Polymer derivatives

Details Polymer derivatives Polymer derivatives

2007-06-12

2007-06-12

Sellers, Robert (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From heterocyclic reactant containing as ring atoms oxygen,...

C525S058000, C525S403000, C525S404000, C525S405000, C525S407000, C525S408000

Reexamination Certificate

active

10960674

ABSTRACT:
The invention provides water-soluble compounds that include a polymer and at least one terminal azide or acetylene moiety. Also provided are highly efficient methods for the selective modification of proteins with PEG derivatives, which involves the selective incorporation of non-genetically encoded amino acids, e.g., those amino acids containing an azide or acetylene moiety, into proteins in response to a selector codon and the subsequent modification of those amino acids with a suitably reactive PEG derivative.

REFERENCES:
patent: 4289872 (1981-09-01), Denkewalter et al.
patent: 4670417 (1987-06-01), Iwasaki et al.
patent: 5191034 (1993-03-01), Ahad
patent: 5229490 (1993-07-01), Tam
patent: 5252714 (1993-10-01), Harris et al.
patent: 5281698 (1994-01-01), Nitecki
patent: 5468478 (1995-11-01), Saifer et al.
patent: 5643575 (1997-07-01), Martinez et al.
patent: 5650234 (1997-07-01), Dolence et al.
patent: 5672662 (1997-09-01), Harris et al.
patent: 5824784 (1998-10-01), Kinstler et al.
patent: 5900461 (1999-05-01), Harris
patent: 5932462 (1999-08-01), Harris et al.
patent: 6448369 (2002-09-01), Bentley et al.
patent: 6602498 (2003-08-01), Shen
patent: 6610281 (2003-08-01), Harris
patent: 2003/0096918 (2003-05-01), Meldal et al.
patent: 2003/0143596 (2003-07-01), Bentley et al.
patent: 0239 770 (1987-10-01), None
patent: 2753975 (1998-04-01), None
patent: 55-092000 (1980-07-01), None
patent: 56067309 (1981-06-01), None
patent: WO 93/21259 (1993-10-01), None
patent: WO 96/21469 (1996-07-01), None
Garanti et al., “MeOPEG-bounded azide cycloadditions to alkenyl dipolarophiles,” Tetrahedron Letters, vol. 44, Dec. 2002, pp. 1133-1135.
Wilson et al., “Synthesis of Novel Energetic Compounds. 4,” Journal of Chemical Engineering Data, vol. 27, May 1982, pp. 472 and 473.
Iyer et al., “Synthesis of orthogonal and functionalized oligoethylene glycols of defined lengths,” Tetrahedron Letters, vol. 45, Apr. 2004, pp. 4285-4288.
CAPLUS accession No. 1986:406904, Zalipsky et al., “Preparation of polyethylene glycol derivatives with two different functional groups at the terminii,” Polymer Preprints, vol. 27, No. 1, abstract.
Abuchowski, A. et al. “Cancer Therapy With Chemically Modified Enzymes. I. Antitumor Properties of Polyethylene Glycol-Asparaginase Conjugates,” Cancer Biochem Biophys. Jun. 1984; 7 (2) :175-86.
Andresz, H. et al. “Chemische Synthese Verzweigter Polysaccharide, 5; Kopplung Von Oligosacchariden Und Amylose An Verschiedene Träger Durch Hydrazonbindung,” Makromol. Chem. 1978;179:301-12.
Beauchamp, Co et al. “A New Procedure for the Synthesis of Polyethylene Glycol-Protein Adducts; Effects on Function, Receptor Recognition, and Clearance of Superoxide Dismutase, Lactoferrin, and Alpha 2-Macroglobulin,” Anal Biochem. May 1983; 131 (1) :25-33.
Bückmann, AF et al. “Functionalization of Poly(Ethylene Glycol) and Monomethoxy-Poly(Ethylene Glycol),” Makromol. Chem. 1981; 182:1379-84.
Chin, JW et al. “An Expanded Eukaryotic Genetic Code,” Science. Aug. 15, 2003;301(5635) :964-7.
Chin, JW et al. “Addition of P-Azido-L-Phenylalanine to the Genetic Code ofEscherichia coli,” J Am Chem Soc. Aug. 7, 2002;124 (31) :9026-7.
Chin, JW & P. G. Schultz. “In Vivo Photocrosslinking with Unnatural Amino Acid Mutagenesis,” Chembiochem. Nov. 4, 2002;3 (11) :1135-7.
Chin, JW et al. “Addition of a Photocrosslinking Amino Acid to the Genetic Code ofEscherichia coli,” Proc Natl Acad Sci USA Aug. 20, 2002;99(17) :11020-4. EPUB Aug. 1, 2002.
