메뉴 건너뛰기




Volumn 5, Issue 1, 1999, Pages 46-55

Solid phase synthesis of glycopeptide dendrimers with Tn antigenic structure and their biological activities. Part I

Author keywords

Glycopeptide dendrimers; Molecular modelling; Multiple antigen glycopeptide systems (MAGs); Solid phase peptide synthesis SPPS); Tn antigens; Tumour associated antigens

Indexed keywords

ANTIGEN; ANTISERUM; DENDRIMER; GLYCOPEPTIDE; MONOCLONAL ANTIBODY; TUMOR VACCINE;

EID: 2442752590     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1387(199901)5:1<46::AID-PSC179>3.0.CO;2-C     Document Type: Article
Times cited : (25)

References (45)
  • 2
    • 0141552213 scopus 로고
    • Blood group a cross-reacting epitope defined by monoclonal antibodies NCC-LU-35 and -81 expressed in cancer of blood group O or B individuals: Its identification as Tn antigen
    • S. Hirohashi, H. Clausen, T. Yamada, Y. Shimosato and S. Hakomori (1985). Blood group A cross-reacting epitope defined by monoclonal antibodies NCC-LU-35 and -81 expressed in cancer of blood group O or B individuals: its identification as Tn antigen. Proc. Natl. Acad. Sci. USA 82, 7039-7043.
    • (1985) Proc. Natl. Acad. Sci. USA , vol.82 , pp. 7039-7043
    • Hirohashi, S.1    Clausen, H.2    Yamada, T.3    Shimosato, Y.4    Hakomori, S.5
  • 3
    • 84965819890 scopus 로고
    • Immunoglobulin G3 monoclonal antibody directed to Tn antigen (tumor-associated alpha-N-acetylgalactosaminyl epitope) that does not cross-react with blood group a antigen
    • H. Takahashi, R. Metoki and S. Hakomori (1988). Immunoglobulin G3 monoclonal antibody directed to Tn antigen (tumor-associated alpha-N-acetylgalactosaminyl epitope) that does not cross-react with blood group A antigen. Cancer Res. 48, 4361-4367.
    • (1988) Cancer Res. , vol.48 , pp. 4361-4367
    • Takahashi, H.1    Metoki, R.2    Hakomori, S.3
  • 4
    • 0021141716 scopus 로고
    • T and Tn, general carcinoma autoantigens
    • G.F. Springer (1984). T and Tn, general carcinoma autoantigens. Science 224, 1198-1206.
    • (1984) Science , vol.224 , pp. 1198-1206
    • Springer, G.F.1
  • 5
    • 0025584540 scopus 로고
    • Pancarcinoma T and Tn epitopes: Autoimmunogens and diagnostic markers that reveal incipient carcinomas and help establish prognosis
    • R.B. Herberman and D.W. Mercer, Eds. Marcel Dekker, New York
    • G.F. Springer and P.R. Desai. Pancarcinoma T and Tn epitopes: Autoimmunogens and diagnostic markers that reveal incipient carcinomas and help establish prognosis, in: Immunodiagnosis of Cancer, 2nd Edition, R.B. Herberman and D.W. Mercer, Eds. p. 587-612, Marcel Dekker, New York, 1990.
    • (1990) Immunodiagnosis of Cancer, 2nd Edition , pp. 587-612
    • Springer, G.F.1    Desai, P.R.2
  • 6
    • 0023880015 scopus 로고
    • Preparation and characterization of monoclonal antibodies directed to the tumor-associated O-linked sialosyl-2-6 alpha-N-acetylgalactosaminyl (sialosyl-Tn) epitope
    • T. Kjeldsen, H. Clausen, S. Hirohashi, T. Ogawa, H. Iijima and S. Hakomori (1988). Preparation and characterization of monoclonal antibodies directed to the tumor-associated O-linked sialosyl-2-6 alpha-N-acetylgalactosaminyl (sialosyl-Tn) epitope. Cancer Res. 48, 2214-2220.
