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(12) United States Patent (10) Patent No.: US 7,037,894 B2 Marshall Et Al

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(12) United States Patent (10) Patent No.: US 7,037,894 B2 Marshall Et Al US007037894B2 (12) United States Patent (10) Patent No.: US 7,037,894 B2 Marshall et al. (45) Date of Patent: May 2, 2006 (54) STABILIZED PROTEINS Malencik and Anderson, 1994, "Dityrosine Formation in Calmodulin: Conditions for Intermolecular Cross-Linking, (75) Inventors: Christopher P. Marshall, Brooklyn, Biochemistry 33: 13363-13372. NY (US); Alexander Hoffman, Los Brown et al., 1995, “Highly Specific Oxidative Cross-Link Angeles, CA (US); Joseph P. Errico, ing of Proteins Mediated by a Nickel-Peptide Complex’, Far Hills, NJ (US); Paul B. Marshall, Biochemistry 34:4733–4739. Munich (DE) Fancy and Kodadek, 1999. “Chemistry for the analysis of protein-protein interactions: rapid and efficient cross-link (73) Assignee: Avatar Medical, LLC, Newark, NJ ing triggered by long wavelength light', PNAS USA (US) 96:6O2O 6O24. Campbell et al., 1998, “Protein Cross-Linking Mediated by (*) Notice: Subject to any disclaimer, the term of this Metalloporphyrins, Biorg. And Medicinal Chem. patent is extended or adjusted under 35 6:1301 7. U.S.C. 154(b) by 390 days. Galeazzi et al., 1999, “In vitro peroxidase oxidation induces stable dimmers of -amyloid (1–42) through dityrosine (21) Appl. No.: 09/837,235 bridge formation'. Amyloid: Int. J. Exp. Clin. Investig. 6:7 13. (22) Filed: Apr. 18, 2001 Baudry et al., 1996, “Dityrosine bridge formation and thy roid hormone synthesis are tightly linked and are both (65) Prior Publication Data dependent on N-glycans', FEBS Lett. 396:223–226. US 2002/0061549 A1 May 23, 2002 Briza et al., 1994, “The sporulation-specific enzymes encoded by the DIT1 and DIT2 genes catalyze a two-step Related U.S. Application Data reaction leading to a soluble LL-dityrosine-containing pre cursor of the yeast spore wall', Proc. Natl. Acad. Sci. USA (63) Continuation of application No. PCT/US00/28595, filed on 91:4524-4528. Oct. 16, 2000. Briza et al., 1990, “Characterization of a DL-dityrosine (60) Provisional application No. 60/159,763, filed on Oct. 15, 1999. containing macromolecule from yeast ascospore walls”. J. Biol. Chem. 265:15118-15123. (51) Int. Cl. Briza et al., 1986, "Dityrosine is a prominent component of A6 IK 38/00 (2006.01) the yeast ascospore wall'. J. Biol. Chem. 261:4288-4294. A6 IK 38/43 (2006.01) DeVore and Gruebel, 1978, “Dityrosine in adhesive formed C07K L/00 (2006.01) by the sea mussel, Mytilus edulis”, Biochem. Biophys. Res. C07K 6/00 (2006.01) Comm 80:993-999. CI2N 9/00 (2006.01) Downie et al. 1972, “An insoluble, dityrosine-containing protein from uterus'. Biochim. Biophys. Acta 263:604-609. (52) U.S. Cl. ..................... 514/12: 424/94.1; 424/130.1; 424/94.3: 530/350; 530/387.1; 530/388.21; (Continued) 530/388.22; 530/388.24; 530/399; 435/183; Primary Examiner Tekchand Saidha 435/198: 514/2 (74) Attorney, Agent, or Firm Jane M. Love; Wilmer (58) Field of Classification Search ..................... 514/2, Cutler Pickering Hale and Dorr LLP 514/12: 424/94.1, 94.3, 130. 