메뉴 건너뛰기




Volumn 54, Issue 20, 2011, Pages 7268-7279

Synthesis and toll-like receptor 4 (TLR4) activity of phosphatidylinositol dimannoside analogues

Author keywords

[No Author keywords available]

Indexed keywords

1 O (1 O HEXADECANOYL 2 O HEXADECYL SN GLYCERO 3 PHOSPHORYL) 2 O (6 O HEXADECANOYL ALPHA DEXTRO MANNOPYRANOSYL) 6 O(ALPHA DEXTRO MANNOPYRANOSYL)DEXTRO MYO INOSITOL; 2 O (1 O HEXADECANOYL 2 O HEXADECYL SN GLYCERO 3 PHOSPHORYL) 1,3 BIS O(ALPHA DEXTRO MANNOPYRANOSYL)GLYCEROL; 2,6 (DI O ALPHA DEXTRO MANNOPYRANOSYL) 1 O(2 DEOXY 1 O HEXADECANOYL 2 N HEXADECANOYLAMINO SN GLYCERO 3 PHOSPHORYL)DEXTRO MYO INOSITOL; 2,6 (DI O ALPHA DEXTRO MANNOPYRANOSYL) 1 O(2 O HEXADECANOYL 1 O HEXADECYL SN GLYCERO 3 PHOSPHORYL)DEXTRO MYO INOSITOL; AMIDE; ESTER DERIVATIVE; ETHER; FATTY ACID ESTER; GLYCEROL; INOSITOL; INTERLEUKIN 6; LIPOPOLYSACCHARIDE; MANNOSIDE; PHOSPHATIDYLGLYCEROL DIMANNOSIDE DERIVATIVE; PHOSPHATIDYLINOSITOL; PHOSPHATIDYLINOSITOL MANNOSIDE; PHOSPHORAMIDOUS ACID DERIVATIVE; RECEPTOR BLOCKING AGENT; TOLL LIKE RECEPTOR 4; TOLL LIKE RECEPTOR AGONIST; UNCLASSIFIED DRUG;

EID: 80054927544     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2008419     Document Type: Article
Times cited : (16)

References (48)
  • 2
    • 77953044679 scopus 로고    scopus 로고
    • Chemical approaches for the study of the mycobacterial glycolipids phosphatidylinositol mannosides, lipomannan and lipoarabinomannan
    • Cao, B.; Williams, S. J. Chemical approaches for the study of the mycobacterial glycolipids phosphatidylinositol mannosides, lipomannan and lipoarabinomannan Nat. Prod. Rep. 2010, 27, 919-947
    • (2010) Nat. Prod. Rep. , vol.27 , pp. 919-947
    • Cao, B.1    Williams, S.J.2
  • 4
    • 70349433667 scopus 로고    scopus 로고
    • Mycobacterium tuberculosis cell wall glycolipids directly inhibit CD4+ T-cell activation by interfering with proximal T-cell-receptor signaling
    • Mahon, R. N.; Rojas, R. E.; Fulton, S. A.; Franko, J. L.; Harding, C. V.; Boom, W. H. Mycobacterium tuberculosis cell wall glycolipids directly inhibit CD4+ T-cell activation by interfering with proximal T-cell-receptor signaling Infect. Immun. 2009, 77, 4574-4583
    • (2009) Infect. Immun. , vol.77 , pp. 4574-4583
    • Mahon, R.N.1    Rojas, R.E.2    Fulton, S.A.3    Franko, J.L.4    Harding, C.V.5    Boom, W.H.6
  • 6
    • 0043032571 scopus 로고    scopus 로고
    • Acylation state of the phosphatidylinositol hexamannosides from Mycobacterium bovis bacillus Calmette Guerin and Mycobacterium tuberculosis H37Rv and its implication in Toll-like receptor response
    • Gilleron, M.; Quesniaux, V. F.; Puzo, G. Acylation state of the phosphatidylinositol hexamannosides from Mycobacterium bovis bacillus Calmette Guerin and Mycobacterium tuberculosis H37Rv and its implication in Toll-like receptor response J. Biol. Chem. 2003, 278, 29880-29890
    • (2003) J. Biol. Chem. , vol.278 , pp. 29880-29890
    • Gilleron, M.1    Quesniaux, V.F.2    Puzo, G.3
  • 9
    • 57549098955 scopus 로고    scopus 로고
    • Chemical synthesis of all phosphatidylinositol mannoside (PIM) glycans from Mycobacterium tuberculosis
    • Boonyarattanakalin, S.; Liu, X.; Michieletti, M.; Lepenies, B.; Seeberger, P. H. Chemical synthesis of all phosphatidylinositol mannoside (PIM) glycans from Mycobacterium tuberculosis J. Am. Chem. Soc. 2008, 130, 16791-16799