    • (1988) Cancer Res. , vol.48 , pp. 2214-2220
    • Kjeldsen, T.1    Clausen, H.2    Hirohashi, S.3    Ogawa, T.4    Iijima, H.5    Hakomori, S.6
  • 7
    • 0024528006 scopus 로고
    • Human lung carcinoma monoclonal antibody specific for the Thomsen-Friedenreich antigen
    • R. Stein, S. Chen, W. Grossman and M. Goldenberg (1989). Human lung carcinoma monoclonal antibody specific for the Thomsen-Friedenreich antigen. Cancer Res. 49, 32-37.
    • (1989) Cancer Res. , vol.49 , pp. 32-37
    • Stein, R.1    Chen, S.2    Grossman, W.3    Goldenberg, M.4
  • 8
    • 0024547438 scopus 로고
    • Tn epitope (N-acetyl-D-galactosamine-O-serine/threonine) density in primary breast carcinoma: A functional predictor of aggresiveness
    • G.F. Springer (1989). Tn epitope (N-acetyl-D-galactosamine-O-serine/threonine) density in primary breast carcinoma: A functional predictor of aggresiveness. Mol. Immunol. 26, 1-5.
    • (1989) Mol. Immunol. , vol.26 , pp. 1-5
    • Springer, G.F.1
  • 9
    • 0024288294 scopus 로고
    • Blood group Tn-active macromolecules from human carcinomas and erythrocytes: Characterization of and specific reactivity with monoand poly-clonal anti-Tn antibodies induced by various immunogens
    • G.F. Springer, E.V. Chanderasekaran, P.R. Desai and H. Tegtmeyer (1988). Blood group Tn-active macromolecules from human carcinomas and erythrocytes: characterization of and specific reactivity with monoand poly-clonal anti-Tn antibodies induced by various immunogens. Carbohydr. Res. 178, 271-292.
    • (1988) Carbohydr. Res. , vol.178 , pp. 271-292
    • Springer, G.F.1    Chanderasekaran, E.V.2    Desai, P.R.3    Tegtmeyer, H.4
  • 10
    • 0026488299 scopus 로고
    • Monoclonal antibodies against partially deglycosylated colon cancer mucin that recognize Tn antigen
    • J. Huang, J.C. Byrd. B. Siddiki, M. Yuan, E. Lau and Y.S. Kim (1992). Monoclonal antibodies against partially deglycosylated colon cancer mucin that recognize Tn antigen. Disease Markers 10, 81-94.
    • (1992) Disease Markers , vol.10 , pp. 81-94
    • Huang, J.1    Byrd, J.C.2    Siddiki, B.3    Yuan, M.4    Lau, E.5    Kim, Y.S.6
  • 11
    • 0024371948 scopus 로고
    • Are pancarcinoma T and Tn differentiation antigens?
    • N. Barr, C.R. Taylor, T. Young and G.F. Springer (1989). Are pancarcinoma T and Tn differentiation antigens? Cancer 64, 834-841.
    • (1989) Cancer , vol.64 , pp. 834-841
    • Barr, N.1    Taylor, C.R.2    Young, T.3    Springer, G.F.4
  • 12
    • 0026451818 scopus 로고
    • An O-linked carbohydrate neutralization epitope of HIV-1 gp 120 is expressed by HIV-1 env gene recombinant vaccinia virus
    • J.E.S. Hansen, H. Clausen, S.L. Hu, J.O. Nielsen and S. Olofsson (1992). An O-linked carbohydrate neutralization epitope of HIV-1 gp 120 is expressed by HIV-1 env gene recombinant vaccinia virus. Arch. Virol. 126, 11-20.
    • (1992) Arch. Virol. , vol.126 , pp. 11-20
    • Hansen, J.E.S.1    Clausen, H.2    Hu, S.L.3    Nielsen, J.O.4    Olofsson, S.5
  • 13
    • 0026562970 scopus 로고
    • The human repertoire of antibody specifities against Thomsen-Friedenreich and Tn-carcinoma associated antigens as defined by human monoclonal antibodies
    • B. Jansson and C.A. Borrebaeck (1992). The human repertoire of antibody specifities against Thomsen-Friedenreich and Tn-carcinoma associated antigens as defined by human monoclonal antibodies. Cancer Immunol. Immunother. 34, 294-298.
