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Volumn 4, Issue , 2014, Pages

A 'Clicked'tetrameric hydroxamic acid glycopeptidomimetic antagonizes sugar-lectin interactions on the cellular level

Author keywords

[No Author keywords available]

Indexed keywords

BIOMIMETIC MATERIAL; GLYCOPEPTIDE; HYDROXAMIC ACID; LECTIN; PEPTIDE;

EID: 84903735944     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep05513     Document Type: Article
Times cited : (19)

References (34)
  • 2
    • 54949106904 scopus 로고    scopus 로고
    • Mammalian glycosylation in immunity
    • Marth, J. D. & Grewal, J. D. Mammalian glycosylation in immunity. Nat. Rev. Immunol. 8, 874-887 (2008).
    • (2008) Nat. Rev. Immunol. , vol.8 , pp. 874-887
    • Marth, J.D.1    Grewal, J.D.2
  • 3
    • 0016322758 scopus 로고
    • The role of surface carbohydrates in the hepatic recognition and transport of circulating glycoproteins
    • Drickamer, K. The role of surface carbohydrates in the hepatic recognition and transport of circulating glycoproteins. Adv. Enzymol. Relat. Areas Mol. Biol. 41, 99-128 (1974).
    • (1974) Adv. Enzymol. Relat. Areas Mol. Biol. , vol.41 , pp. 99-128
    • Drickamer, K.1
  • 4
    • 0025043480 scopus 로고
    • The asialoglycoprotein receptor: A model for endocytic transport receptors
    • Spiess, M. The asialoglycoprotein receptor: a model for endocytic transport receptors. Biochemistry 29, 10009-10018 (1990). (Pubitemid 20365657)
    • (1990) Biochemistry , vol.29 , Issue.43 , pp. 10009-10018
    • Spiess, M.1
  • 5
    • 0028998769 scopus 로고
    • The asialoglycoprotein receptor: Relationships between structure, function, and expression
    • Stockert, R. J. The asialoglycoprotein receptor: relationships between structure, function, and expression. Physiol. Rev. 75, 591-609 (1995).
    • (1995) Physiol. Rev. , vol.75 , pp. 591-609
    • Stockert, R.J.1
  • 6
    • 0034686416 scopus 로고    scopus 로고
    • The N-glycans determine the differential blood clearance and hepatic uptake of human immunoglobulin (Ig) a1 and Iga2 isotypes
    • Rifai, A., Fadden, K., Morrison, S. L. & Chintalacharuvu, K. R. The N-glycans determine the differential blood clearance and hepatic uptake of human immunoglobulin (Ig)a1 and Iga2 isotypes. J. Exp. Med. 191, 2171-2182 (2000).
    • (2000) J. Exp. Med. , vol.191 , pp. 2171-2182
    • Rifai, A.1    Fadden, K.2    Morrison, S.L.3    Chintalacharuvu, K.R.4
  • 7
    • 80052026748 scopus 로고    scopus 로고
    • Hepatocyte cytotoxicity is facilitated by asialoglycoprotein receptor
    • Guy, C. S., Rankin, S. L. & Michalak, T. I. Hepatocyte cytotoxicity is facilitated by asialoglycoprotein receptor. Hepatology 54, 1043-1050 (2011).
    • (2011) Hepatology , vol.54 , pp. 1043-1050
    • Guy, C.S.1    Rankin, S.L.2    Michalak, T.I.3
  • 8
    • 0034467243 scopus 로고    scopus 로고
    • Hepatitis A virus-specific immunoglobulin a mediates infection of hepatocytes with hepatitis A virus via the asialoglycoprotein receptor
    • DOI 10.1128/JVI.74.23.10950-10957.2000
    • Dotzauer, A. et al.Hepatitis Avirus-specific immunoglobulin amediates infection of hepatocytes with hepatitis A virus via the asialoglycoprotein receptor. J. Virol. 74, 10950-10957 (2000). (Pubitemid 32223959)
    • (2000) Journal of Virology , vol.74 , Issue.23 , pp. 10950-10957