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 16791-16799
    • Boonyarattanakalin, S.1    Liu, X.2    Michieletti, M.3    Lepenies, B.4    Seeberger, P.H.5
  • 11
    • 4544288852 scopus 로고    scopus 로고
    • Activation of dendritic cells by liposomes prepared from phosphatidylinositol mannosides from Mycobacterium bovis bacillus Calmette-Guérin and adjuvant activity in vivo
    • DOI 10.1128/IAI.72.9.5235-5246.2004
    • Sprott, G. D.; Dicaire, C. J.; Gurnani, K.; Sad, S.; Krishnan, L. Activation of dendritic cells by liposomes prepared from phosphatidylinositol mannosides from Mycobacterium bovis bacillus Calmette-Guérin and adjuvant activity in vivo Infect. Immun. 2004, 72, 5235-46 (Pubitemid 39223409)
    • (2004) Infection and Immunity , vol.72 , Issue.9 , pp. 5235-5246
    • Sprott, G.D.1    Dicaire, C.J.2    Gurnani, K.3    Sad, S.4    Krishnan, L.5
  • 14
    • 69949141910 scopus 로고    scopus 로고
    • Mycobacterial phosphatidylinositol mannosides negatively regulate host Toll-like receptor 4, MyD88-dependent proinflammatory cytokines, and TRIF-dependent co-stimulatory molecule expression
    • Doz, E.; Rose, S.; Court, N.; Front, S.; Vasseur, V.; Charron, S.; Gilleron, M.; Puzo, G.; Fremaux, I.; Delneste, Y.; Erard, F.; Ryffel, B.; Martin, O. R.; Quesniaux, V. F. Mycobacterial phosphatidylinositol mannosides negatively regulate host Toll-like receptor 4, MyD88-dependent proinflammatory cytokines, and TRIF-dependent co-stimulatory molecule expression J. Biol. Chem. 2009, 284, 23187-23196
    • (2009) J. Biol. Chem. , vol.284 , pp. 23187-23196
    • Doz, E.1    Rose, S.2    Court, N.3    Front, S.4    Vasseur, V.5    Charron, S.6    Gilleron, M.7    Puzo, G.8    Fremaux, I.9    Delneste, Y.10    Erard, F.11    Ryffel, B.12    Martin, O.R.13    Quesniaux, V.F.14
  • 17
    • 33745616513 scopus 로고    scopus 로고
    • Phosphatidylinositol mannosides: Synthesis and suppression of allergic airway disease
    • DOI 10.1016/j.bmc.2006.04.037, PII S0968089606003178
    • Ainge, G. D.; Hudson, J.; Larsen, D. S.; Painter, G. F.; Gill, G. S.; Harper, J. L. Phosphatidylinositol mannosides: synthesis and suppression of allergic airway disease Bioorg. Med. Chem. 2006, 14, 5632-5642 (Pubitemid 43994476)
    • (2006) Bioorganic and Medicinal Chemistry , vol.14 , Issue.16 , pp. 5632-5642
    • Ainge, G.D.1    Hudson, J.2    Larsen, D.S.3    Painter, G.F.4    Gill, G.S.5    Harper, J.L.6
  • 18
    • 33645418472 scopus 로고    scopus 로고
    • Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis
    • Liu, X.; Stocker, B. L.; Seeberger, P. H. Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis J. Am. Chem. Soc. 2006, 128, 3638-3648
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 3638-3648
    • Liu, X.1    Stocker, B.L.2    Seeberger, P.H.3
  • 19
    • 2942562479 scopus 로고    scopus 로고
    • Synthesis of a key Mycobacterium tuberculosis biosynthetic phosphoinositide intermediate
    • DOI 10.1016/j.bmcl.2004.04.103, PII S0960894X04005906
    • Jayaprakash, K. N.; Lu, J.; Fraser-Reid, B. Synthesis of a key Mycobacterium tuberculosis biosynthetic phosphoinositide intermediate Bioorg. Med. Chem. Lett. 2004, 14, 3815-3819 (Pubitemid 38760086)
    • (2004) Bioorganic and Medicinal Chemistry Letters , vol.14 , Issue.14 , pp. 3815-3819