    • (1992) Cancer Immunol. Immunother. , vol.34 , pp. 294-298
    • Jansson, B.1    Borrebaeck, C.A.2
  • 14
    • 0026673512 scopus 로고
    • Immunization of colorectal cancer patients with modified ovine submaxilary mucin and adjuvants induces IgM and IgG antibodies to sialylated Tn
    • K.P. O'Boyle, R. Zamore, S. Adluri, A. Cohen, N. Kemeny, S. Welt, K.O. Lloyd, H.F. Oettgen, L.J. Old and P.O. Livingston (1992). Immunization of colorectal cancer patients with modified ovine submaxilary mucin and adjuvants induces IgM and IgG antibodies to sialylated Tn. Cancer Res. 52, 5663-5667.
    • (1992) Cancer Res. , vol.52 , pp. 5663-5667
    • O'Boyle, K.P.1    Zamore, R.2    Adluri, S.3    Cohen, A.4    Kemeny, N.5    Welt, S.6    Lloyd, K.O.7    Oettgen, H.F.8    Old, L.J.9    Livingston, P.O.10
  • 15
    • 0027411101 scopus 로고
    • Idiotypes of pre-existing human anti-carcinoma anti-T and anti-Tn antibodies
    • M. Zanetti, G. Lenert and G.F. Springer (1992). Idiotypes of pre-existing human anti-carcinoma anti-T and anti-Tn antibodies. Int. Immunol. 5, 113-119.
    • (1992) Int. Immunol. , vol.5 , pp. 113-119
    • Zanetti, M.1    Lenert, G.2    Springer, G.F.3
  • 17
    • 0027218906 scopus 로고
    • Pancarcinoma T/Tn antigen detects human carcinoma long before biopsy does and its vaccine prevents breast carcinoma recurrence
    • Annals of the New York Academy of Sciences, J.C. Bystryn, S. Ferrone, P. Livingston, Eds
    • G.F. Springer, P.R. Desai, H. Tegtmeyer, B.D. Spencer and E.F. Scanlon. Pancarcinoma T/Tn antigen detects human carcinoma long before biopsy does and its vaccine prevents breast carcinoma recurrence, in: Specific Immunotherapy of Cancer with Vaccines, Annals of the New York Academy of Sciences, Vol. 690, J.C. Bystryn, S. Ferrone, P. Livingston, Eds, 1993, p. 355-357.
    • (1993) Specific Immunotherapy of Cancer with Vaccines , vol.690 , pp. 355-357
    • Springer, G.F.1    Desai, P.R.2    Tegtmeyer, H.3    Spencer, B.D.4    Scanlon, E.F.5
  • 18
    • 0028539094 scopus 로고
    • Synthetic carbohydrate vaccines: Synthesis and immunogenicity of Tn antigen conjugates
    • T. Toyokuni, S. Hakomori and A.K. Singhal (1994). Synthetic carbohydrate vaccines: Synthesis and immunogenicity of Tn antigen conjugates. Bioorg. Med. Chem. 2, 1119-1132.
    • (1994) Bioorg. Med. Chem. , vol.2 , pp. 1119-1132
    • Toyokuni, T.1    Hakomori, S.2    Singhal, A.K.3
  • 19
    • 0025287472 scopus 로고
    • Synthetic vaccines: I. Synthesis of multivalent Tn antigen cluster-lysyllysine conjugates
    • T. Toyokuni, B. Dean and S. Hakomori (1990). Synthetic vaccines: I. Synthesis of multivalent Tn antigen cluster-lysyllysine conjugates. Tetrahedron Lett. 31, 2673-2676.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2673-2676
    • Toyokuni, T.1    Dean, B.2    Hakomori, S.3
  • 20
    • 0000260020 scopus 로고
    • Synthetic carbohydrate vaccines based on tumour-associated antigens
    • T. Toyokuni and A.K. Singhal (1995). Synthetic carbohydrate vaccines based on tumour-associated antigens. Chem. Soc. Rev., 231-242.