Clark, R et al. “Long-Acting Growth Hormones Produced by Conjugation with Polyethylene Glycol,” J Biol Chem. Sep. 6, 1996;271 (36) :21969-77.
Elling, L et MR Kula. “Immunoaffinity Partitioning: Synthesis and Use of Polyethylene Glycol-Oxirane for Coupling to Bovine Serum Albumin and Monoclonal Antibodies,” Biotechnol Appl Biochem. Jun. 1991;13 (3) :354-62.
Goodson RJ et NV Katre. “Site-Directed Pegylation of Recombinant Interleukin-2 at its Glycosylation Site,” Biotechnology (N Y). Apr. 1990;8(4) :343-6.
Harris, JM et al. “Synthesis and Characterization of Poly(Ethylene Glycol) Derivatives,” J. Polym. Sci. Chem. Ed. 1984; 22:341-352.
Huisgen, R. “1, 3-Dipolar Cycloadditions -Introduction, Survey, Mechanism,” In1,3-Dipolar Cycloaddition Chemistry,(1984) Ed. Padwa, A., Wiley, New York, p. 1-176.
Joppich, M et PL Luisi. “Peptides Flanked by Two Polymer Chains, 1; Synthesis of Glycyl-L-Tryptophylglycine Substituted by Poly(Ethylene Oxide) at Both the Carboxy and the Amino End Groups,” Makromol. Chem. 1979;180:1381-4.
Kogan, TP. “The Synthesis of Substituted Methoxy-Poly(Ethyleneglycol) Derivatives Suitable for Selective Protein Modification,” Synthetic Comm. 1992; 22(16) :2417-24.
Olson, K et al. “Preparation and Characterization of Poly(Ethylene Glycol)ylated Human Growth Hormone Anatagonist,” InPoly(Ethylene Glycol) Chemistry&Biological Applications, (1997) Harris, JM & Zapliipsky, S Eds., ACS, Washington, D.C., p. 170-181.
Padwa, A. “Intermolecular 1,3-Dipolar Cycloadditions,” InComprehensive Organic Synthesis,vol. 4, (1991) Ed. Trost, BM, Pergamon Press, Oxford, p. 1069-1109.
Pitha J et al. “Detergents Linked to Polysaccharides: Preparation and Effects on Membranes and Cells,” Eur J Biochem. Feb. 15, 1979;94(1) :11-8.
Romani, S et al. “Synthesis of Unsymmetrical Cystine Peptides: Directed Disulfide Pairing with the Sulfenohydrazide Method,” InChemistry of Peptides and Proteins,vol. 2 (1984) Volter, W et al., Eds., Walter De Gruyter, Berlin, p. 29-34.
Rostovtsev, VV et al. “A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes,” Angew Chem Int Ed Engl. Jul. 15, 2002;41(14) :2596-9.
Sartore, L et al. “Enzyme Modification by MPEG with an Amino Acid or Peptide as Spacer Arms,” Appl Biochem Biotechnol. Jan. 1991;27(1) :45-54.
Sawhney, AS et al., “Bioerodible Hydrogels Based on Photopolymerized Poly(Ethylene Glycol) -Co-Poly(Alpha-Hydroxy Acid) Diacrylate Macromers,” Macromolecules 1993; 26:581-7.
Tondelli, L et al. “Poly(Ethylene Glycol) Imidazolyl Formates as Oligometric Drug-Binding Matrices,” J. Controlled Release 1985;1:251-7.
Tornoe, CW et al. “Peptidotriazoles on Solid Phase: [1,2,3]—Triazoles By Regiospecific Copper(I) -Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides,” J Org Chem. May 3, 2002;67(9) :3057-64.
Veronese, FM et al. “Surface Modification of Proteins. Activation of Monomethoxy-Polyethylene Glycols by Phenylchloroformates and Modification of Ribonuclease and Superoxide Dismutase,” Appl Biochem Biotechnol. Apr. 1985;11 (2) :141-52.
Wang, L et al. “Expanding the Genetic Code ofEscherichia coli,” Science. Apr. 20, 2001;292 (5516) :498-500.
Wang, L & PG Schultz. “Expanding the Genetic Code,” Chem Commun (CAMB) . Jan. 7, 2002; (1) :1-11.
Woghiren, C et al. “Protected Thiol-Polyethylene Glycol: A New Activated Polymer for Reversible Protein Modification,” Bioconjug Chem. Sep.-Oct. 1993;4 (5) :314-8.
Zalipsky, S et al. “Attachment of Drugs to Polyethylene Glycols,” Eur. Polym. J. 1983 19(12) :1177-83.
Zalipsky, S. et G. Barany. “Preparation of Polyethylene Glycol Derivatives with Two Different Functional Groups at the Termini,” Polymer Preprints (1986) , 27 (1) , 1-2.

Affiliated with

Also associated with

Rating

Polymer derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Polymer derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Polymer derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3881824