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Collect. Czech. Chem. Commun. 1980, 45, 933-940
https://doi.org/10.1135/cccc19800933

Investigation of drug-protein interactions and the drug-carrier concept by the use of branched polypeptides as model systems. Synthesis and characterization of the model peptides

Ferenc Hudecz and Mária Szekerke

Research Group for Peptide Chemistry, Hungarian Academy of Sciences, Budapest, Hungary

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  • Orosz Ádám, Bősze Szilvai, Mező Gábor, Szabó Ildikó, Herényi Levente, Csík Gabriella: Oligo- and polypeptide conjugates of cationic porphyrins: binding, cellular uptake, and cellular localization. Amino Acids 2017, 49, 1263. <https://doi.org/10.1007/s00726-017-2428-z>
  • Sebestyén Mónika, Szabó Rita, Kőhidai László, Pállinger Éva, Mező Gábor, Kóczán György, Hudecz Ferenc: Synthesis, conformation and cytotoxicity of new, branched polymeric polypeptides containing hydrophobic amino acid or arginine moiety. Struct Chem 2017, 28, 527. <https://doi.org/10.1007/s11224-016-0901-z>
  • Mező Gábor, Herényi Levente, Habdas Jan, Majer Zsuzsa, Myśliwa-Kurdziel Beata, Tóth Katalin, Csík Gabriella: Syntheses and DNA binding of new cationic porphyrin–tetrapeptide conjugates. Biophysical Chemistry 2011, 155, 36. <https://doi.org/10.1016/j.bpc.2011.02.007>
  • Szabó Rita, Peiser Leanne, Plüddemann Annette, Bösze Szilvia, Heinsbroek Sigrid, Gordon Siamon, Hudecz Ferenc: Uptake of Branched Polypeptides with Poly[l-Lys] Backbone by Bone-Marrow Culture-Derived Murine Macrophages:  The Role of the Class A Scavenger Receptor. Bioconjugate Chem. 2005, 16, 1442. <https://doi.org/10.1021/bc050168f>
  • Szabó R, Hudecz F, Reig F: Interfacial interactions between poly[L-lysine]-based branched polypeptides and phospholipid model membranes. Journal of Colloid and Interface Science 2003, 267, 18. <https://doi.org/10.1016/S0021-9797(03)00604-0>
  • Mezö Gábor, de Oliveira Eliandre, Krikorian Dimitrios, Feijlbrief Matty, Jakab Annamária, Tsikaris Vassilios, Sakarellos Constantinos, Welling-Wester Sytske, Andreu David, Hudecz Ferenc: Synthesis and Comparison of Antibody Recognition of Conjugates Containing Herpes Simplex Virus Type 1 Glycoprotein D Epitope VII1. Bioconjugate Chem. 2003, 14, 1260. <https://doi.org/10.1021/bc0341122>
  • Nagy Ildik� B., Majer Zsuzsa, Hudecz Ferenc: Effect of phospholipid bilayers on solution conformation of branched polymeric polypeptides and peptide-polymer conjugates. Biopolymers 2001, 58, 152. <https://doi.org/10.1002/1097-0282(200102)58:2<152::AID-BIP40>3.0.CO;2-V>
  • Mezö Gábor, Reményi Judit, Kajtár Judit, Barna Krisztina, Gaál Dezsö, Hudecz Ferenc: Synthesis and conformational studies of poly(l-lysine) based branched polypeptides with Ser and Glu/Leu in the side chains. Journal of Controlled Release 2000, 63, 81. <https://doi.org/10.1016/S0168-3659(99)00175-3>
  • Nagy Ildikó B., Alsina Maria A., Haro Isabel, Reig Francesca, Hudecz Ferenc: Phospholipid−Model Membrane Interactions with Branched Polypeptide Conjugates of a Hepatitis a Virus Peptide Epitope. Bioconjugate Chem. 2000, 11, 30. <https://doi.org/10.1021/bc9900385>
