Multivalent and flexible PEG-nitrilotriacetic acid derivatives for non-covalent protein pegylation

Pharmaceutical Research

Volumn 28, Issue 10, 2011, Pages 2412-2421

  Mero, Anna ^a   Ishino, Tetsuya ^b,c   Chaiken, Irwin ^b   Veronese, Francesco M ^a   Pasut, Gianfranco ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b DREXEL UNIVERSITY COLLEGE OF MEDICINE   (United States)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

bioconjugation; drug delivery; PEGylation; protein delivery

Indexed keywords

ACETIC ACID DERIVATIVE; CHELATING AGENT; CUPRIC ION; GRANULOCYTE COLONY STIMULATING FACTOR; HISTIDINE; MACROGOL; NITRILOTRIACETIC ACID; NITRILOTRIACETIC ACID DERIVATIVE; NITROGEN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; COVALENT BOND; DRUG CLEARANCE; DRUG CONJUGATION; DRUG HALF LIFE; DRUG STRUCTURE; IMMOBILIZED METAL AFFINITY CHROMATOGRAPHY; IN VIVO STUDY; LIGHT SCATTERING; MALE; METAL BINDING; MOLECULAR INTERACTION; NONHUMAN; PRIORITY JOURNAL; PROTEIN MODIFICATION; PROTEIN PEGYLATION; PROTEIN SECONDARY STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SURFACE PLASMON RESONANCE;

ANIMALS; CHELATING AGENTS; CHROMATOGRAPHY, AFFINITY; COORDINATION COMPLEXES; DRUG DELIVERY SYSTEMS; GRANULOCYTE COLONY-STIMULATING FACTOR; HISTIDINE; MALE; NITRILOTRIACETIC ACID; POLYETHYLENE GLYCOLS; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY; PROTEINS; RATS; RATS, SPRAGUE-DAWLEY; SURFACE PLASMON RESONANCE;

EID: 80054769432     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-011-0468-8     Document Type: Article

References (27)

