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Volumn 58, Issue 3, 2015, Pages 1372-1379

Glycosylated enfuvirtide: A long-lasting glycopeptide with potent anti-HIV activity

Author keywords

[No Author keywords available]

Indexed keywords

2 AZIDOETHYL O (5 ACETAMIDO 3,5 DIDEOXY DEXTRO GLYCERO ALPHA DEXTRO GALACTO 2 NONULOPYRANOSYLICACID) (2-6) O BETA DEXTRO GALACTOPYRANOSYL (1-4) O BETA DEXTRO GLUCOPYRANOSIDE; ENFUVIRTIDE; N [2 [2 [2 (2 PROPYNYLOXY)ETHOXY]ETHOXY]ETHYL]MALEIMIDE; N [2 [2 [2 [[1 (BETA DEXTRO GALACTOPYRANOSYL (1-4) O BETA DEXTRO GLUCOPYRANOSYLOXYETHYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]ETHOXY]ETHOXY]ETHYL]MALEIMIDE; N [2 [2 [2 [[1 [O (5 ACETAMIDO 3,5 DIDEOXY DEXTRO GLYCERO ALPHA DEXTRO GALACTO 2 NONULOPYRANOSYLONIC ACID) (2-6) O BETA DEXTRO GALACTOPYRANOSYL (1-4) BTEA DEXTRO GLUCOPYRANOSYLOXYETHYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]ETHOXY]ETHOXY]ETHYL]MALEIMIDE; SIALIC ACID; UNCLASSIFIED DRUG; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; GLYCOPEPTIDE; GLYCOPROTEIN GP 41; PEPTIDE FRAGMENT;

EID: 84922767939     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm5016582     Document Type: Article
Times cited : (28)

References (52)
  • 1
    • 0001094662 scopus 로고    scopus 로고
    • Glycobiology: Toward understanding the function of sugars
    • Dwek, R. A. Glycobiology: toward understanding the function of sugars Chem. Rev. 1996, 96, 683-720
    • (1996) Chem. Rev. , vol.96 , pp. 683-720
    • Dwek, R.A.1
  • 2
    • 75149183678 scopus 로고    scopus 로고
    • Glycosylation of therapeutic proteins: An effective strategy to optimize efficacy
    • Solá, R. J.; Griebenow, K. Glycosylation of therapeutic proteins: an effective strategy to optimize efficacy BioDrugs 2010, 24, 9-21
    • (2010) BioDrugs , vol.24 , pp. 9-21
    • Solá, R.J.1    Griebenow, K.2
  • 3
    • 0015217323 scopus 로고
    • The role of sialic acid in determining the survival of glycoproteins in the circulation
    • Morell, A. G.; Gregoriadis, G.; Scheinberg, I. H.; Hickman, J.; Ashwell, G. The role of sialic acid in determining the survival of glycoproteins in the circulation J. Biol. Chem. 1971, 246, 1461-1467
    • (1971) J. Biol. Chem. , vol.246 , pp. 1461-1467
    • Morell, A.G.1    Gregoriadis, G.2    Scheinberg, I.H.3    Hickman, J.4    Ashwell, G.5
  • 5
    • 33947545682 scopus 로고    scopus 로고
    • Sialic acids: Carbohydrate moieties that influence the biological and physical properties of biopharmaceutical proteins and living cells
    • Byrne, B.; Donohoe, G. G.; O'Kennedy, R. Sialic acids: carbohydrate moieties that influence the biological and physical properties of biopharmaceutical proteins and living cells Drug Discovery Today 2007, 12, 319-326
    • (2007) Drug Discovery Today , vol.12 , pp. 319-326
    • Byrne, B.1    Donohoe, G.G.2    O'Kennedy, R.3
  • 6
    • 68149118066 scopus 로고    scopus 로고
    • Increasing the sialylation of therapeutic glycoproteins: The potential of the sialic acid biosynthetic pathway
    • Bork, K.; Horstkorte, R.; Weidemann, W. Increasing the sialylation of therapeutic glycoproteins: The potential of the sialic acid biosynthetic pathway J. Pharm. Sci. 2009, 98, 3499-3508
    • (2009) J. Pharm. Sci. , vol.98 , pp. 3499-3508
    • Bork, K.1    Horstkorte, R.2    Weidemann, W.3
  • 7
    • 26944452043 scopus 로고    scopus 로고
    • PEGylation, successful approach to drug delivery
    • Veronese, F. M.; Pasut, G. PEGylation, successful approach to drug delivery Drug Discovery Today 2005, 10, 1451-1458