  • Nagy Ildikó B., Dancs Andrea, Kóczán György, Mezö Gábor, Hudecz Ferenc: Conjugation of HS-Oligopeptides with Polymeric Branched Chain Polypeptides Containing Multiple Amino Groups. Journal of Bioactive and Compatible Polymers 2000, 15, 139. <https://doi.org/10.1177/088391150001500203>
  • Sospedra P., Nagy I. B., Haro I., Mestres C., Hudecz F., Reig F.: Physicochemical Behavior of Polylysine-[HAV-VP3 Peptide] Constructs at the Air−Water Interface. Langmuir 1999, 15, 5111. <https://doi.org/10.1021/la981305i>
  • Pató Janos, Ulbrich Karel, Subr Vladimir, Baker Peter, Mezö Gábor, Hudecz Ferenc: Synthesis of Macromolecular Conjugates of a Urokinase Inhibitor: Amiloride. Journal of Bioactive and Compatible Polymers 1999, 14, 99. <https://doi.org/10.1177/088391159901400201>
  • Nagy I. B., Haro I., Alsina M. A., Reig F., Hudecz F.: Interaction of branched chain polymeric polypeptides with phospholipid model membranes. Biopolymers 1998, 46, 169. <https://doi.org/10.1002/(SICI)1097-0282(199809)46:3<169::AID-BIP4>3.0.CO;2-J>
  • Wilkinson Katalin A., Vordermeier Hans, R. J. Wilkinson,, Ivanyi Juraj, Hudecz Ferenc: Synthesis and in Vitro T-Cell Immunogenicity of Conjugates with Dual Specificity:  Attachment of Epitope Peptides of 16 and 38 kDa Proteins from Mycobacterium tuberculosis to Branched Polypeptide. Bioconjugate Chem. 1998, 9, 539. <https://doi.org/10.1021/bc970159+>
  • García M., Nagy I. B., Alsina M. A., Mezö G., Reig F., Hudecz F., Haro I.: Analysis of the Interaction with Biomembrane Models of the HAV-VP3(101−121) Sequence Conjugated to Synthetic Branched Chain Polypeptide Carriers with a Poly[l-Lysine] Backbone. Langmuir 1998, 14, 1861. <https://doi.org/10.1021/la970443p>
  • Biró Judit, Bösze Szilvia, Hudecz Ferenc, Nagy Zoltán, Rajnavölgyi Éva, Schmidt Béla, Rákász Éva, Falus András: The effect of WSEWS pentapeptide and WSEWS-specific monoclonal antibodies on constitutive and IL-6 induced acute-phase protein production by a human hepatoma cell line, HEPG-2. Immunology Letters 1995, 46, 183. <https://doi.org/10.1016/0165-2478(95)00039-8>
  • Pimm Malcolm V, Gribben Sandra J, Bogdán Katalin, Hudecz Ferenc: The effect of charge on the biodistribution in mice of branched polypeptides with a poly(l-lysine) backbone labelled with 125I, 111In or 51Cr. Journal of Controlled Release 1995, 37, 161. <https://doi.org/10.1016/0168-3659(95)00080-R>
  • Hudecz F., Clegg J. A., Kajtar J., Embleton M. J., Pimm M. V., Szekerke M., Baldwin R. W.: Influence of carrier on biodistribution and in vitro cytotoxicity of methotrexate-branched polypeptide conjugates. Bioconjugate Chem. 1993, 4, 25. <https://doi.org/10.1021/bc00019a004>
  • Hudecz F., Gaál D., Kurucz I., Lányi Á., Kovács A.L., Mezö G., Rajnavölgyi É., Szekerke M.: Carrier design: cytotoxicity and immunogenicity of synthetic branched polypeptides with poly(L-lysine) backbone. Journal of Controlled Release 1992, 19, 231. <https://doi.org/10.1016/0168-3659(92)90079-7>
