Target specific hyaluronic acid-interferon alpha conjugate for the treatment of hepatitis C virus infection

Biomaterials

Volumn 32, Issue 33, 2011, Pages 8722-8729

  Yang, Jeong A ^a   Park, Kitae ^a   Jung, Hyuntae ^a   Kim, Hyemin ^a   Hong, Sung Woo ^b   Yoon, Seung Kew ^b   Hahn, Sei Kwang ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

^b The Catholic University of Korea   (South Korea)

Author keywords

Conjugate; Hepatitis C virus; Hyaluronic acid; Interferon alpha; Targeted delivery

Indexed keywords

BIO-CONJUGATION; BIO-IMAGING; CONJUGATE; COUPLING REACTION; DAUDI CELLS; HEPATITIS C VIRUS; HYALURONIC ACIDS; IN-VITRO; IN-VIVO; INNATE IMMUNE RESPONSE; LIVER TISSUE; N-TERMINALS; NEAR-INFRARED FLUORESCENCE; PEGYLATION; PHARMACOKINETIC ANALYSIS; RESIDENCE TIME; SIDE EFFECT; SYNTHETASES; TARGETED DELIVERY; VIRAL INFECTIONS;

ALDEHYDES; ANTIBIOTICS; GLYCOLS; MAMMALS; ORGANIC ACIDS; POLYETHYLENE GLYCOLS; TISSUE; VIRUSES;

GLYCOPROTEINS;

2',5' OLIGOADENYLATE SYNTHETASE; 2',5' OLIGOADENYLATE SYNTHETASE 1; ALDEHYDE; HYALURONIC ACID; PEGINTERFERON ALPHA2B; RECOMBINANT ALPHA INTERFERON; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; CROSS COUPLING REACTION; DAUDI CELL; DRUG ACTIVITY; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG DETERMINATION; DRUG LABELING; DRUG LIVER LEVEL; DRUG SYNTHESIS; FEMALE; HEPATITIS C; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; INNATE IMMUNITY; MEAN RESIDENCE TIME; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN INDUCTION;

ANIMALS; CARBOHYDRATE SEQUENCE; CHROMATOGRAPHY, GEL; FEMALE; FLUORESCENCE; HEPATITIS C; HYALURONIC ACID; INTERFERON-ALPHA; MICE; MOLECULAR SEQUENCE DATA; RATS; RATS, SPRAGUE-DAWLEY;

HEPATITIS C VIRUS; MURINAE; MUS;

EID: 80052963561     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2011.07.088     Document Type: Article

References (40)