    • (2005) Drug Discovery Today , vol.10 , pp. 1451-1458
    • Veronese, F.M.1    Pasut, G.2
  • 10
    • 33746750608 scopus 로고    scopus 로고
    • Challenges in therapeutic glycoprotein production
    • Sethuraman, N.; Stadheim, T. A. Challenges in therapeutic glycoprotein production Curr. Opin. Biotechnol. 2006, 17, 341-346
    • (2006) Curr. Opin. Biotechnol. , vol.17 , pp. 341-346
    • Sethuraman, N.1    Stadheim, T.A.2
  • 11
  • 12
    • 33747873262 scopus 로고    scopus 로고
    • Glycopeptides as versatile tools for glycobiology
    • Buskas, T.; Ingale, S.; Boons, G.-J. Glycopeptides as versatile tools for glycobiology Glycobiology 2006, 16, 113R-136R
    • (2006) Glycobiology , vol.16 , pp. 113R-136R
    • Buskas, T.1    Ingale, S.2    Boons, G.-J.3
  • 13
    • 0029063811 scopus 로고
    • Glycosylated peptide hormones: Pharmacological properties and conformational studies of analogues of [1-desamino,8- d -arginine]vasopressin
    • Kihlberg, J.; Ahman, J.; Walse, B.; Drakenberg, T.; Nilsson, A.; Söderberg-ahlm, C.; Bengtsson, B.; Olsson, H. Glycosylated peptide hormones: pharmacological properties and conformational studies of analogues of [1-desamino,8- d -arginine]vasopressin J. Med. Chem. 1995, 38, 161-169
    • (1995) J. Med. Chem. , vol.38 , pp. 161-169
    • Kihlberg, J.1    Ahman, J.2    Walse, B.3    Drakenberg, T.4    Nilsson, A.5    Söderberg-Ahlm, C.6    Bengtsson, B.7    Olsson, H.8
  • 15
    • 84860808531 scopus 로고    scopus 로고
    • Site-selective glycosylation of hemoglobin with variable molecular weight oligosaccharides: Potential alternative to PEGylation
    • Styslinger, T. J.; Zhang, N.; Bhatt, V. S.; Pettit, N.; Palmer, A. F.; Wang, P. G. Site-selective glycosylation of hemoglobin with variable molecular weight oligosaccharides: Potential alternative to PEGylation J. Am. Chem. Soc. 2012, 134, 7507-7515
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 7507-7515
    • Styslinger, T.J.1    Zhang, N.2    Bhatt, V.S.3    Pettit, N.4    Palmer, A.F.5    Wang, P.G.6
  • 20
    • 70350534041 scopus 로고    scopus 로고
    • Enfuvirtide: A safe and effective antiretroviral agent for human immunodeficiency virus-infected patients shortly after liver transplantation
    • Teicher, E.; Abbara, C.; Duclos-Vallée, J. C.; Antonini, T.; Bonhomme-Faivre, L.; Desbois, D.; Samuel, D.; Vittecoq, D. Enfuvirtide: A safe and effective antiretroviral agent for human immunodeficiency virus-infected patients shortly after liver transplantation Liver Transplant. 2009, 15, 1336-1342
    • (2009) Liver Transplant. , vol.15 , pp. 1336-1342
    • Teicher, E.1    Abbara, C.2    Duclos-Vallée, J.C.3    Antonini, T.4    Bonhomme-Faivre, L.5    Desbois, D.6    Samuel, D.7    Vittecoq, D.8
  • 21
    • 84868624085 scopus 로고    scopus 로고
    • Enfuvirtide and cutaneous injection-site reactions
    • Mirza, R.; Turiansky, G. Enfuvirtide and cutaneous injection-site reactions J. Drugs Dermatol. 2012, 11, e35-e38
    • (2012) J. Drugs Dermatol. , vol.11 , pp. 35-e38
    • Mirza, R.1    Turiansky, G.2
  • 23
    • 84865113199 scopus 로고    scopus 로고
    • Site-specific PEGylation of HR2 peptides: Effects of PEG conjugation position and chain length on HIV-1 membrane fusion inhibition and proteolytic degradation
    • Danial, M.; Van Dulmen, T. H.; Aleksandrowicz, J.; Pötgens, A. J.; Klok, H.-A. Site-specific PEGylation of HR2 peptides: Effects of PEG conjugation position and chain length on HIV-1 membrane fusion inhibition and proteolytic degradation Bioconjugate Chem. 2012, 23, 1648-1660
    • (2012) Bioconjugate Chem. , vol.23 , pp. 1648-1660