1. B Leader QJ Baca DE Golan 2008 Protein therapeutics: a summary and pharmacological classification Nat Rev Drug Discov 7 21 39 18097458 10.1038/nrd2399 1:CAS:528:DC%2BD1cXht1ygtQ%3D%3D
2. A Abuchowski R Mccoy NC Palczuk T Van Es FF Davis 1977 Effect of covalent attachment of polyethylene glycol on immunogenicity and circulating life of bovine liver catalase J Biol Chem 252 3582 3586 16907 1:CAS:528: DyaE2sXksV2ntL4%3D (Pubitemid 8116088)
3. A Abuchowski T Van Es NC Palczuk FF Davis 1977 Alteration of immunological properties of bovine serum albumin by covalent attachment of polyethylene glycol J Biol Chem 252 3578 3581 405385 1:CAS:528: DyaE2sXksV2it7c%3D (Pubitemid 8116087)
4. G Pasut FM Veronese 2005 Polymer-drug conjugation, recent achievements and general strategies Prog Pol Sci. 32 933 961 10.1016/j.progpolymsci.2007.05. 008 (Pubitemid 47198290)
5. G Pasut A Mero F Caboi S Scaramuzza L Sollai FM Veronese 2008 A new PEG-beta-alanine active derivative for releasable protein conjugation Bioconj Chem 19 2427 2431 10.1021/bc800281s 1:CAS:528:DC%2BD1cXhsVWksrbJ
6. RB Greenwald K Yang H Zhao CD Conover S Lee D Filpula 2003 Controlled release of proteins from their poly(ethylene glycol) conjugates: drug delivery systems employing 1,6-elimination Bioconj Chem. 14 395 403 10.1021/bc025652m 1:CAS:528:DC%2BD3sXhsF2ksLY%3D (Pubitemid 36348663)
7. H Zhao K Yang A Martinez A Basu R Chintala HC Liu A Janjua M Wang D Filpula 2006 Linear and branched bicin linkers for releasable PEGylation of macromolecules: controlled release in vivo and in vitro from mono- and multi-PEGylated proteins Bioconj Chem. 17 341 351 10.1021/bc050270c
8. T Peleg-Shulman H Tsubery M Mironchik M Fridkin G Schreiber Y Shechter 2004 Reversible PEGylation: a novel technology to release native interferon alpha2 over a prolonged time period J Med Chem 7 4897 4904 10.1021/jm0497693 (Pubitemid 39238265)
9. G Pasut F Caboi R Schrepfer G Tonon O Schiavon FM Veronese 2007 React Funct Polym 67 529 539 10.1016/j.reactfunctpolym.2007.03.005 1:CAS:528:DC%2BD2sXlslGju7Y%3D (Pubitemid 46823915)
10. J Porath J Carlsson I Olsson G Belfrage 1975 Metal chelate affinity chromatography, a new approach to protein fractionation Nature 258 598 599 1678 10.1038/258598a0 1:CAS:528:DyaE28XhtVWksLs%3D
11. J Nilsson S Ståhl J Lundeberg M Uhlén P-Å Nygren 1997 Affinity fusion strategies for detection, purification, and immobilization of recombinant proteins Protein Expr Purif 11 11 16 10.1006/prep.1997.0767 (Pubitemid 27434126)
12. S Lata M Gavutis R Tampe J Piehler 2006 Specific and stable fluorescence labeling of histidine-tagged proteins for dissecting multi-protein complex formation J Am Chem Soc 128 2365 2372 16478192 10.1021/ja0563105 1:CAS:528:DC%2BD28XpsVKjtg%3D%3D
13. CR Goldsmith J Jaworski M Sheng SJ Lippard 2006 Selective labeling of extracellular proteins containing polyhistidine sequences by a fluorescein-nitrilotriacetic acid conjugate J Am Chem Soc 128 418 419 16402822 10.1021/ja0559754 1:CAS:528:DC%2BD2MXhtlSmtrvJ (Pubitemid 43157528)
14. SH Kim M Jeyakumar JA Katzenellenbogen 2007 Dual-mode fluorophore-doped nickel nitrilotriacetic acid-modified silica nanoparticles combine histidine-tagged protein purification with site-specific fluorophore labeling J Am Chem Soc 129 13254 13264 17910454 10.1021/ja074443f 1:CAS:528: DC%2BD2sXhtFShtLnJ (Pubitemid 350058367)
15. F Cheng LJ Gamble DG Castner 2008 XPS, TOF-SIMS, NEXAFS, and SPR characterization of nitrilotriacetic acid-terminated self-assembled monolayers for controllable immobilization of proteins Anal Chem 80 2564 2573 18302347 10.1021/ac702380w 1:CAS:528:DC%2BD1cXitl2ksLc%3D (Pubitemid 351499841)
16. S Lata A Reichel R Brock R Tampe J Piehler 2005 High-affinity adaptors for switchable recognition of histidine-tagged proteins J Am Chem Soc 127 10205 10215 16028931 10.1021/ja050690c 1:CAS:528:DC%2BD2MXlsFKrtrw%3D (Pubitemid 41045486)
17. CL Van Broekhoven JG Altin 2005 The novel chelator lipid 3(nitrilotriacetic acid)-ditetradecylamine (NTA(3)-DTDA) promotes stable binding of His-tagged proteins to liposomal membranes: potent anti-tumor responses induced by simultaneously targeting antigen, cytokine and costimulatory signals to T cells Biochim Biophys Acta 1716 104 116 16225839 10.1016/j.bbamem.2005.09. 003 (Pubitemid 41532288)
18. ZH Huang JI Park DS Watson P Hwang FC Szoka 2006 Facile synthesis of multivalent nitrilotriacetic acid (NTA) and NTA conjugates for analytical and drug delivery applications Bioconj Chem. 17 1592 600 10.1021/bc0602228 1:CAS:528:DC%2BD28Xht1WqtLfN (Pubitemid 44851506)
19. Z Huang P Hwang DS Watson L Cao Jr 2009 Tris-nitrilotriacetic acids of subnanomolar affinity toward hexahistidine tagged molecules Bioconjug Chem 20 1667 1672 19650657 10.1021/bc900309n 1:CAS:528:DC%2BD1MXptlSgtbo%3D
20. V Platt Z Huang L Cao M Tiffany K Riviere FC Szoka Jr 2010 Influence of multivalent nitrilotriacetic acid lipid-ligand affinity on the circulation half-life in mice of a liposome-attached His6-protein Bioconjug Chem 21 892 902 20384362 10.1021/bc900448f 1:CAS:528:DC%2BC3cXksFeqt7Y%3D
21. EP Sablin A Woods IN Krylova P Hwang HA Ingraham RJ Fletterick 2008 The structure of corepressor Dax-1 bound to its target nuclear receptor LRH-1 Proc Natl Acad Sci U.S.A. 105 18390 18395 19015525 10.1073/pnas.0808936105 1:CAS:528:DC%2BD1cXhsVyhsrvJ
22. Guideline on the specification limits for residues of metal catalysts or metal reagents (2008) Committee for medicinal products for human use. London, 21 February 2008. Doc. Ref. EMEA/CHMP/SWP/4446/2000.Available from: www.ema.europa.eu/pdfs/human/swp/444600enfin.pdf
23. SL Snyder PZ Sobocinski 1975 An improved 2,4,6-trinitrobenzenesulfonic acid method for the determination of amines Anal Biochem 64 284 288 1137089 10.1016/0003-2697(75)90431-5 1:CAS:528:DyaE2MXhsFWlsbc%3D
24. G Pasut S Scaramuzza O Schiavon R Mendichi FM Veronese 2005 PEG-epirubicin conjugates with high drug loading J Bioac Comp Pol. 20 213 230 10.1177/0883911505053377 1:CAS:528:DC%2BD2MXks1Wjur4%3D (Pubitemid 40663645)
25. J Porath B Olin 1983 Immobilized metal ion affinity adsorption and immobilized metal ion affinity chromatography of biomaterials. Serum protein affinities for gel-immobilized iron and nickel ions Biochemistry 22 1621 1630 6849872 10.1021/bi00276a015 1:CAS:528:DyaL3sXht1ahsL0%3D
26. S Knecht D Ricklin AN Eberle B Ernst 2009 Oligohis-tags: mechanisms of binding to Ni2+-NTA surfaces J Mol Recognit 22 270 279 19235144 10.1002/jmr.941 1:CAS:528:DC%2BD1MXnslGis70%3D
27. T Ishino U Pillalamarri D Panarello M Bhattacharya C Urbina S Horvat S Sarkhel B Jameson I Chaiken 2006 Asymmetric usage of antagonist charged residues drives interleukin-5 receptor recruitment but is insufficient for receptor activation Biochemistry 45 1106 1115 16430207 10.1021/bi0518038 1:CAS:528:DC%2BD28XhtF2mtg%3D%3D (Pubitemid 43167178)