    • Jayaprakash, K.N.1    Lu, J.2    Fraser-Reid, B.3
  • 20
    • 0001260735 scopus 로고
    • Biomimetic synthesis of enantiomerically pure d - Myo -inositol derivatives
    • Bender, S. L.; Budhu, R. J. Biomimetic synthesis of enantiomerically pure d-myo -inositol derivatives J. Am. Chem. Soc. 1991, 113, 9883-9885
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9883-9885
    • Bender, S.L.1    Budhu, R.J.2
  • 22
    • 0001347785 scopus 로고
    • Efficient and systematic syntheses of enantiomerically pure and regiospecifically protected myo -inositols
    • Bruzik, K. S.; Tsai, M. D. Efficient and systematic syntheses of enantiomerically pure and regiospecifically protected myo -inositols J. Am. Chem. Soc. 1992, 114, 6361-6374
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6361-6374
    • Bruzik, K.S.1    Tsai, M.D.2
  • 23
    • 0031012215 scopus 로고    scopus 로고
    • Synthesis of 2,6-di-O-α-D-mannopyranosylphosphatidyl-D-myo- inositol. Utilization of glycosylation and phosphorylation based on phosphite chemistry
    • DOI 10.1016/S0040-4020(96)01038-1, PII S0040402096010381
    • Watanabe, Y.; Yamamoto, T.; Okazaki, T. Synthesis of 2,6-di- O -α- d -mannopyranosylphosphatidyl- d-myo -inositol. Utilization of glycosylation and phosphorylation based on phosphite chemistry Tetrahedron 1997, 53, 903-918 (Pubitemid 27006721)
    • (1997) Tetrahedron , vol.53 , Issue.3 , pp. 903-918
    • Watanabe, Y.1    Yamamoto, T.2    Okazaki, T.3
  • 24
    • 0030039461 scopus 로고    scopus 로고
    • Regiospecific synthesis of 2,6-di- O -(α- d -mannopyranosyl) phosphatidyl- d - Myo- inositol
    • Watanabe, Y.; Yamamoto, T.; Ozaki, S. Regiospecific synthesis of 2,6-di- O -(α- d -mannopyranosyl)phosphatidyl- d-myo- inositol J. Org. Chem. 1996, 61, 14-15
    • (1996) J. Org. Chem. , vol.61 , pp. 14-15
    • Watanabe, Y.1    Yamamoto, T.2    Ozaki, S.3
  • 25
    • 33750020536 scopus 로고    scopus 로고
    • Synthesis of a core arabinomannan oligosaccharide of Mycobacterium tuberculosis
    • DOI 10.1021/jo061233x
    • Hölemann, A.; Stocker, B. L.; Seeberger, P. H. Synthesis of a core arabinomannan oligosaccharide of Mycobacterium tuberculosis J. Org. Chem. 2006, 71, 8071-8088 (Pubitemid 44571813)
    • (2006) Journal of Organic Chemistry , vol.71 , Issue.21 , pp. 8071-8088
    • Holemann, A.1    Stocker, B.L.2    Seeberger, P.H.3
  • 26
    • 0025224783 scopus 로고
    • Synthesis of 6- O -(α- d -mannopyranosyl)- d - Myo -inositol: A fragment from mycobacteria phospholipids
    • Elie, C. J. J.; Verduyn, R.; Dreef, C. E.; Brounts, D. M.; van der Marel, G. A.; van Boom, J. H. Synthesis of 6- O -(α- d -mannopyranosyl)- d-myo -inositol: a fragment from mycobacteria phospholipids Tetrahedron 1990, 46, 8243-8254
    • (1990) Tetrahedron , vol.46 , pp. 8243-8254
    • Elie, C.J.J.1    Verduyn, R.2    Dreef, C.E.3    Brounts, D.M.4    Van Der Marel, G.A.5    Van Boom, J.H.6
  • 27
    • 0035190541 scopus 로고    scopus 로고
    • A phosphatidylinositol 3,4,5-trisphosphate analogue with low serum protein-binding affinity
    • DOI 10.1016/S0968-0896(00)00227-3, PII S0968089600002273
    • Wang, D.-S.; Hsu, A.-L.; Chen, C.-S. A phosphatidylinositol 3,4,5-trisphosphate analogue with low serum protein-binding affinity Bioorg. Med. Chem. 2001, 9, 133-139 (Pubitemid 32007970)