    • Danial, M.1    Van Dulmen, T.H.2    Aleksandrowicz, J.3    Pötgens, A.J.4    Klok, H.-A.5
  • 26
    • 45749149625 scopus 로고    scopus 로고
    • Increasing solubility of proteins and peptides by site-specific modification with betaine
    • Xiao, J.; Burn, A.; Tolbert, T. J. Increasing solubility of proteins and peptides by site-specific modification with betaine Bioconjugate Chem. 2008, 19, 1113-1118
    • (2008) Bioconjugate Chem. , vol.19 , pp. 1113-1118
    • Xiao, J.1    Burn, A.2    Tolbert, T.J.3
  • 29
    • 84864218519 scopus 로고    scopus 로고
    • A novel class of anti-HIV agents with multiple copies of enfuvirtide enhances inhibition of viral replication and cellular transmission in vitro
    • Chang, C.-H.; Hinkula, J.; Loo, M.; Falkeborn, T.; Li, R.; Cardillo, T. M.; Rossi, E. A.; Goldenberg, D. M.; Wahren, B. A novel class of anti-HIV agents with multiple copies of enfuvirtide enhances inhibition of viral replication and cellular transmission in vitro PloS One 2012, 7, e41235
    • (2012) PloS One , vol.7 , pp. 41235
    • Chang, C.-H.1    Hinkula, J.2    Loo, M.3    Falkeborn, T.4    Li, R.5    Cardillo, T.M.6    Rossi, E.A.7    Goldenberg, D.M.8    Wahren, B.9
  • 31
    • 1642299756 scopus 로고    scopus 로고
    • Design and synthesis of αgal-conjugated peptide T20 as novel antiviral agent for HIV-immunotargeting
    • Naicker, K. P.; Li, H.; Heredia, A.; Song, H.; Wang, L. X. Design and synthesis of αGal-conjugated peptide T20 as novel antiviral agent for HIV-immunotargeting Org. Biomol. Chem. 2004, 2, 660-664
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 660-664
    • Naicker, K.P.1    Li, H.2    Heredia, A.3    Song, H.4    Wang, L.X.5
  • 32
    • 0037257999 scopus 로고    scopus 로고
    • Synthesis of maleimide-activated carbohydrates as chemoselective tags for site-specific glycosylation of peptides and proteins
    • Ni, J.; Singh, S.; Wang, L. X. Synthesis of maleimide-activated carbohydrates as chemoselective tags for site-specific glycosylation of peptides and proteins Bioconjugate Chem. 2003, 14, 232-238
    • (2003) Bioconjugate Chem. , vol.14 , pp. 232-238
    • Ni, J.1    Singh, S.2    Wang, L.X.3
  • 33
    • 20444488831 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis of HIV-1 gp41 glycopeptides: Effects of glycosylation on the anti-HIV activity and α-helix bundle-forming ability of peptide C34
    • Wang, L. X.; Song, H.; Liu, S.; Lu, H.; Jiang, S.; Ni, J.; Li, H. Chemoenzymatic synthesis of HIV-1 gp41 glycopeptides: Effects of glycosylation on the anti-HIV activity and α-helix bundle-forming ability of peptide C34 ChemBioChem. 2005, 6, 1068-1074
    • (2005) ChemBioChem. , vol.6 , pp. 1068-1074
    • Wang, L.X.1    Song, H.2    Liu, S.3    Lu, H.4    Jiang, S.5    Ni, J.6    Li, H.7
  • 34
    • 67650507291 scopus 로고    scopus 로고
    • Enzymatic glycosylation of triazole-linked GlcNAc/Glc-peptides: Synthesis, stability and anti-HIV activity of triazole-linked HIV-1 gp41 glycopeptide C34 analogues
    • Huang, W.; Groothuys, S.; Heredia, A.; Kuijper, B. H.; Rutjes, F. P.; van Delft, F. L.; Wang, L. X. Enzymatic glycosylation of triazole-linked GlcNAc/Glc-peptides: Synthesis, stability and anti-HIV activity of triazole-linked HIV-1 gp41 glycopeptide C34 analogues ChemBioChem. 2009, 10, 1234-1242
    • (2009) ChemBioChem. , vol.10 , pp. 1234-1242
    • Huang, W.1    Groothuys, S.2    Heredia, A.3    Kuijper, B.H.4    Rutjes, F.P.5    Van Delft, F.L.6    Wang, L.X.7
  • 35
    • 0016906049 scopus 로고
    • Enzyme coupled immunoassay of insulin using a novel coupling reagent