1, 192.1; 530/350, 530/387.1, 388.21,388.22,388.24, 399, (57) ABSTRACT 530/300,387.9; 435/183, 198: 536/23.1, Isolated polypeptides or polypeptide chains are modified by 536/23.2 di-tyrosine cross-linking such that the retain at least one See application file for complete search history. functional activity. In one embodiment, the isolated polypeptide or polypeptide chains comprise at least one (56) References Cited di-tyrosine cross-link, wherein at least one tyrosine of the di-tyrosine cross-link originates from a point mutation to U.S. PATENT DOCUMENTS tyrosine, and wherein the di-tyrosine cross-linked protein 4,650,758 A 3, 1987 Shaked et al. .............. 435/105 retains at least one function displayed by the protein in the 4,904,592 A 2, 1990 Freeman et al. ............ 435/183 absence of di-tyrosine cross-linking. In another 5,538,876 A 7, 1996 Mutsaers et al. ........... 435/141 embodiment, the di-tyrosine cross-linked polypeptide or 5,747,654 A 5/1998 Pastan et al. ............ 530/3917 polypeptide chain has enhanced stability compared to the same polypeptide or polypeptide chain in the absence of FOREIGN PATENT DOCUMENTS di-tyrosine cross-linking. A method for stabilization of a WO WO O1/29247 4/2001 polypeptide or polypeptide complex, by the introduction of WO WO O1, 54486 8, 2001 intra-polypeptide and/or inter-polypeptide di-tyrosine bonds, which simultaneously maintains the structure and OTHER PUBLICATIONS function of the polypeptide or polypeptide complex is also Stachel et al., 1998, “Stabilization of a C7 Equatorial described. Gamma Turn in DMSO–d6 by a Ditryptophan Crosslink', Bioorganic and Medicinal Chemistry 6:1439–1446. 25 Claims, 26 Drawing Sheets US 7,037,894 B2 Page 2 OTHER PUBLICATIONS Nomura et al., 1990, “Pulcherosine, a novel tyrosine-d- erived, trivalent cross-linking amino acid from the fertili Fetterer et al., 1993, “Synthesis of tyrosine-derived zation envelope of sea urchin embryo', Biochem. cross-links in Ascaris suum cuticular proteins”. J. Parasitol. 29:45.25 4534. 79:160 166. Onorato et al., 1998, “Immunohistochemical and ELISA Fetterer and Rhoads, 1990, “Tyrosine-derived cross-linking assays for biomarkers of oxidative stress in aging and amino acids in the sheath of Haemonchus contortus infec disease', Annals NY Acad. Sci. 854:277–290. tive larvae', J. Parasitol. 76:619–624. Pandey and Aronson, 1979. “Properties of the Bacillus Frater et al., 1960, “A role for thiol and disulphide groups in subtilis spore coat, J. Bacteriol. 137: 1208–1218. determining the rheological properties of dough made from Raven et al., 1971, “Occurrence of dityrosine in Tussah silk wheaten flour', Nature 186:451–454. fibroin and keratin, Biochim. Biophys. Acta 251:96–99. Gmeiner and Seelos, 1989, “Phosphorylation of tyrosine Shewry et al., 1992, “High molecular weight subunits of prevents dityrosine formation in vitro, FEBS Lett. wheat glutenin', J. Cereal Sci. 15:105-120. 255:395. 397. Smail et al., 1995, “Candida albicans cell walls contain the Grune et al., 2001, "Age-related changes in protein oxida fluorescent cross-linking amino acid dityrosine'. Infect. tion and proteolysis in mammalian cells'. J. Gerontol. Immun. 63:4078 4083. 56A:B459 B467. Sobel and Ajie, 1992, “Modification in amino acids of Dead Sea scroll parchments', Free Radical Biol. Med. Guptasarma and Balasubramanian, 1992, “Dityrosine for 13: 701 702. mation in the proteins of the eye lens”. Current Eye Res. Souza et al., 2000, "Dityrosine cross-linking promotes 11:1121-1125. formation of a stable C-synuclein polymers'. J. Biol. Chem. Hensley et al., 1998, “Electrochemical analysis of protein 2.75:18344- 18349. nitrotyrosin and dityrosine in the Alzheimer brain indicates Spangler and Erman, 1986, “Cytochrome c peroxidase com region-specific accumulation”. J. Neurosci. 