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Volumn 15, Issue 3, 2011, Pages 751-757

Synthesis and in vitro inhibition properties of siRNA conjugates carrying glucose and galactose with different presentations

Author keywords

Oligonucleotide synthesis; Oligonucleotide carbohydrate conjugates; RNA interference; siRNA; Tumor necrosis factor

Indexed keywords

ASIALOGLYCOPROTEIN RECEPTOR; CARBOHYDRATE; GALACTOSE; GLUCOSE; SMALL INTERFERING RNA; TUMOR NECROSIS FACTOR ALPHA;

EID: 80051576840     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-011-9305-6     Document Type: Article
Times cited : (28)

References (35)
  • 1
    • 11944267365 scopus 로고
    • Antisense oligonucleotides: A new therapeutic principle
    • 10.1021/cr00102a001 10.1021/cr00102a001 1:CAS:528:DyaK3cXktVKluro%3D
    • E Uhlmann A Peyman 1990 Antisense oligonucleotides: a new therapeutic principle Chem Rev 90 543 584 10.1021/cr00102a001 10.1021/cr00102a001 1:CAS:528:DyaK3cXktVKluro%3D
    • (1990) Chem Rev , vol.90 , pp. 543-584
    • Uhlmann, E.1    Peyman, A.2
  • 2
    • 33751430435 scopus 로고    scopus 로고
    • Building oligonucleotide therapeutics using non-natural chemistries
    • DOI 10.1016/j.cbpa.2006.10.001, PII S1367593106001542
    • C Wilson AD Keefe 2006 Building oligonucleotide therapeutics using non-natural chemistries Curr Opin Chem Biol 10 607 614 10.1016/j.cbpa.2006.10. 001 17049298 10.1016/j.cbpa.2006.10.001 1:CAS:528:DC%2BD28Xht1Kgu7jO (Pubitemid 44821893)
    • (2006) Current Opinion in Chemical Biology , vol.10 , Issue.6 , pp. 607-614
    • Wilson, C.1    Keefe, A.D.2
  • 3
    • 23844543479 scopus 로고    scopus 로고
    • Antisense oligonucleotides: The state of the art
    • DOI 10.2174/0929867054864859
    • T Aboul-Fadl 2005 Antisense oligonucleotides: the state of the art Curr Med Chem 12 2193 2214 10.2174/0929867054864859 16178780 10.2174/0929867054864859 1:CAS:528:DC%2BD2MXpsVegurY%3D (Pubitemid 41179707)
    • (2005) Current Medicinal Chemistry , vol.12 , Issue.19 , pp. 2193-2214
    • Aboul-Fadl, T.1
  • 4
    • 33745211255 scopus 로고    scopus 로고
    • Antisense oligonucleotides: From design to therapeutic application
    • 10.1111/j.1440-1681.2006.04403.x 16700890 10.1111/j.1440-1681.2006.04403. x 1:CAS:528:DC%2BD28XlvFCmt70%3D
    • JH Chan S Lim WS Wong 2006 Antisense oligonucleotides: from design to therapeutic application Clin Exp Pharmacol Physiol 33 533 540 10.1111/j.1440-1681.2006.04403.x 16700890 10.1111/j.1440-1681.2006.04403.x 1:CAS:528:DC%2BD28XlvFCmt70%3D
    • (2006) Clin Exp Pharmacol Physiol , vol.33 , pp. 533-540
    • Chan, J.H.1    Lim, S.2    Wong, W.S.3
  • 5
    • 33751099034 scopus 로고    scopus 로고
    • RNAi therapeutics: A potential new class of pharmaceutical drugs
    • DOI 10.1038/nchembio839, PII NCHEMBIO839
    • D Bumcrot M Manoharan V Koteliansky DWY Sah 2006 RNAi therapeutics: a potential new class of pharmaceutical drugs Nat Chem Biol 2 711 719 10.1038/nchembio839 17108989 10.1038/nchembio839 1:CAS:528:DC%2BD28Xht1SrtLfO (Pubitemid 44764213)
    • (2006) Nature Chemical Biology , vol.2 , Issue.12 , pp. 711-719
    • Bumcrot, D.1    Manoharan, M.2    Koteliansky, V.3    Sah, D.W.Y.4
  • 6
    • 11844251207 scopus 로고    scopus 로고
    • RNA interference in vivo: Toward synthetic small inhibitory RNA-based therapeutics