    • (2001) Bioorganic and Medicinal Chemistry , vol.9 , Issue.1 , pp. 133-139
    • Wang, D.-S.1    Hsu, A.-L.2    Chen, C.-S.3
  • 28
    • 0021101291 scopus 로고
    • 3 Na-(1?'6)-alpha-Glc-(1?'6)-alpha-Glc-(1?'3)]- sn -glycerol: A proposed structure for the glyceroglucolipids of human gastric secretion and of the mucous barrier of rat-stomach antrum
    • 3 Na-(1?'6)-alpha-Glc-(1?'6)-alpha-Glc-(1? '3)]- sn -glycerol: a proposed structure for the glyceroglucolipids of human gastric secretion and of the mucous barrier of rat-stomach antrum Carbohydr. Res. 1983, 123, C1-C4
    • (1983) Carbohydr. Res. , vol.123
    • Ogawa, T.1    Horisaki, T.2
  • 29
    • 10444251868 scopus 로고    scopus 로고
    • Small angle X-ray scattering (SAXS) and differential scanning calorimetry (DSC) studies of amide phospholipids
    • Zhai, X.; Bartel, M.; Brezesinski, G.; Rattay, B.; Möhwald, H.; Li, J. Small angle X-ray scattering (SAXS) and differential scanning calorimetry (DSC) studies of amide phospholipids Chem. Phys. Lipids 2005, 133, 79
    • (2005) Chem. Phys. Lipids , vol.133 , pp. 79
    • Zhai, X.1    Bartel, M.2    Brezesinski, G.3    Rattay, B.4    Möhwald, H.5    Li, J.6
  • 30
    • 33749258201 scopus 로고    scopus 로고
    • Phosphatidylinositol mannosides: Synthesis and adjuvant properties of phosphatidylinositol di- and tetramannosides
    • DOI 10.1016/j.bmc.2006.07.003, PII S0968089606005475
    • Ainge, G. D.; Parlane, N. A.; Denis, M.; Hayman, C. M.; Larsen, D. S.; Painter, G. F. Phosphatidylinositol mannosides: synthesis and adjuvant properties of phosphatidylinositol di- and tetramannosides Bioorg. Med. Chem. 2006, 14, 7615-7624 (Pubitemid 44486790)
    • (2006) Bioorganic and Medicinal Chemistry , vol.14 , Issue.22 , pp. 7615-7624
    • Ainge, G.D.1    Parlane, N.A.2    Denis, M.3    Hayman, C.M.4    Larsen, D.S.5    Painter, G.F.6
  • 32
    • 53849104657 scopus 로고    scopus 로고
    • Toward a prostate specific antigen-based prostate cancer diagnostic assay: Preparation of keyhole limpet hemocyanin-conjugated normal and transformed prostate specific antigen fragments
    • Dudkin, V. Y.; Miller, J. S.; Dudkina, A. S.; Danishefsky, S. J.; Antczak, C.; Scheinberg, D. A. Toward a prostate specific antigen-based prostate cancer diagnostic assay: preparation of keyhole limpet hemocyanin-conjugated normal and transformed prostate specific antigen fragments J. Am. Chem. Soc. 2008, 130, 13598-13607
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 13598-13607
    • Dudkin, V.Y.1    Miller, J.S.2    Dudkina, A.S.3    Danishefsky, S.J.4    Antczak, C.5    Scheinberg, D.A.6
  • 33
    • 33846266192 scopus 로고    scopus 로고
    • Donor-bound glycosylation for various glycosyl acceptors: Bidirectional solid-phase semisynthesis of vancomycin and its derivatives
    • Doi, T.; Kinbara, A.; Inoue, H.; Takahashi, T. Donor-bound glycosylation for various glycosyl acceptors: bidirectional solid-phase semisynthesis of vancomycin and its derivatives Chem. Asian J. 2007, 2, 188
    • (2007) Chem. Asian J. , vol.2 , pp. 188
    • Doi, T.1    Kinbara, A.2    Inoue, H.3    Takahashi, T.4
  • 34
    • 65449146342 scopus 로고    scopus 로고
    • Coordinate regulation of TLR-mediated arachidonic acid mobilization in macrophages by group IVA and group v phospholipase A2s