    • Kitagawa, T.; Aikawa, T. Enzyme coupled immunoassay of insulin using a novel coupling reagent J. Biochem. 1976, 79, 233-236
    • (1976) J. Biochem. , vol.79 , pp. 233-236
    • Kitagawa, T.1    Aikawa, T.2
  • 36
    • 0034602404 scopus 로고    scopus 로고
    • Synthesis of the Lewis b hexasaccharide and squarate acid-HSA conjugates thereof with various saccharide loadings
    • Chernyak, A.; Oscarson, S.; Turek, D. Synthesis of the Lewis b hexasaccharide and squarate acid-HSA conjugates thereof with various saccharide loadings Carbohydr. Res. 2000, 329, 309-316
    • (2000) Carbohydr. Res. , vol.329 , pp. 309-316
    • Chernyak, A.1    Oscarson, S.2    Turek, D.3
  • 38
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. 2002, 114, 2596-2599
    • (2002) Angew. Chem., Int. Ed. , vol.114 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 41
    • 79955829103 scopus 로고    scopus 로고
    • Inhibitory activity of 9-phenylcyclohepta[ d ]pyrimidinedione derivatives against different strains of HIV-1 as non-nucleoside reverse transcriptase inhibitors
    • Huang, Y.; Wang, X.; Yu, X.; Yuan, L.; Guo, Y.; Xu, W.; Liu, T.; Liu, J.; Shao, Y.; Ma, L. Inhibitory activity of 9-phenylcyclohepta[ d ]pyrimidinedione derivatives against different strains of HIV-1 as non-nucleoside reverse transcriptase inhibitors Virol. J. 2011, 8, 230
    • (2011) Virol. J. , vol.8 , pp. 230
    • Huang, Y.1    Wang, X.2    Yu, X.3    Yuan, L.4    Guo, Y.5    Xu, W.6    Liu, T.7    Liu, J.8    Shao, Y.9    Ma, L.10
  • 42
    • 34248155890 scopus 로고    scopus 로고
    • HIV gp41 C-terminal heptad repeat contains multifunctional domains: Relation to mechanisms of action of anti-HIV peptides
    • Liu, S.; Jing, W.; Cheung, B.; Lu, H.; Sun, J.; Yan, X.; Niu, J.; Farmar, J.; Wu, S.; Jiang, S. HIV gp41 C-terminal heptad repeat contains multifunctional domains: Relation to mechanisms of action of anti-HIV peptides J. Biol. Chem. 2007, 282, 9612-9620
    • (2007) J. Biol. Chem. , vol.282 , pp. 9612-9620
    • Liu, S.1    Jing, W.2    Cheung, B.3    Lu, H.4    Sun, J.5    Yan, X.6    Niu, J.7    Farmar, J.8    Wu, S.9    Jiang, S.10
  • 43
    • 0029926552 scopus 로고    scopus 로고
    • HIV-1 membrane fusion mechanism: Structural studies of the interactions between biologically-active peptides from gp41
    • Lawless, M. K.; Barney, S.; Guthrie, K. I.; Bucy, T. B.; Petteway, S. R.; Merutka, G. HIV-1 membrane fusion mechanism: Structural studies of the interactions between biologically-active peptides from gp41 Biochemistry 1996, 35, 13697-13708
    • (1996) Biochemistry , vol.35 , pp. 13697-13708
    • Lawless, M.K.1    Barney, S.2    Guthrie, K.I.3    Bucy, T.B.4    Petteway, S.R.5    Merutka, G.6
  • 44
    • 0037936885 scopus 로고    scopus 로고
    • C-Terminal octylation rescues an inactive T20 mutant: Implications for the mechanism of HIV/SIMIAN immunodeficiency virus-induced membrane fusion
    • Peisajovich, S. G.; Gallo, S. A.; Blumenthal, R.; Shai, Y. C-Terminal octylation rescues an inactive T20 mutant: Implications for the mechanism of HIV/SIMIAN immunodeficiency virus-induced membrane fusion J. Biol. Chem. 2003, 278, 21012-21017
    • (2003) J. Biol. Chem. , vol.278 , pp. 21012-21017
    • Peisajovich, S.G.1    Gallo, S.A.2    Blumenthal, R.3    Shai, Y.4
  • 45
    • 57649155175 scopus 로고    scopus 로고
    • Rationally designed anti-HIV peptides containing multifunctional domains as molecule probes for studying the mechanisms of action of the first and second generation HIV fusion inhibitors
