peptide. Chem Biol Drug Des 73 : 545 552.