    • (1995) Chem. Soc. Rev. , pp. 231-242
    • Toyokuni, T.1    Singhal, A.K.2
  • 21
    • 0020210868 scopus 로고
    • Synthese der glycopeptide O-β-D-galactopyranosyl-(1 → 3)-O-2-acetamido-2-desoxy-α-D-galactopyranosyl-(1 → 3)-L-serin und threonin
    • H. Paulsen and J.P. Holck (1982). Synthese der glycopeptide O-β-D-galactopyranosyl-(1 → 3)-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl-(1 → 3)-L-serin und threonin. Carbohydr. Res. 109, 89-107.
    • (1982) Carbohydr. Res. , vol.109 , pp. 89-107
    • Paulsen, H.1    Holck, J.P.2
  • 22
    • 0028220479 scopus 로고
    • Synthetic immunochemistry of glycohexapeptide analogues characteristic of oncofetal fibronectin. Solid phase synthesis and antigenic activity
    • M. Zheng, M. Gobbo, L. Biondi, F. Filira, S. Hakomori and R. Rocchi (1994). Synthetic immunochemistry of glycohexapeptide analogues characteristic of oncofetal fibronectin. Solid phase synthesis and antigenic activity. Int. J. Peptide Protein Res. 43, 230-238.
    • (1994) Int. J. Peptide Protein Res. , vol.43 , pp. 230-238
    • Zheng, M.1    Gobbo, M.2    Biondi, L.3    Filira, F.4    Hakomori, S.5    Rocchi, R.6
  • 23
    • 0028353768 scopus 로고
    • Synthetic vaccines: Synthesis of a dimeric Tn antigen-lipopeptide conjugate that elicits immune responses against Tn-expressing glycoproteins
    • T. Toyokuni, B. Dean, S. Cai, D. Boivin, S. Hakomori and A.K. Singhal (1994). Synthetic vaccines: Synthesis of a dimeric Tn antigen-lipopeptide conjugate that elicits immune responses against Tn-expressing glycoproteins. J. Am. Chem. Soc. 116, 395-396.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 395-396
    • Toyokuni, T.1    Dean, B.2    Cai, S.3    Boivin, D.4    Hakomori, S.5    Singhal, A.K.6
  • 24
    • 0028674359 scopus 로고
    • Neoglycoproteins from synthetic glycopeptides
    • H. Kunz and K. von dem Bruch (1994). Neoglycoproteins from synthetic glycopeptides. Methods Enzymol. 247, 3-30.
    • (1994) Methods Enzymol. , vol.247 , pp. 3-30
    • Kunz, H.1    Von Dem Bruch, K.2
  • 25
    • 0028672776 scopus 로고
    • Solid phase synthesis of O-glycopeptides
    • T. Norberg, B. Luning and J. Tejbrant (1994). Solid phase synthesis of O-glycopeptides. Methods Enzymol. 247, 87-106.
    • (1994) Methods Enzymol. , vol.247 , pp. 87-106
    • Norberg, T.1    Luning, B.2    Tejbrant, J.3
  • 26
    • 0027010377 scopus 로고
    • Developments in the synthesis of glycopeptides containing glycosyl L-asparagine, L-serine, and L-threonine
    • H.G. Garg, K. von dem Bruch and H. Kunz (1994). Developments In the synthesis of glycopeptides containing glycosyl L-asparagine, L-serine, and L-threonine. Adv. Carbohydr. Chem. Biochem. 50, 277-310.
    • (1994) Adv. Carbohydr. Chem. Biochem. , vol.50 , pp. 277-310
    • Garg, H.G.1    Von Dem Bruch, K.2    Kunz, H.3
  • 27
    • 0002490637 scopus 로고
    • Glycopeptide synthesis
    • Y.C. Lee and R.T. Lee, Eds, Academic Press, San Diego
    • M. Meldal. Glycopeptide synthesis, in: Neoglycoconjugates: Preparation and Applications, Y.C. Lee and R.T. Lee, Eds, p. 145-198, Academic Press, San Diego, 1994.