    • DOI 10.1016/S0076-6879(04)92016-2, PII S0076687904920162
    • A De Fougerolles M Manoharan R Meyers HP Vornlocher 2005 RNA interference in vivo: toward synthetic small inhibitory RNA-based therapeutics Method Enzymol 392 278 296 10.1016/S0076-6879(04)92016-2 10.1016/S0076-6879(04)92016-2 1:CAS:528:DC%2BD2MXksFGntrs%3D (Pubitemid 40092520)
    • (2005) Methods in Enzymology , vol.392 , pp. 278-296
    • Fougerolles, A.D.1    Manoharan, M.2    Meyers, R.3    Vornlocher, H.-P.4
  • 7
    • 24144458271 scopus 로고    scopus 로고
    • Ribozymes, DNAzymes and small interfering RNAs as therapeutics
    • DOI 10.2174/1389450054863653
    • M Sioud PO Iversen 2005 Ribozymes, DNAzymes and small interfering RNAs as therapeutics Curr Drug Targets 6 647 653 10.2174/1389450054863653 16178798 10.2174/1389450054863653 1:CAS:528:DC%2BD2MXps12iu7o%3D (Pubitemid 41236548)
    • (2005) Current Drug Targets , vol.6 , Issue.6 , pp. 647-653
    • Sioud, M.1    Iversen, P.O.2
  • 8
    • 0037373763 scopus 로고    scopus 로고
    • Structural modifications of antisense oligonucleotides
    • DOI 10.1016/S0014-827X(03)00022-3
    • E Urban CR Noe 2003 Structural modifications of antisense oligonucleotides Farmaco 58 243 258 10.1016/S0014-827X(03)00022-3 12620420 10.1016/S0014-827X(03)00022-3 1:CAS:528:DC%2BD3sXhs1CktLc%3D (Pubitemid 36279698)
    • (2003) Farmaco , vol.58 , Issue.3 , pp. 243-258
    • Urban, E.1    Noe, C.R.2
  • 9
    • 61849162695 scopus 로고    scopus 로고
    • SiRNA conjugate delivery systems
    • 10.1021/bc800278e 10.1021/bc800278e 1:CAS:528:DC%2BD1cXhtl2ltb3P
    • JH Jeong H Mok YK Oh TG Park 2009 siRNA conjugate delivery systems Bioconjugate Chem 20 5 14 10.1021/bc800278e 10.1021/bc800278e 1:CAS:528:DC%2BD1cXhtl2ltb3P
    • (2009) Bioconjugate Chem , vol.20 , pp. 5-14
    • Jeong, J.H.1    Mok, H.2    Oh, Y.K.3    Park, T.G.4
  • 10
    • 33847642135 scopus 로고    scopus 로고
    • Glycotargeting to improve cellular delivery efficiency of nucleic acids
    • DOI 10.1007/s10719-006-9023-y
    • H Yan K Tram 2007 Glycotargeting to improve cellular delivery efficiency of nucleic acids Glycoconjugate J 24 107 123 10.1007/s10719-006-9023-y 10.1007/s10719-006-9023-y 1:CAS:528:DC%2BD2sXitlCrs70%3D (Pubitemid 46352522)
    • (2007) Glycoconjugate Journal , vol.24 , Issue.2-3 , pp. 107-123
    • Yan, H.1    Tram, K.2
  • 11
    • 77249174795 scopus 로고    scopus 로고
    • Recent developments in carbohydrate-decorated targeted drug/gene delivery
    • 10.1002/med.20171 19626595 10.1002/med.20169 1:CAS:528: DC%2BC3cXktlSku7c%3D
    • H Zhang Y Ma XL Sun 2010 Recent developments in carbohydrate-decorated targeted drug/gene delivery Med Res Rev 30 270 289 10.1002/med.20171 19626595 10.1002/med.20169 1:CAS:528:DC%2BC3cXktlSku7c%3D
    • (2010) Med Res Rev , vol.30 , pp. 270-289
    • Zhang, H.1    Ma, Y.2    Sun, X.L.3
  • 12
    • 38949186041 scopus 로고    scopus 로고
    • Site-specific delivery of oligonucleotides to hepatocytes after systemic administration
    • DOI 10.1021/bc070126m
    • L Zhu Z Ye K Cheng DD Miller RI Mahato 2008 Site-specific delivery of oligonucleotides to hepatocytes after systemic administration Bioconjugate Chem 19 290 298 10.1021/bc070126m 10.1021/bc070126m 1:CAS:528:DC%2BD2sXhtVansbnI (Pubitemid 351213861)