    • Ruiperez, V.; Astudillo, A. M.; Balboa, M. A.; Balsinde, J. Coordinate regulation of TLR-mediated arachidonic acid mobilization in macrophages by group IVA and group V phospholipase A2s J. Immunol. 2009, 182, 3877-83
    • (2009) J. Immunol. , vol.182 , pp. 3877-83
    • Ruiperez, V.1    Astudillo, A.M.2    Balboa, M.A.3    Balsinde, J.4
  • 35
    • 70350244436 scopus 로고    scopus 로고
    • Pseudomonas aeruginosa LPS or flagellin are sufficient to activate TLR-dependent signaling in murine alveolar macrophages and airway epithelial cells
    • e7259
    • Raoust, E.; Balloy, V.; Garcia-Verdugo, I.; Touqui, L.; Ramphal, R.; Chignard, M. Pseudomonas aeruginosa LPS or flagellin are sufficient to activate TLR-dependent signaling in murine alveolar macrophages and airway epithelial cells PLoS One 2009, 4 e7259
    • (2009) PLoS One , vol.4
    • Raoust, E.1    Balloy, V.2    Garcia-Verdugo, I.3    Touqui, L.4    Ramphal, R.5    Chignard, M.6
  • 36
    • 85056050984 scopus 로고    scopus 로고
    • The Toll-like receptor 2/6 ligand MALP-2 reduces the viability of Mycobacterium tuberculosis in murine macrophages
    • Palma, C.; Iona, E.; Ebensen, T.; Guzman, C. A.; Cassone, A. The Toll-like receptor 2/6 ligand MALP-2 reduces the viability of Mycobacterium tuberculosis in murine macrophages Open Microbiol. J. 2009, 3, 47-52
    • (2009) Open Microbiol. J. , vol.3 , pp. 47-52
    • Palma, C.1    Iona, E.2    Ebensen, T.3    Guzman, C.A.4    Cassone, A.5
  • 38
    • 0034780463 scopus 로고    scopus 로고
    • Differential roles of Toll-like receptors in the elicitation of proinflammatory responses by macrophages
    • Jones, B. W.; Heldwein, K. A.; Means, T. K.; Saukkonen, J. J.; Fenton, M. J. Differential roles of Toll-like receptors in the elicitation of proinflammatory responses by macrophages Ann. Rheum. Dis. 2001, 60 (Suppl. 3) iii6-iii12
    • (2001) Ann. Rheum. Dis. , vol.60 , Issue.SUPPL. 3
    • Jones, B.W.1    Heldwein, K.A.2    Means, T.K.3    Saukkonen, J.J.4    Fenton, M.J.5
  • 39
    • 70449097997 scopus 로고    scopus 로고
    • A synthetic analogue of phosphatidylinositol mannoside is an efficient adjuvant
    • In the concentration ranges reported, this class of compound has also previously been shown to be nontoxic in both in vitro and in vivo assay systems. For examples, see ref 14 and the following: Denis, M.; Ainge, G. D.; Larsen, D. S.; Severn, W.; Painter, G. F. A synthetic analogue of phosphatidylinositol mannoside is an efficient adjuvant Immunopharmacol. Immunotoxicol. 2009, 31, 577-582
    • (2009) Immunopharmacol. Immunotoxicol. , vol.31 , pp. 577-582
    • Denis, M.1    Ainge, G.D.2    Larsen, D.S.3    Severn, W.4    Painter, G.F.5
  • 40
    • 0037218547 scopus 로고    scopus 로고
    • Induction of in vitro reprogramming by toll-like receptor (TLR)2 and TLR4 agonists in murine macrophages: Effects of TLR "homotolerance" versus "heterotolerance" on NF-κB signaling pathway components
    • Dobrovolskaia, M. A.; Medvedev, A. E.; Thomas, K. E.; Cuesta, N.; Toshchakov, V.; Ren, T.; Cody, M. J.; Michalek, S. M.; Rice, N. R.; Vogel, S. N. Induction of in vitro reprogramming by Toll-like receptor (TLR)2 and TLR4 agonists in murine macrophages: effects of TLR "homotolerance" versus "heterotolerance" on NF-kappa B J. Immunol. 2003, 170, 508-519 (Pubitemid 36026178)
    • (2003) Journal of Immunology , vol.170 , Issue.1 , pp. 508-519