    • (1994) Neoglycoconjugates: Preparation and Applications , pp. 145-198
    • Meldal, M.1
  • 29
    • 0001331728 scopus 로고
    • Synthetic peptide vaccine design: Synthesis and properties of a high-density multiple antigenic peptide system
    • J.P. Tam (1988). Synthetic peptide vaccine design: Synthesis and properties of a high-density multiple antigenic peptide system. Proc. Natl. Acad. Sci. USA 85, 5409-5413.
    • (1988) Proc. Natl. Acad. Sci. USA , vol.85 , pp. 5409-5413
    • Tam, J.P.1
  • 30
    • 0028947942 scopus 로고
    • Unprotected peptides as building blocks for branched peptides and peptide dendrimers
    • J.C. Spetzler and J.P. Tam (1995). Unprotected peptides as building blocks for branched peptides and peptide dendrimers. Int. J. Peptide Protein Res. 45, 78-85.
    • (1995) Int. J. Peptide Protein Res. , vol.45 , pp. 78-85
    • Spetzler, J.C.1    Tam, J.P.2
  • 31
    • 0028960723 scopus 로고
    • Unprotected peptides as building blocks for the synthesis of peptide dendrimers with oxime, hydrazone and thiazolldine linkages
    • J. Shao and J.P. Tam (1995). Unprotected peptides as building blocks for the synthesis of peptide dendrimers with oxime, hydrazone and thiazolldine linkages. J. Am. Chem. Soc. 117, 3893-3899.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 3893-3899
    • Shao, J.1    Tam, J.P.2
  • 32
    • 0028119946 scopus 로고
    • Immunization and affinity purification of antibodies using resin-immobilized lysine-branched synthetic peptides
    • S. Butz, S. Rawer, W. Rapp and U. Birsner (1994). Immunization and affinity purification of antibodies using resin-immobilized lysine-branched synthetic peptides. Peptide Res. 7, 20-23.
    • (1994) Peptide Res. , vol.7 , pp. 20-23
    • Butz, S.1    Rawer, S.2    Rapp, W.3    Birsner, U.4
  • 33
    • 0029395709 scopus 로고
    • Application of the multiple antigenic peptides (MAP) strategy to the production of prohormone convertases antibodies: Synthesis, characterization and use of 8-branched immunogenic peptides
    • A. Basak, A. Boudreault, A. Chen, M. Chrétien, N.G. Seidah and C. Lazure (1995). Application of the multiple antigenic peptides (MAP) strategy to the production of prohormone convertases antibodies: synthesis, characterization and use of 8-branched immunogenic peptides. J. Peptide Sci. 1, 385-395.
    • (1995) J. Peptide Sci. , vol.1 , pp. 385-395
    • Basak, A.1    Boudreault, A.2    Chen, A.3    Chrétien, M.4    Seidah, N.G.5    Lazure, C.6
  • 34
    • 2442752086 scopus 로고
    • Multiple antigen peptides for immunization
    • N.D. Zegers, W.J.A. Boersma and E. Claassen, Eds, CRC, Boca Raton, FL
    • N.D. Zegers, E. Claassen and W.J.A. Boersma. Multiple antigen peptides for immunization, in: Immunol. Recognit. Peptide Med. Biol., N.D. Zegers, W.J.A. Boersma and E. Claassen, Eds, p. 205-212, CRC, Boca Raton, FL, 1995.
    • (1995) Immunol. Recognit. Peptide Med. Biol. , pp. 205-212
    • Zegers, N.D.1    Claassen, E.2    Boersma, W.J.A.3
  • 35
    • 0029420802 scopus 로고
    • Chemoselective approaches to the preparation of peptide dendrimers and branched artificial proteins using unprotected peptides as building blocks
    • J.P. Tam and J.C. Spetzler (1995). Chemoselective approaches to the preparation of peptide dendrimers and branched artificial proteins using unprotected peptides as building blocks. Biomed. Peptide Proteins Nucleic Acids 1, 123-132.