    • (2008) Bioconjugate Chemistry , vol.19 , Issue.1 , pp. 290-298
    • Zhu, L.1    Ye, Z.2    Cheng, K.3    Miller, D.D.4    Mahato, R.I.5
  • 13
    • 0037254743 scopus 로고    scopus 로고
    • Solid-phase synthesis of multivalent glycoconjugates on a DNA synthesizer
    • DOI 10.1021/bc0256244
    • M Dubber JM Fréchet 2003 Solid-phase synthesis of multivalent glycoconjugates on a DNA synthesizer Bioconjugate Chem 14 239 246 10.1021/bc0256244 10.1021/bc0256244 1:CAS:528:DC%2BD38Xps1Wqtrs%3D (Pubitemid 36169038)
    • (2003) Bioconjugate Chemistry , vol.14 , Issue.1 , pp. 239-246
    • Dubber, M.1    Frechet, J.M.J.2
  • 14
    • 77954874073 scopus 로고    scopus 로고
    • Synthesis, cell-surface binding, and cellular uptake of fluorescently labeled glucose-DNA conjugates with different carbohydrate presentation
    • 10.1021/bc100079n 10.1021/bc100079n 1:CAS:528:DC%2BC3cXotVOmu70%3D
    • B Ugarte-Uribe S Pérez-Rentero R Lucas A Aviñó JJ Reina I Alkorta R Eritja JC Morales 2010 Synthesis, cell-surface binding, and cellular uptake of fluorescently labeled glucose-DNA conjugates with different carbohydrate presentation Bioconjugate Chem 21 1280 1287 10.1021/bc100079n 10.1021/bc100079n 1:CAS:528:DC%2BC3cXotVOmu70%3D
    • (2010) Bioconjugate Chem , vol.21 , pp. 1280-1287
    • Ugarte-Uribe, B.1    Pérez-Rentero, S.2    Lucas, R.3    Aviñó, A.4    Reina, J.J.5    Alkorta, I.6    Eritja, R.7    Morales, J.C.8
  • 15
    • 53849145719 scopus 로고    scopus 로고
    • Experimental measurement of carbohydrate-aromatic stacking in water by using a dangling-ended DNA model system
    • 10.1002/chem.200800335 10.1002/chem.200800335 1:CAS:528: DC%2BD1cXhtF2mu77P
    • JC Morales JJ Reina I Díaz A Aviñó PM Nieto R Eritja 2008 Experimental measurement of carbohydrate-aromatic stacking in water by using a dangling-ended DNA model system Chem Eur J 14 7828 7835 10.1002/chem.200800335 10.1002/chem.200800335 1:CAS:528:DC%2BD1cXhtF2mu77P
    • (2008) Chem Eur J , vol.14 , pp. 7828-7835
    • Morales, J.C.1    Reina, J.J.2    Díaz, I.3    Aviñó, A.4    Nieto, P.M.5    Eritja, R.6
  • 16
    • 12244274312 scopus 로고    scopus 로고
    • Synthesis of antisense oligonucleotides conjugated to a multivalent carbohydrate cluster for cellular targeting
    • DOI 10.1021/bc020028v
    • MA Maier CG Yannopoulos N Mohamed A Roland H Fritz V Mohan G Just M Manoharan 2003 Synthesis of antisense oligonucleotides conjugated to a multivalent carbohydrate cluster for cellular targeting Bioconjugate Chem 14 18 29 10.1021/bc020028v 10.1021/bc020028v 1:CAS:528:DC%2BD38XptFChtrs%3D (Pubitemid 36169013)
    • (2003) Bioconjugate Chemistry , vol.14 , Issue.1 , pp. 18-29
    • Maier, M.A.1    Yannopoulos, C.G.2    Mohamed, N.3    Roland, A.4    Fritz, H.5    Mohan, V.6    Just, G.7    Manoharan, M.8
  • 17
    • 13644254495 scopus 로고    scopus 로고
    • Lactosylated poly(ethylene glycol)-siRNA conjugate through acid-labile β-thiopropionate linkage to construct pH-sensitive polyion complex micelles achieving enhanced gene silencing in hepatoma cells
    • DOI 10.1021/ja044941d