    • Dotzauer, A.1    Gebhardt, U.2    Bieback, K.3    Gottke, U.4    Kracke, A.5    Mages, J.6    Lemon, S.M.7    Vallbracht, A.8
  • 9
    • 0026540432 scopus 로고
    • Abnormal surface distribution of the human asialoglycoprotein receptor in cirrhosis
    • Burgess, J. B., Baenziger, J. U. & Brown, W. R. Abnormal surface distribution of the human asialoglycoprotein receptor in cirrhosis. Hepatology 15, 702-706 (1992).
    • (1992) Hepatology , vol.15 , pp. 702-706
    • Burgess, J.B.1    Baenziger, J.U.2    Brown, W.R.3
  • 10
    • 84870246401 scopus 로고    scopus 로고
    • Asialoglycoprotein receptor (ASGPR) as target autoantigen in liver autoimmunity: Lost and found
    • Rigopoulou, E. I. et al. Asialoglycoprotein receptor (ASGPR) as target autoantigen in liver autoimmunity: lost and found. Autoimmun. Rev. 12, 260-269 (2012).
    • (2012) Autoimmun. Rev. , vol.12 , pp. 260-269
    • Rigopoulou, E.I.1
  • 11
    • 84858798200 scopus 로고    scopus 로고
    • A review of glycosylated carriers for drug delivery
    • Jain, K., Kesharwani, P., Gupta, U. & Jain, N. K. A review of glycosylated carriers for drug delivery. Biomaterials 33, 4166-4186 (2012).
    • (2012) Biomaterials , vol.33 , pp. 4166-4186
    • Jain, K.1    Kesharwani, P.2    Gupta, U.3    Jain, N.K.4
  • 12
    • 84876907626 scopus 로고    scopus 로고
    • Glycopolymer probes of signal transduction
    • Kiessling, L. L. & Grim, J. C. Glycopolymer probes of signal transduction. Chem. Soc. Rev. 42, 4476-4491 (2013).
    • (2013) Chem. Soc. Rev. , vol.42 , pp. 4476-4491
    • Kiessling, L.L.1    Grim, J.C.2
  • 13
    • 84876895649 scopus 로고    scopus 로고
    • Bridging lectin binding sites by multivalent carbohydrates
    • Wittmann, V. & Pieters, R. J. Bridging lectin binding sites by multivalent carbohydrates. Chem. Soc. Rev. 42, 4492-4503 (2013).
    • (2013) Chem. Soc. Rev. , vol.42 , pp. 4492-4503
    • Wittmann, V.1    Pieters, R.J.2
  • 15
    • 57349199922 scopus 로고    scopus 로고
    • A-Aminoxy acids: New possibilities from foldamers to anion receptors and channels
    • Li, X.,Wu, Y.-D. & Yang,D. a-Aminoxy acids: new possibilities from foldamers to anion receptors and channels. Acc. Chem. Res. 41, 1428-1438 (2008).
    • (2008) Acc. Chem. Res. , vol.41 , pp. 1428-1438
    • Li, X.1    Wu, Y.-D.2    Yang, D.3
  • 16
    • 18744373064 scopus 로고    scopus 로고
    • A cyclic hexapeptide comprising alternating α-aminoxy and α-amino acids is a selective chloride ion receptor
    • DOI 10.1002/chem.200500098
    • Yang, D., Li, X., Sha, Y. & Wu, Y-D. A cyclic hexapeptide comprising alternating a-aminoxy and a-amino acids is a selective chloride ion receptor. Chem. Eur. J. 11, 3005-3009 (2005). (Pubitemid 40672457)
    • (2005) Chemistry - A European Journal , vol.11 , Issue.10 , pp. 3005-3009
    • Yang, D.1    Li, X.2    Sha, Y.3    Wu, Y.-D.4
  • 17
    • 34250837547 scopus 로고    scopus 로고
    • A small synthetic molecule forms chloride channels to mediate chloride transport across cell membranes
    • DOI 10.1021/ja071961h
    • Li, X., Shen, B., Yao, X.-Q. & Yang, D. A small synthetic molecule forms chloride channels to mediate chloride transport across cell membranes. J. Am. Chem. Soc. 129, 7264-7265 (2007). (Pubitemid 46980799)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.23 , pp. 7264-7265
    • Li, X.1    Shen, B.2    Yao, X.-Q.3    Yang, D.4
  • 18
    • 43449102815 scopus 로고    scopus 로고