    • Qi, Z.; Shi, W.; Xue, N.; Pan, C.; Jing, W.; Liu, K.; Jiang, S. Rationally designed anti-HIV peptides containing multifunctional domains as molecule probes for studying the mechanisms of action of the first and second generation HIV fusion inhibitors J. Biol. Chem. 2008, 283, 30376-30384
    • (2008) J. Biol. Chem. , vol.283 , pp. 30376-30384
    • Qi, Z.1    Shi, W.2    Xue, N.3    Pan, C.4    Jing, W.5    Liu, K.6    Jiang, S.7
  • 46
    • 0032146060 scopus 로고    scopus 로고
    • A molecular basis for glycosylation-induced conformational switching
    • O'Connor, S. E.; Imperiali, B. A molecular basis for glycosylation-induced conformational switching Chem. Biol. 1998, 5, 427-437
    • (1998) Chem. Biol. , vol.5 , pp. 427-437
    • O'Connor, S.E.1    Imperiali, B.2
  • 47
    • 62549107841 scopus 로고    scopus 로고
    • The core trisaccharide of an N-linked glycoprotein intrinsically accelerates folding and enhances stability
    • Hanson, S. R.; Culyba, E. K.; Hsu, T.-L.; Wong, C.-H.; Kelly, J. W.; Powers, E. T. The core trisaccharide of an N-linked glycoprotein intrinsically accelerates folding and enhances stability Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 3131-3136
    • (2009) Proc. Natl. Acad. Sci. U. S. A. , vol.106 , pp. 3131-3136
    • Hanson, S.R.1    Culyba, E.K.2    Hsu, T.-L.3    Wong, C.-H.4    Kelly, J.W.5    Powers, E.T.6
  • 49
    • 0030970693 scopus 로고    scopus 로고
    • Core structure of gp41 from the HIV envelope glycoprotein
    • Chan, D. C.; Fass, D.; Berger, J. M.; Kim, P. S. Core structure of gp41 from the HIV envelope glycoprotein Cell 1997, 89, 263-273
    • (1997) Cell , vol.89 , pp. 263-273
    • Chan, D.C.1    Fass, D.2    Berger, J.M.3    Kim, P.S.4
  • 50
    • 71649110385 scopus 로고    scopus 로고
    • Determination of pterostilbene in rat plasma by a simple HPLC-UV method and its application in pre-clinical pharmacokinetic study
    • Lin, H. S.; Yue, B. D.; Ho, P. C. Determination of pterostilbene in rat plasma by a simple HPLC-UV method and its application in pre-clinical pharmacokinetic study Biomed. Chromatogr. 2009, 23, 1308-1315
    • (2009) Biomed. Chromatogr. , vol.23 , pp. 1308-1315
    • Lin, H.S.1    Yue, B.D.2    Ho, P.C.3
  • 51
    • 79551537181 scopus 로고    scopus 로고
    • Determination of 3,4-dihydroxyphenylglycol, hydroxytyrosol and tyrosol purified from olive oil by-products with HPLC in animal plasma and tissues
    • Rodríguez-Gutiérrez, G.; Wood, S.; Fernández-Bolaños Guzmán, J.; Duthie, G. G.; De Roos, B. Determination of 3,4-dihydroxyphenylglycol, hydroxytyrosol and tyrosol purified from olive oil by-products with HPLC in animal plasma and tissues Food Chem. 2011, 126, 1948-1952
    • (2011) Food Chem. , vol.126 , pp. 1948-1952
    • Rodríguez-Gutiérrez, G.1    Wood, S.2    Fernández-Bolaños Guzmán, J.3    Duthie, G.G.4    De Roos, B.5
  • 52
    • 7244253012 scopus 로고    scopus 로고
    • N-Substituted pyrrole dericatives as novel human immunodeficiency virus type 1 entry inhibitors that interfere with the gp41 six-helix bundle formation and block virus fusion
    • Jiang, S.; Lu, H.; Liu, S.; Zhao, Q.; He, Y.; Debnath, A. K. N-Substituted pyrrole dericatives as novel human immunodeficiency virus type 1 entry inhibitors that interfere with the gp41 six-helix bundle formation and block virus fusion Antimicrob. Agents Chemother. 2004, 48, 4349-4359
    • (2004) Antimicrob. Agents Chemother. , vol.48 , pp. 4349-4359
    • Jiang, S.1    Lu, H.2    Liu, S.3    Zhao, Q.4    He, Y.5    Debnath, A.K.6


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