    • M Oishi Y Nagasaki K Itaka N Nishiyama K Kataoka 2005 Lactosylated poly(ethylene glycol)-siRNA conjugate through acid-labile β-thiopropionate linkage to construct pH-sensitive polyion complex micelles achieving enhanced gene silencing in hepatoma cells J Am Chem Soc 127 1624 1625 10.1021/ja044941d 15700981 10.1021/ja044941d 1:CAS:528:DC%2BD2MXmsVarsQ%3D%3D (Pubitemid 40229133)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.6 , pp. 1624-1625
    • Oishi, M.1    Nagasaki, Y.2    Itaka, K.3    Nishiyama, N.4    Kataoka, K.5
  • 19
    • 17444393481 scopus 로고    scopus 로고
    • Synthesis and applications of oligonucleotide-carbohydrate conjugates
    • 10.1002/cbdv.200490104 17191787 10.1002/cbdv.200490104 1:CAS:528:DC%2BD2cXpvVCisbs%3D
    • TS Zatsepin TS Oretskaya 2004 Synthesis and applications of oligonucleotide-carbohydrate conjugates Chem Biodivers 1 1401 1417 10.1002/cbdv.200490104 17191787 10.1002/cbdv.200490104 1:CAS:528: DC%2BD2cXpvVCisbs%3D
    • (2004) Chem Biodivers , vol.1 , pp. 1401-1417
    • Zatsepin, T.S.1    Oretskaya, T.S.2
  • 20
    • 67649231388 scopus 로고    scopus 로고
    • Solid-phase synthesis of oligonucleotides conjugates useful for delivery and targeting of potencial nucleic acid therapeutics
    • 10.1021/bc800406a 10.1021/bc800406a
    • H Lönnberg 2009 Solid-phase synthesis of oligonucleotides conjugates useful for delivery and targeting of potencial nucleic acid therapeutics Bioconjugate Chem 20 1065 1094 10.1021/bc800406a 10.1021/bc800406a
    • (2009) Bioconjugate Chem , vol.20 , pp. 1065-1094
    • Lönnberg, H.1
  • 21
    • 0029116896 scopus 로고
    • Synthesis of mono- and dimannoside phosphoramidite derivatives for solid-phase conjugation to oligonucleotides
    • 10.1016/0040-4039(95)01512-G 10.1016/0040-4039(95)01512-G 1:CAS:528:DyaK2MXosVWqu74%3D
    • S Akhtar A Routledge R Patel JM Gardiner 1995 Synthesis of mono- and dimannoside phosphoramidite derivatives for solid-phase conjugation to oligonucleotides Tetrahedron Lett 36 7333 7336 10.1016/0040-4039(95)01512-G 10.1016/0040-4039(95)01512-G 1:CAS:528:DyaK2MXosVWqu74%3D
    • (1995) Tetrahedron Lett , vol.36 , pp. 7333-7336
    • Akhtar, S.1    Routledge, A.2    Patel, R.3    Gardiner, J.M.4
  • 22
    • 85047696800 scopus 로고    scopus 로고
    • Nucleoglycoconjugates: Design and synthesis of a new class of DNA-carbohydrate conjugates
    • 10.1002/1521-3773(20001016)39:20 1:CAS:528:DC%2BD3cXnsFGmtLc%3D
    • TL Sheppard C-H Wong GF Joyce 2000 Nucleoglycoconjugates: design and synthesis of a new class of DNA-carbohydrate conjugates Angew Chem Int Ed 39 3660 3663 10.1002/1521-3773(20001016)39:20 1:CAS:528:DC%2BD3cXnsFGmtLc%3D
    • (2000) Angew Chem Int Ed , vol.39 , pp. 3660-3663
    • Sheppard, T.L.1    Wong, C.-H.2    Joyce, G.F.3
  • 23
    • 3142663253 scopus 로고    scopus 로고
    • Modulating the activity of oligonucleotides by carbohydrate conjugation: Solid phase synthesis of sucrose-oligonucleotide hybrids
    • 10.1039/b401819b 15227540 10.1039/b401819b 1:CAS:528:DC%2BD2cXlt1altr0%3D
    • M Adinolfi L De Napoli G Di Fabio A Iadonisi D Montesarchio 2004 Modulating the activity of oligonucleotides by carbohydrate conjugation: solid phase synthesis of sucrose-oligonucleotide hybrids Org Biomol Chem 2 1879 1886 10.1039/b401819b 15227540 10.1039/b401819b 1:CAS:528:DC%2BD2cXlt1altr0%3D
    • (2004) Org Biomol Chem , vol.2 , pp. 1879-1886
    • Adinolfi, M.1    De Napoli, L.2    Di Fabio, G.3    Iadonisi, A.4    Montesarchio, D.5