18:8126-8132. pound I: formation of covalent protein crosslinks during the Huggins et al., 1992, “Tyrosine and dityrosine concentra endogenous reduction of the active site'. Biochim. Biophys. tions in oxidized proteins and lens proteins with age'. Acta 872:155 157. Annals NY Acad. Sci. 663:436–437. Sullivan et al., 1940, “The action of oxidizing and reducing Kanwar and Balasubramanian, 2000, "Structural studies on agents on flour, Cereal Chem. 17:507–528. some dityrosine-cross-linked globular proteins: stability is Tilley et al., 2001, “Tyrosine cross-links: molecular basis of weakened, but activity is not abolished. Biochem. gluten structure and function.” J. Agric. Food Chem. 49: 39:14976- 14983. 2627 2632. Kanwar and Balasubramanian, 1999, "Structure and stabil Totsune et al., 1993, "Chemiluminescence from bamboo ity of the dityrosine-linked dimer of YB-crystallin'. Exp. shoot cut, Biochem. Biophys. Res. Comm. 194:1025-1029. Eye Res. 68:773–784. Waffenschmidt et al., 1993, “Isodityrosine cross-linking Kato et al., 1995, “Formation of protein-bound 3,4-dihy mediates insolubilization of cell walls in Chlamydomonas', droxyphenylalanine in collagen types I and IV exposed to Plant Cell 5:809–820. ultraviolet light', Photochem. Photobiol. 61:367–372. Waykole and Heidemann, 1976, "Dityrosine in collagen'. Kay and Shapiro, 1987. “Ovoperoxidase assembly into the Connective Tissue Res. 4:219–222. sea urchin fertilization envelope and dityrosine crosslink Wells-Knecht et al., 1993, “Oxidized amino acids in lens ing, Devel. Biol. 121:325–334. protein with age”, J. Biol. Chem. 268:12348–12352. Keeley et al., 1969, "Dityrosine in a non-hydroxyproline, Aeschbach et al., 1976, “Formation of Dityrosine alkali-soluble protein isolated from chick aorta and bovine Cross-Links in Proteins by Oxidation of Tyrosine Resi ligament, Biochem. Biophys. Res. Comm. 34:156–161. dues.” Biochim. Biophys. Acta 439, 292–301 ikas. Bodaness et al., 1984, “An Analysis of the H.O. Mediated LaBella et al., 1967, “Evidence for dityrosine in elastin', Crosslinking of Lens Crytallins Catalyzed by the Heme-Un Biochem. Biophys. Res. Comm. 26:748–753. decapeptide from Cytochrome c.” Arch. Biochem. Biophys. Leonardi et al., 1994, "Presence of dityrosine bridges in 231 (2), 461–469. thyroglobulin and their relationship with iodination, Bio Brown et al., 1998, “Determining Protein-Protein Interac chem. Biophys. Res. Comm. 202:38–43. tions by Oxidative Cross-Linking of a Glycine-Glycine Leeuwenburgh et al., 1999, “Oxidized amino acids in the Histidine Fusion Protein.” Biochemistry 37, 4397–4406. urine of aging rats: potential markers for assessing oxidative Campbell et al., 1998, “Protein Cross-Linking Mediated by stress in vivo”, Am. J. Physiol. 276:R128-R135. Metalloporphyrins,” Bioorg. Med. Chem. 6, 1301–1307. Li et al., 1996, “Involvement of peroxidase in chorion Fancy & Kodadek, 1997, “Site Directed Oxidative Protein hardening in Aedes aegypti. Insect Biochem. Molec. Biol. Crosslinking.” Tetrahedron. 53 (35), 11953–11960. 26:309. 3.17. Fancy & Kodadek, 1999. “Chemistry for the Analysis of Malanik and Ledvina, 1979, “The content of dityrosine in Protein-Protein Interactions: Rapid and Efficient chick and rabbit aorta proteins’.
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