    • Dobrovolskaia, M.A.1    Medvedev, A.E.2    Thomas, K.E.3    Cuesta, N.4    Toshchakov, V.5    Ren, T.6    Cody, M.J.7    Michalek, S.M.8    Rice, N.R.9    Vogel, S.N.10
  • 42
    • 0037189544 scopus 로고    scopus 로고
    • Monomeric recombinant MD-2 binds toll-like receptor 4 tightly and confers lipopolysaccharide responsiveness
    • DOI 10.1074/jbc.M202554200
    • Re, F.; Strominger, J. L. Monomeric recombinant MD-2 binds Toll-like receptor 4 tightly and confers lipopolysaccharide responsiveness J. Biol. Chem. 2002, 277, 23427-23432 (Pubitemid 34952175)
    • (2002) Journal of Biological Chemistry , vol.277 , Issue.26 , pp. 23427-23432
    • Re, F.1    Strominger, J.L.2
  • 43
    • 67349182481 scopus 로고    scopus 로고
    • The structural basis of lipopolysaccharide recognition by the TLR4-MD-2 complex
    • Park, B. S.; Song, D. H.; Kim, H. M.; Choi, B. S.; Lee, H.; Lee, J. O. The structural basis of lipopolysaccharide recognition by the TLR4-MD-2 complex Nature 2009, 458, 1191-1195
    • (2009) Nature , vol.458 , pp. 1191-1195
    • Park, B.S.1    Song, D.H.2    Kim, H.M.3    Choi, B.S.4    Lee, H.5    Lee, J.O.6
  • 44
    • 77954627827 scopus 로고    scopus 로고
    • Crystal structure of soluble MD-1 and its interaction with lipid IVa
    • Yoon, S. I.; Hong, M.; Han, G. W.; Wilson, I. A. Crystal structure of soluble MD-1 and its interaction with lipid IVa Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 10990-10995
    • (2010) Proc. Natl. Acad. Sci. U.S.A. , vol.107 , pp. 10990-10995
    • Yoon, S.I.1    Hong, M.2    Han, G.W.3    Wilson, I.A.4
  • 46
    • 0037124513 scopus 로고    scopus 로고
    • Synthesis of galactoglycerolipids found in the HT29 human colon carcinoma cell line
    • DOI 10.1016/S0040-4020(02)00473-8, PII S0040402002004738
    • Lindberg, J.; Svensson, S. C. T.; Pahlsson, P.; Konradsson, P. Synthesis of galactoglycerolipids found in the HT29 human colon carcinoma cell line Tetrahedron 2002, 58, 5109-5117 (Pubitemid 34634201)
    • (2002) Tetrahedron , vol.58 , Issue.25 , pp. 5109-5117
    • Lindberg, J.1    Svensson, S.C.T.2    Pahlsson, P.3    Konradsson, P.4
  • 47
    • 0035808967 scopus 로고    scopus 로고
    • 2-(Azidomethyl)benzoyl as a new protecting group in nucleosides
    • DOI 10.1016/S0040-4039(00)02183-3, PII S0040403900021833
    • Wada, T.; Ohkubo, A.; Mochizuki, A.; Sekine, M. 2-(Azidomethyl)benzoyl as a new protecting group in nucleosides Tetrahedron Lett. 2001, 42, 1069-1072 (Pubitemid 32149846)
    • (2001) Tetrahedron Letters , vol.42 , Issue.6 , pp. 1069-1072
    • Wada, T.1    Ohkubo, A.2    Mochizuki, A.3    Sekine, M.4
  • 48
    • 0018290773 scopus 로고
    • Effects of immobilized immune complexes on Fc- and complement-receptor function in resident and thioglycollate-elicited mouse peritoneal macrophages
    • DOI 10.1084/jem.150.3.607
    • Michl, J.; Pieczonka, M. M.; Unkeless, J. C.; Silverstein, S. C. Effects of immobilized immune complexes on Fc- and complement-receptor function in resident and thioglycollate-elicited mouse peritoneal macrophages J. Exp. Med. 1979, 150, 607-621 (Pubitemid 9250732)
    • (1979) Journal of Experimental Medicine , vol.150 , Issue.3 , pp. 607-621
    • Michl, J.1    Pieczonka, M.M.2    Unkeless, J.C.3    Silverstein, S.C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.