  • 24
    • 64549094682 scopus 로고    scopus 로고
    • Synthesis of mannose and galactose oligonucleotide conjugates by bi-click chemistry
    • 10.1021/jo802536q 19123843 10.1021/jo802536q 1:CAS:528: DC%2BD1MXktVOhug%3D%3D
    • G Pourceau A Meyer JJ Vasseur F Morvan 2009 Synthesis of mannose and galactose oligonucleotide conjugates by bi-click chemistry J Org Chem 74 1218 1222 10.1021/jo802536q 19123843 10.1021/jo802536q 1:CAS:528: DC%2BD1MXktVOhug%3D%3D
    • (2009) J Org Chem , vol.74 , pp. 1218-1222
    • Pourceau, G.1    Meyer, A.2    Vasseur, J.J.3    Morvan, F.4
  • 25
    • 0035968991 scopus 로고    scopus 로고
    • Efficient preparation of carbohydrate-oligonucleotide conjugates (COCs) using oxime bond formation
    • DOI 10.1016/S0040-4039(01)01682-3, PII S0040403901016823
    • D Forget O Renaudet E Defranq P Dumy 2001 Efficient preparation of carbohydrate-oligonucleotide conjugates (COCs) using oxime bond formation Tetrahedron Lett 42 7829 7832 10.1016/S0040-4039(01)01682-3 10.1016/S0040- 4039(01)01682-3 1:CAS:528:DC%2BD3MXnsV2rs7Y%3D (Pubitemid 32971796)
    • (2001) Tetrahedron Letters , vol.42 , Issue.44 , pp. 7829-7832
    • Forget, D.1    Renaudet, O.2    Defrancq, E.3    Dumy, P.4
  • 26
    • 3242786469 scopus 로고    scopus 로고
    • Solid-phase synthesis of multiantennary oligonucleotide glycoconjugates utilizing on-support oximation
    • DOI 10.1021/bc049955n
    • J Katajisto H Virta H Lönnberg 2004 Solid-phase synthesis of multiantennary oligonucleotide glycoconjugates utilizing on-support oximation Bioconjugate Chem 15 890 896 10.1021/bc049955n 10.1021/bc049955n 1:CAS:528:DC%2BD2cXlt1Sjurs%3D (Pubitemid 38981965)
    • (2004) Bioconjugate Chemistry , vol.15 , Issue.4 , pp. 890-896
    • Katajisto, J.1    Virta, P.2    Lonnberg, H.3
  • 27
    • 0036738585 scopus 로고    scopus 로고
    • Synthesis of N-acetyl-d-galactosamine and folic acid conjugated ribozymes
    • 10.1021/bc025525q 10.1021/bc025525q 1:CAS:528:DC%2BD38XltFKrsLk%3D
    • J Matulic-Adamic V Serebryany P Haeberli VR Mokler L Beigelman 2002 Synthesis of N-acetyl-d-galactosamine and folic acid conjugated ribozymes Bioconjugate Chem 13 1071 1078 10.1021/bc025525q 10.1021/bc025525q 1:CAS:528:DC%2BD38XltFKrsLk%3D
    • (2002) Bioconjugate Chem , vol.13 , pp. 1071-1078
    • Matulic-Adamic, J.1    Serebryany, V.2    Haeberli, P.3    Mokler, V.R.4    Beigelman, L.5
  • 28
    • 2342452008 scopus 로고    scopus 로고
    • The oxime bond formation as an efficient chemical tool for the preparation of 3′,5′-bifunctionalised oligodeoxyribonucleotides
    • DOI 10.1016/j.bmcl.2004.03.053, PII S0960894X0400407X
    • OP Edupuganti O Renaudet E Defrancq P Dumy 2004 The oxime bond formation as an efficient chemical tool for the preparation of 3',5'-bifunctionalised oligodeoxyribonucleotides Bioorg Med Chem Lett 14 2839 2842 10.1016/j.bmcl.2004. 03.053 15125943 10.1016/j.bmcl.2004.03.053 1:CAS:528:DC%2BD2cXjs1amtb4%3D (Pubitemid 38569747)
    • (2004) Bioorganic and Medicinal Chemistry Letters , vol.14 , Issue.11 , pp. 2839-2842
    • Edupuganti, O.P.1    Renaudet, O.2    Defrancq, E.3    Dumy, P.4
  • 29
    • 70349770699 scopus 로고    scopus 로고
    • Synthesis and characterization of mannosylated oligoribonucleotides