1. Tan S.L., Pause A., Shi Y., Sonenberg N. Hepatitis C therapeutics: current status and emerging strategies. Nat Rev Drug Discov 2002, 1:867-881.
2. Borden E.C., Sen G.C., Uze G., Silverman R.H., Ransohoff R.M., Foster G.R., et al. Interferons at age 50: past, current and future impact on biomedicine. Nat Rev Drug Discov 2007, 6:975-990.
3. Sadler A.J., Williams B.R. Interferon-inducible antiviral effectors. Nat Rev Immunol 2008, 8:559-568.
4. Shaunak S., Godwin A., Choi J.W., Balan S., Pedone E., Vijayarangam D., et al. Site-specific PEGylation of native disulfide bonds in therapeutic proteins. Nat Chem Biol 2006, 2:312-313.
5. Bell S.J., Fam C.M., Chlipala E.A., Carlson S.J., Lee J.I., Rosendahl M.S., et al. Enhanced circulating half-life and antitumor activity of a site-specific pegylated interferon-alpha protein therapeutic. Bioconjug Chem 2008, 19:299-305.
6. Veronese F.M., Harris J.M. Introduction and overview of peptide and protein pegylation. Adv Drug Deliv Rev 2002, 54:453-456.
7. Subramanian G.M., Fiscella M., Lamouse-Smith A., Zeuzem S., McHutchison J.G. Albinterferon alpha-2b: a genetic fusion protein for the treatment of chronic hepatitis C. Nat Biotechnol 2007, 25:1411-1419.
8. Freitas S., Merkle H.P., Gander B. Microencapsulation by solvent extraction/evaporation: reviewing the state of the art of microsphere preparation process technology. J Control Release 2005, 102:313-332.
9. Ye M., Kim S., Park K. Issues in long-term protein delivery using biodegradable microparticles. J Control Release 2010, 146:241-260.
10. Zhang Y.M., Yang F., Yang Y.Q., Song F.L., Xu A.L. Recombinant interferon-alpha2b poly(lactic-co-glycolic acid) microspheres: pharmacokinetics-pharmacodynamics study in rhesus monkeys following intramuscular administration. Acta Pharmacol Sin 2008, 29:1370-1375.
11. Bailon P., Palleroni A., Schaffer C.A., Spence C.L., Fung W.J., Porter J.E., et al. Rational design of a potent, long-lasting form of interferon: a 40kDa branched polyethylene glycol-conjugated interferon alpha-2a for the treatment of hepatitis C. Bioconjug Chem 2001, 12:195-202.
12. Foser S., Schacher A., Weyer K.A., Brugger D., Dietel E., Marti S., et al. Isolation, structural characterization, and antiviral activity of positional isomers of monopegylated interferon alpha-2a (PEGASYS). Protein Expr Purif 2003, 30:78-87.
13. Grace M., Youngster S., Gitlin G., Sydor W., Xie L., Westreich L., et al. Structural and biologic characterization of pegylated recombinant IFN-alpha2b. J Interferon Cytokine Res 2001, 21:1103-1115.
14. Wang Y.S., Youngster S., Grace M., Bausch J., Bordens R., Wyss D.F. Structural and biological characterization of pegylated recombinant interferon alpha-2b and its therapeutic implications. Adv Drug Deliv Rev 2002, 54:547-570.
15. Chevaliez S., Pawlotsky J.M. Interferon-based therapy of hepatitis C. Adv Drug Deliv Rev 2007, 59:1222-1241.
16. Fried M.W., Shiffman M.L., Reddy K.R., Smith C., Marinos G., Gonçales F.L., et al. Peginterferon alfa-2a plus ribavirin for chronic hepatitis C virus infection. N Engl J Med 2002, 347:975-982.
17. McHutchison J.G., Lawitz E.J., Shiffman M.L., Muir A.J., Galler G.W., McCone J., et al. Peginterferon alfa-2b or alfa-2a with ribavirin for treatment of hepatitis C infection. N Engl J Med 2009, 361:580-593.
18. Laurent T.C., Fraser J.R. Hyaluronan. Faseb J 1992, 6:2397-2404.
19. Stern R. Hyaluronan catabolism: a new metabolic pathway. Eur J Cell Biol 2004, 83:317-325.
20. Oh E.J., Park K., Kim K.S., Kim J., Yang J.A., Kong J.H., et al. Target specific and long-acting delivery of protein, peptide, and nucleotide therapeutics using hyaluronic acid derivatives. J Control Release 2010, 141:2-12.