  • Hudecz F., Price M.R.: Monoclonal antibody binding to peptide epitopes conjugated to synthetic branched chain polypeptide carriers. Journal of Immunological Methods 1992, 147, 201. <https://doi.org/10.1016/S0022-1759(12)80009-3>
  • Hudecz Ferenc, Clegg J. A., Kajtar J., Embleton M. J., Szekerke M., Baldwin R. W.: Synthesis, conformation, biodistribution and in vitro cytotoxicity of daunomycin-branched polypeptide conjugates. Bioconjugate Chem. 1992, 3, 49. <https://doi.org/10.1021/bc00013a008>
  • Plaue S., Muller S., Briand J.P., Van Regenmortel M.H.V.: Recent advances in solid-phase peptide synthesis and preparation of antibodies to synthetic peptides. Biologicals 1990, 18, 147. <https://doi.org/10.1016/1045-1056(90)90001-G>
  • Clegg J. A., Hudecz F., Mezo G., Pimm M. V., Szekerke M., Baldwin R. W.: Carrier design: biodistribution of branched polypeptides with a poly(L-lysine) backbone. Bioconjugate Chem. 1990, 1, 425. <https://doi.org/10.1021/bc00006a009>
  • Mező G., Hudecz F., Kajtár J., Szókán Gy., Szekerke M.: The influence of the side‐chain sequence on the structure–activity correlations of immunomodulatory branched polypeptides. Synthesis and conformational analysis of new model polypeptides. Biopolymers 1989, 28, 1801. <https://doi.org/10.1002/bip.360281013>
  • Rajnavölgyi É., Lányi Á, Hudecz F., Kurucz I., Kiss K., László G., Szekerke M., Gergely J.: Structural characteristics influencing the carrier function of synthetic branched polypeptides based on poly[Lys-(dl-Ala)3)]backbone. Molecular Immunology 1989, 26, 949. <https://doi.org/10.1016/0161-5890(89)90113-2>
  • Hudecz Ferenc, Kajtȧr Judit, Kurucz IstvȧN, Kovȧcs Attila L., Szekerke MȧRia: Investigation of the carrier function of polypeptides. Synthesis, conformation and cytotoxicity of oxazolone conjugates of poly(Lys) and poly[Lys‐(DL‐ALAm)]. Makromolekulare Chemie. Macromolecular Symposia 1988, 19, 107. <https://doi.org/10.1002/masy.19880190108>
  • Hudecz Ferenc, Kajtár Judit, Szekerke Mária: Influence of side-chain-terminating moieties on the conformation of branched polypeptides and their conjugates with 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone. Biophysical Chemistry 1988, 31, 53. <https://doi.org/10.1016/0301-4622(88)80008-5>
  • Szókán Gyula, Mezö Gábor, Hudecz Ferenc: Application of marfey's reagent in racemization studies of amino acids and peptides. Journal of Chromatography A 1988, 444, 115. <https://doi.org/10.1016/S0021-9673(01)94014-2>
  • Rajnavölgyi Éva, Hudecz Ferenc, Mezö Gábor, Szekerke Mária, Gergely János: Isotype distribution and fine specificity of the antibody response of inbred mouse strains to four compounds belonging to a new group of synthetic branched polypeptides. Molecular Immunology 1986, 23, 27. <https://doi.org/10.1016/0161-5890(86)90168-9>
  • Szókán Gyula, Kelemen Gabriella, Török Angela: High-performance liquid chromatography of isopeptides. Journal of Chromatography A 1986, 366, 283. <https://doi.org/10.1016/S0021-9673(01)93475-2>
  • Hudecz F., Kov�cs P., Kutassi-Kov�cs S., Kajt�r J.: GPC, CD and sedimentation analysis of poly-Lys and branched chain poly-Lys-poly-DL-Ala polypeptides. Colloid & Polymer Sci 1984, 262, 208. <https://doi.org/10.1007/BF01458962>