    • 10.1016/j.carres.2009.08.033 19765694 10.1016/j.carres.2009.08.033 1:CAS:528:DC%2BD1MXht1Ggt7zO
    • Y Zhao K Tram H Yan 2009 Synthesis and characterization of mannosylated oligoribonucleotides Carbohydr Res 344 2137 2143 10.1016/j.carres.2009.08.033 19765694 10.1016/j.carres.2009.08.033 1:CAS:528:DC%2BD1MXht1Ggt7zO
    • (2009) Carbohydr Res , vol.344 , pp. 2137-2143
    • Zhao, Y.1    Tram, K.2    Yan, H.3
  • 30
    • 0141552295 scopus 로고    scopus 로고
    • Gene silencing by systemic delivery of synthetic siRNAs in adult mice
    • DOI 10.1016/S0022-2836(03)00181-5
    • DR Sorensen M Leirdal MJ Sioud 2003 Gene silencing by systemic delivery of synthetic siRNA in adult mice J Mol Biol 327 761 766 10.1016/S0022-2836(03) 00181-5 12654261 10.1016/S0022-2836(03)00181-5 1:CAS:528:DC%2BD3sXitlWgs7o%3D (Pubitemid 36315917)
    • (2003) Journal of Molecular Biology , vol.327 , Issue.4 , pp. 761-766
    • Sorensen, D.R.1    Leirdal, M.2    Sioud, M.3
  • 31
    • 11844271384 scopus 로고
    • Synthesis of glycol glucosides
    • 10.1021/ja01861a058 10.1021/ja01861a058 1:CAS:528:DyaH3cXisVWgtg%3D%3D
    • S Karjala KP Link 1940 Synthesis of glycol glucosides J Am Chem Soc 62 917 920 10.1021/ja01861a058 10.1021/ja01861a058 1:CAS:528:DyaH3cXisVWgtg%3D%3D
    • (1940) J Am Chem Soc , vol.62 , pp. 917-920
    • Karjala, S.1    Link, K.P.2
  • 32
    • 0141648496 scopus 로고    scopus 로고
    • Synthesis of branched oligonucleotides as templates for the assembly of nanomaterials
    • DOI 10.1002/hlca.200390232
    • M Grimau D Iacopino A Aviñó BG de la Torre A Ongaro D Fitzmaurice J Wessels R Eritja 2003 Synthesis of branched oligonucleotides as templates for the assembly of nanomaterials Helv Chim Acta 86 2814 2826 10.1002/hlca.200390232 10.1002/hlca.200390232 1:CAS:528:DC%2BD3sXnsVSqu7Y%3D (Pubitemid 37128249)
    • (2003) Helvetica Chimica Acta , vol.86 , Issue.8 , pp. 2814-2826
    • Grimau, M.G.1    Iacopino, D.2    Avino, A.3    De La Torre, B.G.4    Ongaro, A.5    Fitzmaurice, D.6    Wessels, J.7    Eritja, R.8
  • 33
    • 0035813464 scopus 로고    scopus 로고
    • Synthesis of galactosyl compounds for targeted gene delivery
    • DOI 10.1016/S0968-0896(01)00203-6, PII S0968089601002036
    • T Ren G Zhang D Liu 2001 Synthesis of galactosyl compounds for targeted gene delivery Bioorg Med Chem 9 2969 2978 10.1016/S0968-0896(01)00203-6 11597478 10.1016/S0968-0896(01)00203-6 1:CAS:528:DC%2BD3MXosVGkuro%3D (Pubitemid 32904541)
    • (2001) Bioorganic and Medicinal Chemistry , vol.9 , Issue.11 , pp. 2969-2978
    • Ren, T.1    Zhang, G.2    Liu, D.3
  • 34
    • 0028903260 scopus 로고
    • Synthesis of cluster galactosides with high affinity for the hepatic asialoglycoprotein receptor
    • 10.1021/jm00009a014 7739012 10.1021/jm00009a014 1:CAS:528: DyaK2MXltVyiu7k%3D
    • EAL Biessen DM Beuting HCPF Roelen GA van der Marel JH van Boom TJC Van Berkel 1995 Synthesis of cluster galactosides with high affinity for the hepatic asialoglycoprotein receptor J Med Chem 38 1538 1546 10.1021/jm00009a014 7739012 10.1021/jm00009a014 1:CAS:528:DyaK2MXltVyiu7k%3D
    • (1995) J Med Chem , vol.38 , pp. 1538-1546
    • Biessen, E.A.L.1    Beuting, D.M.2    Hcpf, R.3    Van Der Marel, G.A.4    Van Boom, J.H.5    Van Berkel, T.J.C.6


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