    • Design of a "new motif" with β-amino acids and α-aminoxy acids: Synthesis of hybrid peptides with 12/10-helix
    • DOI 10.1021/jo702242q
    • Sharma, G. V. M.,Manohar, V.,Dutta, S. K., Subash, V. & Kunwar, A. C. Design of a ''new motif'' with b-amino acids and a-aminoxy acids: synthesis of hybrid peptides with 12/10-helix. J. Org. Chem. 73, 3689-3698 (2008). (Pubitemid 351671432)
    • (2008) Journal of Organic Chemistry , vol.73 , Issue.10 , pp. 3689-3698
    • Sharma, G.V.M.1    Manohar, V.2    Dutta, S.K.3    Subash, V.4    Kunwar, A.C.5
  • 19
    • 57449107375 scopus 로고    scopus 로고
    • BβSugar aminoxy peptides as rigid secondary structural scaffolds
    • Chandrasekhar, S. et al. bβSugar aminoxy peptides as rigid secondary structural scaffolds. J. Org. Chem. 73, 9443-9446 (2008).
    • (2008) J. Org. Chem. , vol.73 , pp. 9443-9446
    • Chandrasekhar, S.1
  • 20
    • 70349970662 scopus 로고    scopus 로고
    • Synthesis and solution conformation of homo-b-peptides consisting ofN-mannofuranosyl- 3-ulosonic acids
    • Andreini, M., Taillefumier, C., Chrétien, F., Thery, V. & Chapleur, Y. Synthesis and solution conformation of homo-b-peptides consisting ofN-mannofuranosyl- 3-ulosonic acids. J. Org. Chem. 74, 7651-7659 (2009).
    • (2009) J. Org. Chem. , vol.74 , pp. 7651-7659
    • Andreini, M.1    Taillefumier, C.2    Chrétien, F.3    Thery, V.4    Chapleur, Y.5
  • 21
    • 77249174283 scopus 로고    scopus 로고
    • Self-assembling cyclic tetrapeptide from alternating Clinked carbo-b-amino acid [(S)-b-Caa] and a-aminoxy acid [(R)-Ama]: A selective chloride ion receptor
    • Sharma, G. V. M. et al. Self-assembling cyclic tetrapeptide from alternating Clinked carbo-b-amino acid [(S)-b-Caa] and a-aminoxy acid [(R)-Ama]: a selective chloride ion receptor. J. Org. Chem. 75, 1087-1094 (2010).
    • (2010) J. Org. Chem. , vol.75 , pp. 1087-1094
    • Sharma, G.V.M.1
  • 22
    • 70749117839 scopus 로고    scopus 로고
    • Synthesis of oligosaccharide mimetics with glycoaminoxy acids
    • Gong, Y., Sun, H. & Xie, J. Synthesis of oligosaccharide mimetics with glycoaminoxy acids. Eur. J. Org. Chem. 2009, 6027-6033 (2009).
    • (2009) Eur. J. Org. Chem. , vol.2009 , pp. 6027-6033
    • Gong, Y.1    Sun, H.2    Xie, J.3
  • 23
    • 80051701671 scopus 로고    scopus 로고
    • Synthesis of nucleoside aminoxy acids
    • Gong, Y., Peyrat, S., Sun, H. & Xie, J. Synthesis of nucleoside aminoxy acids. Tetrahedron 67, 7114-7120 (2011).
    • (2011) Tetrahedron , vol.67 , pp. 7114-7120
    • Gong, Y.1    Peyrat, S.2    Sun, H.3    Xie, J.4
  • 24
    • 80052039386 scopus 로고    scopus 로고
    • 6-O-amino-2-O-carboxymethyl glycopyranoside as novel glycoaminoxy acid building block for the construction of oligosaccharide mimetics
    • Song, Z., He, X.-P., Chen, G.-R. & Xie, J. 6-O-amino-2-O- carboxymethyl glycopyranoside as novel glycoaminoxy acid building block for the construction of oligosaccharide mimetics. Synthesis 17, 2761-2766 (2011).
    • (2011) Synthesis , vol.17 , pp. 2761-2766
    • Song, Z.1    He, X.-P.2    Chen, G.-R.3    Xie, J.4
  • 25
    • 84861345548 scopus 로고    scopus 로고
    • Synthesis of thymidine dimers from 59-O-aminothymidine
    • Peyrat, S. & Xie, J. Synthesis of thymidine dimers from 59-O-aminothymidine. Synthesis 44, 1718-1724 (2012).
    • (2012) Synthesis , vol.44 , pp. 1718-1724
    • Peyrat, S.1    Xie, J.2
  • 26