21. Aruffo A., Stamenkovic I., Melnick M., Underhill C.B., Seed B. CD44 is the principal cell surface receptor for hyaluronate. Cell 1990, 61:1303-1313.
22. Entwistle J., Hall C.L., Turley E.A. HA receptors: regulators of signalling to the cytoskeleton. J Cell Biochem 1996, 61:569-577.
23. Zhou B., Weigel J.A., Fauss L.A., Weigel P.H. Identification of the hyaluronan receptor for endocytosis (HARE). J Biol Chem 2000, 275:37733-37741.
24. Banerji S., Ni J., Wang S.X., Clasper S., Su J., Tammi R., et al. LYVE-1, a new homologue of the CD44 glycoprotein, is a lymph-specific receptor for hyaluronan. J Cell Biol 1999, 144:789-801.
25. Asayama S., Nogawa M., Takei Y., Akaike T., Maruyama A. Synthesis of novel polyampholyte comb-type copolymers consisting of a poly(L-lysine) backbone and hyaluronic acid side chains for a DNA carrier. Bioconjug Chem 1998, 9:476-481.
26. Lee H., Mok H., Lee S., Oh Y.K., Park T.G. Target-specific intracellular delivery of siRNA using degradable hyaluronic acid nanogels. J Control Release 2007, 119:245-252.
27. Urashima S., Tsutsumi M., Ozaki K., Tsuchishima M., Shimanaka K., Ueshima Y., et al. Immunohistochemical study of hyaluronate receptor (CD44) in alcoholic liver disease. Alcohol Clin Exp Res 2000, 24:34S. 8S.
28. Kim K.S., Hur W., Park S.J., Hong S.W., Choi J.E., Goh E.J., et al. Bioimaging for targeted delivery of hyaluronic acid derivatives to the livers in cirrhotic mice using quantum dots. ACS Nano 2010, 4:3005-3014.
29. Jia X., Colombo G., Padera R., Langer R., Kohane D.S. Prolongation of sciatic nerve blockade by in situ cross-linked hyaluronic acid. Biomaterials 2004, 25:4797-4804.
30. Wong S.S. Reactive groups of proteins and their modifying agent. Chemistry of protein conjugation and cross-linking 1991, CRC Press, Boca Raton, Florida, p 13.
31. Kinstler O., Molineux G., Treuheit M., Ladd D., Gegg C. Mono-N-terminal poly(ethylene glycol)-protein conjugates. Adv Drug Deliv Rev 2002, 54:477-485.
32. Wetzel R., Halualani R., Stults J.T., Quan C. A general method for highly selective cross-linking of unprotected polypeptides via pH-controlled modification of N-terminal alpha-amino groups. Bioconjug Chem 1990, 1:114-122.
33. Wang Y.S., Youngster S., Bausch J., Zhang R., McNemar C., Wyss D.F. Identification of the major positional isomer of pegylated interferon alpha-2b. Biochemistry 2000, 39:10634-10640.
34. Veiseh M., Gabikian P., Bahrami S.B., Veiseh O., Zhang M., Hackman R.C., et al. Tumor paint: a chlorotoxin:Cy5.5 bioconjugate for intraoperative visualization of cancer foci. Cancer Res 2007, 67:6882-6888.
35. Rebouillat D., Hovanessian A.G. The human 2',5'-oligoadenylate synthetase family: interferon-induced proteins with unique enzymatic properties. J Interferon Cytokine Res 1999, 19:295-308.
36. Yuan L., Wang J., Shen W.C. Lipidization of human interferon-alpha: a new approach toward improving the delivery of protein drugs. J Control Release 2008, 129:11-17.
37. Shrivastava S., Raychoudhuri A., Steele R., Ray R., Ray R.B. Knockdown of autophagy enhances the innate immune response in hepatitis C virus-infected hepatocytes. Hepatology 2011, 53:406-414.
38. Brehin A.C., Casademont I., Frenkiel M.P., Julier C., Sakuntabhai A., Despres P. The large form of human 2',5'-oligoadenylate synthetase (OAS3) exerts antiviral effect against Chikungunya virus. Virology 2009, 384:216-222.
39. Oh E.J., Park K., Choi J.S., Joo C.K., Hahn S.K. Synthesis, characterization, and preliminary assessment of anti-Flt1 peptide-hyaluronate conjugate for the treatment of corneal neovascularization. Biomaterials 2009, 30:6026-6034.
40. Kong J.H., Oh E.J., Chae S.Y., Lee K.C., Hahn S.K. Long acting hyaluronate - exendin 4 conjugate for the treatment of type 2 diabetes. Biomaterials 2010, 31:4121-4128.