    • (1995) Biomed. Peptide Proteins Nucleic Acids , vol.1 , pp. 123-132
    • Tam, J.P.1    Spetzler, J.C.2
  • 36
    • 0030202292 scopus 로고    scopus 로고
    • Structure and properties of Tenta Gel resin beads: Implications for combinatorial library chemistry
    • R. Quarrell, T.D.W. Claridge, G.W. Weaver and G. Lowe (1996). Structure and properties of Tenta Gel resin beads: implications for combinatorial library chemistry. Mol. Diversity 1, 223-232.
    • (1996) Mol. Diversity , vol.1 , pp. 223-232
    • Quarrell, R.1    Claridge, T.D.W.2    Weaver, G.W.3    Lowe, G.4
  • 37
    • 0001926444 scopus 로고
    • Solid-phase peptide synthesis
    • E. Gross and J. Meienhofer, Eds, Academic Press, New York
    • G. Barany and RB. Merrifield. Solid-phase peptide synthesis, in: The Peptides. Analysis, Synthesis, Biology, Vol. 2, Part A, E. Gross and J. Meienhofer, Eds, p. 1-284, Academic Press, New York, 1980.
    • (1980) The Peptides. Analysis, Synthesis, Biology , vol.2 , Issue.PART A , pp. 1-284
    • Barany, G.1    Merrifield, R.B.2
  • 38
    • 0014772602 scopus 로고
    • Color test for the detection of free terminal amino groups in the solid-phase synthesis of peptides
    • E. Kaiser, R.L. Colescott, C.D. Bossinger and P.I. Cook (1970). Color test for the detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal Biochem. 34, 595-598.
    • (1970) Anal Biochem. , vol.34 , pp. 595-598
    • Kaiser, E.1    Colescott, R.L.2    Bossinger, C.D.3    Cook, P.I.4
  • 40
    • 84988080209 scopus 로고
    • New strategy for the solid phase synthesis of O-glycopeptides via 2-azido-glycopeptides
    • H. Paulsen, T. Bielfeldt, S. Peters, M. Meldal and K. Bock (1994). New strategy for the solid phase synthesis of O-glycopeptides via 2-azido-glycopeptides. Liebigs Ann. Chem. 369-379.
    • (1994) Liebigs Ann. Chem. , pp. 369-379
    • Paulsen, H.1    Bielfeldt, T.2    Peters, S.3    Meldal, M.4    Bock, K.5
  • 41
    • 0029572443 scopus 로고
    • Coupling difficulty associated with interchain clustering and phase transition in solid phase peptide synthesis
    • J.P. Tam and Y.A. Lu (1995). Coupling difficulty associated with interchain clustering and phase transition in solid phase peptide synthesis. J. Am. Chem. Soc. 117, 12058-12063.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 12058-12063
    • Tam, J.P.1    Lu, Y.A.2
  • 42
    • 0010423097 scopus 로고
    • Design of a new multiple antigen peptide system, using 9-fluorenyl-methoxycarbonyl (Fmoc) strategy
    • J. Bernillon and J.M. Wallach (1993). Design of a new multiple antigen peptide system, using 9-fluorenyl-methoxycarbonyl (Fmoc) strategy. Biotechnol. Tech. 7, 603-608.
    • (1993) Biotechnol. Tech. , vol.7 , pp. 603-608
    • Bernillon, J.1    Wallach, J.M.2
  • 43
    • 26544452925 scopus 로고    scopus 로고
    • preparation
    • M. Pisačka et al. In preparation.
    • Pisačka, M.1
  • 45
    • 2442728452 scopus 로고    scopus 로고
    • Solid phase synthesis of glycopeptide dendrimers with Tn antigenic structure and their biological activities
    • R. Ramage and R Epton, Eds, Mayflower, London
    • J. Ježek, J. Velek, T. Trnka, M. Pisačka and F. Mareček. Solid phase synthesis of glycopeptide dendrimers with Tn antigenic structure and their biological activities, in: Peptides 1996, R. Ramage and R Epton, Eds, p. 503-504, Mayflower, London, 1998.
    • (1998) Peptides 1996 , pp. 503-504
    • Ježek, J.1    Velek, J.2    Trnka, T.3    Pisačka, M.4    Mareček, F.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.