    • 0035906449 scopus 로고    scopus 로고
    • Synthesis of 4-cis-Phenyl-l-proline via Hydrogenolysis
    • DOI 10.1021/jo005625u
    • Makoto, T., Han, G. & Hruby, V. J. Synthesis of 4-cis-phenyl-L- proline via hydrogenolysis. J. Org. Chem. 66, 3593-3596 (2001). (Pubitemid 32878973)
    • (2001) Journal of Organic Chemistry , vol.66 , Issue.10 , pp. 3593-3596
    • Tamaki, M.1    Han, G.2    Hruby, V.J.3
  • 27
    • 85077634689 scopus 로고
    • The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products
    • Mitsunobu, O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 13, 1-28 (1981).
    • (1981) Synthesis , vol.13 , pp. 1-28
    • Mitsunobu, O.1
  • 28
    • 84882455057 scopus 로고    scopus 로고
    • Fluorogenic probing of specific recognitions between sugar ligands and glycoprotein receptors on cancer cells by an economic graphene nanocomposite
    • Zhang, H.-L. et al. Fluorogenic probing of specific recognitions between sugar ligands and glycoprotein receptors on cancer cells by an economic graphene nanocomposite. Adv. Mater. 25, 4097-4101 (2013).
    • (2013) Adv. Mater. , vol.25 , pp. 4097-4101
    • Zhang, H.-L.1
  • 29
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
    • 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. Engl. 41, 2596-2599 (2002). (Pubitemid 34803480)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.14 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 30
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • DOI 10.1021/jo011148j
    • Tornøe, C. W., Christensen, C. & Meldal, M. 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. 67, 3057-3064 (2002). (Pubitemid 34457265)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.9 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 31
    • 84881176472 scopus 로고    scopus 로고
    • Capturing intercellular sugar-mediated ligand-receptor recognitions via a simple yet highly biospecific interfacial system
    • Li, Z. et al. Capturing intercellular sugar-mediated ligand-receptor recognitions via a simple yet highly biospecific interfacial system. Sci. Rep. 3, 2293 (2013).
    • (2013) Sci. Rep. , vol.3 , pp. 2293
    • Li, Z.1
  • 32
    • 84897639621 scopus 로고    scopus 로고
    • Substitution pattern reverses the fluorescence response of coumarin glycoligands upon coordination with silver (I)
    • Shi, D.-T. et al. Substitution pattern reverses the fluorescence response of coumarin glycoligands upon coordination with silver (I). Sci. Rep. 4, 4252 (2014).
    • (2014) Sci. Rep. , vol.4 , pp. 4252
    • Shi, D.-T.1
  • 33
    • 84884287162 scopus 로고    scopus 로고
    • Targeting C-type lectin receptors with multivalent carbohydrate ligands
    • Lepenies, B., Lee, J. & Sonkaria, S. Targeting C-type lectin receptors with multivalent carbohydrate ligands. Adv. Drug Delivery Rev. 65, 1271-1281 (2013).
    • (2013) Adv. Drug Delivery Rev. , vol.65 , pp. 1271-1281
    • Lepenies, B.1    Lee, J.2    Sonkaria, S.3
  • 34
    • 84901777244 scopus 로고    scopus 로고
    • Target-specific imaging of transmembrane receptors using quinonyl glycosides functionalized quantum dots
    • Ma,W. et al. Target-specific imaging of transmembrane receptors using quinonyl glycosides functionalized quantum dots. Anal. Chem. 86, 5502-5507 (2014).
    • (2014) Anal. Chem. , vol.86 , pp. 5502-5507
    • Ma, W.1


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